Fungal endophytes live widely inside plant tissues and some have been revealed to provide benefits to their host and ecological environment. Considering the fact that endophytes are engaged in remarkably stable long-term interactions with the host for their whole life cycle, it’s conceivable that both partners have substantial influence on each other’s metabolic processes. Here, we investigated the fermented products of an endophytic fungus Umbelopsis dimorpha SWUKD3.1410 grown on host–plant Kadsura angustifolia and wheat bran, respectively, to assess the impact of SWUKD3.1410 on the secondary metabolites of K. angustifolia. Twenty compounds (1–20) were isolated and identified as 11 schitriterpenoids (1–9, 17–18), two lignans (10, 20), two sesquiterpenoids (11–12), one trinorsesquiterpenoid (13), one monoterpene (14), one sterol (19), and two simple aromatic compounds (15–16) by the extensive 1D-, 2D-NMR and HR-ESI-MS data analysis. Except for nigranoic acid (1), compounds 2–19 have been firstly found from K. angustifolia. Of them, metabolites 2, 11, and 14 were identified to be new. Obtained results indicated that U. dimorpha SWUKD3.1410 could not only produce the same/similar components as its host does, and modify the host–plant components, but also enhance the production of these highly oxygenated schitriterpenoids/schinortriterpenoids in plants. This study suggested an interesting prospective for setting up alternative processing techniques to improve the quality of crude drugs derived from K. angustifolia and increase their values.
The objective of this study was to determine whether endophytic fungi, isolated from Kadsura angustifolia produce nigranoic acid and its highly oxygenated derivatives. From the 426 endophytic fungi screened, Trichoderma harzianum SWUKD3.1610 was detected to have a component with the same TLC R value and HPLC retention time as authentic nigranoic acid. This component was further confirmed as nigranoic acid by investigating the chemical composition of the fungal extracts. Besides (1), one new triterpenoid, 7β- schinalactone C (2), and two known minor compounds were isolated and characterized by HRESIMS, 1D and 2D NMR spectroscopic methods. Our study indicates that endophytic fungus may play an important role in increasing the quality of the crude drugs from Chinese medicinal plant K. angustifolia. This study is the first to isolate, characterize, and identify schitriterpenes-producing Trichoderma spp.
The ability of the endophytic fungus Umbelopsis dimorpha SWUKD3.1410 to transform the triterpene nigranoic acid (3, 4-secocycloarta-4(28), 24-(Z)-diene-3, 26-dioic acid; 1) was investigated. Co-culture of nigranoic acid with U. dimorpha SWUKD3.1410 yielded six major products, including a new triterpene (2) and 5 known compounds (3-7). Their structures were identified by the extensive 1D, 2D NMR and HR-ESI-MS Data analysis, and by comparison with those reported data. Among them, 2-4 were transformed from nigranoic acid (1), while 5-7 were derived from the culture medium stimulated by the substrate. On the basis of the structures of 2-4, it was proposed that the transformative process probably involved isomerase and hydroxylase, in which the former was rare in fungi. Additionally, all the compounds (1-7) were evaluated for their cytotoxic activity. As a result, compounds 1, 3-5 exhibited weak cytotoxicity against the tested cell lines, while others showed no cytotoxicity.
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