4.7 Article

Polyhydroxylated sesquiterpenes and ergostane glycosides produced by the endophytic fungus Xylaria sp. from Azadirachta indica

Journal

PHYTOCHEMISTRY
Volume 199, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2022.113188

Keywords

Xylaria sp; Xylariaceae; Sesquiterpene; Eremophilane; Guaiane glycoside; Ergostane glycoside; Antiphytopathogenic activity

Funding

  1. National Natural Science Foundation of China [81860634]
  2. Applied Basic Research Key Project of Yunnan Province [202001BB050029]
  3. Project of Innovative Research Team of Yunnan Province [202005AE160005]

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The investigation of metabolites from the endophytic fungus Xylaria sp. YM 311647 led to the discovery of six undescribed compounds with strong antifungal activities. Among them, xylarioxide E exhibited excellent antifungal properties.
The investigation of the metabolites from the endophytic fungus Xylaria sp. YM 311647 in solid fermentation resulted in the isolation of six undescribed compounds, namely xylarioxides A-F, respectively. These included one eremophilane sesquiterpene, three guaiane sesquiterpene glycosides, and two ergostane glycosides. The structures of the compounds were determined by extensive analyses of spectroscopic data, including 1D and 2D NMR, as well as HRESIMS data. The stereochemistry of xylarioxide A was confirmed by X-ray crystallographic analysis. All of the isolated compounds were assayed for their antifungal activities against seven phytopathogenic fungi and two human pathogenic fungi. Among them, xylarioxides A, E and F showed potent activities against the tested phytopathogens. Particularly, xylarioxide E exhibited the highest activity against Gibberella saubinetii, Curvularia lunata, and Colletotrichum gloeosporioides with MIC values of 4, 4, and 8 mu g/mL, respectively, which were comparable to the positive control of nystatin. Interestingly, guaiane sesquiterpene glycosides have been rarely reported from fungal sources. Additionally, xylarioxide E represented an unusual naturally occurring 3,4seco-steroidal glycoside with a seven-membered lactone in ring A.

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