Abstract
Chemical investigation of the ethyl acetate extract of an endophytic fungus, Alternaria brassicae JS959 derived from a halophyte, Vitex rotundifolia, led to the isolation of a new chromone, (2′S)-2-(2-acetoxypropyl)-7-hydroxy-5-methylchromone (1), along with sixteen known compounds: a chromone (2), twelve benzopyranones (3−14) and three perylenequinones (15−17). The chemical structures of the isolated compounds were identified by extensive spectroscopic data analysis including 1D, 2D NMR, HRESIMS, and optical rotation. Of these compounds, 1 and 2 showed inhibitory activity on Cu2+‒induced low density lipoprotein (LDL) and high density lipoprotein (HDL) oxidation in human blood plasma. The results suggest that metabolites of endophytic microbes could provide the basis for developing treatments for heart disease.
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Guo B, Wang Y, Sun X, Tang K. Bioactive natural products from endophytes: a review. Prikl Biokhim Mikrobiol. 2008;44:153–8.
Kim JW, Choi HG, Song JH, Kang KS, Shim SH. Bioactive secondary metabolites from an endophytic fungus Phoma sp. PF2 derived from Artemisia princeps Pamp. J Antibiot. 2019;72:174–7. Epub ahead of print.
Buchwaldt L, Green H. Phytotoxicity of destruxin B and its possible role in the pathogenesis of Alternaria brassicae. Plant Pathol. 1992;41:55–63.
Lee HW, Kim YJ, Nam SJ, Kim H. Potent Selective inhibition of monoamine oxidase A by alternariol monomethyl ether isolated from Alternaria brassicae. J Microbiol Biotechnol. 2017;27:316–20.
Dahiya JS, Tewari JP, Woods DL. Abscisic acid from Alternaria brassicae. Phytochemistry. 1988;27:2983–4.
Meisinger C, Baumert J, Khuseyinova N, Loewel H, Koenig W. Plasma oxidized low-density lipoprotein, a strong predictor for acute coronary heart disease events in apparently healthy, middle-aged men from the general population. Circulation. 2005;112:651–7.
Wang X, Greilberger J, Ledinski G, Kager G, Paigen B, Jürgens G. The hypolipidemic natural product Commiphora mukul and its component guggulsterone inhibit oxidative modification of LDL. Atherosclerosis. 2004;172:239–46.
Cho KH. 1,8-cineole protected human lipoproteins from modification by oxidation and glycation and exhibited serum lipid-lowering and anti-inflammatory activity in zebrafish. BMB Rep. 2012;45:565–70.
Xu J, Kjer J, Sendker J, Wray V, Guan H, Edrada R, Lin W, Wu J, Proksch P. Chromones from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata. J Nat Prod. 2009;72:662–5.
Ayer WA, Racok JS. The metabolites of Talaromyces flavus: Part 1. Metabolites of the organic extracts. Can J Chem. 1990;68:2085–94.
Wang Y, Yang MH, Wang XB, Li TX, Kong LY. Bioactive metabolites from the endophytic fungus Alternaria alternata. Fitoterapia. 2014;99:153–8.
Jiao P, Gloer JB, Campbell J, Shearer CA. Altenuene derivatives from an unidentified freshwater fungus in the family Tubeufiaceae. J Nat Prod. 2006;69:612–5.
Naganuma M, Nishida M, Kuramochi K, Sugawara F, Yoshida H, Mizushina Y. 1-deoxyrubralactone, a novel specific inhibitor of families X and Y of eukaryotic DNA polymerases from a fungal strain derived from sea algae. Bioorg Med Chem. 2008;16:2939–44.
Ye F, Chen GD, He JW, Li SX, Guo LD, Li Y, Gao H. Xinshengin, the first altenusin with tetracyclic skeleton core from Phialophora spp. Tetrahedron Lett. 2013;54:4551–4.
Stack ME, Mazzola EP. Stemphyltoxin III from Alternaria alternata. J Nat Prod. 1989;52:426–7.
Stack ME, Mazzola EP, Page SW, Pohland AE, Highet RJ, Tempesta MS, Corley DG. Mutagenic perylenequinone metabolites of Alternaria alternata: altertoxins I, II and III. J Nat Prod. 1986;49:866–71.
Liu R, Meng F, Bai H, Liu Y, Liu BW. Inhibitory effect of isorhamnetin and hesperidin on the oxidation of high-density lipoproteins (HDL) induced by Cu2+. Sichuan Da Xue Xue Bao Yi Xue Ban. 2007;38:961–4.
Wang Y, Che J, Zhao H, Tang J, Shi G. Osthole alleviates oxidized low-density lipoprotein-induced vascular endothelial injury through suppression of transforming growth factor-β1/Smad pathway. Int Immunopharmacol. 2018;65:373–81.
Yu J, Wang L, Walzem RL, Miller EG, Pike LM, Patil BS. Antioxidant activity of citrus limonoids, flavonoids, and coumarins. J Agric Food Chem. 2005;53:2009–14.
Patel RP, Svistunenko D, Wilson MT, Darley-Usmar VM. Reduction of Cu(II) by lipid hydroperoxides: implications for the copper-dependent oxidation of low-density lipoprotein. Biochem J. 1997;322:425–33.
Acknowledgements
This work was supported by the National Research Foundation of Korea (NRF) and the center for Women In Science, Engineering and Technology (WISET) grant funded by the Ministry of Science and ICT (MSIT) under the program for returners into R&D (WISET-201700780001, WISET-201700260002) and also supported by the National Research Foundation of Korea (NRF-2018R1A2B6001733) and the National Institute of Biological Resources (NIBR201921101).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher’s note: Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
41429_2019_198_MOESM1_ESM.docx
Chromones with lipoprotein oxidation inhibitory activity from an endophytic fungus Alternaria brassicae JS959 derived from Vitex rotundifolia
Rights and permissions
About this article
Cite this article
Kim, J.W., Kim, JY., Li, W. et al. Chromones with lipoprotein oxidation inhibitory activity from an endophytic fungus Alternaria brassicae JS959 derived from Vitex rotundifolia. J Antibiot 72, 709–713 (2019). https://doi.org/10.1038/s41429-019-0198-4
Received:
Revised:
Accepted:
Published:
Version of record:
Issue date:
DOI: https://doi.org/10.1038/s41429-019-0198-4
This article is cited by
-
Metabolomics-guided identification of compounds with antibacterial and antioxidant activities from Polygonatum sibiricum-derived endophytic fungi
Beni-Suef University Journal of Basic and Applied Sciences (2023)
-
Biological potential of bioactive metabolites derived from fungal endophytes associated with medicinal plants
Mycological Progress (2021)
