Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

Journal of Natural Products
Kam-Weng ChongToh-Seok Kam

Abstract

Reexamination of the absolute configuration of recently isolated eburnane alkaloids from Malaysian Kopsia and Leuconotis species by X-ray diffraction analysis and ECD/TDDFT has revealed the existence of biosynthetic enantiodivergence. Three different scenarios are discerned with respect to the composition of the enantiomeric eburnane alkaloids in these plants: first, where the new eburnane congeners possess the same C-20, C-21 absolute configurations as the common eburnane alkaloids (eburnamonine, eburnamine, isoeburnamine, eburnamenine) occurring in the same plant; second, where the new eburnane congeners possess opposite or enantiomeric C-20, C-21 absolute configurations compared to the common eburnane alkaloids found in the same plant; and, third, where the four common eburnane alkaloids were isolated as racemic or scalemic mixtures, while the new eburnane congeners were isolated as pure enantiomers with a common C-20, C-21 configuration (20α, 21α). Additionally, the same Kopsia species (K. pauciflora) found in two different geographical locations (Peninsular Malaysia and Malaysian Borneo) showed different patterns in the composition of the enantiomeric eburnane alkaloids. Revision of the absolute configurations of a number ...Continue Reading

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May 8, 2013·Journal of Natural Products·Chew-Yan GanToh-Seok Kam
May 17, 2014·Journal of Natural Products·Yun-Yee LowToh-Seok Kam
Apr 21, 2016·Angewandte Chemie·Cyril PiemontesiJieping Zhu

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Citations

Nov 4, 2020·Natural Products and Bioprospecting·Zong-Qing HuoYu Zhang
Jan 9, 2021·Angewandte Chemie·Ren-Xiao LiangYi-Xia Jia
Mar 17, 2020·Fitoterapia·Tian-Zhen XieXiao-Dong Luo
Jul 21, 2020·Journal of Natural Products·Jian ZhangXiao-Qi Zhang

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