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来自图尔巴辛链丝菌的羟基链烯基间苯二酚。

Hydroxyalkenylresorcinols from Stylogyne turbacensis.

作者信息

Jiménez-Romero Carlos, Torres-Mendoza Daniel, Ureña González Luis David, Ortega-Barría Eduardo, McPhail Kerry L, Gerwick William H, Cubilla-Rios Luis

机构信息

Laboratory of Tropical Bioorganic Chemistry, Faculty of Natural, Exact Sciences and Technology, Apartado 0824-10835, University of Panama, Panama City, Republic of Panama.

出版信息

J Nat Prod. 2007 Aug;70(8):1249-52. doi: 10.1021/np070081d. Epub 2007 Jul 13.

DOI:10.1021/np070081d
PMID:17629327
Abstract

Two new compounds, 5-(11'(S)-hydroxy-8'-heptadecenyl)resorcinol (3) and 5-(12'(S)-hydroxy-8',14'-heptadecadienyl)resorcinol (4), were isolated from the leaves of Stylogyne turbacensis together with the known analogue metabolites 1 and 2. Compounds 3 and 4 showed the strongest activity in the leishmania assay, 7 and 3 microM, respectively, while compounds 1, 2, and 4 showed moderate activity against a drug-resistant strain of Trypanosoma cruzi with IC(50) values of 30, 25, and 22 microM, respectively. Additional testing in MCF-7 and NCI-H460 was performed for compounds 3 and 4. The structures of compounds 1-4 were elucidated using NMR, MS, and other spectroscopic data. The absolute stereochemistry of compounds 3 and 4 was also investigated using the Mosher ester approach. Peracetylated derivatives of these four metabolites were produced and their activities determined in the Trypanosoma cruzi assay.

摘要

从苏氏旋柱苣苔(Stylogyne turbacensis)叶片中分离出两种新化合物,5-(11'(S)-羟基-8'-十七碳烯基)间苯二酚(3)和5-(12'(S)-羟基-8',14'-十七碳二烯基)间苯二酚(4),以及已知的类似代谢产物1和2。化合物3和4在利什曼原虫试验中表现出最强活性,分别为7和3 microM,而化合物1、2和4对克氏锥虫耐药菌株表现出中等活性,IC(50)值分别为30、25和22 microM。对化合物3和4在MCF-7和NCI-H460中进行了额外测试。使用NMR、MS和其他光谱数据阐明了化合物1-4的结构。还使用莫舍尔酯法研究了化合物3和4的绝对立体化学。制备了这四种代谢产物的全乙酰化衍生物,并在克氏锥虫试验中测定了它们的活性。

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