Abstract
Five new hybrid monoterpenoid indole alkaloids bearing an unusual 2,2-dimethyl-4-oxopiperidin-6-yl moiety, namely rauvotetraphyllines F–H (1, 3, 4), 17-epi-rauvotetraphylline F (2) and 21-epi-rauvotetraphylline H (5), were isolated from the aerial parts of Rauvolfia tetraphylla. Their structures were established by extensive spectroscopic analysis. The new alkaloids were evaluated for their cytotoxicity in vitro against five human cancer cell lines.Graphical Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-015-0074-2) contains supplementary material, which is available to authorized users.
Highlights
Rauvolfia genus of the Apocynaceae family, comprising about 60 species, is mainly distributed in America, Africa, Asia, and Oceania [1]. Plants of this genus are a rich source of monoterpenoid indole alkaloids, which have attracted great interests from biological and therapeutic aspects [2,3,4,5]
As part of a BioBioPha [http://www.chemlib.cn] objective to assemble a large-scale natural product library valuable in the discovery of new drug leads from nature, previous chemical study on the ethanolic extract of Rauvolfia tetraphylla had resulted in the isolation of five new indole alkaloids, rauvotetraphyllines A–E [6]
Li State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China rauvotetraphylline B [6] revealed a remarkable resemblance except for a prominent difference as follows: the carbon signals assigned to 4,6-dimethylpyrid-2-yl unit in rauvotetraphylline B were not present, and there was a set of newly arisen resonances [dC 56.5 (d), 47.4 (t), 213.2 (s), 55.7 (t), 55.5 (s), 25.6 (q), and 31.9 (q)] determined as a
Summary
Rauvolfia genus of the Apocynaceae family, comprising about 60 species, is mainly distributed in America, Africa, Asia, and Oceania [1]. Plants of this genus are a rich source of monoterpenoid indole alkaloids, which have attracted great interests from biological and therapeutic aspects [2,3,4,5]. As part of a BioBioPha [http://www.chemlib.cn] objective to assemble a large-scale natural product library valuable in the discovery of new drug leads from nature, previous chemical study on the ethanolic extract of Rauvolfia tetraphylla had resulted in the isolation of five new indole alkaloids, rauvotetraphyllines A–E [6]. The present paper describes the isolation, structure elucidation, and cytotoxic evaluation of the new compounds
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