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

Chao Liu; Zhi-Xin Liao; Shi-Jun Liu; Lan-Ju Ji; Hong-Fa Sun

doi:10.1055/s-0034-1368612

Planta Medica, Table of Contents

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

¹Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China

³Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing, P. R. China

,

Zhi-Xin Liao

¹Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China

³Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing, P. R. China

,

Shi-Jun Liu

¹Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China

,

Lan-Ju Ji

²Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, P. R. China

,

Hong-Fa Sun

²Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, P. R. China

› Author Affiliations

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

Full Text

References

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