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Review
. 2021 Feb 7;26(4):883.
doi: 10.3390/molecules26040883.

Lignans of Sesame (Sesamum indicum L.): A Comprehensive Review

Mebeaselassie Andargie  1 , Maria Vinas  2 , Anna Rathgeb  1 , Evelyn Möller  1 , Petr Karlovsky  1
Affiliations
Review

Lignans of Sesame (Sesamum indicum L.): A Comprehensive Review

Mebeaselassie Andargie et al. Molecules. .

Abstract

Major lignans of sesame sesamin and sesamolin are benzodioxol--substituted furofurans. Sesamol, sesaminol, its epimers, and episesamin are transformation products found in processed products. Synthetic routes to all lignans are known but only sesamol is synthesized industrially. Biosynthesis of furofuran lignans begins with the dimerization of coniferyl alcohol, followed by the formation of dioxoles, oxidation, and glycosylation. Most genes of the lignan pathway in sesame have been identified but the inheritance of lignan content is poorly understood. Health-promoting properties make lignans attractive components of functional food. Lignans enhance the efficiency of insecticides and possess antifeedant activity, but their biological function in plants remains hypothetical. In this work, extensive literature including historical texts is reviewed, controversial issues are critically examined, and errors perpetuated in literature are corrected. The following aspects are covered: chemical properties and transformations of lignans; analysis, purification, and total synthesis; occurrence in Seseamum indicum and related plants; biosynthesis and genetics; biological activities; health-promoting properties; and biological functions. Finally, the improvement of lignan content in sesame seeds by breeding and biotechnology and the potential of hairy roots for manufacturing lignans in vitro are outlined.

Keywords: biological function; health-promoting properties; lignan biosynthesis; lignan glycosides; plant biotechnology; sesame lignans; sesamin; sesamol; sesamolin.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of major lignans of sesame.
Figure 2
Figure 2
Minor lignans of sesame (first two rows) and transformation products (bottom row).
Figure 3
Figure 3
Dimerization of cinnamyl alcohol forms pinoresinol. Numbering according to IUPAC recommendation [34].
Figure 4
Figure 4
Structures of major lignan glycosides of sesame.
Figure 5
Figure 5
Degradation and transformation products of sesame lignans during industrial processing. (A) Degradation products of sesamolin. (B) Degradation products of sesamin.
Figure 6
Figure 6
Conversion of sesamolin into sesamol by roasting. Seeds were roasted for 25 min in an electric oven at a designated temperature. The graph was constructed using data published by Yoshida and Tagaki [126].
Figure 7
Figure 7
Colorimeter for Villavecchia test used in Aarhus Oliefabrik (Aarhus, Denmark).
Figure 8
Figure 8
Variation of lignan content in sesame seeds. Lignan content is given in mg/g. Asterisk indicates that sesamolin content was not determined.
Figure 9
Figure 9
Lignan biosynthetic pathway in Sesamum indicum. 1 = laccase, 2 = dirigent protein, 3 = piperitol/sesamin synthase (CYP81Q1), 4 = sesamolin/sesaminol synthase (CYP92B14), 5 = UGT71A9, 6 = UGT94AG1, 7 = UGT94D1/UGT94AA2. Identified and postulated conversions are represented by solid and broken lines, respectively. The sequential conversion from pinoresinol to secoisolariciresinol and to matairesinol is proposed in sesame based on Forsythia intermedia biosynthetic pathway [244,245]. The convertion of sesamin to 7′-episesantalin has been recently proposed to occur in S. radiatum [92].
Figure 10
Figure 10
Biosynthetic pathway of selected lignans in different plant species. 1 = laccase, 2 = dirigent protein, 3 = CYP81Q3 in S. alatum [89], 4 = PLR1 in L. perenne [243], 5 = SDH in F. intermedia [244], 6 = CYP719A23 in P. hexandrum [249], 7–12 = OMT3, CYP71Cu1, OMT1, 2-ODD, CYP71BE54 and CYP82D61 in P. hexandrum, 13–14 = DOP6H, βP6OMT in L. flavum. Identified and postulated conversions are represented by solid and broken lines, respectively. Two arrows indicate several consecutive steps.
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