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Planta Med 2014; 80(11): 936-941
DOI: 10.1055/s-0034-1368612
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Two New 2,3-Seco-Hopane Triterpene Derivatives from Megacodon stylophorus and Their Antiproliferative and Antimicrobial Activities

Chao Liu
1   Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China
3   Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing, P. R. China
,
Zhi-Xin Liao
1   Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China
3   Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing, P. R. China
,
Shi-Jun Liu
1   Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China
,
Lan-Ju Ji
2   Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, P. R. China
,
Hong-Fa Sun
2   Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, P. R. China
› Author Affiliations
Further Information

Publication History

received 28 November 2013
revised 18 May 2014

accepted 20 May 2014

Publication Date:
04 July 2014 (online)

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Abstract

Chemical investigation of the ethanol extract of the whole plant of Megacodon stylophorus led to the isolation and identification of two new seco-hopane triterpenoids, 2,3-seco-22(29)-hopene-2-carboxyl-3-aldehyde (1) and 2,3-seco-4(23),22(29)-hopene-2-carboxyl-3-aldehyde (2), along with 10 known compounds, 3–12. All the isolates were reported from this plant for the first time. The structures of compounds 1 and 2 were determined by detailed analysis of their spectral data including 1D and 2D NMR. In addition, compound 1 was further analyzed by X-ray crystallography. Compounds 1–3 were evaluated for their in vitro anti-proliferative activities on HeLa, MCF-7, and Hep-G2 tumor cell lines. Compound 2 was active against the three cell lines with IC50 values of 3.6, 7.5, and 13.6 µM, respectively, while compound 1 exhibited cytotoxicity on MCF-7 (IC50 14.0 µM) and HeLa (IC50 18.2 µM) cell lines. Antimicrobial activities of compounds 1–2 (minimum inhibitory concentration values in the range of 3.12–12.50 mg/mL) were also observed.

Key words

Megacodon stylophorus - Gentianaceae - 2,3-seco-hopane triterpenoids - antiproliferative - antimicrobial

Supporting Information

 

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