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Contents
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
2 Bioactive Compounds in Sesame . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
2.1 Phenolics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
2.2 Minor Phenolics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9
2.3 Phytosterols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9
2.4 Phytates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10
2.5 Polyunsaturated Fatty Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10
2.6 Short-Chain Peptides, Protein Hydrolysates, and Their Functional Properties . . . . . . . 11
3 Quantitative Insight in Lignan and Tocopherol Content: Interspecific and Intraspecific
Variation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
4 Biotechnological Approaches for Sesame . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
4.1 Genome Sequencing of Sesame Crop: Unraveling the Oil Biosynthetic Pathway . . . 12
4.2 Functional Gene Expression: “Lignan Biosynthetic Genes” . . . . . . . . . . . . . . . . . . . . . . . . . . 13
5 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14
Abstract
Sesame is a valuable oilseed crop that contains various nutritionally rich bioactive
compounds including lignans, tocopherol homologues, phytosterols, etc. Lignans
are the product of oxidative coupling of β-hydroxyphenylpropane. Sesame has a
N. Pathak
Department of Botany, Deshbandhu College, University of Delhi, Delhi, India
e-mail: [email protected]
A. Bhaduri
Cluster Innovation Centre, University of Delhi, Delhi, India
e-mail: [email protected]
A.K. Rai (*)
Department of Botany, Banaras Hindu University, Varanasi, India
e-mail: [email protected]
Keywords
Bioactive compounds Sesame Sesamin Sesamolin Sesamol Pinoresinol
Tocopherol Phytosterols
Abbreviations
CYP81Q1 Sesamin synthase
DIR1 Dirigent protein
DMPQ 2,3-Dimethyl-5-phytyl-1,4-hydroquinol
VTE1 Tocopherol cyclase
γ-TMT γ-Tocopherol methyltransferase
1 Introduction
are saturated fatty acids (myristic acid, 0.1% or less; palmitic acid, 8–12%; stearic
acid, 3.5–7%; arachidonic acid, 0.5–1%). The unsaponifiable matter (1.2%) includes
tocopherols and the lignans sesamin (0.1–0.6%), sesamolin (0.25–0.3%), sesamol,
and sesaminol, which give the oil its resistance to rancidity. Extracted sesame cake
varies in color from light yellow to grayish black, depending on the dominant seed
coat color. Its chemical composition also varies according to cultivar, method of oil
extraction, and the presence of testa. The sesame cake has ample amount of calcium
and phosphate; protein content ranges from 35% to 47% but is deficient in lysine.
Sesame seed color show variation in different species which could partly be
attributed to changes in composition of bioactive phenolics i.e., lignans and tocoph-
erols (Fig. 1). The present chapter provides detailed and updated information on the
bioactive components present in sesame seeds, their importance, and health benefits.
In particular, sesame lignans and tocopherols have been focused at length: the
biosynthetic pathway, the gene regulation, and the biotechnological approaches to
enhance the concentration of lignans and tocopherols in sesame crop.
Bioactive compounds are beneficial components in food and are accountable for
disease-preventing properties. They include a range of chemical compounds includ-
ing phenolics, carotenoids, phytosterols, and polyunsaturated fatty acids. These
compounds are often utilized as antioxidants and other purposes such as inhibiting
cholesterol absorption, blocking the activity of bacterial toxins, etc. Our recent
review on value addition in sesame crop has elaborated the production of value-
added products such as sesame oil and meal, thereby enhancing its economic
importance [7]. The target candidates for this study are bioactive compounds
such as lignans, tocopherols, phytates, phytosterols, and polyunsaturated fatty
acids (Fig. 2).
4 N. Pathak et al.
2.1 Phenolics
Natural phenolic compounds are secondary metabolites, which are widely distrib-
uted in the plant kingdom. Plant phenols are noted for their role in prevention of
various ailments associated with oxidative stress such as cardiovascular and neuro-
degenerative diseases and cancer [8]. Phenolics are characterized by the presence of
aromatic ring (at least one) coupled with a few hydroxyl groups. The antioxidative
potential of phenolics is very high as these compounds can produce stable radical
intermediates utilizing electrons. Due to their antioxidative potential, they play an
important role in the stabilization of edible oils and protection from off-flavor
formation [8]. Recent findings suggest that phenolics could play an important role
in conditions associated with oxidative stress [9, 10]. The antioxidant property of
sesame seed and its oil along with various health properties is attributed to the
presence of lignans such as sesamin, sesamolin, sesaminol, sesangolin, 2-episalatin,
and tocopherol isomers [11]. Sesame oil is extremely resistant to oxidative rancidity
due to the presence of chemically related compounds sesamol and sesamol dimer.
Haworth was first to suggest (1936) [13] that the class of compounds derived from
two C6C3 units having β,β0 linkage (8–80 bond) should be called as lignans. Lignan is
actually a constituent of lignin, a generic name for the compound resulting from two
p-hydroxyphenylpropane molecules. Sesame seed contains two major groups of
lignans: (1) oil-soluble lignans (sesamin, sesamolin, sesaminol, sesamolinol, and
pinoresinol) and (2) glycosylated water-soluble lignans (sesaminol triglucoside,
pinoresinol triglucoside, sesaminol monoglucoside, pinoresinol monoglucoside,
and two isomers of pinoresinol diglucoside and sesaminol diglucoside) [14–16].
The antioxidative property of sesame seed is associated with lignan components
present in the oil and are unique to sesame. The lignans, sesamin, and sesamolin and
their derivatives prevent oxidation of the oil and give it a long shelf life and stability
[17]. Lignans and tocopherols are also reported to act in coordination resulting in
enhanced vitamin E activity [18]. Namiki [19] suggested that the bioactive com-
pounds present in sesame seed cannot individually describe the high oxidative
stability of roasted sesame oil, but the cumulative effect of all the components of
sesame oil protects the roasted sesame oil from oxidative deterioration.
The oil fraction of most oilseeds comprises mainly of triacylglycerols (95–99%)
acting as a dispersing media for a wide range of lipophilic and amphiphilic second-
ary metabolites, together known as the unsaponifiable fraction of the seed. These
unsaponifiable portions can be extracted with lipophilic solvents after saponification
of acyl lipids [20] and are of importance as the presence of the lignans may be taken
as marker for genuineness of the oil. Other constituents, tocopherols and
tocotrienols, are strong antioxidants and provide stability to the oil. Also, lignans,
especially sesamin, have currently been recognized for possessing interesting phys-
iological bioactivities against chronic diseases.
Sesaminol, a water-soluble glycoside along with fat-soluble sesamin and
sesamolin, constitutes the major lignans of sesame seeds. The isomer of sesamin
called episesamin is generated in the process of refining sesame oil. The functional
methylenedioxyphenyl group of most of these lignans especially sesamin,
sesamolin, and sesangolin initiates the activities [21, 22], and these molecules in
turn utilize their effect via inhibition of liver microsome oxidases [23].
Sesamin Biosynthesis
Phenylalanine and tyrosine are precursors for various plant substances such as
tannins, polymeric lignin, and lignans. Phenylalanine is converted to cinnamic
acid by the enzyme phenylalanine ammonia lyase (PAL). This is followed by a
series of hydroxylation, methylation, and reduction leading to production of
coumaric acid, caffeic acid, ferulic acid, and eventually E-coniferyl alcohol [24].
However, it has also been claimed that [14C]-labeled tyrosine is incorporated into
sesamin when administered to the cell suspension cultures of Sesamum indicum [25].
E-coniferyl alcohol has also been shown to undergo stereoselective coupling
to synthesize (þ)-pinoresinol in Sesamum indicum seeds (Fig. 3). (þ)-Pinoresinol
is then metabolized further, and methylenedioxyphenyl group is added in matur-
ing sesame seeds which result in production of (þ)-piperitol and (þ)-sesamin and
(þ)-sesamolin [26]. A 78 kDa dirigent protein is known to assist in a stereoselective
6 N. Pathak et al.
aliphatic side chain containing two methyl groups in the middle and two more
methyl groups at the end. Plants synthesize eight different vitamin E forms, includ-
ing α-, β-, γ-, and δ-tocopherols and α-, β-, γ-, and δ-tocotrienols [33]. All tocoph-
erols and tocotrienols consist of a chromanol ring and varying number of methyl
groups on the chromanol ring. Metabolic fate and biological activities of tocols
depend upon their structural features. The entire isoforms act as lipid antioxidants,
and α-tocopherol has the highest vitamin E activity [34, 35]. The difference between
tocopherols and tocotrienols is that tocopherols have a saturated tail, while
tocotrienols have an unsaturated tail.
Higher plants like dicots have tocopherols in almost all parts including roots,
stems, leaves, flowers, fruits, and seeds [36, 37]. However, the total tocopherol
content and different forms of tocopherols in these tissues differ considerably.
Among the tocopherols, α-tocopherol is the predominant form in photosynthetic
tissues such as stems and leaves. In most seed crops, α-tocopherol is present only in a
minor form, and γ- and δ-tocopherols tend to predominate [38].
Tocopherol Biosynthesis
The hydroquinone ring of tocopherol is derived from the shikimate pathway
of aromatic amino acid synthesis (Fig. 4). Biosynthesis of homogentisate, the
precursor for tocopherol, tocotrienol, and plastoquinone, is catalyzed by p-
hydroxyphenylpyruvate dioxygenase (HPPD) [39]. After attachment of the hydro-
phobic side chain by homogentisate phytyl transferase (HPT1/VTE2) [40, 41] and on
methylation (VTE3) [42, 43], 2,3-dimethyl-5-phytyl-1,4-hydroquinol (DMPQ) is
formed, which is converted to γ-tocopherol by tocopherol cyclase (VTE1) [44, 45].
Tocopherol cyclase is considered as a key enzyme in tocopherol biosynthesis. Final
methylation by γ-tocopherol methyltransferase (γ-TMT, VTE4) results in the pro-
duction of α-tocopherol.
Sesame lignans have antioxidant and tocopherol-sparing activities [59–62]. They are
reported to reduce cholesterol level [48, 50, 63] and exhibit antihypertensive [64] and
anti-inflammatory activities [65] as well as affect lipid metabolism by enhancing gene
expression and hepatic enzyme (acyl CoA oxidase, carnitine palmitoyltransferase,
bifunctional enzyme, and 3-ketoacyl-CoA-thiolase) activities involved in fatty acid
oxidation [66, 67]. On the other hand, lignans reduce the activities of enzymes involved
in lipogenesis (acetyl-CoA carboxylase, fatty acid synthase, ATP citrate lyase, glucose-
6-phosphate dehydrogenase, and pyruvate kinase) by altering the gene expression [66].
Hence, sesame plays a crucial role in minimizing the vulnerability and increasing the
safety against atherosclerosis, cancer, and cardiovascular diseases [48, 64, 68].
Thus, sesame has both preventive and therapeutic values in a variety of chronic
diseases, owing to its rich lignan content and its antioxidative, anticholesterolemic,
and antihypertensive properties. Sesame lignans, especially sesamin, are absorbed in
human body, undergo enterohepatic circulation, and are converted into strong
antioxidative metabolites. Intestinal bacteria metabolize them into other bioactive
compounds such as mammalian lignans enterolactone and enterodiol compounds,
which the role in breast, prostate, and colon cancers, bone health, and cardiovascular
diseases is understudy [69–71].
In traditional Chinese and Indian systems of medicine like Ayurveda, sesame
occupies an important position with diverse pharmaceutical application. In China,
Sesame: Bioactive Compounds and Health Benefits 9
sesame oil is used in treatment of toothaches and gum diseases [72]. In India, it is
being used as an antibacterial mouthwash to relieve anxiety and insomnia and in the
treatment of blurred vision, dizziness, and headache [72]. Sesame oil is also noted
for burn-healing effect [73]. Moist-exposed burn ointment (MEBO) a purely herbal
formulation from China contains sesame oil as an active ingredient along with β-
sitosterol, berberine, and other plant extracts in trace amount [74] and is usually used
in managing the burns of the face, neck, and hand [73].
The main antioxidant activity of α-tocopherol is to break the radical chain in
membranes and lipoproteins [75]. Its antioxidant potential along with various func-
tions at the molecular level mitigates the possibility of cardiovascular diseases and
cancers [76, 77]. Other tocols that are present in lesser amount can also perform the
antioxidative and biological activities. Gamma-tocopherol (γ-T), for instance, is
more potent in decreasing platelet aggregation and LDL oxidation and delaying
intra-arterial thrombus formation than that of α-tocopherol [78, 79]. Tocotrienols
inhibit cholesterol biosynthesis [80] and are found effective in reducing the tendency
of breast cancer [81]. Thus, tocopherols have high antioxidant, antitumor, and
hypocholesterolemic potential. γ-Tocopherol is the major tocopherol in sesame,
whereas α- and δ-tocopherols are present in very small amounts. It has been reported
that γ-tocopherol is a more effective antioxidant compared to other tocopherols [82]
but has poor vitamin E activity in biological systems [76].
Tocopherols terminate the recyclable chain reaction of polyunsaturated fatty acid
(PUFA) radicals produced by oxidation of lipid [83]. The lipid peroxy radicals that
are scavenged by tocopherols are converted into tocopheroxyl radicals, which with
the help of ascorbate and other antioxidants are recycled back as the corresponding
tocopherol [84]. In this manner, a tocopherol molecule can undergo in multiple lipid
peroxidation chain-breaking events before it is finally degraded.
2.3 Phytosterols
Phytosterols (sterols and stanols) are plant triterpenes with preventive functions
in many diseases especially cancer. They have been shown to possess antioxidant
[90], anti-inflammatory [91], and antibacterial properties [92]. Similar in structure
to cholesterol (phytosterols have extra methyl group at C-24 position), these plant
sterols, when digested, compete with cholesterol for small intestine absorption leading
to lowering of the cholesterol level in blood [93]. The recommended functional foods
usually contain phytosterols extracted from plant sources, or at times processed foods
10 N. Pathak et al.
2.4 Phytates
Phytic acid is a bioactive compound with wide distribution in plant foods. Due to its
molecular structure, phytic acid has affinity to polyvalent cations such as minerals
and trace elements. Phytic acid is one of the most important sources of phosphorus in
plant seeds, and sesame is no exception. In fact, sesame seeds are richer in phytate
than the commonly known legumes. In oil seeds such as sunflower, soybean,
sesame, linseed, and rapeseed, the phytic acid content ranges from 1% to 5.4%
compared to 0.2–2.9% in legumes. A defatted sesame meal has much higher phytate
concentration than that of soybean meal [98]. Graf and Dintzis [99] have measured
5.36% phytic acid content in sesame seeds. Often, phytates are termed as anti-
nutrient for preventing mineral absorption from meal, but it is also seen that phytates
have anticancerous and hypocholesterolemic activities [100, 101].
Fatty acids are carboxylic acids with long-chain hydrocarbon side groups derived
from or contained as esterified molecular form in lipids (fat, oil, or wax) of microbes,
animals, and plants usually ranging from 1 to 30 carbon atoms in length attached to a
terminal carboxyl group [102]. Polyunsaturated fatty acids (PUFAs) are long-chain
fatty acids containing two or more double bonds introduced by specific desaturase
enzymes. Over the years, vegetable oils rich in various PUFAs have emerged as
potential dietary elements for normal growth and development of human beings with
considerable biomedical significance. LC-x-3-PUFAs are important for human
health in maintaining the cellular membrane by regulating cholesterol synthesis,
transportation [103], and eicosanoid synthesis [104].
Sesame is a high-energy food containing approximately 50% oil. The fatty acid
composition of sesame oil is highly desirable with about 80–85% unsaturated acids
and only 15–20% of saturated acids. Sesame oil consists mainly of linoleic
Sesame: Bioactive Compounds and Health Benefits 11
(35–50%) and oleic (35–50%) acids, with small amount of palmitic (7–12%) and
stearic (3.5–6%) acids, but with only traces of linolenic acid [105, 106]. Studies
indicate that a high intake of n-6 fatty acids shifts the physiologic state to one that is
pro-thrombotic and pro-aggregatory, characterized by increase in blood viscosity,
vasospasm, and vasoconstriction and decrease in bleeding time. The n-3 fatty acids,
however, have anti-inflammatory, antithrombic, hypolipidemic, and vasodilatory
properties [103]. Sesame in combination with soybean oil increases the vitamin E
activity along with nutritive value of the lipid [19, 107].
Sesame varieties differ greatly in fatty acid contents of their seeds, and this under-
standing could lead to crop engineering with an aim to develop better quality edible oil in
future [108]. Indian sesame germplasms have lower level of saturated fatty acids
compared to other sesame varieties with palmitic acid being the prominent one. C18:1
and C18:2 are the major unsaturated fatty acids present in Indian varieties [109]. In
unsaturated fatty acids, while the content of C18:1 and C18:2 is quite high in sesame oil
(38–49% and 17–43%, respectively), the C18:3 content is below par (<1%) [110]. A
critical analysis of different cultivars is the need of hour, if we are assertive to improve the
nutritional quality of oil by engineering the fatty acid biosynthetic pathway.
The bioactive polypeptides are amino acid chains joined by amide or peptide bonds,
with molecular weight not exceeding beyond 20 kDa. These are protein fragments
that have independent function in various biochemical, physiological, or cellular
processes. While some of these peptides are formed naturally, it is the artificial
protein hydrolysates that are much in use and are structurally and functionally a
diverse group of peptides. Proteins can be digested by proteases, or specific fragment
can be created in bio-fermenters utilizing microbes [111]. Sesame food preparation is
also an important source of protein [112]. Protein hydrolysates are widely in use as
nutritional supplement, functional ingredient, food flavor enhancer, pharmaceuticals,
and cosmetics [113, 114]. They display hormone- or drug-like activities and based
on the mode of action can be classified as antimicrobial, antithrombotic, antihyper-
tensive, opioid, immunomodulatory, mineral binding, and antioxidative [115]. Use
of papain for producing sesame protein hydrolysates having better functional prop-
erties, high storability, and emulsifying properties than that of the original sesame
protein lysate has been studied by Bandyopadhyay and Ghosh [116].
Sesame crops are of high nutritional value owing to the presence of antioxidants
lignans (sesamin, sesamolin, and sesamol) and tocopherols (α-, γ-, and δ-forms).
Separation of tocopherol homologues in sesame by RPLC on triacontyl (C30)
12 N. Pathak et al.
stationary phase has been successfully optimized. The reproducibility of the procedure
is in the range 1.7–3.9%, and recovery ranged from 91% to 99% [117]. Lignans and
tocopherol homologue contents in a wide collection of 143 sesame lines (wild species,
landraces, introgressed lines, and cultivars) collected from diverse agroecological
zones of India have been determined by reverse-phase HPLC (RP-HPLC) [118].
Screening of sesame germplasm revealed an exploitable level of variation in major
bioactive compounds. High levels of sesamin and γ-tocopherol suggested for the
efficient introduction of these lines in the trait enhancement of other oilseed crops.
Sesame crop is relatively superior in oil quantity and quality compared to many
major oil crops. The oil content varies from 35% to 60%, but mostly it is about 50%
of seed weight [119]. Therefore, genetic engineering of sesame directed toward
creation of sesame oil having diverse composition of lignans and tocopherols with
high nutritional value is an important biotechnological aspect. With high genetic
diversity, sesame becomes a promising oilseed crop for performing genetic manip-
ulations to obtain high yield and quality oil [120].
Higher oil content compared to other oilseed crops, combined with small genome
related to oil quality enhancement, makes sesame an invaluable model plant for
studying oil biosynthesis. Wang et al. [121] have done de novo assembling of the
genome, where a set of 12 transcriptomes and 29 resequenced accessions provided
a large resource for exploring the mechanisms underlying different oil content
between sesame and soybean, as well as among the sesame accessions. The results
reveal the presence of whole genome duplication and absence of the Toll/interleukin-
1 receptor domain in resistance genes. Genes and oil biosynthetic pathways respon-
sible for high oil content were determined employing comparative genomic and
transcriptomic analyses. That has indicated for the expansion of type 1 lipid transfer
genes by tandem duplication, the contraction of lipid degradation genes, and the
differential expression of essential genes in the triacylglycerol biosynthesis pathway
in the early stage of seed development [121].
Resequencing data study in 29 sesame accessions from 12 countries suggests that
the high genetic diversity of lipid-related genes is linked with the wide variation in
oil content. Additionally, the results shed light on the pivotal stage of seed develop-
ment, oil accumulation, and potential key genes for sesamin production, an impor-
tant lignan with numerous health benefits. Recently, two more sesame landraces and
the chloroplast genome have been sequenced [121, 122] enriching the sesame
genome dataset. A recent genome-wide association study has identified SiNST1as
the candidate gene for lignin and cellulose biosynthesis, and this gene could
Sesame: Bioactive Compounds and Health Benefits 13
indirectly be associated with sesamin and sesamolin content [123]. Thankfully, a few
open access platform like Sinbase is also being maintained where all these datasets
are managed for further analysis and utilization by sesame researchers [121].
malabaricum, whereas other cultivars had low expression, indicating that sesamin
synthase was not favored during domestication.
5 Conclusions
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