Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai, 201210, P. R. China.
Institute of Science, Technology and Humanities, Shanghai University of Traditional Chinese Medicine, Shanghai, 201210, P. R. China.
Chem Biodivers. 2020 Dec;17(12):e2000676. doi: 10.1002/cbdv.202000676. Epub 2020 Nov 17.
This study aimed to investigate the metabolic effects of endophytic fungi in Gentiana rigescens. From the 100 selected morphospecies, strain 7-2 (Penicillium brasilianum) showed a remarkable biocatalytic activity for gentiopicroside and swertiamarin, yielding seven products, including one new compound, 5-ethylidene-8-hydroxy-4,5,6,8-tetrahydropyrano[3,4-c]pyran-1-one (M04), alongside six known compounds. Gentianine (M01) was the only metabolite of swertiamarin in this study, while the remaining ones were all gentiopicroside metabolites. Among these, five compounds: gentianine (M01), (5S,6S)-5-(hydroxymethyl)-6-methyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (M02), (5R,6S)-5-(hydroxymethyl)-6-methyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (M03), 2-(3-formyl-2-oxo-3,6-dihydro-2H-pyran-4-yl)but-3-enoic acid (M06), and 2-oxo-4-(1-oxobut-3-en-2-yl)-3,6-dihydro-2H-pyran-3-carboxylic acid (M07) were similar to gentiopicroside metabolites in humans. Screening the metabolic potential of endophytic fungi in Gentiana rigescens provides an outstanding source for assessing the bioactive metabolites of iridoid glycosides. The above findings suggested that the endophytic fungi of G. rigescens possess multi-enzyme systems that mimic metabolic reactions in mammalian organisms.
本研究旨在探讨内生真菌对獐牙菜苦苷的代谢作用。从 100 种形态种中，菌株 7-2（棒曲霉）对龙胆苦苷和当药苦苷显示出显著的生物催化活性，生成了 7 种产物，包括一种新化合物 5-亚乙基-8-羟基-4,5,6,8-四氢吡喃并[3,4-c]吡喃-1-酮（M04），以及 6 种已知化合物。在本研究中，獐牙菜苦苷的唯一代谢产物是獐牙菜苦苷（M01），而其余的都是当药苦苷的代谢产物。其中，有 5 种化合物：獐牙菜苦苷（M01）、（5S，6S）-5-羟甲基-6-甲基-5,6-二氢-1H，3H-吡喃并[3,4-c]吡喃-1-酮（M02）、（5R，6S）-5-羟甲基-6-甲基-5,6-二氢-1H，3H-吡喃并[3,4-c]吡喃-1-酮（M03）、2-（3-甲酰基-2-氧代-3,6-二氢-2H-吡喃-4-基）丁-3-烯酸（M06）和 2-氧代-4-（1-氧代丁-3-烯-2-基）-3,6-二氢-2H-吡喃-3-羧酸（M07）与人体内的龙胆苦苷代谢物相似。筛选獐牙菜内生真菌的代谢潜力为评估裂环环烯醚萜苷类生物活性代谢物提供了一个极好的来源。上述发现表明，獐牙菜内生真菌具有多酶系统，模拟哺乳动物体内的代谢反应。
