Sesquiterpenoids and mycotoxin swainsonine from the locoweed endophytic fungus Alternaria oxytropis

Oxytropiols A-J, ten undescribed guaiane-type sesquiterpenoids, and the mycotoxin swainsonine (SW) were isolated from the locoweed endophytic fungus Alternaria oxytropis. The chemical structures of these sesquiterpenoids were elucidated on the basis of HR-ESI-MS and NMR data including 1H, 13C, HSQC,...

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Published in:Phytochemistry (Oxford) 2019-08, Vol.164, p.154-161
Main Authors: Tan, Xiangmei, Zhang, Xiaoyan, Yu, Meng, Yu, Yongtao, Guo, Zhe, Gong, Ting, Niu, Shubin, Qin, Jianchun, Zou, Zhongmei, Ding, Gang
Format: Article
Language:English
Subjects:
Alternaria oxytropis
Bioactivities
Desert plant
Endophytic fungus
Oxytropiols
Oxytropis glabra (Leguminosae)
Swainsonine
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Summary:Oxytropiols A-J, ten undescribed guaiane-type sesquiterpenoids, and the mycotoxin swainsonine (SW) were isolated from the locoweed endophytic fungus Alternaria oxytropis. The chemical structures of these sesquiterpenoids were elucidated on the basis of HR-ESI-MS and NMR data including 1H, 13C, HSQC, 1H-1H COSY, HMBC, and NOESY spectra, and the absolute configurations of these compounds were determined using a modified Mosher's method and X-ray diffraction spectroscopy. A possible biosynthetic pathway of these guaiane-type sesquiterpenoids is discussed, and proposed that post-modification oxidative enzymes might form these highly polyhydroxylated structures. Compound 1 displayed biological effects on the root growth of Arabidopsis thaliana, and SW displayed cytotoxicity against A549 and HeLa cancer cell lines. [Display omitted] •Only a toxic alkaloid swainsonine was isolated from the endophytic fungus Alternaria oxytropis.•Ten new sesquiterpenoids oxytropiols A-J were isolated from the desert plant endophytic fungus A. oxytropis.•Structural elucidation, biological evaluation and possible biosynthesis of these undescribed compounds were presented.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2019.05.012