Enantiomeric ratio of sesamin in the bark of Pentaspadon motleyi (Anacardiaceae)

  • CHINAMI KITAMURA FUKUYAMA UNIVERSITY
  • PARTOMUAN SIMANJUNTAK INDONESIA INSTITUTE OF SCIENCE
  • KAZUYOSHI KAWAZOE UNIVERSITY OF TOKUSHIMA
  • SHOJI MAEHARA FUKUYAMA UNIVERSITY
  • KOZUYOSHI OHASHI FUKUYAMA UNIVERSITY
  • HIROTAKA SHIBUYA FUKUYAMA UNIVERSITY

Abstract

The barks of Pentaspadon motleyi Hook. f. (Anacardiaceae) were collected from the Poso district in Central Sulawesi, Indonesia, in 1992 which it has been used traditionally as a remedy for malaria and tuberculosis in the local area. It was found that a mixture of (+)-sesamin (1) and (-)-sesamin (2) in a ratio of 100:86 were present together with lupeol in the bark of Pentaspadon motleyi. This was the first evidence of sesamin being isolated in almost equivalent amounts of (+)- and (-)-forms from a single plant species, and indicates that the biosynthetic pathway of sesamin in the plant is not enantioselective or fuzzy.

References

1. Tocher JF. Isolation of another substance from sesame oil. Pharm J Trans 1890/1891. 639-40.

2. Tocher JF. A further note on sesamin. Pharm J Trans 1892/1893. 700-2.

3. Kanu PJ, Zhu K, Kanu JB , Zhou H, Qian H, Zhu K. Biologically active components and nutraceuticals in sesame and related products: a review and prospect. Trends Food Sci Technol. 2007. (18): 599-608. 4. Suzuki S, Umezawa T’ Biosynthesis of lignans and norlignans. J Wood Sci. 2007. (53): 273-84.

5. Paré PW, Wang H-B, Davin LB, Lewis NG. (+)-Pinoresinol synthesis: a stereoselective oxidase catalysing 8,8’-lignan formation in Forsythia intermedia.Tetrahedron Lett .1994. (35): 4731-34.

6. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent)protein without an active center. Science. 1997. (275): 362-6.

7. Ono E, Nakai M, Fukui Y, Tominori N, Fukuchi-Mizunati M, Saito M, Satake H, Tanaka K, Katsuta M, Umezawa T, Tanaka Y. Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin. Proc Natl Acad Sci USA. 2006. (103): 10116-21.

8. Lin R-W, Tsai I-L, Duh C-Y, Lee K-H, Chen I-S. New lignans and cytotoxic constituents from Wikstroemia lanceolata. Planta Med. 2004. (70): 234-8. 9. Antonaccio LD, Gottlieb OR . Sesamin and lupeol in the bark of two Brazilian Fagara species. Anais assoc brasil quim .1959. (18): 183-4.

10. Carnmalm B, Erdtman H, Pelchowicz Z. Constitution of resin phenols and their biogenetic relations XIX. The structure of sesamolin, the configuration of sesamin and the nature of fagarol. Acta Chem Scand. 1955. (9): 1111-8.
Published
2011-09-30
How to Cite
KITAMURA, CHINAMI et al. Enantiomeric ratio of sesamin in the bark of Pentaspadon motleyi (Anacardiaceae). JURNAL ILMU KEFARMASIAN INDONESIA, [S.l.], v. 9, n. 2, p. 101-103, sep. 2011. ISSN 2614-6495. Available at: <http://jifi.farmasi.univpancasila.ac.id/index.php/jifi/article/view/294>. Date accessed: 05 nov. 2024.
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Articles