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Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB‐121, and endophytic fungus in Quercus variabilis
Author(s) -
Shu R. G.,
Wang F. W.,
Yang Y. M.,
Liu Y. X.,
Tan R. X.
Publication year - 2004
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-004-1280-9
Subject(s) - chemistry , stereochemistry , cerebroside , antibacterial activity , heteronuclear molecule , fusarium solani , xanthine oxidase , two dimensional nuclear magnetic resonance spectroscopy , nuclear chemistry , nuclear magnetic resonance spectroscopy , biochemistry , microbiology and biotechnology , biology , enzyme , bacteria , genetics
Two antibacterial and xanthine oxidase inhibitory cerebrosides, one of which is chemically new, were characterized from the chloroform‐methanol (1∶1) extract of Fusarium sp. IFB‐121, an endophytic fungus in Quercus variabilis . By means of chemical and spectral methods [IR, electrospray ionization MS (ESI‐MS), tandem ESI‐MS, 1 H and 13 C NMR, distortionless enhancement by polarization transfer, COSY, heteronuclear multiple‐quantum coherence, heteronuclear multiple‐bond correlation, and 2‐D nuclear Overhauser effect correlation spectroscopy], the structure of the new metabolite named fusaruside was established as (2 S ,2′ R ,3 R ,3′ E ,4 E ,8 E ,10 E )‐1‐ O ‐β‐ d ‐glucopyranosyl‐2‐ N ‐(2′‐hydroxy‐3′‐octadecenoyl)‐3‐hydroxy‐9‐methyl‐4,8,10‐sphingatrienine, and the structure of the other was identified as (2 S ,2′ R ,3 R ,3′ E ,4 E ,8 E )‐1‐ O ‐β‐ d ‐glucopyranosyl‐2‐ N ‐(2′‐hydroxy‐3′‐octadecenoyl)‐3‐hydroxy‐9‐methyl‐4,8‐sphingadienine. Both new and known cerebrosides, although inactive to Trichophyton rubrum and Candida albicans , showed strong antibacterial activities against Bacillus subtilis, Escherichia coli , and Pseudomonas fluorescens , with their minimum inhibitory concentrations being 3.9, 3.9, and 1.9 μg/mL, and 7.8, 3.9, and 7.8 μg/mL, respectively. Furthermore, both metabolites were inhibitory to xanthine oxidase, with the IC 50 value of fusaruside being 43.8±3.6 μM and the known cerebroside being 55.5±1.8 μM.