Unusual fatty acid composition of cerebrosides from the filamentous soil fungus Mortierella alpina

Batrakov, S. G.; Konova, I. V.; Шейченко, В. И.; Esipov, S. E.; Galanina, L. A.; Istratova, Larisa N.

doi:10.1016/s0009-3084(02)00028-2

Cited by 27 publications

(13 citation statements)

References 22 publications

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“…Precoated C 18 reversed-phase TLC plates were purchased from Merck (Darmstadt, Germany), and normal-phase TLC was carried out on silica gel 60-precoated plates (Macherey-Nagel, Düren, Germany). Substances on all developed TLC plates were visualized under UV light, followed by heating after being stained with either 10% methanolic H 2 SO 4 or 10% ethanolic phosphomolybdic acid as detailed earlier (7). XO from cow's milk, xanthine, and the standard inhibitor allopurinol were purchased from Sigma Chemical Co. (St. Louis, MO).…”

Section: Methodsmentioning

confidence: 99%

Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB‐121, and endophytic fungus in Quercus variabilis

Shu

Wang

Yang

et al. 2004

Lipids

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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, 1H and 13C 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 (2S,2'R,3R,3'E,4E,8E,10E)-1-O-beta-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 (2S,2'R,3R,3'E,4E,8E)-1-O-beta-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 microg/mL, and 7.8, 3.9, and 7.8 microg/mL, respectively. Furthermore, both metabolites were inhibitory to xanthine oxidase, with the IC50 value of fusaruside being 43.8 +/- 3.6 microM and the known cerebroside being 55.5 +/- 1.8 microM.

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Section: Methodsmentioning

confidence: 99%

Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB‐121, and endophytic fungus in Quercus variabilis

Shu

Wang

Yang

et al. 2004

Lipids

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“…In our continuous research into chemical constituents of T. indicum, much attention was paid to the fact that sphingolipids, including cerebrosides and ceramides, displayed structural features uncommon for the fungal sphingosine derivatives. Since sphingolipids represent not only structural components of the cell membrane, but burden also other vitally important functions in the fungal cell (Gao et al, 2003c;Batrakov et al, 2002). Recently, some have also been reported to show antinociceptive (Koyama et al, 2002), neurotrophic (Kwon et al, 2003), antitumor and immunostimulatory (Natori et al, 1994), anti-phospholipase A 2 (Gao et al, 2003d), cholesteryl ester transfer protein inhibitory (Venkateswarlu et al, 1998) activity.…”

Section: Introductionmentioning

confidence: 99%

Molecular species of ceramides from the ascomycete truffle Tuber indicum

Gao

Zhang

Chen

et al. 2004

Chemistry and Physics of Lipids

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“…Seven sterols (1-4, 6-8) and a cerebroside (5) (Batrakov et al, 2002) were isolated from the n-hexane and ethylacetate extracts of the fruits of C. cibarius using a combination of silica gel column chromatography and preparative TLC. Compounds 1-4, 6-8 were identified as ergosterol (Zhang et al, 2002), cerevisterol, tuberoside (Jinming et al, 2001), β-sitosterol glucoside (Faizi et al, 2001), ergosterol peroxide (Yue et al, 2001), β-sitosterol (Chaurasia and Wichtl, 1987) and 7-dehydrostigmasterol (Yates et al, 1992), respectively.…”

Section: Resultsmentioning

confidence: 99%

NF‐κB inhibitory activity of compounds isolated from Cantharellus cibarius

Kim

Tay

Blanco

2008

Phytotherapy Research

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The inhibitory activities of the extracts of Cantharellus cibarius and isolated compounds were investigated in an enzyme-based ELISA NF-kappaB assay. Of the tested compounds, ergosterol, ergosterol peroxide and cerevisterol were noted to have the most potent inhibition of NF-kappaB activation. The ability of the active metabolites to inhibit the NF-kappaB translocation from the cytoplasm to the nucleus was assessed using a cell-based NF-kappaB assay. The isolated compounds were elucidated through the analysis of various spectroscopic methods.

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Unusual fatty acid composition of cerebrosides from the filamentous soil fungus Mortierella alpina

Cited by 27 publications

References 22 publications

Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB‐121, and endophytic fungus in Quercus variabilis

Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB‐121, and endophytic fungus in Quercus variabilis

Molecular species of ceramides from the ascomycete truffle Tuber indicum

NF‐κB inhibitory activity of compounds isolated from Cantharellus cibarius

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