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Planta Med 2011; 77(9): 922-928
DOI: 10.1055/s-0030-1250673
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Triterpenoids and Steroids from the Bark of Melia azedarach

Shi-Biao Wu1 , Qiu-Ying Bao1 , Wen-Xuan Wang1 , Yun Zhao1 , Gang Xia1 , Zheng Zhao1 , Huaqiang Zeng2 , Jin-Feng Hu1
  • 1Department of Natural Products for Chemical Genetic Research, Key Laboratory of Brain Functional Genomics, Ministry of Education and Shanghai Key Laboratory of Brain Functional Genomics, East China Normal University, Shanghai, PR China
  • 2Department of Chemistry, National University of Singapore, Singapore
Further Information

Publication History

received Sept. 16, 2010 revised Nov. 9, 2010

accepted Dec. 7, 2010

Publication Date:
17 January 2011 (online)

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Abstract

Two new triterpenoids (1, 2) and two new steroids (3, 4) along with twelve related known compounds (5–16) were isolated from the bark of Melia azedarach. The new structures were elucidated by means of spectroscopic methods and molecular modeling studies and found to be 21,24-cycloeupha-7-ene-3β,16β,21α,25-tetrol (1), 3β-acetoxy-12β-hydroxy-eupha-7,24-dien-21,16β-olide (2), 29-hydroperoxy-stigmasta-7,24(28)E-dien-3β-ol (3), and 24ξ-hydroperoxy-24-vinyl-lathosterol (4). All isolated compounds were tested for their cytotoxic activity against three human cancer cell lines (A549, H460, HGC27) using the CellTiter Glo™ luminescent cell viability assay. Among them, compounds 2–4, 24ξ-hydroperoxy-24-vinyl-cholesterol (6), kulinone (7), meliastatin 3 (8), 3-oxo-olean-12-en-28-oic acid (10), and (22E,24S)-5α,8α-epidioxy-24-methyl-cholesta-6,22-dien-3β-ol (12) were found to have cytotoxic effects, with IC50 values of 5.6–21.2 µg/mL.

Key words

Melia azedarach - Meliaceae - triterpenoids - steroids - cytotoxicity

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Prof. Dr. Jin-Feng Hu

Department of Natural Products for Chemical Genetic Research
Key Laboratory of Brain Functional Genomics
Ministry of Education & Shanghai Key Laboratory of Brain Functional Genomics
East China Normal University

3663 Zhongshan Road N

Shanghai 200062

China

Phone: +86 21 62 23 75 10

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Email: jfhu@brain.ecnu.edu.cn

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