The Cerebrosides

Asperamides A (1) and B (2), a sphingolipid and their corresponding glycosphingolipid possessing a hitherto unreported 9-methyl-C20-sphingosine moiety, were characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from marine brown alga Colpomenia sinuosa. The structures were elucidated by spectroscopic and chemical methods as (2S,2'R,3R,3'E,4E,8E)-N-(2'-hydroxy-3'-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (1) and 1-O-beta-D-glucopyranosyl-(2S,2'R,3R,3'E,4E,8E)-N-(2'-hydroxy-3'-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (2). In the antifungal assay, asperamide A (1) displayed moderate activity against Candida albicans.

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Sphingolipids with a Previously Unreported 9‐Methyl‐C₂₀‐sphingosine Moiety from a Marine Algous Endophytic Fungus Aspergillus niger EN‐13

Zhang

Wang

et al. 2007

“…Moreover, the cerebrosides play significant or even essential biological roles in cellular membranes as cell surface antigens and receptors. In particular, an increasing amount of evidence has indicated that cerebrosides perform a wide range of biological functions, all being potentially related to the common amphipathic and/or ionophoretic nature of this type of molecule (1).…”

mentioning

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

Self Cite

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.

“…Some cerebrosides have been proven to serve as structural support and texture determinants of cell membranes, and act as mediators of biological events such as activation, cell agglutination, intracellular communication and cell development. The biological activities of cerebrosides are very wide, for example, immunomodulatory, antitumor/cytotoxic, COX-2 and histidine decarboxylase inhibitory, anti-HIV-1, and so on [10].…”

Section: Introductionmentioning

confidence: 99%

An Isomeric Mixture of Novel Cerebrosides Isolated from Impatiens pritzellii Reduces Lipopolysaccharide‐Induced Release of IL‐18 from Human Peripheral Blood Mononuclear Cells

Zhou

Tang

Liu

2009

An isomeric mixture of two cerebrosides, soya-cerebrosides I and II, was isolated from an ethno drug, the rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f., and their structures were identified by spectroscopic (NMR, MS) analysis. In order to determine the immunomodulatory activities of soya-cerebrosides I and II, the effects of the mixture of cerebrosides (MC) on cytotoxicity of human peripheral blood mononuclear cells (PBMC) and the inhibitory activities to lipopolysaccharide (LPS)-induced interleukin (IL)-18 in PBMC were studied. The MC at concentrations of 10 and 1 microM, without toxicity to PBMC in 24 h, showed obvious inhibitory activity on IL-18 secretion. Because of this effect of modulating the cellular immune response, soya-cerebrosides I and II were considered to be the active substances of this ethno drug.