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Fitoterapia. 2018 Jun;127:47-55. doi: 10.1016/j.fitote.2018.01.013. Epub 2018 Jan 31.

New zwitterionic monoterpene indole alkaloids from Uncaria rhynchophylla.

Author information

1
State Key Laboratory of Natural and Biomimetic Drugs and Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, People's Republic of China.
2
State Key Laboratory of Natural and Biomimetic Drugs and Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, People's Republic of China. Electronic address: qyzhang@hsc.pku.edu.cn.

Abstract

Four new zwitterionic monoterpene indole alkaloids, rhynchophyllioniums A-D (1-4), together with eight known alkaloids (5-12), were isolated from the hook-bearing stems of Uncaria rhynchophylla. Their structures were elucidated by extensive spectroscopic data analysis of MS, 1D and 2D NMR, and ECD, and the zwitterionic forms and absolute configurations of 1 and 2 were unambiguously confirmed by single crystal X-ray diffraction analysis. All the isolates, including the monoterpene indole alkaloids with free C-22 carboxyl group and those with C-22 carboxyl methyl ester, were proved to be naturally coexisting in the herb by LC-MS analysis. This is the first report of monoterpene indole alkaloids that exist in the form of zwitterion. Additionally, the cytotoxic activities of all isolates against A549, HepG2, and MCF-7 cell lines are reported.

KEYWORDS:

Cytotoxicity; Monoterpene indole alkaloid; Rhynchophyllionium; Uncaria rhynchophylla; Zwitterion

PMID:
29373834
DOI:
10.1016/j.fitote.2018.01.013
[Indexed for MEDLINE]

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