Isolation and structure characterization of cytotoxic alkaloids from Micromelum integerrimum

Nan-Kai Cao; Yue-Mei Chen; Si-Si Zhu; Ke-Wu Zeng; Ming-Bo Zhao; Jun Li; Peng-Fei Tu; Yong Jiang

doi:10.1016/j.phytochem.2020.112463

Isolation and structure characterization of cytotoxic alkaloids from Micromelum integerrimum

Phytochemistry. 2020 Oct:178:112463. doi: 10.1016/j.phytochem.2020.112463. Epub 2020 Jul 22.

Authors

Nan-Kai Cao¹, Yue-Mei Chen¹, Si-Si Zhu¹, Ke-Wu Zeng¹, Ming-Bo Zhao¹, Jun Li¹, Peng-Fei Tu¹, Yong Jiang²

Affiliations

¹ State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, People's Republic of China.
² State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, People's Republic of China. Electronic address: yongjiang@bjmu.edu.cn.

PMID: 32888669
DOI: 10.1016/j.phytochem.2020.112463

Abstract

Ten undescribed alkaloids, named integerrines A-J, including one racemic heterodimer of carbazole and indole, two racemic, two scalemic, and one enantiomerically enriched biscarbazoles, two aldoximes, and one racemic pyrrolone, were isolated from the dried leaves and stems of Micromelum integerrimum. The racemic or scalemic compounds were resolved using chiral-phase HPLC and their configurations were determined by comparison of experimental and calculated ECD data. Four compounds exhibited moderate to weak cytotoxicities against HepG2, HTC-116, HeLa, and PANC-1 cell lines, with IC₅₀ values of 14.1-67.5 μM.

Keywords: Aldimine; Atropisomers; Carbazole; Cytotoxicity; Heterodimers; Micromelum integerrimum (Buch.-ham.) roem.; Pyrrolone; Rutaceae.

MeSH terms

Alkaloids*
Antineoplastic Agents*
Cell Line, Tumor
Humans
Molecular Structure
Plant Leaves
Rutaceae*

Substances

Alkaloids
Antineoplastic Agents