New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp.
New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp.
复制标题
DOI：
10.1021/np020128p
复制
发表时间：
2002-11-01
影响因子：
5.1
通讯作者：
Wright, AD
中科院分区：
文献类型：
--
作者：
Abdel-Lateff, A;König, GM;Wright, AD
一种被鉴定为顶孢霉属的海洋真菌分离株经过大规模培养，发现可产生两种新型氢醌衍生物：7-异丙烯基双环[4.2.0]八-1,3,5-三烯-2,5-二醇 (1) 和 7-异丙烯基双环[4.2.0]八-1,3,5-三烯-2,5-二醇-5-β-D-吡喃葡萄糖苷（2）。化合物 I 及其葡萄糖苷 2 具有最不寻常的环系统。新天然产物(3S*,4S*)-3,4-二羟基-7-甲基-3,4-二氢-1(2H)-萘酮(3)和(3S*,4S*)-3,4-二羟基-7-甲基-3,4-二氢-1(2H)-萘酮(4)以1:0.8的混合物形式获得。 2-(1-甲基亚乙基)戊二酸(5)首次作为天然产物分离出来，并通过X射线分析证实了其结构。除了这些化合物之外，还获得了三种新异构体化合物的不可分离的混合物：戊二酸2-(1-甲基亚乙基)-5-甲酯(6)、戊二酸2-(1-甲基亚乙基)-1-甲酯(7)和戊二酸2-(1-甲基乙烯基)-5-甲酯(8)。与新化合物一起分离出的是三种已知的氢醌衍生物 9、10 和 11。所有化合物的结构均通过解释其光谱数据（1D 和 2D NMR、MS、UV 和 IR）来确定。测试了每种分离物的抗氧化特性，发现化合物 1 和 9-11 具有显着的活性。
A marine fungal isolate, identified as Acremonium sp., was mass cultivated and found to produce two novel hydroquinone derivatives, 7-isopropenylbicyclo [4.2.0]octa-1,3,5-triene-2,5-diol (1) and 7-isopropenylbicyclo[4.2.0]octa-1,3,5-triene-2,5-diol-5-beta-D-glucopyranoside (2). Compound I and its glucoside 2 possess a most unusual ring system. The new natural products (3S*,4S*)-3,4-dihydroxy-7-methyl-3,4-dihydro-1(2H)-naphthalenone (3) and (3S*,4S*)-3,4-dihydroxy-7-methyl-3,4-dihydro-1(2H)-naphthalenone (4) were obtained as a 1:0.8 mixture. 2-(1-Methylethylidene)pentanedioic acid (5) was isolated for the first time as a natural product and its structure proven by X-ray analysis. In addition to these compounds an inseparable mixture of three new isomeric compounds, pentanedioic acid 2-(1-methylethylidene)-5-methyl ester (6), pentanedioic acid 2-(1-methylethylidene)-1-methyl ester (7), and pentanedioic acid 2-(1-methylethenyl)-5-methyl ester (8), was also obtained. Isolated together with the new compounds were three known hydroquinone derivatives, 9, 10, and 11. The structures of all compounds were determined by interpretation of their spectroscopic data (1D and 2D NMR, MS, UV, and IR). Each isolate was tested for its antioxidant properties, and compounds 1 and 9-11 were found to have significant activity.