Isolation and structure determination of Pachybasium cerebrosides which potentiate the antifungal activity of aculeacin.

Sitrin, Robert D.; Chan, George; Dingerdissen, John J.; DeBrosse, Charles W.; Mehta, R. J.; Roberts, Gerald D.; Rottschaefer, Sue; Staiger, David B.; Valenta, Joseph R.; Snader, Kenneth M.; Stedman, R. J.; Hoover, John R. E.

doi:10.7164/antibiotics.41.469

Cited by 52 publications

(59 citation statements)

References 14 publications

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“…Methanolysis of 1 gave long chain base (LCB) and fatty methyl ester (FAME). The FAME in the n-hexane layer was identified as pentacosanoic acid methyl ester based on the GCMS molecular ion peak at m/ The trans (E) configuration of the double bond was proven by the large vicinal coupling constant value (J5,6 = 15.3 Hz) and the chemical shifts of the carbons next to the double bond at δH 32.2 (C-4) and 32.0 (C-7) [24][25][26]. The location of the olefinic moiety at C-6/C-7 was established based on the HMBC cross peaks from H-5 to C-3, C-4, and C-7 and from H-6 to C-4, C-5, and C-7.…”

Section: Structure Elucidation Of Compoundmentioning

confidence: 99%

New Cerebroside and Nucleoside Derivatives from a Red Sea Strain of the Marine Cyanobacterium Moorea producens

et al. 2016

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Abstract:In the course of our ongoing efforts to identify marine-derived bioactive compounds, the marine cyanobacterium Moorea producens was investigated. The organic extract of the Red Sea cyanobacterium afforded one new cerebroside, mooreaside A (1), two new nucleoside derivatives, 3-acetyl-2 1 -deoxyuridine (2) and 3-phenylethyl-2 1 -deoxyuridine (3), along with the previously reported compounds thymidine (4) and 2,3-dihydroxypropyl heptacosanoate (5). The structures of the compounds were determined by different spectroscopic studies (UV, IR, 1D, 2D NMR, and HRESIMS), as well as comparison with the literature data. Compounds 1-5 showed variable cytotoxic activity against three cancer cell lines.

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Section: Structure Elucidation Of Compoundmentioning

confidence: 99%

New Cerebroside and Nucleoside Derivatives from a Red Sea Strain of the Marine Cyanobacterium Moorea producens

et al. 2016

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“…174.27 [25,27], which indicated that the glucose was present as its D-isomer. [34]. It is thus clear that 1 possesses a branched sphingoid moiety with (4E,8E) geometry, 2-amino-1,3-dihydroxy-9-methyl-4,8-octadecanediene.…”

Section: Resultsmentioning

confidence: 97%

“…Further methanolysis gave a methyl 2-hydroxystearate identified by GC/MS. From the above evidence and comparison of the data with those in the literature [26,34], the structure of compound 2 was therefore characterized as shown in Fig. 1.…”

Section: Resultsmentioning

confidence: 99%

“…A number of reports have described physiological activities for fungal cerebrosides [13,26,34,[38][39][40][41][42][43][44][45]. These two cerebrosides have been reported to inhibit the activities of replicative animal or mushroom DNA polymerase a [38], cerebroside 2 was determined as an antinociceptive component by the acetic acid-induced writhing methods [13], and 1 inhibited phospholipase A 2 (Crotalus adamenteus) [26].…”

Section: Resultsmentioning

confidence: 99%

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Sphingolipids from the edible fungus Tuber indicum

Gao

Zhu

Zhang

et al. 2004

Euro J Lipid Sci & Tech

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Two sphingolipids, 1‐O‐β‐D‐glucopyranosyl‐(2S,3R,4E,8E)‐2‐[(2R)‐2‐hydroxyhexade‐canoylamino]‐9‐methyl‐4,8‐octadecadiene‐1,3‐diol (1) and 1‐O‐β‐D‐glucopyranosyl‐(2S,3R,4E,8E)‐2‐[(2R)‐2‐hydroxyoctadecanoylamino]‐9‐methyl‐4,8‐octadecadiene‐1,3‐diol (2), have been isolated from the fruiting bodies of the ascomycete fungus Tuber indicum Cooke et Massee. Their structures were established on the basis of spectroscopic and chemical methods. Sphingolipids are reported from the truffle for the first time.

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“…Consequently, the two elicitors were identified as cerebrosides A and C (Fig. 2), sphingolipids that were previously isolated from Penicillium funiculosum (14) and Pachybasium species (34).…”

Section: Purification and Structural Determination Of Elicitors From mentioning

confidence: 99%

Cerebrosides A and C, Sphingolipid Elicitors of Hypersensitive Cell Death and Phytoalexin Accumulation in Rice Plants

Koga¹,

Yamauchi²,

Shimura³

et al. 1998

Journal of Biological Chemistry

149

128

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When plants interact with certain pathogens, they protect themselves by generating various chemical and physical barriers called the hypersensitive response. These barriers are induced by molecules called elicitors that are produced by pathogens. In the present study, the most active elicitors of the hypersensitive response in rice were isolated from the rice pathogenic fungus Magnaporthe grisea, and their structures were identified as cerebrosides A and C, sphingolipids that were previously isolated as inducers of cell differentiation in the fungus Schizophyllum commune. Treatment of rice leaves with cerebroside A induced the accumulation of antimicrobial compounds (phytoalexins), cell death, and increased resistance to subsequent infection by compatible pathogens. The degradation products of cerebroside A (fatty acid methyl ester, sphingoid base, and glucosyl sphingoid base) showed no elicitor activity. Hydrogenation of the 8E-double bond in the sphingoid base moiety or the 3E-double bond in the fatty acid moiety of cerebroside A did not alter the elicitor activity, whereas hydrogenation of the 4E-double bond in the sphingoid base moiety led to a 12-fold decrease in elicitor activity. Furthermore, glucocerebrosides from Gaucher's spleen consisting of (E)-4-sphingenine and cerebrosides from rice bran mainly consisting of (4E,8E)-4,8-sphingadienine and (4E,8Z)-4,8-sphingadienine showed no elicitor activity. These results indicate that the methyl group at C-9 and the 4E-double bond in the sphingoid base moiety of cerebrosides A and C are the key elements determining the elicitor activity of these compounds. This study is the first to show that sphingolipids have elicitor activity in plants.

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Isolation and structure determination of Pachybasium cerebrosides which potentiate the antifungal activity of aculeacin.

Cited by 52 publications

References 14 publications

New Cerebroside and Nucleoside Derivatives from a Red Sea Strain of the Marine Cyanobacterium Moorea producens

New Cerebroside and Nucleoside Derivatives from a Red Sea Strain of the Marine Cyanobacterium Moorea producens

Sphingolipids from the edible fungus Tuber indicum

Cerebrosides A and C, Sphingolipid Elicitors of Hypersensitive Cell Death and Phytoalexin Accumulation in Rice Plants

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