Abstract

The biotransformation of glabranin (1) with Aspergillus niger and Cunninghamella blakesleeana favoured the formation of benzofuran derivatives (3 and 4), while in contrast, its acid-catalysed chemical transformation favoured the formation of benzopyran derivatives (6 and 7). Compound 6 was further biooxidised at C-4′. Biotransformation of 7-O-methylglabranin (2) proceeded via oxidation of the prenyl group and C-4' by the same fungi, and the obtention of 11 mimics the biosynthesis of this last compound. Some compounds displayed moderate antiproliferative activity against selected human cancer cell lines, with glabranin being the most active, suggesting that the prenyl group and the phenol at C-7 are important structural determinants for cytotoxicity.

摘要

光甘草素 ( 1 ) 与黑曲霉和Cunninghamella blakesleeana的生物转化有利于苯并呋喃衍生物 ( 3和4)的形成，而相反，其酸催化的化学转化有利于苯并吡喃衍生物 ( 6和7 ) 的形成。化合物6在C-4'处被进一步生物氧化。7- O-甲基光甘草素 ( 2 )的生物转化是通过异戊二烯基和 C-4' 被相同的真菌氧化，得到11模拟最后一种化合物的生物合成。一些化合物对选定的人类癌细胞系表现出中等的抗增殖活性，其中光甘草宁是最活跃的，这表明异戊二烯基和 C-7 上的苯酚是细胞毒性的重要结构决定因素。