Highly oxygenated schitriterpenoids are interesting for study of their structures, bioactivities and synthesis. From Kadsura angustifolia fermented by an associated symbiotic endophytic fungus, Penicillium sp. SWUKD4.1850, nine undescribed triterpenoids, kadhenrischinins A-H, and 7β-schinalactone C together with four known triterpenoids, henrischinins A and B, schinalactone C and nigranoic acid were isolated and established by the extensive 1D-, 2D-NMR, HR-ESI-MS and ECD data analysis. Except nigranoic acid, all these metabolites have been first detected in non-fermented K. angustifolia. Structurally, kadhenrischinins A-D belong to the relatively rare class of highly oxygenated schitriterpenoids that contain a unique 3-one-2-oxabicyclo [3,2,1]-octane motif, while kadhenrischinins E-H feature a cyclopentane ring in a side chain rarely found in the family Schisandraceae. These results indicated that fermentation of K. angustifolia with SWUKD4.1850 induced the production of highly oxygenated schitriterpenoids from nigranoic acid, which provided a guidance to obtain desired compounds from those plants initially thought not to produce. This is the first report on the fermentation of K. angustifolia medical plant and the first discovery of highly oxygenated schitriterpenoids by microbial technology.

中文翻译：

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由共生内生真菌 Penicillium sp. 发酵的 Kadsura angustifolia 提高了不寻常的三萜类化合物的产量。SWUKD4.1850

高度氧化的半萜类化合物对于研究它们的结构、生物活性和合成很有趣。来自由相关共生内生真菌 Penicillium sp. 发酵的 Kadsura angustifolia。SWUKD4.1850，九种未描述的三萜类化合物，kadhenrischinins AH 和 7β-schinalactone C 以及四种已知的三萜类物质，henrischinins A 和 B、schinalactone C 和 nigranoic acid 通过广泛的 1D-、2D-NMR、HR-ESI-分离和建立MS 和 ECD 数据分析。除黑质酸外，所有这些代谢物均首次在非发酵 K. angustifolia 中检测到。从结构上讲，kadhenrischinins AD 属于相对稀有的一类高度氧化的半三萜，它含有独特的 3-one-2-oxabicyclo [3,2,1]-辛烷基序，而 kadhenrischinins EH 在侧链中具有环戊烷环，很少在五味子科中发现。这些结果表明，用 SWUKD4.1850 发酵 K. angustifolia 诱导了从黑酸中产生高度氧化的半萜类化合物，这为从最初认为不会产生的那些植物中获得所需化合物提供了指导。这是第一篇关于狭叶金缕梅药用植物发酵的报道，也是首次通过微生物技术发现高含氧半萜类化合物。