链霉菌CPCC 200510产生的大黄酚及其类似物的鉴定

Identification of chrysophenol and its congeners from Streptomyces sp. CPCC 200510

目的链霉菌具有丰富次级代谢产物合成能力,对链霉菌CPCC 200510 产生的色素类次级代谢产物进行研究。方法对该菌株的次级代谢产物进行乙酸乙酯提取、ODS色谱柱分离、半制备 HPLC 分离纯化、NMR 结构解析和生物活性检测。结果得到 6 个黄色化合物,分别为 1,8-二羟基-3-甲基蒽醌(大黄酚,1)、2-乙酰-1,8-二羟基-3-甲基蒽醌(2)、2-乙酰-1,8-二羟基-3-羧甲基蒽醌(3)、1,2,8-三羟基-3-甲基蒽醌(4)、1-(7-乙酰-8-羟基苯并[de]色烯-2-基)-2-丙酮(5)和1-(8-羟基-2-甲基苯并[de]色烯-7-基)乙酮(6),为一组生物合成相关的芳香聚酮类化合物。其中,1 ~ 3 为链霉菌 CPCC 200510 产生的主要组分。生物活性测定表明,1 ~ 3 具有抗肿瘤细胞或抗病毒活性。结论链霉菌 CPCC 200510 有望作为大黄酚类化合物的微生物产生菌。

Objective To identify secondary metabolite(s) produced by Streptomyces sp. CPCC 200510. Methods TLC and LC-MS were used to analyze the EtOAc extract of fermentation culture of Streptomyces sp. CPCC 200510. EtOAc extraction, ODS column chromatography and preparative HPLC were employed to purify secondary metabolites from Streptomyces sp. CPCC 200510. Chemical structures of the purified metabolites were assayed by NMR. Results Six yellow compounds (1 - 6) were purified from Streptomyces sp. CPCC 200510, with 1 - 3 as main components. The structures of 1 - 6 were determined as 1,8-dihydroxy-3-methyl-9,10-anthraquinone (1, chrysophenol), 2-acetyl-1,8-dihydroxy-3- methyl-9,10-anthraquinone (2), 2-acetyl-1,8-dihydroxy-3-carboxymethyl-9,10-anthraquinone (3), 1,2,8-trihydroxy-3-methyl-9,10- anthraquinone (4), 1-(7-acetyl-8-hydroxybenzo[de]chromen-2-yl) propan-2-one (5) and 1-(8-hydroxy-2-methylbenzo[de]chromen- 7-yl)ethanone (6), respectively. 1 - 3 showed moderate cytotoxicity against cancer cell line HCT116, and 1 - 2 displayed some activity against HSV-1. 1 - 6 are a group of biosynthetically related aromatic polyketides. Conclusion Streptomyces sp. CPCC 200510 is a promising microbial producer for chrysophenol or its congeners.