Macropodumines A-C: novel pentacyclic alkaloids with an unusual skeleton or zwitterion moiety from Daphniphyllum macropodum Miq

Chemistry : a European Journal
Wen ZhangKarsten Krohn

Abstract

Three novel alkaloids, macropodumines A-C (1-3), were isolated from the stem of Daphniphyllum macropodum Miq. Interestingly, the structure of macropodumine A (1) was characterized as having a fused pentacyclic system including an unusual eleven-membered macrolactone ring, whereas macropodumine B (2) contains a rare cyclopentadienyl carbanion, which is stabilized as a zwitterion by an internal iminium cation. The structures of these new metabolites were established on the basis of their detailed spectroscopic analysis. In particular, the unique structure of zwitterion 2 was further confirmed by using single-crystal X-ray diffraction analysis.

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May 31, 2011·Journal of Asian Natural Products Research·Jian-Rong WangYue-Wei Guo
Feb 17, 2009·Journal of Asian Natural Products Research·Zhen-Yu LiYue-Wei Guo
Mar 13, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yunyang LuHaifeng Tang
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Jan 31, 2009·Chemistry & Biodiversity·Zhen-Yu LiYue-Wei Guo
Oct 7, 2011·Organic & Biomolecular Chemistry·Jian-Rong WangYue-Wei Guo

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