Microbial Biotransformation of Iridoid Glycosides from Gentiana rigescens Franch by Penicillium brasilianum,Chemistry & Biodiversity

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Microbial Biotransformation of Iridoid Glycosides from Gentiana rigescens Franch by Penicillium brasilianum
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2020-11-17 , DOI: 10.1002/cbdv.202000676
Li-Li Xu _{1,

2} , Chang Liu _{1,

3} , Zhu-Zhen Han ₁ , Han Han _{1,

4} , Li Yang ₁ , Zheng-Tao Wang ₁

Affiliation

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.

中文翻译：

巴西青霉对龙胆花环烯醚萜苷的微生物转化

本研究旨在研究内生真菌在龙胆中的代谢作用。从 100 个选定的形态种中，菌株 7-2（Penicillium brasilianum）对龙胆苦苷和芥子素显示出显着的生物催化活性，产生了七种产品，包括一种新化合物，5-亚乙基-8-羟基-4,5,6,8-四氢吡喃[3,4-c]pyran-1-one (M04)，以及六种已知化合物。龙胆碱 (M01) 是本研究中唯一的 swertiamarin 代谢物，其余均为龙胆苦苷代谢物。其中，五种化合物：龙胆素（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-one (M02), (5R,6S)-5-(羟甲基)-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), 和 2-oxo-4-(1-oxobut-3-en-2-yl)-3,6-dihydro-2H-pyran-3-羧酸 (M07) 与人体中的龙胆苦苷代谢物相似。筛选龙胆内生真菌的代谢潜力为评估环烯醚萜苷的生物活性代谢物提供了一个很好的来源。上述发现表明 G. rigescens 的内生真菌具有多酶系统，可模拟哺乳动物生物体的代谢反应。

更新日期：2020-11-17

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