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塔贝纳蒙坦那 Corymbosa 中的两种 Vobasinyl-Ibogan 型双吲哚生物碱:塔伯考利明 A 和 B。

Tabercorymines A and B, Two Vobasinyl-Ibogan-Type Bisindole Alkaloids from Tabernaemontana corymbosa.

机构信息

Yunnan University of Traditional Chinese Medicine , Kunming 650500, China.

Natural Product Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina , Chapel Hill, North Carolina 27599-7568, United States.

出版信息

Org Lett. 2017 Sep 15;19(18):4964-4967. doi: 10.1021/acs.orglett.7b02445. Epub 2017 Sep 6.

DOI:10.1021/acs.orglett.7b02445
PMID:28876071
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6421835/
Abstract

Tabercorymines A (1) and B (2), two new vobasinyl-ibogan-type bisindole alkaloids with an unprecedented skeleton, were isolated from Tabernaemontana corymbosa. Their structures were established by a combination of spectroscopic data, chemical transformation, single-crystal X-ray diffraction, and ECD calculation. Compound 1 represents a novel bisindole alkaloid, characterized by a caged heteropentacyclic ring system incorporating an unprecedented C-7/C-20 bond in the vobasinyl unit. Alkaloids 1 and 2 showed potent antiproliferative activity against several human cancer cell lines, including vincristine-resistant KB.

摘要

从 Tabernaemontana corymbosa 中分离得到了两种新的 vobasinyl-ibogan 型双吲哚生物碱 Tabercorymines A (1) 和 B (2),它们具有前所未有的骨架。通过光谱数据、化学转化、单晶 X 射线衍射和 ECD 计算的组合,确定了它们的结构。化合物 1 代表了一种新型的双吲哚生物碱,其特征在于在 vobasinyl 单元中包含一个前所未有的 C-7/C-20 键的笼状杂五环体系。生物碱 1 和 2 对包括长春新碱耐药的 KB 在内的几种人类癌细胞系表现出强烈的抗增殖活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/c488602352d1/nihms-1016651-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/deb2c96f73f6/nihms-1016651-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/925b15d4e0e2/nihms-1016651-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/4084d8c6bf20/nihms-1016651-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/a68a452d2d08/nihms-1016651-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/964398ef01f0/nihms-1016651-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/d6d44f506ede/nihms-1016651-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/c488602352d1/nihms-1016651-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/deb2c96f73f6/nihms-1016651-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/925b15d4e0e2/nihms-1016651-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/4084d8c6bf20/nihms-1016651-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/a68a452d2d08/nihms-1016651-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/964398ef01f0/nihms-1016651-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/d6d44f506ede/nihms-1016651-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afe5/6421835/c488602352d1/nihms-1016651-f0008.jpg

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