2013
DOI: 10.1002/hlca.201200235
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Novel Cerebrosides Isolated from the Fermentation Mycelia of Tuber indicum

Abstract: The four new cerebrosides 1–4 possessing a unique C18 9‐methylsphinga‐4,8‐dienine‐related moiety and a cyclic octapeptide, 5, possessing alternating proline and glycine moietes were isolated from the Tuber indicum fermentation mycelium. Their structures were established on the basis of a spectroscopic analysis including NMR and HR‐ESI‐MS, as well as an acidic methanolysis experiment. To the best of our knowledge, the cerebrosides identified in the present study are quite different from those isolated from Tube… Show more

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Cited by 4 publications
(3 citation statements)
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“…Reduction of the aldehyde in A-3 into the primary alcohol give A-4, and formation of 1, 2 by nucleophilic attack of the primary alcohol on either site of the carbons in one of the two epoxide groups and hydration in the rest epoxide group, and the similar biosynthetic conversion was also reported in aspilactonol B, C [5]. Other known compounds were isolated and determined as chrysogeside D (3) [7], aspinonene (4) [6], aspinotriols A (5) and B (6) [6], 22E,24R-ergosta-7,22-diene-3,5,6-triol (7) [8], mellein (8) [9], 4-hydroxymellein ( 9) [10].…”
Section: Resultsmentioning
confidence: 58%
See 1 more Smart Citation
“…Reduction of the aldehyde in A-3 into the primary alcohol give A-4, and formation of 1, 2 by nucleophilic attack of the primary alcohol on either site of the carbons in one of the two epoxide groups and hydration in the rest epoxide group, and the similar biosynthetic conversion was also reported in aspilactonol B, C [5]. Other known compounds were isolated and determined as chrysogeside D (3) [7], aspinonene (4) [6], aspinotriols A (5) and B (6) [6], 22E,24R-ergosta-7,22-diene-3,5,6-triol (7) [8], mellein (8) [9], 4-hydroxymellein ( 9) [10].…”
Section: Resultsmentioning
confidence: 58%
“…The mixture of compound 1 and 2, and other isolated compounds (3)(4)(5)(6)(7)(8)(9) were evaluated for antimicrobial activity against the pathogenic bacteria and fungi, Escherichia coli, Bacillus subtilis, Candida albicans, Fusarium oxysporum, Fusarium solani. Compound 8 indicated the broad spectrum antibiotic activity against all five pathogens with MICs at 128-256 µg/mL.…”
Section: Resultsmentioning
confidence: 99%
“…By the same manner, the geometry of the double bond at C-3 was presumed to be E due to the large vicinal coupling constant of the olefinic protons (J H3 -4 = 15.3 Hz) [36]. The geometry of the double bond at C-8 was presumed to be E due to the 13 C-NMR signal of the methyl group attached to C-8 at δ C 16.1, while that of a (Z)-C=C bond appeared at δ C 22.7 [38]. The 2-amino-1,3-dioxigenated-4-ene moiety was confirmed by COSY correlations for H-1 through H-8 ( Figure 1, Figure S5).…”
Section: Structural Elucidation Of Compounds 1-4mentioning
confidence: 99%