Anti‐Neuroinflammatory Activity of New Naturally Occurring Benzylated Hydroxyacetophenone Analogs from the Endophytic Fungus Alternaria sp. J030

Abstract

Chemical studies on the culture broth of the endophytic fungus Alternaria sp. J030 led to the identification of three benzylated hydroxyacetophenone derivatives, bauvaroalterins A -C (1 -3), and 34 structurally diverse metabolites (4 -37). The new structures were elucidated by extensive spectroscopic analyses including UV, IR, 1D and 2D NMR, HR-ESI-MS, and further confirmed using single crystal X-ray diffraction. The in vitro antineuroinflammatory effects of the co-isolated metabolites were evaluated in lipopolysaccharide (LPS)-stimulated microglial cells. Compounds 1-3 were shown to significantly reduce LPS-induced NO production by inhibiting the expression of iNOS, as well as inhibiting LPS-induced production of the inflammatory factors TNF-α, IL-1β and IL-6. Further studies revealed that 1-3 were capable of down-regulating the expression of NF-кB subunits p50 and p65, thereby suppressing the activation of NF-кB by inhibiting the LPS-induced phosphorylation of IкBα. Together these findings demonstrate that bauvaroalterins AÀ C (1 -3) exert anti-neuroinflammatory effects via inhibition of the NF-кB/iNOS signalling pathway in LPS induced BV-2 cells.

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

“…Z184. The structures of these compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) were identified by comparing the spectral data to those reported in the respective references (Figures S80-S105).…”

“…Z184. Moreover, we co-isolated 14 previously reported compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18), and reported the first complete set of spectroscopic data for pyranone 5. In vitro bioassays were performed on a number of the isolated compounds and crude fungal extract.…”

“…As part of our group's ongoing effort to identify bioactive natural products from medicinal plants and endophytic fungi [9][10][11], the fungus Xylaria sp. Z184, isolated from the leaves of Fallopia convolvulus (L.) Á. Löve for the first time, has attracted our attention for Molecules 2024, 29, 1728 2 of 13 its impressive compound abundance in TLC and HPLC analyses (Figure S106).…”

“…Molecules 2024, 29, x FOR PEER REVIEW 2 of 13 leaves of Fallopia convolvulus (L.) Á. Löve for the first time, has attracted our attention for its impressive compound abundance in TLC and HPLC analyses (Figure S106). Our current investigation on this strain led to the isolation of three new pyranone derivatives, called fallopiaxylaresters A-C (1-3), a new bisabolane-type sesquiterpenoid fallopiaxylarol A (4) (Figure 1), and the first complete set of the spectroscopic data for the previously disclosed pestalotiopyrone M (5), as well as a suite of known compounds consisting of six pyranone derivatives (6)(7)(8)(9)(10)(11), three sesquiterpenoids (12)(13)(14), three isocoumarin derivatives (15)(16)(17), and one aromatic allenic ether (18). Herein, the details of the isolation, structure elucidation of all new compounds and their anti-inflammatory, antimicrobial, and α-glucosidase-inhibitory activities were described.…”

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

“…As part of our group's ongoing effort to identify bioactive natural products from medicinal plants and endophytic fungi [9][10][11], the fungus Xylaria sp. Z184, isolated from the leaves of Fallopia convolvulus (L.) Á. Löve for the first time, has attracted our attention for its impressive compound abundance in TLC and HPLC analyses (Figure).…”