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苦楝树皮中的细胞毒性三萜类化合物和甾体化合物。

Cytotoxic triterpenoids and steroids from the bark of Melia azedarach.

机构信息

Department 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.

出版信息

Planta Med. 2011 Jun;77(9):922-8. doi: 10.1055/s-0030-1250673. Epub 2011 Jan 17.

DOI:10.1055/s-0030-1250673
PMID:21243584
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-3 β,16 β,21 α,25-tetrol (1), 3 β-acetoxy-12 β-hydroxy-eupha-7,24-dien-21,16 β-olide (2), 29-hydroperoxy-stigmasta-7,24(28) E-dien-3 β-ol (3), and 24 ξ-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, 24 ξ-hydroperoxy-24-vinyl-cholesterol (6), kulinone (7), meliastatin 3 ( 8), 3-oxo-olean-12-en-28-oic acid (10), and (22 E,24 S)-5 α,8 α-epidioxy-24-methyl-cholesta-6,22-dien-3 β-ol (12) were found to have cytotoxic effects, with IC₅₀ values of 5.6-21.2 µg/mL.

摘要

从苦楝树皮中分离得到两个新的三萜(1,2)和两个新的甾体(3,4)以及十二个相关的已知化合物(5-16)。通过光谱方法和分子建模研究阐明了新结构,发现它们分别是 21,24-环羊毛甾-7-烯-3β,16β,21α,25-四醇(1)、3β-乙酰氧基-12β-羟基羊毛甾-7,24-二烯-21,16β-内酯(2)、29-过氧甾烷-7,24(28)E-二烯-3β-醇(3)和 24ξ-过氧-24-乙烯胆甾醇(4)。所有分离得到的化合物均采用 CellTiter Glo™发光细胞活力测定法,对三种人癌细胞系(A549、H460、HGC27)进行了细胞毒性活性测试。其中,化合物 2-4、24ξ-过氧-24-乙烯胆甾醇(6)、苦楝酮(7)、美拉他汀 3(8)、3-氧代-齐墩果-12-烯-28-酸(10)和(22E,24S)-5α,8α-表过氧-24-甲基胆甾-6,22-二烯-3β-醇(12)具有细胞毒性,IC₅₀值为 5.6-21.2µg/mL。

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