Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184

Version 1 : Received: 3 April 2024 / Approved: 7 April 2024 / Online: 8 April 2024 (16:42:40 CEST)

A peer-reviewed article of this Preprint also exists.

Zhang, Y.; Jin, Y.; Yan, W.; Gu, P.; Zeng, Z.; Li, Z.; Zhang, G.; Wei, M.; Xue, Y. New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184. Molecules 2024, 29, 1728. Zhang, Y.; Jin, Y.; Yan, W.; Gu, P.; Zeng, Z.; Li, Z.; Zhang, G.; Wei, M.; Xue, Y. New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184. Molecules 2024, 29, 1728.

Abstract

The fungus Xylaria sp. Z184, harvested from the leaves of Fallopia convolvulus (L.) Á. Löve, has been isolated for the first time. Chemical investigation of the methanol extract of this strain’s culture broth led to the discovery of three new pyranone derivatives fallopiaxylaresters A-C (1–3) and a new bisabolane-type sesquiterpenoid named fallopiaxylarol A (4), along with the first complete set of spectroscopic data for the previously-reported pestalotiopyrone M (5). Known pyranone derivatives (6–11), sesquiterpenoids (12–14), isocoumarin derivatives (15–17), and an aromatic allenic ether (18) were co-isolated. Their structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy and quantum chemical computation method. The antimicrobial, anti-inflammatory, and α-glucosidase inhibitory activities of selected compounds and crude extract were evaluated in vitro. The extract inhibited nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells, with an inhibition rate of 77.28 ± 0.82% at a concentration of 50 μg/mL. The compounds 5, 7 and 8 displayed weak antibacterial activity against Staphylococcus areus subsp. aureus at a concentration of 100 μM.

Keywords

Xylaria sp.; pyranone derivative; sesquiterpenoid; antimicrobial activity

Subject

Chemistry and Materials Science, Organic Chemistry

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