Organic Letters
Organic Letters
3 years ago

Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria

Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria
Jian-Jun Chen, Qi-Li Zhang, Dong-Bo Zhang, Jun Zeng, Lei Zhao, Kun Gao, Pan-Pan Zhou
Two unusual normonoterpenoid indole alkaloids rauvomine A (1) and rauvomine B (2), together with two known compounds peraksine (3) and alstoyunine A (4), were isolated from the aerial parts of Rauvolfia vomitoria. The structures with absolute configurations of 1 and 2 were elucidated by spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compound 2 is a novel C18 normonoterpenoid indole alkaloid with a substituted cyclopropane ring that forms an unusual 6/5/6/6/3/5 hexcyclic rearranged ring system. The plausible biogenetic pathways of 1 and 2 were proposed. Compound 2 exhibited significant anti-inflammatory activity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01723

DOI: 10.1021/acs.orglett.7b01723

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