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从泰氏红厚壳中分离出的阿纳酮及其结构修饰与细胞毒性活性

Isolation and structural modifications of ananixanthone from Calophyllum teysmannii and their cytotoxic activities.

作者信息

Kar Wei Lee, Zamakshshari Nor Hisam, Ee Gwendoline Cheng Lian, Mah Siau Hui, Mohd Nor Siti Mariam

机构信息

a Faculty of Science, Department of Chemistry , Universiti Putra Malaysia , Serdang , Malaysia.

b School of Biosciences , Taylor's University , Selangor , Malaysia.

出版信息

Nat Prod Res. 2018 Sep;32(18):2147-2151. doi: 10.1080/14786419.2017.1367781. Epub 2017 Aug 22.

DOI:10.1080/14786419.2017.1367781
PMID:28826239
Abstract

Two naturally occurring xanthones, ananixanthone (1) and β-mangostin (2), were isolated using column chromatographic method from the n-hexane and methanol extracts of Calophyllum teysmannii, respectively. The major constituent, ananixanthone (1), was subjected to structural modifications via acetylation, methylation and benzylation yielding four new xanthone derivatives, ananixanthone monoacetate (3), ananixanthone diacetate (4), 5-methoxyananixanthone (5) and 5-O-benzylananixanthone (6). Compound 1 together with its four new derivatives were subjected to MTT assay against three cancer cell lines; SNU-1, K562 and LS174T. The results indicated that the parent compound has greater cytotoxicity capabilities against SNU-1 and K562 cell lines with IC values of 8.97 ± 0.11 and 2.96 ± 0.06 μg/mL, respectively. Compound 5 on the other hand exhibited better cytotoxicity against LS174T cell line with an IC value of 5.76 ± 1.07 μg/mL.

摘要

采用柱色谱法分别从红厚壳的正己烷提取物和甲醇提取物中分离得到两种天然存在的氧杂蒽酮,即异红厚壳素(1)和β-山竹黄酮(2)。对主要成分异红厚壳素(1)进行乙酰化、甲基化和苄基化结构修饰,得到4种新的氧杂蒽酮衍生物,即异红厚壳素单乙酸酯(3)、异红厚壳素二乙酸酯(4)、5-甲氧基异红厚壳素(5)和5-O-苄基异红厚壳素(6)。将化合物1及其4种新衍生物对3种癌细胞系;SNU-1、K562和LS174T进行MTT检测。结果表明,母体化合物对SNU-1和K562细胞系具有更强的细胞毒性,IC值分别为8.97±0.11和2.96±0.06μg/mL。另一方面,化合物5对LS174T细胞系表现出更好的细胞毒性,IC值为~5.76±1.07μg/mL。

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