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  • 1
    Electronic Resource
    Electronic Resource
    Cytotoxic Triterpene Glycosides from Far-Eastern Sea Cucumbers Belonging to the Genus Cucumaria (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2351-2356 
    Details
    ISSN: 0947-3440
    Keywords: Carbohydrates ; Cucumaria japonica ; Cucumaria miniata ; Sea cucumbers ; Cucumariosides ; Triterpene glycosides ; Antitumor activity ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New cytotoxic triterpene oligoglycoside disulfates, cucumariosides A3 (1) and A6-2 (2), have been isolated from the sea cucumber Cucumaria japonica. The trisulfated cucumarioside A7-3 (4) was found to be the major component in the glycoside fraction of Cucumaria miniata. The structures were assigned on the basis of extensive spectral data (NMR and MS), selective solvolysis of desulfated derivative 3 and other chemical evidence. The presence or absence of a carbonyl group at C-16 of the aglycone and of sulfate groups at C-6 of the glucose and 3-O-methylglucose units are interpreted in terms of the functional evolution of sea cucumbers in order to improve their defensive system. Both (1) and (2) are cytotoxic in vitro at IC50 = 1 μg/ml against a selection of five human and mice tumoral cell lines.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971125
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  • 2
    Electronic Resource
    Electronic Resource
    Mitrariosides, Five Bitter Labdane Glycosides from Mitraria coccinea (Gesneriaceae) (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 665-668 
    Details
    ISSN: 0170-2041
    Keywords: Mitraria coccinea ; Gesneriaceae ; Labdane glycosides, bitter ; Mitrariosides A  -  D ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From Mitraria coccinea Cav. (Gesneriaceae), five strongly bitter labdane glycosides named mitrariosides A1, A2, B, C and D (1  -  5) were obtained. The structures were deduced by chemical and spectroscopic evidence (COSY, 13C-1H CORR, NOESY and MS-FAB) and found to be: mitrarioside A1 (1): (6S)-19-(β-D-galactopyranosyloxy)-6-hydroxy-15-(α-Lrhamno-pyranosyloxy)labda-8(17),13-diene, mitrarioside A2 (2): (6S)-19-(β-D-glucopyranosyloxy)-6-hydroxy-15-(α-L-rhamnopyranosyloxy)labda-8(17),13-diene, mitrarioside B (3):(6S)-19-(β-D-glucopyranosyloxy)-6-hydroxy-15-(β-D-glucopyranosyloxy)-labda-8(17),13-diene, mitrarioside C (4): (6S)-19-(β-D-glucopyranosyloxy)-6,15-dihydroxylabda-8(17), 13-diene, and mitrarioside D (5): (6S)-19-(α-L-rhamnopyranosyloxy)-6,15-dihydroxy-labda-8(17),13-diene. The known compounds acteoside and calceolarioside C were also isolated.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201113
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  • 3
    Electronic Resource
    Electronic Resource
    Antarctic Marine Metabolites: New Polyhydroxylated Steroidal Glycosides from the Starfish Odontaster validus (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1257-1262 
    Details
    ISSN: 0170-2041
    Keywords: Odontaster validus ; Antarctic starfish ; Asterosaponin ; Validoside ; Steroidal glycosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two new asterosaponins, validosides A and B, were isolated from the butanolic extract of the starfish Odontaster validus and their structures established as (24S)-24-O-[2,4-di-O-methyl-β-xylopyranosyl-(1→2)-α-arabinofuranosyl]-5α-cholestane-3β,4β,6α,8,15β,24-hexaol 6-O-sodium sulfate (1) and (24S)-24-O-(3-O-methyl-β-xylopyranosyl)-5α-cholestane-3β,6α,8,15β,24-pentaol 2′-O-sodium sulfate (2) on the basis of extensive spectroscopic investigations and chemical correlations. Validoside A and B are extremely rarely occurring saponins due to the presence of a sulfated group at C-6 of the aglycone in 1 and at C-2′ of a pyranose in 2. The absolute configuration at C-24 was found to be S by the application of the Trost-Mosher methodology.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301205
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