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  • 1
    Electronic Resource
    Electronic Resource
    Thermal Degradation of Glycosides, IV. Degradation of flavonoid glycosides (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 1285-1289 
    Details
    ISSN: 0170-2041
    Keywords: Degradation, thermal ; Glycosides ; Flavonoid glycosides ; FDMS fragmentation ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: By mere heating, the flavone (1, 7), flavanone (4, 10), and flavonol glycosides (13, 14) are converted into their aglycones and monoglycosides. The products of pyrolysis have been isolated by chromatography and their structures elucidated by chemical and spectroscopic methods. The compound derived from the sugar moiety in the pyrolysis of glucosides has been identified as levoglucosan (17). From the structures of some minor products (16, 18, 19), generated by the thermal degradation, a mechanism of their generation and the elucidation of the structures of rearranged ions (for example [M + 146 + H]+), often generated in the FD-mass spectra of glycosides, are presented.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101221
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  • 2
    Electronic Resource
    Electronic Resource
    Thermal Degradation of Glycosides, V. Hydrothermolysis of Triterpenoid and Steroid Glycosides (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 453-459 
    Details
    ISSN: 0170-2041
    Keywords: Degradation, thermal ; Thermolysis ; Glycosides ; Carbohydrates ; Triterpenoids ; Steroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In this paper the hydrothermolysis of triterpenoid and steroid glycosides is described. By mere heating with water or water/1,4-dioxane solution, the triterpenoid and steroid glycosides 1, 4 and 15, 16, 25, 29, respectively, are converted into their aglycones and prosapogenins. Furthermore, hydrothermolysis of the triterpenoid 3,28-O-bisglycosides 5, 6, 8, 9, 12 affords the corresponding 3-O-glycosides and reduced oligosaccharides formed by selective cleavage of the ester glycosidic linkage. It is expected that this hydrothermolysis is useful for the structure determination of some triterpenoid and steroid glycosides and for yielding new oligosaccharides. The hydrothermolyzed products have been isolated by chromatography and their structures elucidated by spectroscopic methods.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920181
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  • 3
    Electronic Resource
    Electronic Resource
    Thermal Degradation of Glycosides, VI. Hydrothermolysis of Cardenolide and Flavonoid Glycosides (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 575-579 
    Details
    ISSN: 0170-2041
    Keywords: Thermolysis ; Degradation, thermal ; Carbohydrates ; Glycosides ; Cardenolides ; Steroids ; Flavonoids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The hydrothermolysis of cardenolide and flavonoid glycosides is described. On heating with water or water/dioxane, cardenolide (1, 5, 11) and flavonoid glycosides (16, 20, 23, 27) are converted into their genuine aglycones and partially hydrolyzed products, together with saccharide components. Meanwhile, the glycosidic linkage of 2-deoxy sugar moieties in cardenolide glycosides is more readily cleaved than that of the common sugar moieties by means of hydrothermolysis. Therefore, hydrothermolysis of the uzarigenin triglycoside (13), bearing a 2-deoxy sugar moiety which is directly attached to the aglycone, leads to selective cleavage of the sugar - aglycone linkage. The hydrothermolyzed products have been isolated by chromatography and their structures elucidated by spectroscopic methods.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201100
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  • 4
    Electronic Resource
    Electronic Resource
    Thermal degradation of glycosides, III. Degradation of cardenolide glycosides (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 943-947 
    Details
    ISSN: 0170-2041
    Keywords: Thermal degradation ; Glycosides ; Cardiac glycosides ; Cardenolide glycosides ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The thermal degradation of cardenolide glycosides consisting of different sugar moieties and aglycones was examined. On simple heating, the sugar - aglycone linkage of cardenolide glycosides having 2,6-dideoxy sugar moieties in readily cleaved, to afford their genuine aglycones. On the contrary, cardenolide glycosides possessing 6-deoxy sugar moieties are resistant to the degradative reaction. Besides the fission of the glycosidic linkages, some interesting reactions also took place. The pyrolyzed products were isolated by chromatography, and the structures were elucidated by spectroscopic evidence.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001174
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  • 5
    Electronic Resource
    Electronic Resource
    Thermal Degradation of Glycosides, VII. Application of Hydrothermolysis to the Studies on the Constituents of the Merck Saponin (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 941-946 
    Details
    ISSN: 0170-2041
    Keywords: Thermolysis ; Degradation, thermal ; Carbohydrates ; Merck saponin ; Triterpenoids ; Glycosides ; Gypsophyla paniculata ; Gypsogenin ; Quillaic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two new triterpenoid 3,28-O-bisglycosides, MS-1 and MS-2, were isolated from the Merck Saponin (origin: Gypsophila paniculata L.). Their structures were elucidated on the basis of chemical and spectral data as follows. MS-1 (1): 3-O-β-D-galactopyranosyl-(→2)-[α-L-arabinopyranosyl-(→3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(→3)- β-D-xylopyranosyl-(→4)-α-L-rhamnopyranosyl-(→4)-[β-D-quinovopyranosyl-(→2)]-β-D- fucopyranoside. MS-2(2): 3-O-β-D-galactopyranosyl-(→2)-[α-L- arabinopyranosyl-(→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(→3)-β-D-xylopyranosyl-(→4)-α-L-rhamnopyranosyl-(→4)-[β-D-quinovopyranosyl -(→2)]-β-D-fucopyranoside. The hydrothermal degradation, which led to selective cleavage of the ester glycosidic linkage, was useful for the structure elucidation.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201155
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