Abstract
Intestinal fungi, which are important parts of the gut microbiota, have the ability to produce specialized metabolites that significantly contribute to maintaining the balance of the gut microbiota and promoting the health of the host organism. In the present study, two new glycosides, including fusintespyrone A (1) and cerevisterolside A (4), as well as ten known compounds were isolated from the intestinal fungus Fusarium sp. LE06. The structures of the new compounds were elucidated by a combination of spectroscopic methods, such as mass spectrometry (MS) and nuclear magnetic resonance (NMR), along with chemical reactions and calculations of NMR and ECD spectra. Compounds 1–3 showed significant growth inhibition against Aspergillus fumigatus, Fusarium oxysporum, and Verticillium dahliae with MIC values in the range of 1.56–6.25 μg ml−1.
References
Vos T, Flaxman AD, Naghavi M, Lozano R, Michaud C, Ezzati M, et al. Years lived with disability (YLDs) for 1160 sequelae of 289 diseases and injuries 1990-2010: a systematic analysis for the global burden of disease study 2010. Lancet. 2012;380:2163–96.
Park BJ, Wannemuehler KA, Marston BJ, Govender N, Pappas PG, Chiller TM. Estimation of the current global burden of cryptococcal meningitis amongpersons living with HIV/AIDS. AIDS. 2009;23:525–30.
Lee A. Ibrexafungerp: first approval. Drugs. 2021;81:1445–50.
Underhill DM, Iliev ID. The mycobiota: interactions between commensal fungi and the host immune system. Nat Rev Immunol. 2014;14:405–16.
Chen Y, Jiang N, Wei YJ, Li X, Ge HM, Jiao RH, et al. Citrofulvicin, an antiosteoporotic polyketide from Penicillium velutinum. Org Lett. 2018;20:3741–44.
Huo XK, Li DW, Wu F, Li SH, Qiao YL, Wang C, et al. Cultivated human intestinal fungus Candida metapsilosis M2006B attenuates colitis by secreting acyclic sesquiterpenoids as FXR agonists. Gut. 2022;71:2205–17.
Mcalester G, O’Gara F, Morrissey JP. Signal-mediated interactions between Pseudomonas aeruginosa and Candida albicans. J Med Microbiol. 2008;57:563–69.
Evidente A, Conti L, Altomare C, Bottalico A, Sindona G, Segre AL, et al. Fusapyrone and deoxyfusapyrone, two antifungal a-pyrones from Fusarium semitectum. Nat Toxins. 1994;2:4–13.
Ayer WA, Ma YT. Sirosterol and dehydroazasirolsterol, unusual steroidal adducts from a Sirococcus species,. Can J Chem. 1992;70:1905–13.
Guo JP, Zhu CY, Zhang CP, Chu YS, Wang YL, Zhang JX, et al. Thermolides, potent nematocidal PKS-NRPS hybrid metabolites from thermophilic fungus Talaromyces thermophilus. J Am Chem Soc. 2012;134:20306–9.
Negera A, Matthias H, Jacob OM, Ndakala A, Majer Z, Neumann B, et al. A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochem Lett. 2014;9:67–73.
Zhou M, Lou J, Li YK, Wang YD, Zhou K, Ji BK, et al. Butyrolactones from the endophytic fungus Aspergillus versicolor and their anti-tobacco mosaic virus activity. J Braz Chem Soc. 2015;26:545–49.
Smith SG, Goodman JM. Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 prob-ability. J Am Chem Soc. 2010;132:12946–59.
Gao JM, Hu L, Liu JK. A novel sterol from Chinese truffles Tuber indicum. Steroids. 2001;66:771–5.
Emanuele A, Giorgio C, Felicia D’A. A new stereocontrolled access to β-D-mannopyranosides and 2-acetamido-2-deoxy-β-D-mannopyranosides starting from β-D-galactopyranosides. Tetrahedron Lett. 2002;43:8815–18.
Kasai R, Okihara M, Asakawa J, Mizutani K, Tanaka O. 13C nmr study of α- and β-anomeric pairs of D-mannopyranosides and L-rhamnopyranosides. Tetrahedron. 1979;35:1427–32.
Ishizuka T, Yaoita Y, Kikuchi M. Sterols from the fruit bodies of Grifola frondosa. Chem Pharm Bull. 1997;45:1756–60.
Iorizzi M, Minale L, Riccio R, Lee JS, Yasumoto T. Polar steroids from the marine Scallop Patinopecten yessoensis. J Nat Prod. 1988;51:1098–103.
Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull. 2007;55:899–901.
Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, et al. Fungal glycosides: structure and biological function. Trends Food Sci Tech. 2021;110:611–51.
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Financial support of the National Key Research and Development Program of China (grant No. 2022YFA1304200) and the National Natural Science Foundation of China (grant Nos. 22177131 and 82073723) are gratefully acknowledged.
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Zhang, M., Chen, B., Dai, H. et al. Discovery of antifungal secondary metabolites from an intestinal fungus Fusarium sp.. J Antibiot 77, 193–198 (2024). https://doi.org/10.1038/s41429-023-00692-1
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DOI: https://doi.org/10.1038/s41429-023-00692-1
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