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Radhakrishna Chennur (480-46-925)
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IP Address: 14.139.127.9
Algal lipids, fatty acids and sterols

P. Kumari, M. Kumar, C. R. K. Reddy and
B. Jha, CSIR-Central Salt and Marine Chemicals
Research Institute, India
DOI: 10.1533/9780857098689.1.87
Abstract: Algae are photosynthetic organisms with ubiquitous distribution and
contain varied forms of lipids owing to their extreme habitat diversity. This chapter
presents detailed information on the structure and distribution of lipids, fatty
acids and sterols in algae together with the genes and enzymes involved in their
metabolism. The developments in acclimatory roles of lipids, fatty acids and sterols
in response to changes in environmental factors such as nutrients, light, temperature
and salinity have been discussed. Further, the current status of lipidomics in algae
has also been discussed presuming its promising implications in elucidation of novel
lipids and understanding of complex metabolic pathways.
Key words: algae, lipids, fatty acids, sterols, polyunsaturated fatty acids (PUFAs),
seasonal variations.
3.1
Introduction
Algae comprise a diverse group of photosynthetic organisms that exist in

various forms and sizes ranging from unicellular microscopic microalgae to
multicellular macrophytic forms inhabiting a broad range of extreme habitats that encompass both the aquatic (marine and freshwater) and terrestrial
ecosystems. As a result of thriving in such diverse and extreme environments,
they produce an array of unique bioactive, complex, exotic acyl lipids and
fatty acids that are not generally present in terrestrial plants. Algal lipids are
of immense commercial value as alternative sources of nutritionally important n-3 polyunsaturated fatty acids (PUFAs) and are therefore, widely
employed as ingredients in functional food formulations (Mendis and Kim,
2011; Miurcov et al., 2011). The study of algal lipids mostly encompasses
Woodhead Publishing Limited, 2013

IP Address: 14.139.127.9
88 Functional ingredients from algae for foods and nutraceuticals

the elucidation of lipid and fatty acid composition, their metabolic pathways,
lipid signaling, the genes and enzymes involved as well as their roles in stress
response, innate immunity and defense against pathogens. Recently, the thrust
on biofuel has renewed the interest in algal lipid biochemistry to manipulate
these renewable reservoirs using modern, advanced tools of mass spectrometry and genetic engineering. However, most of the lipid research has been
focused on a few model organisms such as Chlamydomonas reinhardtii and
Dunaliella spp. (Goss and Wilhelm, 2009; Guschina and Harwood, 2006;
Guschina and Harwood, 2009; Harwood and Guschina, 2009; Thompson,
1996) but with relatively less emphasis on macroalgae. Thus, the present chapter will summarize the information available on lipid, fatty acid and sterol
compositions of algae and their responses to environmental variations in the
light of recent developments, with more emphasis on macrophytes.
3.2
Structure and occurrence of algal lipids
Algal lipids consist of phospholipids, glycolipids (glycosylglycerides) and

non-polar glycerolipids (neutral lipids) analogous to higher plants along with
betaine and some unusual lipids that may be characteristic of a particular
genus or species. Their chain length and degree of unsaturation are also significantly higher than those of higher plants. The basic structure of glycerolipids consists of a glycerol backbone metabolically derived from glycerol
3-phosphate to which hydrophobic acyl groups are esterified at sn-1 and sn-2
positions. Phospholipids are characterized by the presence of a phosphate
group at sn-3 position which is further linked to a hydrophilic head group
that classifies individual phospholipid molecules. The major phospholipids
found in algae are phosphatidylglycerol (PG), phosphatidylcholine (PC),
phosphatidylethanolamine (PE), phosphatidylserine (PS), phosphatidylinositol (PI) and phoshatidic acid (PA) containing glycerol, choline, ethanolamine,
serine, myo-inositol, and phosphomonoester as their characteristic head
groups, respectively (Fig. 3.1). Glycolipids contain 1,2-diacyl-sn-glycerol
moiety with mono- or oligosaccharide groups attached at sn-3 position of
the glycerol backbone. The typical algal glycolipids include monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG) and sulfolipid,
sulfoquinovosyldiacylglycerol (SQDG) with their respective structures as
1,2-di-O-acyl-3-O--D-galactopyranosyl-sn-glycerol, 1,2-di-O-acyl-3-O-(6O--D-galactopyranosyl--D-galactopyranosyl)-sn-glycerol and 1,2-di-Oacyl-3-O-(6-deoxy-6-sulfo--D-glucopyranosyl)-sn-glycerol, respectively
(Fig. 3.1). MGDG and DGDG contain one and two galactose molecules,
respectively, and are uncharged at physiological pH, while SQDG carries a
negative charge due to its sulfonic acid residue at position 6 of the monosaccharide moiety. In non-polar glycerolipids, either one, two or all the
three positions (sn-1, sn-2 and sn-3) are esterified to the hydrophobic acyl
groups that may be saturated or unsaturated, forming monoacylglycerol,
Algal lipids, fatty acids and sterols 89

CH2OH
CH2 OOCR
RCOO CH
OH
CH2 O P O
O
OO
OH
CH2
CH2OH
RCOO
O
O
+
O CH2CH2N(CH3)3
Phosphatidylcholine (PC)
CH2
RCOO
OOCR
CH
CH2
CH2CH2NH3
Phosphatidylethanolamine (PE)

IP Address: 14.139.127.9
RCOO CH
CH2
RCOO
OOCR
O
NH+
3
O P O CH2CHCOO
O
CH2 O
CH
CH2 O
O
C
RCOO
CH2
CHOCOR1
OH
OH
Phosphatidic acid (PA)
CH2
CH
+
CH2 N(CH3)3
RCOO
OOCR
CH
CH2
CH
CH2CH2
+
N(CH3)3
COO
Diacylglycerl carboxyhydroxymethylcholine
(DGCC)
OH
O
CH2
CHOCOR1
CH2OCOR2
Sulfoquinovosyldiacylglycerol
(SQDG)
CH2
CH
O
O
CH2
Diacylglyceryl hydroxymethyltrimethyl--alanine
(DGTA)
CH2SO3
R1
O
P O
O
OOCR
CH
CH2
COO
Digalactosyldiacylglycerol
(DGDG)
OH
Phosphatidylinositol (PI)
CH2
+
N(CH3)3
OOCR
CH
CH2
CH2
O
OH OH O O
OH
Phosphatidylserine (PS)
O
R2 C O
CH
CH2OCOR2
OH
CH2
CH2CH2
Diacylglycerol-O-(N.N.N.-trimethyl)-homoserine
(DGTS)
CH2
CH2OH
OH
O
OH
O
O
COO
OH
CH2
CH
OH
Monogalactosyldiacylglycerol
(MGDG)
OOCR
CH
CH2
RCOO
CH2OCOR2
Phosphatidylglycerol (PG)
CH2
CHOCOR1
CHOH
OOCR
CH2
CH2
CH2
OOC
OOC
OOC
R
R
R
Triacylglycerol
(TAG)
Fig. 3.1 Structure of common lipid molecules found in algae.
diacylglycerol and triacylglycerol, respectively. Betaine lipids contain a betaine

moiety instead of phosphorus or carbohydrate as a polar group linked to
sn-3 position of glycerol by an ether bond with fatty acids esterified in sn-1
and sn-2 positions. The three types of betaine lipids present in algae are
1,2-diacylglyceryl-3-O-4-(N,N,N-trimethyl)-homoserine (DGTS), 1,2-diacylglyceryl-3-O-2-(hydroxymethyl)-(N,N,N-trimethyl)--alanine
(DGTA)
and 1,2-diacylglyceryl-3-O-carboxy-(hydroxymethyl)-choline (DGCC) (see
Fig. 3.1). These betaine lipids are all zwitterionic at neutral pH due to their
positively-charged trimethylammonium group and a negatively charged carboxyl group.
3.2.1 Phospholipids
Phospholipids (PL) represent 1020% of total lipids in algae (Dembitsky
and Rozentsvet, 1990; Dembitsky and Rozentsvet, 1996) except dinophytes
such as Kraenia, Karlodinium, Takayama species (Mooney et al., 2007) and
Polarella glacialis (Thomson et al., 2004) where its content is 7895%. They
are located in extra-chloroplast membranes with the exception of PG which
occurs in significant amounts in thylakoid membranes. Cell membranes

IP Address: 14.139.127.9

utilize the amphiphilic nature of phospholipids to maintain structural
integrity and selective permeability while PG aids glycolipids in maintaining the stability of photosynthetic apparatus. PG is the dominant phospholipid in green algae that accounts for 2047% of phospholipids, while
PC represents >60% of PL in red algae, and both PC and PE are dominant
in brown algae and each ranges from 11.3% to 29.3% of PL (Dembitsky
et al., 1990; Dembitsky and Rozentsvet, 1996; Illijas et al., 2009; Jones and
Harwood, 1992; Khotimchenko et al., 1990; Kulikova and Khotimchenko,
2000; Vakovsky et al., 1996). However, PC is often replaced by DGTS in
green algae and by its homologue, DGTA, in brown algae. PS and PI are
found in appreciable amounts while DPG and PA are present as minor
components. In contrast, Rozentsvet et al. (1995) reported higher PA contents (2.517.1% of PL) for 12 species of freshwater algae. A large number of unidentified lipids were also present in amounts ranging from 2.7%
to 10.3% of PL (Dembitsky and Rozentsvet, 1990; Dembitsky et al., 1990;
Kulikova and Khotimchenko, 2000). Phospholipids are further characterized by higher contents of n-6 fatty acids (FAs) as compared to galactolipids
except PG that has substantial amount of n-3 FAs, especially -linolenic
acid (C18:3 n-3, ALA). Major FAs present are oleic, palmitic, stearic acid,
arachidonic acid (C20:4 n-6, AA), eicosapentaenoic acid (C20:5 n-3, EPA).
Further, an unusual FA, 3-trans-hexadecenoic acid (16:1, 3t) is esterified to
sn-2 position of PG in all eukaryotic photosynthetic organisms (Tremolieres
and Siegenthaler, 1998).
Moreover, red algae also contain small amounts of sphingolipids such
as cerebrosides and ceramides detected in Chondrus crispus, Polysiphonia
lanosa, Ceratodictyon spongiosum and Halymenia sp. (Bano et al., 1990; Lo
et al., 2001; Pettitt et al., 1989). Vakovsky et al. (1996) detected ceramidephosphoinositol (CPI) in 11 red algae. Subsequently, Khotimchenko et al.
(2000) quantified this lipid from 22 red algal species belonging to Nemaliales,
Cryptonemiales, Gigartinales, Rhodymeniales and Ceramiales. They reported
its range from 2.6% to 15.7% of PL in Nemalion vermiculare and Gracilaria
verrucosa, respectively. Further, Khotimchenko and Vakovsky (2004) isolated and characterized inositol containing sphingolipid from G. verrucosa
that contained palmitic (51.7%), stearic (23.2%), myristic (9.8%), oleic (9.8%)
and palmitoleic acids in its acyl chains.
3.2.2 Glycolipids
Glycolipids are predominantly located in photosynthetic membranes with
MGDG and SQDG strictly restricted to the thylakoid membranes of
the chloroplast while DGDG is also found in extraplastidial membranes.
Recently, X-ray crystallographic study of PSI and PSII revealed the presence
of 4 and 25 lipid molecules (MGDG, DGDG, SQDG and PG), respectively,
in Thermosynochococcus elongatus (Guskov et al., 2009). These glycolipids

IP Address: 14.139.127.9

are found to be indispensible for assembly and functional regulation of PSII
(refer to the review by Mizusawa and Wada, 2012). Further, they invariably
constitute more than half of the lipids with MGDG representing 3156%
(Hofmann and Eichenberger, 1997; Khotimchenko, 2002; Muller and
Eichenberger, 1994; Sanina et al., 2004; Yan et al., 2011) with the exception
of a few red algae such as Palmaria stenogona, Ceramium kondoi, Laurencia
nipponica, Anfeltia tobuchiensis and Exophyllum wentii where DGDG was
the characteristic glycolipid (35.764% of total lipids), (Illijas et al., 2009;
Khotimchenko, 2002; Sanina et al., 2004) whereas the members of Fucales
(brown algae) contained higher SQDG content varying between 36.8 and
48.8% (Khotimchenko, 2002; Sanina et al., 2004).
A unique feature of glycolipids is their high n-3 PUFA contents similar
to higher plants. MGDG is the most unsaturated glycolipid in green and red
algae with DGDG in brown algae, while SQDG was the most saturated one.
Their FA composition revealed that they contain a mixture of prokaryotic
and eukaryotic types of FAs (FAs containing one C18 and one C16 PUFA).
Moreover, marine algae also contain long chain C20 and C22 PUFAs such
as AA, EPA and docosahexaenoic acid (C22:6, n-3, DHA) in contrast to
the freshwater algae with ALA as a major FA in galactolipids and palmitic
acid in SQDG. The chain length of these glycolipid FAs (C16 or C18) indicates whether they are synthesized de novo within the plastid or imported
from the endoplasmic reticulum. MGDG and DGDG contain hexadecatetraenoic acid (C16:4 n-3), ALA, stearidonic acid (C18:4 n-3, STA) and
linoleic acid (C18:2 n-6, LA) in green algae, AA and EPA in red, and both
in brown algae, while SQDG contains palmitic and oleic acid as major
FAs (Hofmann and Eichenberger, 1997; Illijas et al., 2009; Khotimchenko,
2002; Khotimchenko, 2003; Sanina et al., 2004). However, higher contents
of AA, EPA and ALA have been reported in SQDG of Ahnfeltia touchiensis, Ulva fenestrata and Undaria pinnatifida (Khotimchenko, 2003; Sanina
et al., 2004).
3.2.3 Betaine lipids

Betaine lipids are widely distributed in algae and extensively reviewed by
Dembitsky (1996) and Kato et al. (1996). DGTS abundantly occurs in green
algae with 5.256.5% of polar lipids and DGTA in brown algae with 7.396.8%
of polar lipids (Dembitsky and Rozentsvet, 1989; Dembitsky and Rozentsvet,
1996; Eichenberger et al., 1993; Jones and Harwood, 1992; Kulikova and
Khotimchenko, 2000; Makewicz et al., 1997; Muller and Eichenberger, 1994).
However, there is no report of betaine lipids in most of the red algal species investigated except the presence of DGTS in Lomentaria articulata,
Mastocarpus stellatus, Phyllophora pseudoceranoides, Membranoptera alata
and Phycodrys rubens (Knzler and Eichenberger, 1997). These two betaine
lipids resemble PC in structure due to the presence of quarternary ammonium

IP Address: 14.139.127.9

group and thus replace PC to traces in most of the marine algae, including
Ulotrichales, Scytosiphonales and Desmarestiales. It was further confirmed
by the study of lipid composition of C. reinhardtii using matrix-assisted laser
desorption ionization-time of flight mass spectrometry (MALDI-TOF MS)
by Vieler et al., 2007, where they detected DGTA as a major membranebound lipid while PC and PS were not present. In contrast, freshwater algae
mainly contain PC and little DGTS. They also vary in their FA compositions, exhibiting saturated fatty acids (SFAs), myristic and palmitic at sn-1
and C18 PUFAs, predominantly LA and ALA at sn-2 position while DGTS
in marine algae are esterified to long-chain PUFAs at both the sn-1 and sn-2
positions. DGTA contain palmitic, myristic, oleic, LA, ALA, AA and EPA as
major FAs (Hofmann and Eichenberger, 1997; Makewicz et al., 1997). DGTA
is considered to play an important role in the redistribution of acyl chains
and the biosynthesis of galactolipids and DGTS in lipid-linked desaturation
of fatty acids (Giroud and Eichenberger, 1989; Hofmann and Eichenberger,
1998). Riekhof et al. (2005) identified and isolated the betaine lipid synthase
(BTA1Cr) gene from C. reinhardtii that encodes DGTS. The heterologous
expression of BTA1Cr led to DGTS accumulation in Escherichia coli (which
normally lacks this lipid) and allowed in vitro analysis of its enzymatic properties. The third betaine lipid, DGCC is the characteristic of Haptophyceae
and contains palmitic, stearic, oleic, AA, EPA, DPA and DHA as major FAs
(Kato et al., 1996).
3.2.4 Non-polar glycerolipids (neutral lipids)

Triacyglycerol (TAG) is the most prevalent neutral lipid accumulated in algae
as a storage product and energy reservoir. Its level is highly plastic in algae and
ranges between 1% and 97% (Dembitsky and Rozentsvet, 1996; Dembitsky
et al., 1992; Fan et al., 2007; Hofmann and Eichenberger, 1997; Illijas et al.,
2009; Kamenarska et al., 2004; Khotimchenko and Kulikova, 1999; Kulikova
and Khotimchenko, 2000; Rozentsvet et al., 1995). Algal lipids are mostly
characterized by saturated and monounsaturated fatty acids but many oleaginous algae exhibit the potential to accumulate long-chain PUFAs (AA,
EPA and DHA). Parietochloris incisa accumulates AA; Phaeodactylum tricornutum, Porphyridium cruentum, Nitzschia laevis and Nannochloropsis sp.
accumulate EPA; Pavlova lutheri accumulates both AA and EPA; and S.
mangrovei, Isochrysis galbana accumulate DHA (Bigognoa et al., 2002; Chen
et al., 2007; Khozin-Goldberg et al., 2000; Khozin-Goldberg and Boussiba,
2011; Meireles et al., 2003; Patil et al., 2007). TAGs are mostly synthesized in
light, stored in cytosolic lipid bodies and reutilized for polar lipid synthesis in
the dark (Thompson, 1996). PUFA-rich TAGs act as reservoirs for FAs and
donate acyl groups for polar lipid biosynthesis especially under adverse conditions, when de novo syntheses of PUFAs are impaired (Khozin-Goldberg
et al., 2000).

3.2.5 Unusual lipids
In addition, a large number of unusual lipids have been reported in various
algal species and are mentioned in Table 3.1.

IP Address: 14.139.127.9
3.3
Structure and occurrence of algal fatty acids, oxylipins

and sterols
Algae contain a wide variety of fatty acids and their oxidized products (oxylipins), and sterols of nutritional and chemo-taxonomic importance. The fatty
acid carbon skeleton mainly ranges from C12 to C24 with one or more double
bonds in algae. The oxylipins are mainly derived from C16, C18, C20 or C22
PUFAs depending on the nature of PUFAs present in the algae. The algal sterols consists of cholesterol, fucosterol, isofucosterol, clionosterol, dihydroxysterols and others biosynthesized from isoprenoid metabolic pathways of both
the mevalonate and methyl-D-erythritol 4-phosphate. Numerous studies have
confirmed that the occurrence of fatty acids, oxylipins and sterols in algae
are highly specific to their respective classes and their evolutionary history.
A large number of studies have been undertaken in recent years deciphering
the novel structures of algal fatty acids, oxylipins and sterols in the context
of chemotaxonomic, nutritional and abiotic stresses in algae. The individual
components are discussed in great detail in the following sections.
3.3.1 Fatty acids

Fatty acids are carboxylic acids with long aliphatic chains that may be straight
or branched, saturated or unsaturated. Most of the naturally occurring FAs
contain even carbon numbers (C4C28); however, odd chain FAs are also
prevalent in algae. On the basis of the number of double bonds present, FAs
are classified as monounsaturated FAs (MUFAs, with 1 double bond), and
polyunsaturated FAs (PUFAs, with 2 double bonds). Further, PUFAs are
classified as n-3 or n-6 FAs depending on the position of the first double bond
from the methyl end. n-3 PUFAs are of nutritional importance as these cannot be synthesized by humans and thus obtained through diet. Often FAs
also contain other groups such as hydroxyl, halogens, keto, epoxy groups and
others thereby forming hydroxyl-, halogenated-, oxo- and epoxy-FAs.
Algae are extensively explored for fatty acids, especially PUFAs (representing 1070% of total fatty acids; TFAs) due to their chemotaxonomic and
nutritional importance, with their compositions varying even within the same
phyla. A list of FA chemotaxonomic markers characteristic of algae is presented in Table 3.2. FA compositions of freshwater green algae are comparable to vascular plants and contain C16 PUFAs > C18 PUFAs while PUFAs
greater than C18 are abundantly found in marine species, with green algae
being rich in C18 PUFAs (ALA, STA and LA) and red algae being rich in
Euglenophyta, Rhodophyta and

diatoms
Brown algae
10
7
8
Unusual sulfur-containing PL,

phosphatidylsulfocholine (PSC)
Phosphatidyl-O-[N-(2-hydroxyethyl) glycine]
(PHEG) containing glycine head group (3%25%
of PL) and rich in AA (80%) and EPA (10%)
Amino acid (-CH2- CH2-NH- CH (NH2) CH2CH2-COOH) containing PL
Carboxylated glycoglycerolipid, diacylglyceryl
glucuronide (DGGA) containing AA and DPA
Acylated and diacylated SQDG
Novel lipids
Sulfonoglycolipid crassiculisine (C39H73O12SNa)

containing -O-(6-sulpho-
-D-quinovopyranosyl)-glycerol as sugar moiety
and methyl myristate and palmitate as acyl chains
Freshwater and marine algae both Chlorosulfolipids
Botryococcus braunii
Unusual hydrocarbons (C23- C40) and ether lipids
accounting to 80% of cell dry wt.
Emiliania huxleyi, Isochrysis
Long chain (C35-C40) alkenes, alkenones and
alkenoates
galbana
Arainvillea nigricans
Arainvilloside containing a 6-deoxy-6-aminoglucose
moiety
Ochromonas danica and Pavlova

lutheri
P. lutheri, Scytonema sp. and
Oscillatoria raoi
Chondria armata
Brown algae
Algae
List of unusual lipids reported from algae
S. No.
Table 3.1
Andersen and Taglialatela-Scafati

(2005)
Dembitsky and Srebnik (2002)

Achitouv et al. (2004), Metzger and
Largeau (2005)
Eltgroth et al. (2005)
Shao et al. (2002)
Reshef et al. (1997)
Eichenberger and Gribi (1997)
Eichenberger et al. (1995), Makewicz

et al. (1997), Kulikova and
Khotimchenko (2000)
Khotimchenko and Titlyanova (1996)
Harwood and Jones (1989)
References

IP Address: 14.139.127.9
16
15
14
13
12
11
Six minor new glycolipids in crude methanolic

extracts that included 1,2-di-O-acyl-3-O-(acyl-6galactosyl)-glycerol (GL1a) and sulfonoglycolipids
2-O-palmitoyl-3-O-(6sulfoquinovopyranosyl)glycerol and its ethyl ether derivative
Arainvillea nigricans
Antimitotic ether-linked glycoglycerolipids
nigricanosides A and B
Sargassum thunbergii
(2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)
-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3O--D-galactopyranosyl-sn-glycerol and
(2S)-1-O-(9Z,12Z,15Z-octadecatrienoyl)-2O-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-3-O--Dgalactopyranosyl-sn-glycerol
Gymnodinium sp.
Trigalactosyldiacylglycerol containing 18:1/14:0,
18:1/16:0 and 18:1/18:1 at sn-1 and sn-2 positions.
Phaeodactylum tricornutum
SQDG and acylated SQDG containing sn-1:
C16:0/ sn-2: C16:0/2 C20:5 and sn-1: C20:5/sn-2:
C16:0/2 C20:5
Ulva fasciata and Dilophys fasciola Mannose and rhamnose containing glycolipids
Chondria armata
El-Baroty et al. (2011)
Naumann et al. (2011)
Gray et al. (2009)
Kim et al. (2007)
Williams et al. (2007)
Al-Fadhli et al. (2006)

IP Address: 14.139.127.9
C16:0, C18:4 (n-3), C18:5 (n-3), C22:6 (n-3), C28:7 (n-6),

C28:8 (n-3)
C16:0, C20:1, C20:5 (n-3)
C16:0, C16:1, C18:1, C20:5 (n-3), C22:5 (n-3), C22:6

(n-3)
C16:0, C16:1, C18:1, C18:2 (n-6), C18:3 (n-3), C20:5 (n3), C22:6 (n-3)
C16:0, C16:1 (n-13t), C 18:4 (n-3), C18:5 (n-3), C20:5
(n-3)
C16:0, C22:5 (n-3), C20:5 (n-3)
C16:0, C18:1, C20:3, C20:4 (n-3), C20:5 (n-3)
Dinophyceae
(Dinoflagellates)
Cryptophyceae
Chrysophyceae
C14:0, C16:0, C16:1, C16:3, C20:4 (n-6), C20:5 (n-3)

C16:0, C16:1, C18:1, C18:2 (n-6), C18:3 (n-3)
Xanthophyceae
Cyanobacteria
Prasinophyceae
C16:0, C16:1,C18:1, C18:2 (n-6), C18:3 (n-3), C20:4 (n6), C20:5 (n-3)
C16:0, C18:1, C18:3 (n-3), C20:4 (n-6), C20:5 (n-3)
Euglenophyceae
Chlororachinophyceae
Eustigmatophyceae
Pyemnesiophyceae
(Haptophyceae)
Raphidophyceae
C16:0, C16:1, EPA, C20:5 (n-3), C22:6 (n-3), High

C16:1(n-7)/C16:0 ratio, High C16:0/C18:0 ratio
Phaeophyta
Microalgae
Bacillariophyceae
(Diatoms)
C16 and C18 PUFAs, High C18/C20 PUFA ratio

C20:4 (n-6), C20:5 (n-3), High C20/C18 PUFA ratio,
High C18:1
C20 PUFA C18 PUFA, High C18:1 and C14:0
Biomarkers/characteristic fatty acids
Fatty acid biomarkers characteristic of different algal groups
Macroalgae
Chlorophyta
Rhodophyta
Algae
Table 3.2
Zhukova and Aizdacher (1995), Pratoomyot et al.

(2005), Lang et al. (2011)
Patil et al. (2007), Lang et al. (2011)
Patil et al. (2007), Pratoomyot et al. (2005)
Leblond et al. (2005)

Zhukova and Aizdacher (1995), Patil et al. (2007),
Lang et al. (2011)
Lang et al. (2011)
Zhukova and Aizdacher (1995), Basova (2005),

Patil et al. (2007), Lang et al. (2011)
Marshall et al. (2002)
Zhukova and Aizdacher (1995), Gatenby et al.

(2003), Liang et al. (2005), Pratoomyot et al.
(2005), Patil et al. (2007)
Zhukova and Aizdacher (1995), Leblond et al.
(2003), Leblond et al. (2006), Mooney et al.
(2007), Lang et al. (2011)
Zhukova and Aizdacher (1995), Patil et al. (2007),
Lang et al. (2011)
Basova (2005)
Khotimchenko et al. (2002), Li et al. (2002),

Kumari et al. (2010), Kumari et al. (2012)
References

IP Address: 14.139.127.9

IP Address: 14.139.127.9

C20 PUFAs (AA and EPA), while brown algae exhibit both in appreciable
amounts (Galloway et al., 2012; Khotimchenko et al., 2002; Kumari et al.,
2010; Kumari et al., 2013; Li et al., 2002). These long chain PUFAs are indispensible for proper growth and development of organisms with n-3 PUFAs
(ALA, STA and EPA) being beneficial for the prevention of cardiovascular
and other chronic diseases such as diabetes, hypertension and autoimmune
diseases, DHA for visual and neurological health, while AA and EPA are precursors of bioregulators prostaglandins, thromboxanes and other eicosanoids,
which influence inflammation processes and immune reactions (Calder and
Grimble, 2002).
Recently, Lang et al. (2011) screened 2071 strains of SAG cultures belonging to 17 microalgal taxonomic groups and found 76 different fatty acids.
Their study revealed that Glaucophytes, Rhohophytes, Eustigmatophytes and
Phaeophytes were rich sources of AA and EPA, Haptophytes and Dinophytes
of EPA and DHA, Euglenoids of AA and DHA, Xanthophytes of AA and
Cryptophytes of EPA. Moreover, unusual, very long chain PUFAs, C28:7
(n-6) and C28:8 (n-3), have also been reported for Dinophytes (Kraniaceae
members), although in low levels <1% (Leblond et al., 2003; Mooney et al.,
2007). Further, some novel FAs have also been found in algae such as fatty
acid amides from freshwater green algae Rhizoclonium hieroglyphicum
(Dembitsky et al., 2000), halogenated fatty acid amides, grenadamides B and
C from cyanobacteria Lyngbya majuscula (Jimnez et al., 2009), polyhalogenated homosesquiterpenic fatty acids containing chlorine, bromine and diene
groups from Plocamium cartilageneum (ezanka and Dembitsky, 2001) and
mono and diunsaturated -hydroxy FAs in ester bound lipids of green algal
cell wall from Tetrahedron minimum, Scendesmus communis and Pediastrum
boryanum (Allard and Templier, 2000; Blokker et al., 1998). A detailed
account of halogenated fatty acid occurrence in green, brown and red algae
exhibiting biological activities have been discussed by Dembitsky and Srebnik
(2002). Very long chain iso- and anteiso-branched FAs, up to 33-methyltetratricontanoic acid have been identified as picolinyl ester derivatives using
GC-MS in N-acylphosphatidylethanolamines from a natural cyanobacterial
mat of Calothrix sp. (ezanka et al., 2009). Chang et al. (2011) identified a
series of odd-chain fatty acids (OC-FAs) in thraustochytrids with 19 strains
showing high proportions of saturated OC-FAs, 12 strains with long chain
OC-PUFAs, such as C21:5 (n-5) and C21:4 (n-7) accounting for 3.5% and
4.1%, respectively, and proposed their biosynthetic pathways.
Our knowledge of algal lipid metabolism at molecular level is in its infancy;
however, genome information available in the last decade has revealed anticipated progress in elucidating fatty acid and glycerolipid metabolism and prediction of genes encoding proteins involved in membrane and storage lipid
biogenesis in microalgae. These developments have been extensively reviewed
by Harwood and coworkers (Harwood and Guschina, 2009; Guschina and
Harwood, 2006) and Khozin-Goldberg and Cohen (2011) where they discussed
the isolation and characterization of various desaturases, elongases, acyl

IP Address: 14.139.127.9
CoA carboxylases, acyl CoA synthases, acyl transferases (acyl-CoA:glycerol3-phosphate acyltransferase (GPAT), acyl-CoA:diacylglycerol acyltransferase (DGAT2), phospholipid:diacylglycerol acyltransferase (PDAT),
acyl-CoA:lysophosphatidic acyltransferase (LPAAT) and lysophosphatidylcholine acyltransferase (LPCAT) from C. reinhardtii, P. tricornutum, I. galbana, T. pseudonana, Euglena gracilis, Pavlova salina, Thraustochytrium sp.,
Parietochloris incisa, Galdieria sulpharia, Ochromonas tauri, O. lucimarinus,
Micromonas pusilla and Mantoniella squamata. Metz et al. (2001) reported
polyketide synthase (PKS) pathway in Schizochytrium spp. and found plenty
of PKS-homologous sequences in 8500 randomly-selected clones from a
Schizochytrium cDNA library instead of desaturases expected in the aerobic
pathway.
3.3.2 Oxylipins
Oxylipins are oxygenated derivatives of PUFAs formed enzymatically either
by lipoxygenases (LOX) and dioxygenases or by chemical (auto) oxidation.
The occurrence and distribution of these molecules are widespread within the
lineage with considerable species-specific differences due to the variability of
both FAs and enzymatic transformations. Algae possess octadecanoid, eicosanoid as well as hexadecanoid pathways emanating from C18, C20 and C16
PUFAs, respectively. Green algae metabolize C18 PUFAs at C-9 and C-13 via
9- and 13-LOX, respectively, while red algae transform C20 PUFAs via 5-, 8-,
9-, 12- and 15-LOX action as well as C18 PUFAs via 9S-, 11R- and 13S-LOX;
brown algae metabolize both C18 and C20 PUFAs and diatoms C16 and C20
PUFAs via 9-, 11-, 1214- and 15-LOX forming respective hydroperoxides
(see reviews by Andreou et al., 2009 and Guschina and Harwood, 2006).
Further, these hydroperoxides are transformed into hydroxy-, oxo-, epoxyfatty acids and polyunsaturated aldehydes (PUAs) by the action of LOX,
peroxygenases, oxygenases, epoxygenases and hydroperoxide lyases (HPL),
respectively. Moreover, some red algae also form prostaglandins and leukotrienes either non-enzymatically or by the enzymatic action of allele oxide synthase/cyclase (AOS/AOC) (see reviews by Andreou et al., 2009 and Guschina
and Harwood, 2006). Recently, Kanamoto et al. (2011) identified COX gene
in Gracilaria vermiculophylla and cloned it in E. coli for the production of
PGF2. Apart from these simple oxylipins, macroalgae contain various complex oxylipins such as polycyclic oxylipins, cyclopropyl hydroxyeicosanoids,
egregialactones, ecklonialactones, hybridialactones, bicyclic cymathere ethers,
cymatherelactones and cymatherols (Choi et al., 2012; Kousaka et al., 2003;
Lion et al., 2006; Nagle and Gerwick, 1990; Proteau and Gerwick, 1993;
Rempt et al., 2012; Weinberger et al., 2011). The various oxylipins found in
algae are presented in Table 3.3. Similar to phyto-oxylipins, algal oxylipins
also confer innate immunity in response to biotic and abiotic stress such as
pathogenic bacteria, herbivores, wounding and metal toxicity (Bouarab et al.,
2004; Fontana et al., 2007; Ritter et al., 2008).
Algae
Macroalgae
CHLOROPHYTA
Acrosiphonia coalita
Cladophora columbiana
Chlorella pyrenoidosa
Enteromorpha
intestinalis
Ulva conglobata
Ulva lactuca
PHAEOPHYTA
Cymathere triplicata
Ecklonia stolonifera
Egregia menziesii
Eisenia spp.
Laminaria angustata
Laminaria digitata
S. No.
2
3
8
9
10
11
12
Arachidonate 12S- and 15SLOX, linoleate 13-LOX,

HPL
LOX, epoxygenase
LOX
LOX
13-LOX
LOX
Linoleate and linolenate 9LOX, arachidonate 11-LOX

n-9 and n-6 LOX
12-, 8-, 15- LOX
Linoleate and linolenate 9-LOX,

16-LOX
Linoleate 9-LOX
Anaerobic 9/13-LOX
Biosynthetic enzymes
Table 3.3 Different types of oxylipins reported from algae
(Bicyclic cymathere ethers)1, (polycyclic

oxylipins cymatherelactone and
cymatherols)2
Ecklonialactones
Egregialactones
Carbocyclic eiseniachlorides, eiseniaiodides
and bicyclic cymathere ethers
13-HPODE, 13-HPOTrE, 12S-, 15-, 11-,
9-, 8-HpETE, C-9 aldehydes from C20
PUFAs and C-6 from C18/C20-PUFAs
Hydroxy-, hydroperoxy FAs derived from
LA, ALA, AA, prostaglandins (PGE1,
PGD1, 15 keto-PGF2),12,13- epoxyoctadecaenoic acid, 18-hydroxy-17-oxoeicosatetraenoic acid
9(R)-HPODE, 9(R)-HPOTrE, 11-HPETE,

aldehydes (2,4-decadienal)
9- and 13-HODE, 9-HOTrE, 12- and 15HETE, 12-HEPE, 14-HDHE
Hydroxy and hydroperoxy FAs

Coalital (C10-oxylipin), Epoxy alcohol
Hydroxy and hydroperoxy FAs
13-oxo-trideca-9,11-dienoic acid, (2Z)pentane, pentanol, hexanal
12-, 8- and 15-HETE
Oxylipins

IP Address: 14.139.127.9
(Continued)
Kpper et al. (2006);

Ritter et al. (2008);
Kpper et al. (2009)
Boonprab et al. (2003,

2004)
Proteau and Gerwick

(1992, 1993); 2Choi
et al. (2012)
Todd et al. (1994)
Todd et al. (1993)
Kousaka et al. (2003)
Akakabe et al. (2002,

2003)
Kuo et al. (1997)
Kuo et al. (1997)
Gerwick et al. (1993)

Nunez et al. (2000)
Bernart et al. (1993)
References
Gracilariopsis
lemaneiformis
Murrayella periclados
Gracilaria asiatica
Gracilaria spp. (G.

verrucosa and G.
lichenoides)
Gracilaria chilensis
Lithothaamnion
coralloides
Rhodymenia pertusa
15
16
17
18
20
21
19
Constantinea simplex
RHODOPHYTA
Chondrus crispus
13
14
Algae
Continued
S. No.
Table 3.3
Arachidonate (12R)- and (5S)LOX
Arachidonate and linoleate

LOX, BAH
References
Prostaglandins (PGE2 , 15 keto-PGE2, PGA2,

LTB4), 8-HETE
Prostaglandins
Eicosanoids
12 (S)-HpETE, hydroxy FAs2, vicinal

dihydroxy FAs (12R, 13S-diHETE)1, 3,
Eicosanoids2
Cyclopropyl hydroxyeicosanoids
5-, 11-, 12-, 15-HETE, 11-, 13- and

9-HODE, 11-keto-9Z-12Zoctadecadienoic acid
Eicosanoids (5R,6S-diHETE, 5R,6SdiHEPE, 5-HETE, 5-HEPE)
Jiang et al. (2000)
Gerwick et al. (1993)
Lion et al. (2006)
Nagle and Gerwick

(1990)
1
Gerwick et al. (1991);
2
Jiang and Gerwick
(1991); 3Hamberg
and Gerwick (1993)
Bernart and Gerwick
(1994)
Sajiki and Kakimi
(1997)
Imbs et al. (2001)
Hydroperoxy FAs, hydroxy FAs, diols, epoxy Bouarab et al. (2004);

FAs, prostaglandins (PGB1, PGB2, PGA2,
Gaquerel et al.
15-keto-PGE2 and leukotrienes.
(2007)
Oxylipins
Arachidonate LOX, peroxidase (8R)- HETE, 7S,8R-di-HETE
Arachidonate 8-LOX, AOS/

AOC
Arachidonate 8-LOX, AOS/
AOC
Arachidonate (12S)- LOX
Arachidonate (12S)- LOX,

Hydroperoxide isomerase
Arachidonate (5R)-, (8R)-,

(9S)- and (15S)- LOX,
linoleate (9S)- and (13S)LOX, (n-7) Bisallylic
hydroxylase (BAH)
Arachidonate (12S)- LOX
Biosynthetic enzymes

IP Address: 14.139.127.9
LOX, HPL
9(S)-LOX, 14-LOX
9-LOX
9(S)-LOX, arachidonate LOX,
HPL, AOS hydroperoxide
halolyase
(9S)- LOX, DES, peroxidase
Jiang and Gerwick

(1997)
9(S)- and 14-hydroperoxides

Fontana et al. (2007)
Dictyoterpene A derived from 9(S)-HpETE Hombeck et al. (1998)
1
dIppolito et al.
(9-HHTrE, 9-HHTE)1, (heptadienal,
octadienal, octatrienal)1, 3, (12-ODTE
(2004); 2Wichard
2
and 3-chloro-octenes from AA) , (15(S)and pohnert (2006);
3
HEPE, 5R-HEPE, epoxy alcohols
Fontana et al.
3
7,8-HepETE, 13, 14-HepETE)
(2007),
(9-HHTrE, 9-HHTE from C16 PUFAs, 11- 1dIppolito et al. (2005);
2
HEPE from AA, octadienal, octatrienal)1,
Barofsky and
(2,4-decadienal, 2,4,7-decatrienals)2,(
Pohnert (2007)
hydroxyl FAs 10-hydroxydeca-5,8-dienoic
acid, 6-hydroxy-7-octenoic acid, 8-hydroxy6-octenoic acid)2
Hepoxilin like metabolite, Polyneuric acid,

9(S)-HETE, 9,15-diHETE
Note: The superscript numbers 13 represent the respective citations for the oxylipin compounds mentioned in each column.
Thalassiosira rotula
Microalgae
Chaetoceros spp.
Gomphonema parvulum
Skeletonema spp.
23
24
25
26
Polyneura latissima
22

IP Address: 14.139.127.9

IP Address: 14.139.127.9

3.3.3 Sterols
Sterols are important structural components of cell membranes ubiquitously
present in all eukaryotic organisms regulating membrane fluidity and permeability. They are amphipathic compounds that originate in isoprenoid
biosynthesis forming a group of triterpenes with a tetracyclic cyclopenta()
phenanthrene structure and a side chain at C17. The four rings (A, B, C, D)
have trans-ring junctions, side chain and two methyl groups at C18 and C19
at an angle to the rings above the plane with stereochemistry. Accordingly,
it possesses four indispensible domains (Fig. 3.2). In domain A, the polarity and tilt of the C3-OH group imparts functionality to hydrogen bond
interactions, while C4 and C14-methyl groups in domain B affect the A ring
conformation and back-face planarity, respectively. In domain C, the natural configuration at C20, R determines the configuration of the side chain
to orient into a right-handed side chain. In domain D, the conformation,
length of side chain and stereochemistry of the C24-alkyl group are critical
to intermolecular contacts (Nes, 2011). 5-cholestan-3-ol is the basic sterol
from which other sterol structures are defined (Fig. 3.2). They can be further
classified on the basis of their structure or biosynthesis, as 4-desmethyl sterols
(with no substituent at C4), 4-monomethyl sterols (1 methyl group at C4)
and 4,4-dimethyl sterols (2 methyl groups at C4). Further, 4-desmethyl sterols
can be sub-divided into 5-sterols, 7-sterols and 5,7-sterols depending on
the position of double bonds in the B ring.
Algal sterols are extremely diverse with both the mevalonate (MVA) and
methyl-D-erythritol 4-phosphate (MEP) pathways of isoprenoid biosynthesis
existing in algae. The choice of the pathway depends on their evolutionary history (Lohr et al., 2012). It has been suggested that cyanobacteria exhibit MVA;
algae arising from primary endosymbiosis (green algae and prasinophytes)
have the MEP pathway with the exception of red algae Galdieria sulpharia
and Cyanidium caldarium, while those arising from secondary endosymbiosis
such as Euglenophytes, Chlororachinophytes, Chrysophytes, Bacillariophytes,
Pelagophytes and Haptophytes have both the MVA and MEP pathways active
in cytosol and plastids, respectively (Lohr et al., 2012).
20
12
19
27
D
2
HO
25
23
11
1
3
24
22
21
18
16
15
Fig. 3.2
Basic skeleton of sterol.
26

IP Address: 14.139.127.9

The major sterol compositions of different macro- and microalgae are listed
in Table 3.4. Among macroalgae, cholesterol is the dominant sterol in all the
Rhodophyta, fucosterol in Phaeophyta, while the dominant sterol seems to
vary within the orders among Chlorophyta (Al Easa et al., 1995) such as isofucosterol in Ulvales and clionasterol in Bryopsidales and Siphonocladales.
Among microalgae, Haptophytes are characterized by the presence of unusual
dihydroxysterols (pavlovols), pelagophytic algae by 24-propylidenecholesterol,
diatoms by 4-desmethyl-23,24-dimethyl steroids, chlororachinophytes by
crinosterols, stigmasterols, dinophytes by dinosterols and dinostanols except
for the Kareniaceae members and Polarella glacialis (Leblond et al., 2003;
Leblond et al., 2005; Leblond et al., 2011; Mooney et al., 2007; Thomson
et al., 2004; Volkman et al., 1997). These algal sterols possess beneficial healthpromoting effects such as hypercholesterolemic, antioxidant, anticancer, antidiabetic, antihypertensive, anti-inflammatory responses (refer to the review by
Kim and Ta, 2011). Two novel sterol glycosides, 19-O--D-glucopyranosyl-19hydroxy-cholest-4-en-3-one and 19-O--D-N-acetyl-2-aminoglucopyranosyl19-hydroxy-cholest-4-en-3-one, exhibiting anticancer properties have also been
reported from Fijian red alga Peyssonnelia sp. (Lin et al., 2010).
3.4
Recent advances in algal lipid methodology

and lipidomics
The detection, identification and precise quantification of lipid compounds

are prerequisite for their potential utilization and exploration. Traditionally,
lipids are extracted from algae by solvent extraction methods using chloroform, methanol, dichloromethane, diethyl ether and hexane, or a combination
of two or more of these solvents (Christie, 1993; de Boer et al., 2012; Mercer
and Armenta, 2011). Often, these methods are applied to algae in conjunction
with various cell disruption techniques such as mechanical pressing, homogenization, bead beating, sonication (ultrasound), microwave, osmotic shock
and pulsed electric field (de Boer et al., 2012; Mercer and Armenta, 2011; Xu
and Mi, 2012). The accuracy of different lipid extraction methods depends on
the solubility of their constituent lipid classes in the solvents employed and
the nature of sample matrix as both could influence the extent of lipid extraction. According to Christie (1993), extraction solvents/mixtures should be
polar enough to remove lipids from their associating cell constituents, but not
too polar that the solvents do not readily solubilize all the TAGs and other
non-polar lipids. Chloroform-methanol based Bligh and Dyer (Bligh and
Dyer, 1959) and Folch (Folch et al., 1957) methods have been the most popular methods among algal researchers, and various modifications have been
proposed to suit different types of sample matrices (Khotimchenko, 2003;
Kumari et al., 2011; Mattos et al., 2011; Sanina et al., 2004). Further, fatty
acids are extracted either by conventional lipid extraction followed by transmethylation reactions or by one-step direct transesterification (DT) methods
12
13
6
7
8
9
10
11
Macroalgae
Enteromorpha spp.
Characteristic sterols
Isofucosterol (88.694.1%),a cholesterol, clerosterol, clionasterol

24-methylenecholesterol, dihydrobrassicasterol, poriferasterol,
22-(E)-dihydrocholesterol
Ulva spp.
Isofucosterol (8385.5%), cholesterol, desmosterol, fucosterol,
24-methylenecholesterol, dihydrobrassicasterol, poriferasterol,
Bryopsis plumosa
Clionasterol (88.3%), clerosterol, dihydrobrassicasterol,
24-methylenecholesterol, isofucosterol, cholesterol, desmesterol,
Caulerpa spp.
Clionasterol (5877%), fucosterol (1617%), cholesterol (13.1%),
24-methylenecholesterol, clerosterol, poriferasterol, 22-(E)dihydrocholesterol, dihydrobrassicasterol
Codium dichotomum
Clerosterol (83.3%), Codisterol (8.3%), cholesterol, isofucosterol,
porifersterol, 24-methylenecholesterol, brassicasterol, 22-(E)dihydrocholesterol
Laminaria ochroleuca
Fucosterol (85.9%), 24-ethylenecholesterol (clionasterol) 14.1%)
Undaria pinnatifida
Fucosterol (82.9%), 24-ethylenecholesterol (16.8%)
Himanthalia elongata
Fucosterol (97.3%), 24-ethylenecholesterol (2.6%)
Fucus virsoides
Clerosterol
Fucus spiralis
Fucosterol, cholesterol, campesterol, stigmasterol, desmosterol
Cystoseira spp.
Fucosterol, cholesterol, desmosterol, stigmasterol, desmosterol,
-sitosterol
Cladostephus spongiosus Fucosterol, cholesterol, campesterol, stigmasterol, desmosterol
Stypocaulon scoparium Fucosterol, cholesterol, campesterol, stigmasterol, desmosterol,
ergosterol, -sitosterol
Algae
Sterols reported from different algae
S. No.
Table 3.4

IP Address: 14.139.127.9
Lopes et al. (2011)
Kapetanovi et al. (2005)
Snchez-Machado et al.
(2004); Lopes et al. (2011)
Aknin et al. (1992);

Kapetanovi et al. (2005);
Shevchenko et al. (2009)
References
Asparagopsis armata
Plocamium
cartilagineum
Osmundea pinnatifida
Gracilaria salicornia
Hypnea flagelliformis
Ceramium spp.
Corallina spp.
Bangia fuscopurpurea
21
22
24
25
26
27
28
23
Chondria collinsiana
Laurencia papillosa
Polysiphonia brodiei
17
18
20
Hormophysa triquetra
16
Spyridia filamentosa
Padina gymnospora
15
19
Sargassum spp.
14
Fucosterol, cholesterol, desmosterol, -sitosterol, campesterol,

stigmasterol
Chlolesterol, 22-dehydrocholesterol, stigmasterol
Chlolesterol, 22-dehydrocholesterol, 22-(E)-cholesta-5,22-dien-3-ol70one
Cholesterol (9596%), desmosterol, cholesta-5,7-diene-3-ol, 24-ethylcholesta-5,24(28)E-dien-3-ol
Cholesterol (87.891.8%), (22E)-cholesta-5,22-dien-3-ol
Cholesterol (59.8%), desmosterol (16.2%), 24-methyl-cholesta-5,
24(28)-dien-3-ol (12.1%), 24-ethyl-cholest-5-en-3-ol (11%),
24-methyl-cholest-5-en-3-ol
(Continued)
Kamenarska et al. (2006)
Nasir et al. (2011)
Cholesterol (21.343.2%), fucosterol (28.138.4%), brassicasterol

Al Easa et al. (1995); Lopes
(9.6%), 24-methylenecholesterol (7.415.5%), stigmasterol,
et al. (2011); Kamenarska
ergosterol, 22-(E)-dihydrocholesterol
et al. (2006)
Fucosterol (72.4%), 24-methylenecholesterol (10.4%), cholesterol
(14.4%), brassicasterol
Fucosterol (86.7%), 24-methylenecholesterol (10.1%), cholesterol
(3.2%)
Cholesterol (68.7%), stigmasterol (31.3%)
Cholesterol (32%), clionsterol (14%), desmosterol (13.7%), 22-(E)dehydrocholesterol (11.6%), ergosterol (9.3%), stigmasterol (9.3%),
22-(Z)-dehydrocholesterol, cholestanol
Clionasterol (30.5%), cholesterol (23.8%), stigmasterol (13.7%),
desmosterol, ergosterol, 22-(Z)-dehydrocholesterol, 22-(E)dehydrocholesterol
Cholesterol (72.9%), clionasterol (12.7%), 24-methylenecholesterol,
24-nor-cholesta-5,22-dien-3-ol, stigmasterol, 22-dehydrocholesterol,
Lopes et al. (2011)
Fucosterol, cholesterol, desmosterol, -sitosterol
Fucosterol, cholesterol, campesterol, stigmasterol, desmosterol,

IP Address: 14.139.127.9
Karlodinium spp.
Takayama spp.
Peridinium aciculiferum
Scrippsiella hangoei
Polarella glacialis
40
41
42
36
37
35
38
39
Microalgae
Neochloris oleabundans
31
Bigelowiella natans
Gymnochlora stellata
Lotharella
amoeboformis
Karenia brevis, K.
mikimotoi
K. umbella
K. papilionacea
Porphyra sp.
Palmaria sp.
29
30
32
33
34
Algae
Continued
S. No.
Table 3.4
Leblond et al. (2003); Mooney

et al. (2007)
Gatenby et al. (2003)
Snchez-Machado et al.
(2004)
References
(Continued)
Gymnodinosterol (59.3%)
23-methyl-27-norergosta-8(14), 22-dien-3-ol (59.366.4%), cholesterol,
24-methylenecholesterol
Brevesterol (40.3%), gymnodinosterol (70.583.1%)
Brevesterol (84%), gymnodinosterol ((21.6%), cholesterol, 3-keto form
of brevesterol and gymnodinosterol
Dinostanol (4453%), cholestanol (1433%), dinosterol (8.615.4%),
4,23,24-trimethyl-5-cholest-7-en-3-ol
Dinostanol (29.635.4%), cholestanol (1831%), dinosterol (5.56.7%),
4,23,24-trimethyl-5-cholest-7-en-3-ol, cholestanol, 24-methyl5-cholestan-3-ol
Thomson et al. (2004)
27-Nor-24-methylcholest-5,22Edien- 3-ol (64%), 4-desmethylsterols,
cholesterol, 4-methyl sterols and stanols
Brevesterol (45.338.1%) gymnodinosterol (3348.1%)
5,7,22- ergostatrienol (45.3%), 5,7-ergostadienol (28.1%), 7-ergostenol

(26.6%)
Crinosterol (29.7%), stigmasterol (70.3%)
Crinosterol (8%), stigmasterol (92%)
Crinosterol (5%), stigmasterol (95%)
Desmosterol (87%), cholesterol, campesterol, 24-ethylenecholesterol

Desmosterol (92.6%), cholesterol, campesterol, 24-ethylenecholesterol,
fucosterol
Characteristic sterols

IP Address: 14.139.127.9
Cryptthecodinium cohnii Dinosterol, dehydrodinosterol, 4,24-dimethyl-cholestan-3-ol, 4,24dimethyl-cholest-5en-3-ol, dinosterone

Phaeodactylum
Brassicasterol, (89.5%), 7,22-ergostadienol (10.5%), cholesterol
tricornutum
Chattonella spp.
24-Ethylcholesterol (6469.9%), cholesterol, isofucosterol,
24-dihydrozymosterol
Fibrocapsa japonica
24-Ethylcholesterol (84.492.2%), cholesterol (511%), isofucosterol
(1.91.7%)
Heterosigma akashiwo
24-Ethylcholesterol (84.694.3%)
Olisthodiscus luteus
Cholesterol (36.9%), fucosterol (31.3%), poriferasterol (23.8%),
brassicasterol (0.51%)
Cyanophora paradoxa
24-Ethylcholesterol (72.5%), 24-methylcholesterol (19.4%),
24-ethylcholesta-5, 22E-dien-3-ol (5.5%)
Glaucocystis
24-Ethylcholesterol (7172%), 24-Methylcholesterol (16.919.7%),
nostochinearum
24-ethylcholesta-5, 22E-dien-3-ol (9%)
Pavlova spp.
24-Methyl and 24-ethylpavlovols, 4-methylsterols (4-methyl24-ethyl-5-cholest-22E-en-3-ol ) 4-desmethylsterols (cholesterol,
24-ethylcholesterol, brassicasterols and others)
Percentage data given in parentheses are the concentration of respective sterols in algae.
50
49
48
46
47
45
44
43

IP Address: 14.139.127.9
Volkman et al. (1997)
Giner et al. (2008), Marshall

et al. (2002)
Gatenby et al. (2003)
Mendes et al. (2008)

IP Address: 14.139.127.9

where methylation reagent is added directly to the algal samples without
previous lipid extraction (Christie, 1993; de Boer et al., 2012; Griffiths et al.,
2010; Laurens et al., 2012; Mercer and Armenta, 2011). Both methods have
their own advantages and disadvantages. Kumari et al., (2011) studied different solvent extraction methods and direct transesterification methods, where
it was proposed to choose an extraction method according to the desired purpose. For example, DT methods are suggested for FA research whereas conventional methods for study of lipid classes as DT does not separate the lipid
fractions, with extraction and methylation being accomplished in a single
step. Moreover, the different types of lipid classes (PL, GL and NL) are separated from their crude lipid extracts by TLC, HPLC, LC-MS and characterized by various spectrometric techniques such as ESI-MS, FT-IR and NMR
(Al-Fadhli et al., 2006; Beal et al., 2010; Kim et al., 2011).
It is only in the last decade that the importance of biodiesel has provided an impetus for undertaking research aimed at manipulation of lipid
and fatty extraction techniques to obtain higher yields of lipid and FAs
(de Boer et al., 2012; Laurens et al., 2012; Mercer and Armenta, 2011).
Recently, Kim et al. (2011) used ionic liquids for lipid and FA extraction
from Chlorella vulgaris, and Jones et al. (2012) reported that 2-ethoxyethanol yield >150200% lipid recovery as compared to other commonly used
extraction solvents such as chloroform, methanol and hexane in Chlorella
sp. Further, Cheng et al. (2011) used supercritical CO2 for lipid extraction
in Pavlova sp. and obtained a 98.7% yield of TAGs, while Patil et al. (2011)
employed supercritical methanol for direct liquefaction and conversion
of wet algal biomass containing about 90% of water to biodiesel. Chen
et al. (2012a) obtained 88% recovery rate of total lipids by the method of
subcritical co-solvent extraction (hexane/ethanol, 3/1; v/v) from wet algal
pastes of Nannochloropsis sp. in 50 min. Recently, Reep and Green (2012)
patented a technology for extracting lipids from alga without cell sacrifice.
They accomplished it by exposing algal cells in an aqueous medium to an
electric field sufficient to cause release of lipids from the cells.
A further, recent advance in mass spectrometry has allowed lipidomics to
take the forefront in lipid analysis. Lipidomics aims to quantify the full complement of lipid molecules in cells or tissues. However, this omics approach
remains largely unexplored with a few exceptions for microalgae that utilized
the potential of LC-Q-TOF-MS, ESI-MS, FT-IR and NMR for the elucidation of different lipid molecules. Leblond and co-workers extensively studied
the glycolipid profiles of dinoflagellate Pyrocystis spp., glaucocystophytes
Cyanophora paradoxa and Glaucocystis nostochinearum, raphidophytes
Chattonella, Fibrocapsa and Heterosigma spp. and chlororachinophytes
Bigelowiella natans, Gymnochlora stellata and Lotharella spp., with the latter
chlororachinophytic algae exhibiting a novel lauric acid containing MGDG
(C20:5/C12:0, sn-1/sn-2) (Leblond and Roche, 2009; Leblond et al., 2010a;
Leblond et al., 2010b; Roche and Leblond, 2011). Wu et al. (2010) developed

IP Address: 14.139.127.9

a direct quantitative method for in vivo lipid profiling in oil-producing
microalgae using single-cell laser-trapping Raman spectroscopy that provides real-time chemical information in a label-free manner. They determined
the degree of unsaturation and transition temperatures of constituent lipids
within microalgae, thus providing a facile technique that can be exploited to
understand fast dynamics of metabolites, pathways and lipid compositions in
a desired organism. Further, Laurens and Wolfrum (2011) developed a multivariate calibration model for screening algae for accurate lipid quantification,
utilizing NIR and FT-IR, while Beal et al. (2010) employed liquid state NMR
for lipid analysis of Neochloris oleabundus. Recently, He et al. (2011) characterized the polar lipid profile of Nannochloropsis occulata and identified 200
unique lipid species by online nanoscale high-performance liquid chromatography (HPLC) followed by electrospray ionization and mass analysis with
a linear ion trap (LTQ) coupled with 14.5 T Fourier transform ion cyclotron
resonance mass spectrometry (FT-ICR MS).
Sterols are extracted as lipid extracts by using solvents such as ethanol,
methanol, chloroform and petroleum ether. Thereafter, they are purified
and characterized using TLC, HPLC, LC-MS, FT-IR, NMR or, by GC-MS
after saponifiaction of lipid extracts by ethanolic/methanolic KOH followed
by derivatization as TMS ethers (Dahmen and Leblond, 2011; Kamenarska
et al., 2006; Leblond and Lasiter, 2012; Lopes et al., 2011; Rampen et al.,
2009; Snchez-Machado et al., 2004).
3.5
Seasonal variations
The lipid, fatty acid and sterol compositions often vary with the seasonal
changes owing to the combined influence of environmental factors such as
temperature, light, nutrient availability and the physiological state of the
algae. High lipid content in winter and autumn as compared to summer has
been observed in Undaria pinnatifida, Laminaria japonica, Fucus serratus,
Egregia menziesii, Condrocanthus canaliculatus and Ulva lobata (Gerasimenko
et al., 2011; Kim et al., 1996; Nelson et al., 2002). However, high TAG contents are observed in summer while polar lipids (PL and GL) depended on
the algal development stages throughout the year (Gerasimenko et al., 2011;
Kim et al., 1996). Gerasimenko et al. (2010) reported higher TAG contents
in May at the time of sporulation in brown alga Costaria costata and different classes of GL were in the following order MGDG > SQDG > DGDG in
April (growth period) and May (sporogenesis period) compared to MGDG >
DGDG > SQDG in July (beginning of senescence). These lipid changes are
often accompanied by high PUFAs, high unsaturation index (UI) and n-3 >
n-6 PUFAs in winter versus summer season as observed in A. touchiensis, L.
japonica, U. fenestrata, S. pallidum, U. pinnatifida, C. taxifolia (Gerasimenko
et al., 2011; Ivea et al., 2004; Kim et al., 1996; Nelson et al., 2002; Sanina

IP Address: 14.139.127.9

et al., 2008). The higher percentage of PUFAs in winter aids in low-temperature acclimatization and protects photosynthetic machinery from low
temperature photoinhibition (Blankenship, 2002; Gombos et al., 1994). The
substitution of n-6 by n-3 PUFAs, occurring during the change in season from
summer to winter, was also accompanied by the partial substitution of C20
by C18 PUFAs in GLs and PG in contrast to PC and PE in A. touchiensis, L.
japonica, U. fenestrata, S. pallidum, U. pinnatifida, C. costata and F. serratus
(Gerasimenko et al., 2011; Gerasimenko et al., 2010; Kim et al., 1996; Sanina
et al., 2008). The sampling season also affects the concentration of CPI in
red algae but the effect is species-specific with T. crinitus and Rhodoglossum
japonicum exhibiting higher CPI levels in summer (12.9% and 13.9% of PL)
than fall (8.9% and 6.5%, respectively) while Rhodomela larix reported 1% of
PL as CPI in summer increasing to 3.7% in fall (Khotimchenko et al., 2000).
Further, sterol content is also reported to be higher in winter than in summer
(Gerasimenko et al., 2010; Gerasimenko et al., 2011). Moreover, FA composition in microalgae changes during annual cycles and is accompanied by
seasonal succession of species composition of the community and temperature adaptations of the algal populations. The FA composition of littoral
microalgae in Yenisei River reflected the actively growing spring population
of psychrophilic filamentous green algae summer communities of diatoms
fall populations of cyanobacteria detritus derived from decaying eukaryotic algae in late fall and winter (Sushchik et al., 2010).
3.6
Environmental variations
Algae in their natural habitats experience severe environmental stresses including salinity variations, intense radiation, temperature, desiccation, and chemical pollution that limit their distribution, production and fecundity (Aguilera
and Rautenberger, 2011). Such fluctuating and dynamic environmental conditions have been shown to be associated with cellular increase in the formation
of reactive oxygen species (ROS) as a consequence of photosynthetic inhibition with excess energy, resulting in the production of singlet oxygen (Dring,
2006) causing oxidative stress. In algae such climatic stresses cause fluctuations in the fluidity of cell membranes which are considered critical for the
initiation of regulatory reactions that eventually lead to acclimation to these
stresses, though the precise mechanism for the perception of changes of membrane fluidity have not been fully characterized. It is generally admitted that
membrane lipids undergo certain changes to alter the physiological properties
of membrane bilayer for maintaining normal cell functioning (ion permeability, photosynthesis, respiration and other metabolic activities) (Mikami
and Murata, 2003).The most commonly observed change in membrane lipids
following adverse environmental conditions in algae is the alteration in fatty
acid unsaturation (Guschina and Harwood, 2006).

IP Address: 14.139.127.9

3.6.1 Nutrients
Nutrient limitation, which generally causes a reduced cell division rate in
algae, surprisingly activates the biosynthesis of storage lipids, primarily TAGs.
Researchers in biodiesel industries are gaining from this fact for increasing
the lipid productivity in algal cells while culturing them in nutrient-starved
conditions. In biodiesel industries, NLs, mainly TAGs, are preferred over
PLs or GLs due to their higher percentage of FAs (Chisti, 2007). Microalgae
share common carbon precursors for starch and lipid biosynthesis, and thus
blocking of starch synthesis has been suggested as a way to increase oil accumulation in algal cells. The inactivation of ADP-glucose pyrophosphorylase
in Chlamydomonas starchless mutant, leading to a 10-fold increase in TAG,
suggested that shunting of photosynthetic carbon partitioning from starch to
TAG synthesis may represent a more effective strategy than direct manipulation of the lipid biosynthesis pathway to accumulate TAG (Li et al., 2010a
and 2010b). Similarly, nitrogen starvation in the presence of acetate and
blocking of starch biosynthesis in sta6 mutant exhibited a 30-fold increase
in lipid bodies (Wang et al., 2009). To develop cost-effective algal oil production, culturing of microalgae in heterotrophic conditions where sugars and
organic acids serve as carbon sources has also been suggested as the alternative strategy to autotrophic conditions. Heterotrophic algal cultivation
has been reported to provide not only a high algal biomass productivity, but
high cellular oil content as well. This mode of culture minimizes the light
requirement and, therefore, offers the possibility of increased cell density and
productivity (Chisti, 2007). In case of C. vulgaris, heterotrophic growth on
glucose (1%) and glycerol (2%) has evidenced fast growth rate with greater
lipid productivity (3.55.5 fold) when compared to autotrophic cultivation
practices (Liang et al., 2009). Similarly, Liu et al. (2011) demonstrated a
9-fold increase in lipid yield in Chlorella zofingiensis fed with 30 g L1 of glucose cultivated under heterotrophic conditions. Furthermore, heterotrophic
cells accumulated predominantly neutral lipids that accounted for 79.5% of
total lipids of which 88.7% was TAG (rich in oleic acid), whereas photoautotrophic cells contained mainly the membrane lipids (GL and PL). Increasing
NL production in response to nitrogen starvation and increased concentration of metal ions such as iron or cobalt has also been reported in Dunaliella
species (Chen et al., 2011). A considerable increase in total lipid content (56%
biomass by dry weight) in C. vulgaris supplemented with 1.2105 mol L1
FeCl3 was reported, corresponding to 37-fold more than the medium supplemented with a lower iron concentration (Liu et al., 2008). Nitrogen deficiency
has resulted in a significant increase in lipid yield (4046%) but lower biomass
in Chlorella minutissima strains when cultured in medium containing a range
of nitrogen concentrations (7700 mg L1 N) for 15 days (rdg et al., 2011).
Further, culture conditions for C. vulgaris with 1.0 mM KNO3, 1.0% CO2 and
60 mol photons m2 s1 at 25C were found ideal for obtaining the highest
lipid productivity of 40 mg L1 d1 (Lv et al., 2010). In conditions of nitrogen

IP Address: 14.139.127.9

(2.5 mg L1) or phosphorus (0.1 mg L1) limitation, Scenedesmus sp. LX1
could accumulate lipids as high as 30% and 53%, respectively, of its algal biomass (Xin et al., 2010). Further, high light (270 E.m2.s1) and nitrogen deprivation has also been shown to trigger a rapid accumulation of TAG enriched
in n-6 AA or DGLA, along with a deposition of -carotene in the oil bodies
in wild green microalga P. incisa and its mutant strain P127 (5-desaturase
deficient) (Solovchenko et al., 2008, Solovchenko et al., 2010). A combination
of nitrogen deficiency, moderately high light intensity (82.5 E m2 s1) and
high iron content (0.74 mM) improved lipid accumulation in TRG, KB, SK
and PSU strains of Botryococcus spp. up to 35.9%, 30.2%, 28.4% and 14.7%,
respectively, from their corresponding lipid contents of 25.8%, 17.8%, 15.8%
and 5.7%, respectively, in nitrogen-rich medium (Yeesang and Benjamas,
2011). Recently, Choi et al. (2011) evidenced 2.6-fold higher expression of
the stearoyl-ACP desaturase gene (sad) encoding a stearoyl-ACP desaturase
involved in the synthesis of oleic acid together with maximum lipid content
(63%) under N-limited conditions (0.04 mM nitrate) in B. braunii. On the
contrary, marine microalgae Isochrysis zhangjiangensis had higher lipid accumulation during sustained nitrate addition and showed a high carbohydrate
content under nitrate-deplete conditions. These results revealed that this algal
strain can accumulate lipids under nitrogen-replete conditions and accumulate carbohydrate under nitrogen-deplete conditions. This special characteristic of lipid accumulation registered I. zhangjiangensis as an ideal candidate for
producing biodiesel using N-rich wastewater (Feng et al., 2011).
Tsuzuki (1990) reported that increasing CO2 concentration from 0.036%
to 2% could increase the composition of SFAs in C. vulgaris. Muradyan
(2004) and Hoshida (2005) demonstrated a decrease in FA content with the
increase of CO2 concentration from 2% to 10% and 5% to 20%, in D. salina
and Thalassiosira weissflogii, respectively. Further, in contrast to the results
with Chlamydomonas spp., elevated CO2 or added organic carbon sources
significantly enhanced EPA production in Nannochloropsis sp. (Hu and Gao
2006). Recently, Tang et al. (2011) demonstrated high PUFA production in
Scenedesmus obliquus SJTU-3 and Chlorella pyrenoidosa SJTU-2 when cultivated at high levels of CO2 (3050%). The contents of PUFAs such as hexadecatrienoic acid (16:3), ALA and EPA were high at 3050% CO2.
3.6.2 Salinity stress

Salinity is an important environmental factor that affects growth and productivity of algae. Salinity fluctuations influence algae mainly by altering membrane permeability and fluidity by creating: 1) osmotic stress with decreased
cellular water potential, 2) ion toxicity caused by the excessive uptake of Na+
or Cl ions, and 3) cellular ion imbalance due to the selective ion permeability
of the membrane (Mansour and Salama, 2004). Lipids are reported to play
crucial roles in regulating these functions under different salinities through
compositional changes in sterols and membrane lipids (PLs and GLs) (Parida

IP Address: 14.139.127.9

and Das, 2005). The restructuring of membrane lipid composition is one of
the adaptations to survive in high salt concentration, which is mainly achieved
by increasing the unsaturation of its phospholipid FAs (Lu et al. 2009).
Unicellular green algae of genus Dunaliella are exceptional in their ability to proliferate over the entire range of salinities (<0.1M to near saturation). Their outstanding salt tolerance has been attributed to salt-induced
increased expression of -ketoacyl-coenzyme A synthases (KCS) and other
desaturases resulting in a higher ratio of C18 (mostly unsaturated) to C16
(mostly saturated) FAs, when cells were grown in 3.5 M NaCl compared to
the 0.5 M control (Azachi et al., 2002). An increase in the initial salt concentration from 0.5 M NaCl to 1 M followed by further addition of 1 M NaCl
during cultivation of D. tertiolecta resulted in an increase in intracellular total
lipid and TAG content (Takagi and Karseno, 2006). Further, in wild-type
Synechocystis sp., PUFAs in membrane lipids have shown to play an important role in protecting the photosynthetic machinery under salt stress when
compared to mutant cells (Sakamoto and Murata, 2002).
In Antarctic microalga C. vulgaris, the expression levels of CvFAD2 and
CvFAD6 (C. vulgaris fatty acid desaturases) has been shown to increase by
20-fold and 8.5-fold, respectively, when cultures of C. vulgaris NJ-7 were
shifted from 30 to 60 NaCl (Lu et al. 2009, 2010). Recently, Zhang
et al. (2011) have demonstrated the enhanced mRNA level of CiFAD3 in
Chlamydomonas sp. ICE-L that increased 3.8-fold at salinity 62 in comparison to control. Further, a rapid increase in the putative lipid second messengers, PA and lyso-PA has been suggested as a major contributor to LA
accumulation during hypersalinity stress in Chlamydomonas sp. (Arisz and
Munnik, 2011). Further, seven types and 35 kinds of polar lipid molecules
were identified as biomarkers against salt stress in snow alga Chlamydomonas
nivalis, including MGDG, DGDG, SQDG, DGTS, PG, PE and PI using a
lipidomics approach by UPLC/Q-TOF-MS (Lu et al., 2012). In diatom N.
laevis, high salt concentration induced a decrease in neutral lipids with a
concomitant increase in polar lipids. The degree of FA unsaturation of both
neutral and polar lipid fractions increased sharply when salt concentration
increased from 10 to 20 g L1 but decreased at 30 g L1. The amount of total
free sterols was also found to increase with the increase in salt concentration
(Chen et al., 2008). An increase in relative proportion of oleic acid, LA and
ALA (by 1.31.6-fold) with a parallel decrease in palmitoleic acid at hypersalinities were observed while shifting the cultures of marine macroalgae
Gracilaria corticata from 30 to 45 NaCl (Kumar et al., 2010a). These
findings suggested that hypersalinity-induced activation of 9 FAD enzyme
was responsible for converting stearic to oleic acid.
3.6.3 Light stress

Light has been reported to produce many effects on algal lipid metabolism and
lipid composition. The qualitative changes in lipids as a result of various light

IP Address: 14.139.127.9

conditions have been shown to be associated with alterations in chloroplast
development (Harwood 1998). The increase in irradiance results in decreased
UFAs, especially n-3, due to a considerable decrease in EPA in Nanochloropsis
sp., P. tricornutum and M. subterraneus (Adlerstein et al., 1997; Fbregas
et al., 2004). Further, an increase in MGDG and DGDG together with
increased levels of palmitoleic acid and ALA has been noticed in Cladophora
spp. under low light conditions (6 mol photon m2 s1), (Napolitano, 1994).
The effect of light on FA composition in seaweeds has been examined only
for a few algal species and these studies yielded contradictory results. In
Gracilaria sp., the content of EPA, the main PUFA, increased with increasing
photon flux density (Levy et al., 1992), whereas in G. verrucosa, the proportion of the main PUFA, AA, decreased under high light conditions (Floreto
and Teshima, 1998; Levy et al., 1992). In G. tikvahiae and Grateloupia sparsa,
FA composition was not affected by light (Dawes et al., 1993). In the green
alga Ulva fenestrata, grown under different solar irradiances in field experiments, MGDG, SQDG and PG increased 23.5 fold when grown at 24% of
photosynthetically active radiations (PAR) compared with algae cultured at
80% of PAR (Khotimchenko and Yakovleva, 2004). Exposure of algae to low
light resulted in an increase in the content of EPA in MGDG while decrease
in PG in Tichocarpus crinitus. Light conditions influenced the total lipid
content, wherein algae exposed to 810% PAR accumulated lipid at 4.2 mg
g1 FW and at 3.4 mg g1 FW lipid with 7080% PAR, (Khotimchenko and
Yakovleva, 2005). However, G. tenuistipitata cultures exposed to low (100
mol photons m2 s1) and high light intensity (1000 mol photons m2 s1)
for five days showed no statistically significant differences in the FA contents
(Pinto et al., 2011).
3.6.4 Temperature
The ability of algae to survive in extreme temperatures indicates their unique
mechanisms to cope with temperature stress. One such adaptation is the ability
to adjust lipids and their molecular species in cell membranes with a process
referred to as homeoviscous adaptation (Guschina and Harwood, 2006). The
detrimental effects of low temperature on the rigidification of the membrane
lipid bilayers such as loss of ion permeability have been clearly demonstrated
in many psychrophilic and psychrotrophic organisms (Morgan-Kiss et al.,
2006). These organisms utilize a combination of changes in FA composition
to regulate the fluidity of the membrane at low temperatures, including incorporation of polyunsaturated, short-chain, branched or cyclic FAs (White
et al., 2000). Owing to the availability of genome-wide DNA microarrays
of cyanobacteria and Synechocystis, they have been exploited as a model
for lipid unsaturation studies under cold stress. In genus Synechocystis, the
expression of three desaturases (encoded by desA, desB and desD) has been
reported under cold temperatures (Sakamoto and Murata, 2002). Further, the

IP Address: 14.139.127.9

cold senser histidine kinase 33 (Hik33) has been identified in Synechocystis
as a regulator of cold inducible expression of desB gene, which encodes desaturases. A considerable increase in lipids (PG, SQDG) and PUFAs (EPA
and DHA) was observed upon shifting the cultures from 25C to 15C in
P. tricornutum (Jiang and Gao, 2004). Further, a significant rise in ALA/16:1
(3t)-PG with a parallel decrease in LA/16:1 (3t)-PG has been reported in
green algae D. salina at 12C (Thompson, 1996). Similarly, increased ALA
has also been found in two Antarctic species, Stichococcus bacillaris and
S. minutus, at 4C15C (Chen et al., 2012b). The positive correlation between
the accumulation of CvFAD6 and temperature has been evidenced by real
time PCR wherein a 4-fold expression of CvFAD6 was observed, when cultures of C. vulgaris were shifted from 25C to 4C, contributing to a considerable accumulation of LA (Lu et al., 2010). Recently, Fuschino et al. (2011)
demonstrated the possible impact of global warming on lipid dynamics while
culturing Scenedesmus obliquus at 20C and 28C. Increasing the water temperature to 28C decreased TL yield, PUFAs (ALA and STA) along with
the proportional contribution of PG and DGDG in PL with concomitant
increase in palmitic and oleic acid at 28C. Furthermore, the low temperature
adaptability of ice algae Chlamydomonas sp. ICE-L has been attributed to
the upregulation of CiFAD3 gene expression which increased by 2.6-fold at
0C and 1.8-fold at 12C, accounting for increased TL and UFA contents
under low-temperature conditions (Zhang et al., 2011). The Rhodophycean
Gracilaria spp. inhabiting low temperature waters also contain high PUFAs,
with a higher n-3/n-6 FA ratio (Gressler et al., 2010). Durmaz et al. (2008)
studied the sterol composition of I. galbana at two different temperatures
(18C and 28C) and found stigmasterol to be the main sterol in all the growth
phases at 28C, while at 18C -sitosterol dominated the exponential phase
followed by stigmasterol during stationary and decay phases.
3.6.5 Ultra violet radiation and anthropogenic activities

The depletion of the stratospheric ozone layer by anthropogenic activities and
natural destruction has caused a remarkable increase in UV radiation (UV-R)
reaching the earths surface, especially in the Polar regions and at lower latitudes of the northern hemisphere (Karentz and Bosch, 2001). Alteration in
FA composition in microalgae exposed to UV-R has been addressed in many
reports; however, the results are extremely contradictory. Some authors have
observed an overall increase in the levels of SFAs and MUFAs and a decrease
in PUFAs (EPA and DHA) when microalgae P. lutheri, I. galbana and others were exposed to UVB-R (Wang and Chai, 1994; Guihneuf et al., 2010).
These findings indicate a switch to the synthesis of more SFA, which is a more
efficient energy source than PUFAs for stress adaptation. It is also proposed
that the low availability of ATP could account for the decreased proportions
of PUFAs in microalgae exposed to UV-R stress. Inhibition of enzymes such

IP Address: 14.139.127.9

as desaturases and elongases could be one more explanation for the decrease
in PUFAs induced by UV-R (Guihneuf et al., 2010). Indeed, Leu et al.
(2006) suggested that low levels of oleic acid observed in Selenastrum capricornutum could result from the inhibition of 9-desaturase induced by UV-R
stress. On the contrary, some authors have also reported increased PUFAs in
P. tricornutum, C. muelleri and C. vulgaris (Skerratt et al. 1998; Liang et al.
2006; Wong et al., 2007) while no change was observed in Odontella aurita
(Guihneuf et al., 2010) after UV exposure.
In recent years, the release of toxic pollutants by a growing number of
diverse anthropogenic sources (industrial effluents and wastes, urban runoff, sewage treatment plants, agricultural fungicide runoff, domestic garbage
dumps, and mining operations) have become a major threat for the aquatic
ecosystem, negatively affecting the benthic flora and fauna assemblages
(Pinto et al., 2003). These pollutants have been shown to alter the degree
of unsaturation of membrane lipids in algae to combat the oxidative stress
conditions. For example, a significant accumulation of di- and tri-unsaturated FAs, LA and ALA at the expense of palmitic, palmitoleic and oleic
acids has been demonstrated during cadmium stress in Ulva lactuca (Kumar
et al., 2010b). On the contrary, a considerable reduction in LA, -linolenic
acid (18:3 n-6, GLA), octapentadecanoic acid (18:5 n-4), dihomogammalinolenic acid (20:3 n-6, DGLA), AA, EPA and DHA have been observed in
red algae G. tenuistipitata and G. dura exposed to higher concentrations of
Cd and Cu (Kumar et al., 2012, Pinto et al., 2011). Similarly, the exposure
to imidazolium ionic liquids in U. lactuca resulted in significant decrease
in n-3 and n-6 PUFAs with a concomitant increase in SFAs (Kumar et al.,
2011). Recently, the release of polyunsaturated aldehyde (PUA) class oxylipins such as (2E,4E)-octa-2,4,7-trienal and (2E,4E,7Z)-deca-2,4,7-trienal
as signal molecules related to defence mechanisms in response to various
biotic and abiotic stress conditions has also been addressed (Goulitquer
et al., 2009).
3.7
Nutritional implications
Algae are renewable reservoirs of bioactive pharmaceutical and nutraceutical

compounds with potential food applications. Macroalgae are considered as
low-calorie food due to their low lipid contents, high PUFAs (both n-3 and
n-6) and C28 and C29 sterols that exhibit anti-hypercholesterolemic, antioxidant, anticancer, antidiabetic, antihypertensive, anti-inflammatory, antifungal and antibacterial activities (Mendis et al., 2011; Miurcov et al., 2011).
Recently, Kumari et al. (2013) reported FA profiles of 100 macroalgae from
the Indian coast and found that most of them possessed nutritionally beneficial n-6/n-3 ratio of 0.1:13.9:1, demonstrating the potential for increasing the
availability of n-3 PUFAs in the diet. In addition, the PUFA/SFA ratio, which

IP Address: 14.139.127.9

is one of the important parameters for assessing the nutritional quality of
the lipid fraction of food, was in accordance with the nutritional guidelines,
0.4 in 93% of the macroalgal species investigated (Department of Health,
1994). The artherogenic (AI) and thrombogenic (TI) indices were <3 in 97%
of the macroalgal species studied (Kumari et al., 2013). Macroalgal lipids are
also better alternatives to fish oil, this being attributed to their greater resistance to oxidation and higher bioavailability (Mendis et al., 2011). Prolonged
consumption of algal sterols reduces the tendency to form a fatty liver and
excessive fat deposition in the human heart (Mendis et al., 2011). Thus, they
are increasingly being employed as ingredients in various food products such
as addition of Enteromorpha sp., U. pinnatifida, H. elongata, P. umblicalis,
S. thubergii and Gelidium amanasii in snack food, pasta, patties, bakery products, low fat frankfurters, meat products and hamburger patties (Chun et al.,
1999; Prabhasankar et al., 2009). Further, microalgae have been considered
more promising sustainable sources of these FAs (especially EPA and DHA)
for use in food as they are capable of producing higher amounts of lipids than
any conventional crops. The species of Schizochytrium and Crypthecodinium
have been used for the production of DHA, Nannochloropsis, Nitzschia and
Phaeodactylum for EPA, Porphyridium for AA and EPA and Arthrospira for
AA (Spolaore et al., 2006), for nutritional supplements, infant formula and
aquaculture applications. However, only DHA is currently commercially
available from an algal source (AlgaeMac 2000, Docosa gold) and no purified algal oil is economically competitive with other sources. EPA and AA
had also been purified a decade earlier from Porphyridium sp. with 39.5%
and 50.8% recovery, respectively, at 97% purity for both the FAs (GuilGuerrero et al., 2001) but is still not commercialized. However, Kumari et al.
(2013) reported that many of the macroalgal species contain comparable
ALA, AA and EPA contents. For example, green macroalgal species such
as Ulva, Caulerpa, Monostroma, Bryopsis, Udotea and Acrosiphonia contain
ALA in the range of 1448% of TFAs comparable to those of Dunaliella
and Chlorella commercially utilized for ALA (Lang et al. 2011; Zhukova and
Aizdacher, 1995). Cryptonemia undulata and Rhodymenia sonderi had AA
content >30% of TFAs while G. corticata showed higher content >50% of
TFAs which is higher than commercial sources of microalgal AA such as
Porphyridium sp. (34.7% of TFA) and Parietochloris sp. (46% of TFA) (GuilGuerrero et al. 2001; Lang et al. 2011). Similarly, EPA contents of the species Pyropia, Halymenia, Polysiphonia, Acanthophora, Gelidium and Gelidiella
(2035% of TFAs) were comparable to those of Phaeodactylum tricornutum (1214% of TFAs), Pavlova lutheri (1028% of TFAs), Nannochloropsis
spp., Thalassiosira sp., Chaetoceros spp. (1218% of TFAs), Nitzschia sp.,
Skeletonema sp., Chattonella spp. and Navicula sp. (2026% of TFAs) (Lang
et al. 2011; Marshall et al. 2002; Pratoomyot et al. 2005). The only bottleneck
in the utilization of macroalgae for pure oil-based products such as PUFA-oils
is the low lipid content of macroalgae as compared to microalgae. Conversely,

IP Address: 14.139.127.9
this low lipid, PUFA-rich content is a boon for their utilization as whole macroalgae in both fresh and dried form in human nutrition and aquaculture as
it helps in improving cardiac and mental health and combating inflammatory diseases. However, in a recent study, Gosch et al. (2012) reported a lipid
content of 1012% on dry weight basis for the macroalgae of genus Dictyota,
Spatoglossum, Derbesia and Caulerpa, which is quite comparable to those
reported for several microalgal species such as Tetraselmis, Rhodomonas,
Scendesmus and a few strains of Skeletonema and Isochrysis (Huerlimann
et al., 2010; Mata et al., 2010). Thus, appropriately chosen macro/microalgae
can be used as ingredients in the formulation of low-fat foods and PUFArich nutraceuticals, which would improve the quality of human diet and also
reduce the dependency on traditional, terrestrial sources.
3.8
Conclusions and future trends
Algae exhibit heterogeneous forms of lipids that are not found in other organisms owing to their habitat diversity. The development of advanced spectroscopic
techniques for isolation and characterization of lipids such as by LC-FTIR-QTOF-MS, ESI-MS, NIR and NMR has greatly enriched the algal lipid database. The latest approach of lipidomics has further accelerated the algal lipid
research leading to the identification of whole lipidomes that would further provide new insights into algal lipid metabolism. Moreover, the impetus to obtain
biodiesel from algae has further aroused great interest in lipid biochemistry in
the last decade. This has led to the investigation of genes and enzymes involved
in lipid metabolism for developing genetically modified algal strains with high
lipid yields. The development of high throughput methods with greater recovery of algal lipids, fatty acids and sterols would greatly enhance their utilization
in functional foods in a cost-effective manner.
3.9
Sources of further information and advice
We recommend the online website The Lipid Library, AOCS (www.lipidlibrary.aocs.org), edited at present by W. W. Christie, for information regarding
the structure, function and recent developments in the field of lipids.
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3.11 Appendix: acronyms

15-keto- PGF2
AA
ALA
AOC
AOS
BAH
CPI
DGAT2
DGCC
DGDG
DGLA
15-keto-Prostaglandin F2
arachidonic acid
-Linolenic acid
allene oxide cyclase
allene oxide synthase
bisallylic hydroxylase
ceramidephosphoinositol
acyl-CoA:diacylglycerol acyltransferase
1, 2-diacylglyceryl-3-O-carboxy-(hydroxymethyl)-choline
digalactosyldiacylglycerol
dihomogamma-linolenic acid

DGTA

IP Address: 14.139.127.9
DGTS
DHA
di-HETE
DPA
DT
EPA
ESI-MS
FA
FAD
FT-ICR MS
FT-IR
GLA
GPAT
HDHE
HEPE
HepETE
HETE
HHTE
HHTrE
HPETE
HPL
HPODE
HPOTrE
KCS
LC-Q-TOF-MS
LOX
LPCAT
LPPAT
LTB4
MGDG
MUFA
NL
NMR
OC-FAs
PA
PAR
PC
PDAT
PE
PG
1, 2-diacylglyceryl-3-O-2-(hydroxymethyl)-(N,N,Ntrimethyl)--alanine
1, 2-diacylglyceryl-3-O-4-(N,N,N-trimethyl)-homoserine
docosahexaenoic acid
di-hydroxyeicosatetraenoic acid
docosapentaenoic acid
direct transesterification
eicosapentaenoic acids
electrospray ionization mass spectrometry
fatty acid
fatty acid desaturase
Fourier transform ion cyclotron resonance mass
spectrometry
Fourier transform infrared radiation
-linolenic acid
acyl-CoA: glycerol-3-phosphate acyltransferase
hydroxydocosahexaenoic acid
hydroxyeicosapentaenoic acid
hydroxyepoxyeicosatetraenoic acid
hydroxyeicosatetraenoic acid
hydroxyhexatetraenoic acid
hydroxyhexatrienoic acid
hydroperoxyeicosatetraenoic acid
hydroperoxide lyase
hydroperoxyoctadecaenoic acid
hydroperoxyoctadecatrienoic acid
-ketoacyl-coenzyme A synthases
liquid chromatography quadrupole time-of-flight mass
spectrometry
lipoxygenase
lysophosphatidylcholine acyltransferase
acyl-CoA:lysophosphatidic acyltransferase
leukotriene B4
monogalactosyldiacylglycerol
monounsaturated fatty acid
neutral lipid
nuclear magnetic resonance
odd-chain fatty acids
phoshatidic acid
photosynthetically active radiation
phosphatidylcholine
phospholipid:diacylglycerol acyltransferase
phosphatidylethanolamine
phosphatidylglycerol

IP Address: 14.139.127.9

PGA2
PGB1
PGB2
PGD1
PGE1
PHEG
PI
PKS
PL
PS
PSC
PUFAs
ROS
SQDG
STA
TAG
TFAs
UI
UV-R
prostaglandin A2
prostaglandin B1
prostaglandin B2
prostaglandin D1
prostaglandin E1
phosphatidyl-O-[N-(2-hydroxyethyl) glycine]
phosphatidylinositol
polyketide synthase
phospholipids
phosphatidylserine
phosphatidylsulfocholine
polyunsaturated fatty acids
reactive oxygen species
sulfoquinovosyldiacylglycerol
stearidonic acid
triacylglycerol
total fatty acids
unsaturation index
UV radiation

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Algal lipids, fatty acids and sterols

Algae comprise a diverse group of photosynthetic organisms that exist in

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88 Functional ingredients from algae for foods and nutraceuticals

Structure and occurrence of algal lipids

Algal lipids consist of phospholipids, glycolipids (glycosylglycerides) and

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Algal lipids, fatty acids and sterols 89

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Phosphatidic acid (PA)

Fig. 3.1 Structure of common lipid molecules found in algae.

diacylglycerol and triacylglycerol, respectively. Betaine lipids contain a betaine

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90 Functional ingredients from algae for foods and nutraceuticals

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Algal lipids, fatty acids and sterols 91

3.2.3 Betaine lipids

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92 Functional ingredients from algae for foods and nutraceuticals

3.2.4 Non-polar glycerolipids (neutral lipids)

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Algal lipids, fatty acids and sterols 93

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Structure and occurrence of algal fatty acids, oxylipins

3.3.1 Fatty acids

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Euglenophyta, Rhodophyta and

Unusual sulfur-containing PL,

Sulfonoglycolipid crassiculisine (C39H73O12SNa)

Ochromonas danica and Pavlova

List of unusual lipids reported from algae

Andersen and Taglialatela-Scafati

Dembitsky and Srebnik (2002)

Shao et al. (2002)

Reshef et al. (1997)

Eichenberger and Gribi (1997)

Eichenberger et al. (1995), Makewicz

Harwood and Jones (1989)

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Six minor new glycolipids in crude methanolic

El-Baroty et al. (2011)

Naumann et al. (2011)

Gray et al. (2009)

Kim et al. (2007)

Williams et al. (2007)

Al-Fadhli et al. (2006)

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C16:0, C18:4 (n-3), C18:5 (n-3), C22:6 (n-3), C28:7 (n-6),

C16:0, C20:1, C20:5 (n-3)

C16:0, C16:1, C18:1, C20:5 (n-3), C22:5 (n-3), C22:6

C14:0, C16:0, C16:1, C16:3, C20:4 (n-6), C20:5 (n-3)

C16:0, C16:1, EPA, C20:5 (n-3), C22:6 (n-3), High

C16 and C18 PUFAs, High C18/C20 PUFA ratio