Biosynthesis of Lamiide and Ipolamiide from 8-epi-Deoxyloganin Studied by 2H N.M.R. Spectroscopy
2H N.m.r. spectroscopy shows that selectively labelled 8-epi-deoxyloganin is efficiently incorporated into lamiide and ipolamiide in Hebenstreitia dentata, whereas selectively labelled deoxyloganin provides no observable incorporation.
Synthetic analogues of durantoside I from Citharexylum spinosum L. and their cytotoxic activity
New iridoid glycoside derivatives from durantoside I, the latter from the dried flowers and leaves of Citharexylum spinosum, were synthesized by variously modifying a sugar moiety by silylation or acetylation and/or removal of cinnamate group at C-7 posit
BIOSYNTHESIS OF IRIDOID GLUCOSIDES IN HEBENSTRETIA DENTATA
Deuterium-labelled samples of 8-epi-iridodial, 8-epi-iridotrial and their glucosides were fed to Hebenstretia dentata.The aglucones were better precursors than their glucosides of ipolamiide and lamiide, the iridoid glucosides of the plant.A feeding experiment with (13)C-labelled 10-hydroxy-geraniol showed that C-3 and C-11 are equivalent during biosynthesis of the iridoid glucosides and, thus, glucosidation must take place after formation of 8-epi-iridotrial.Isolation of the minor metabolites after feeding with 8-epi-deoxyloganic acid suggested that the route from this compound proceeds by oxidation at C-8 followed by esterification and that oxidation at C-5 is the final step. Key Word Index: Hebenstretia dentata; Scrophulariaceae; iridoid glucosides; ipolamiide; lamiide; biosynthesis; (2)H NMR.
Damtoft, Soeren,Jensen, Soeren Rosendal,Nielsen, Bent Juhl,Thorsen, Jesper
p. 3839 - 3844
(2007/10/02)
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