Unusual cycloartane triterpenoids from Kadsura ananosma

Jian-Hong Yang; Jian-Xin Pu; Jin Wen; Xiao-Nian Li; Fei He; Jia Su; Yan Li; Han-Dong Sun

doi:10.1016/j.phytochem.2014.10.014

Unusual cycloartane triterpenoids from Kadsura ananosma

Phytochemistry. 2015 Jan:109:36-42. doi: 10.1016/j.phytochem.2014.10.014. Epub 2014 Nov 14.

Authors

Jian-Hong Yang¹, Jian-Xin Pu², Jin Wen³, Xiao-Nian Li⁴, Fei He⁴, Jia Su⁴, Yan Li⁴, Han-Dong Sun⁵

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People's Republic of China; Graduate University of Chinese Academy of Sciences, Beijing 100039, People's Republic of China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People's Republic of China. Electronic address: pujianxin@mail.kib.ac.cn.
³ Yunnan Academy of Forest Sciences Institute of Tropical Forestry, Kunming 650204, Yunnan, People's Republic of China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People's Republic of China.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People's Republic of China. Electronic address: hdsun@mail.kib.ac.cn.

PMID: 25457490
DOI: 10.1016/j.phytochem.2014.10.014

Abstract

Five 3,4-seco-cycloartane triterpenoids were isolated from the stems of Kadsura ananosma, two of which had rearranged 5/6 consecutive carbocycle rings C/D (trivially named ananosins A (1) and B (2)), one had a migrated CH3-18 (named ananosins C (3)), and two were analogs, ananosins D (4) and E (5). Their structures were characterized by comprehensive spectroscopic analysis, especially using 2D NMR spectra. A biogenetic pathway to 1 was proposed. These 5 compounds, together with 5 known analogs isolated from the same origin, were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549, PANC-1, and SK-BR-3 human cancer cells, but were inactive.

Keywords: Ananosins; Cycloartane triterpenoids; Kadsura ananosma; Schisandraceae.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Kadsura / chemistry
Lignans / chemistry
Lignans / isolation & purification
Molecular Structure
Triterpenes / chemistry*
Triterpenes / isolation & purification

Substances

Lignans
Triterpenes
ananosin A
cycloartane