Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2024 Apr 11;29(8):1728.
doi: 10.3390/molecules29081728.

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

Yan Zhang  1 , Yang Jin  1 , Wensi Yan  1 , Peishan Gu  1 , Ziqian Zeng  1 , Ziying Li  2 , Guangtao Zhang  2 , Mi Wei  3 , Yongbo Xue  1
Affiliations

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

Yan Zhang et al. Molecules. .

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 on the methanol extract of the culture broth of the titles strain led to the discovery of three new pyranone derivatives, called 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 also co-isolated in this study. All new structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy, and quantum chemical computation approach. The in vitro antimicrobial, anti-inflammatory, and α-glucosidase-inhibitory activities of the selected compounds and the crude extract were evaluated. The extract was shown to inhibit 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.; antimicrobial activity; pyranone derivative; sesquiterpenoid.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 1–18.
Figure 2
Figure 2
The key 1H–1H COSY and HMBC correlations of 1–4.
Figure 3
Figure 3
Experimental ECD spectrum of fallopiaxylarester A (1) (black); calculated ECD of (6R)–1 (red); mirrored spectrum of calculated ECD (blue).
Figure 4
Figure 4
1D-TOCSY spectra of compounds 2 (purple) and 3 (green).
Figure 5
Figure 5
Energy-minimized structures of 2 and 4 with the key ROESY correlations.
Figure 6
Figure 6
Photo of the fungus Xylaria sp. Z184.
See this image and copyright information in PMC

Similar articles

See all similar articles

References

    1. Newman D.J., Cragg G.M. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J. Nat. Prod. 2020;83:770–803. doi: 10.1021/acs.jnatprod.9b01285. - DOI - PubMed
    1. Liu H., Tan H., Chen Y., Guo X., Wang W., Guo H., Liu Z., Zhang W. Cytorhizins A-D, four highly structure-combined benzophenones from the endophytic fungus Cytospora rhizophorae. Org. Lett. 2019;21:1063–1067. doi: 10.1021/acs.orglett.8b04107. - DOI - PubMed
    1. Han W.B., Wang G.Y., Tang J.J., Wang W.J., Liu H., Gil R.R., Navarro-Vázquez A., Lei X.X., Gao J.M. Herpotrichones A and B, two intermolecular [4+2] adducts with anti-neuroinflammatory activity from a Herpotrichia Species. Org. Lett. 2020;22:405–409. doi: 10.1021/acs.orglett.9b04099. - DOI - PubMed
    1. Yoiprommarat S., Unagul P., Suvannakad R., Klaysuban A., Suetrong S., Bunyapaiboonsri T. Eremophilane sesquiterpenes from the mangrove fungus BCC 60405. Phytochem. Lett. 2019;34:84–90. doi: 10.1016/j.phytol.2019.09.005. - DOI
    1. Wu W., Dai H., Bao L., Ren B., Lu J., Luo Y., Guo L., Zhang L., Liu H. Isolation and structural elucidation of proline-containing cyclopentapeptides from an endolichenic Xylaria sp. J. Nat. Prod. 2011;74:1303–1308. doi: 10.1021/np100909y. - DOI - PubMed

MeSH terms

LinkOut - more resources