A furofuran lignan from Sesamum alatum

Kamal‐Eldin, Afaf; Yousif, G.

doi:10.1016/0031-9422(92)83664-k

Cited by 22 publications

(11 citation statements)

References 9 publications

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“…Sesangolin was later reported from S. angustifolium [ 87 ], S. alatum [ 88 ], and S. radiaum [ 92 ]. Both alatumin [ 89 ] and episesalatin [ 90 ] were found in S. alatum . The most recent contribution to the diversity of sesame lignans is (+)-7′-episesantalin, which was purified from S. radiatum [ 92 ].…”

Section: Chemistry Of Sesame Lignansmentioning

confidence: 99%

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

et al. 2021

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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.

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Section: Chemistry Of Sesame Lignansmentioning

confidence: 99%

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

et al. 2021

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“…Chemical investigations of the active fractions led to seven (1 -7, l " Fig. 1) known compounds: the chromanes 3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(2′′-methyl-2′′-butenyl)-2-(4′-methyl-1′, 3′-pentadienyl)-2H-1-benzopyran-6-carboxylic acid (1) [9], peperobtusin A (6) [6] and clusifoliol (7) [6], [10]; the furofuran lignans 2-episesalatin (3) [11] and sesartemin (4) [12]; and the flavone C-diglycosides isoswertisin-4′-methyl-ether-2′′α-L-rhamnoside (2) and isoswertisin-2′′α-L-rhamnoside (5) [13,14]. The structures of 1 -7 were confirmed by IR, MS, 1 H-, 13 C-NMR and 2D NMR spectral data, which were in agreement with the reported data for the respective compounds.…”

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confidence: 99%

In vitroTrypanocidal Activity of Phenolic Derivatives fromPeperomia obtusifolia

et al. 2009

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The trypanocidal activity of crude extracts and fractions from the leaves and stems of Peperomia obtusifolia (Piperaceae) was evaluated in vitro against the epimastigote forms of Trypanosoma cruzi. Bioactivity-guided fractionation of the most active extracts afforded seven known compounds, including three chromanes, two furofuran lignans and two flavone C-diglycosides. The most active compounds were the chromanes peperobtusin A and 3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(2''-methyl-2''-butenyl)-2-(4'-methyl-1',3'-pentadienyl)-2 H-1-benzopyran-6-carboxylic acid, with IC (50) values of 3.1 microM (almost three times more active than the positive control benznidazole, IC (50) 10.4 microM) and 27.0 microM, respectively. Cytotoxicity assays using peritoneal murine macrophages indicated that the chromanes were not toxic at the level of the IC (50) for trypanocidal activity. This is the first report on the trypanocidal activity besides unspecific cytotoxicity of chromanes from Peperomia species. Additionally it represents the first time isolation of 3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(2''-methyl-2''-butenyl)-2-(4'-methyl-1',3'-pentadienyl)-2 H-1-benzopyran-6-carboxylic acid from P. obtusifolia.

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“…It is interesting to note that in spite of cooking in presence of aqueous decoction SO did not show high increase in peroxide value indicating oxidative damage to SO, though hydrolytic damage was seen by increasing in acid value to as much as three to four times of the acceptable range. Authors feel this could be due to presence of antioxidants naturally occurring in SO, mainly sesamol and sesamin[ 5 ] and herbal components dissolving in the oil providing additional stabilizing properties. The study also shows that cooking oil with qwatha perhaps help get extractive values and components in to the oil.…”

Section: Resultsmentioning

confidence: 99%

A comparative evaluation of medicated oils prepared using ayurvedic and modified processes

et al. 2009

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Medicated oils prepared using process as mentioned in Ayurveda are used for external and internal administrations to treat various disorders. Taila pak vidhi provides detailed description of such processes. Medicated oils are prepared by prolonged cooking of sesame oil with pasty mass of herbs and decoction of herbs in presence of large quantity of water. We report preliminary findings of physicochemical and chromatographic profiles of changes brought out by such processes and the role of each component. Changes observed when the processes were altered to deviate from those prescribed in Ayurveda are also reported.

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A furofuran lignan from Sesamum alatum

Cited by 22 publications

References 9 publications

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

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

In vitroTrypanocidal Activity of Phenolic Derivatives fromPeperomia obtusifolia

A comparative evaluation of medicated oils prepared using ayurvedic and modified processes

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