Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl.

Chen, Xuesong; Wu, Yonggang; Chen, Di-Hua

doi:10.1016/s0040-4039(02)00583-x

Cited by 38 publications

(31 citation statements)

References 20 publications

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“…732.5620)) and 13 C-NMR data analysis. The C-atom chemical shifts at d(C) 54.5 (C(2)), 71.2 (C(3)), and 72.4 (C(2')) indicated the (2S), (3S), and (2'R) configurations, respectively, in agreement with those reported cerebrosides [20]. The NMR spectra of 1 (Table) (2)) and the C-atom signals at d(C) 70.4 (C(1)), 51.4(C(2)), 75.8 (C(3)), and 72.4 (C(4)) in the NMR spectra of 1 were in good agreement with those of a reported cerebroside with a 1,3,4trihydroxy long-chain base [17].…”

supporting

confidence: 87%

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Zhao

Chen

et al. 2012

Helvetica Chimica Acta

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Two new cerebrosides, (2R)‐N‐{(1S,2S,3R,8E)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2,3‐dihydroxyheptadec‐8‐en‐1‐yl}‐2‐hydroxyhexadecanamide (1) and (2R)‐N‐{(1S,2R,8E)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2‐hydroxyheptadec‐8‐en‐1‐yl}‐2‐hydroxyhexadecanamide (2), were isolated from the aerial parts of Tithonia diversifolia (Hemsl.) A. Gray. Their structures were determined on the basis of spectroscopic analysis (IR, HR‐ESI‐MS, and 1D‐, and 2D‐NMR).

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supporting

confidence: 87%

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Zhao

Chen

et al. 2012

Helvetica Chimica Acta

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“…The negatively and positively charged ESIMS of 1 showed significant [24,25]. On the other hand, the presence of 2-amino and 1, 2 0 , 3, 5, 6 pentahydroxyl groups as well as C-8 and C-9 double bond in the main chain were also able to be established from the fragments observed after McLafferty rearrangement [26] (Scheme 3). The 1 H-1 H COSY spectra of 1 showed a pair of double doublets of oxygenated methylene at d H 4.50 (1H, dd, J = 11.0, 4.5 Hz) and 4.40 (1H, dd, J = 10.5, 5.0 Hz) coupled to the nitrogen bearing methane signal at d H 5.08 (1H, m), which coupled further to the signal at d H 4.33 (1H, m).…”

Section: Resultsmentioning

confidence: 96%

Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from Zephyranthes candida

Chen

Xia

et al. 2008

Lipids

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Two novel ceramides, Candidamide A (1) with a phytosphingolipid structure, and Candidamide B (2) with a tertiary amide structure, together with 12 known compounds (3-14) have been isolated from the bulbs of Zephyranthes candida, The structures of 1 and 2 have been elucidated to be 1,3,5,6-tetrahydroxy-2-(2'-hydroxytetracosanoyl amino)-8-(E)-octadecadiene (1) and (2S,3S,4R,8E,2'R)-2-[N-(2'-hydroxyoctadecanoyl)-N-(1'',2''-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol (2) on the basis of spectroscopic evidence including IR, MS, NMR ((1)H-NMR, (13)C-NMR, DEPT, (1)H-(1)H COSY, HSQC, HMBC). The known compounds were identified as (2S)-3',7-dihydroxy-4'-methoxyflavan (3), (2S)-4'-hydroxy-7-methoxyflavan (4), (2S)-4',7-dihydroxyflavan (5), 7-hydroxy-3', 4'-methylenedioxyflavan (6), ambrettolide (7), beta-sitostero1 (8), beta-daucosterin (9), rutin (10), pancratistatin (11), lycorine (12), haemanthidine (13), and haemanthamine (14). In the antimicrobial assay, candidamide A (1) and candidamide B (2) displayed moderate activities against bacteria Staphylococcus aureus and Escherichia coli, and fungi Aspergillus niger, Candida albicans and Trichophyton rubrum.

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“…The absolute stereochemistry for sphingolipids is commonly characterized by the comparison of the NMR data with related literature reports [1,7,11,12]. For 1, the configurations at C-2, C-2¢, and C-3 were determined based on the proton chemical shifts and coupling constants at d [13].…”

Section: Resultsmentioning

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

Lipids

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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.

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Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl.

Cited by 38 publications

References 20 publications

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from Zephyranthes candida

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

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Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl.

Cited by 38 publications

References 20 publications

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from Zephyranthes candida

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

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