Au\ den oberirdischen Teilen yon Luphorhiu rsula L. (Euphurbiiiceae) wurde ein Flabonglykosid isolicrt und als 3.5.7.4'-Tetrahydroxy-flavon~Kampferol)-3-~-~-glucuroi~id (8) identifiziert. Seine Struktur wurde durch Kupplung von 7.4-Dibenzyl-kimpferol mit n-Acetobromglucuronsaure-methylester, Darstellung dcs Vollacetats, Entbenzylierung und Verseirung zu 8 bewicsen.
Synthesis of Glucuronides in the Flavonoid-Scries, TI
Isolation of Kaempferol-3-~-D-glucuronide from Euphouhiu esulu L.From the aerial part4 ot Euplaurbi(z esuln L. (Euphorbiacrae) a flavone-glycojide wasisoldted and identified as 3,5,7,4'-tetrahydroxyflavone( kaempferol)-3-~-~-gIucuron1de (8) Its structure W~S confirmed by coupling of 7,4'-dibenzylkaempferoI with methyl(tr1-0-acetyl-1-u-glucopyranosyl bromide)-uronate, followed by total acetylation, debenzylation and saponification to 8
Durch Kupplung von 7.4'-Dibewyl-quercetin mit a-Acetobromglucuron~aure-methylester, Darstellung des Vollacetats, Entbenzylierung und Verseifung wurde das aus zahlreichen Pflanzen isolierte Quercetin-3-~-D-glucopyrdno~uronid (3) als erstes natiirlich vorkommendes Glucuronid des Pflanzenreiches synthetisiert und in seiner Struktur bewiesen.The first synthesis, and thereby confirmation of its structure, of a naturally occurring flavonoid glucuronide, quercetin-3-P-~-g~ucuronide (3) i s achieved by coupling of 7,4'-dibenzylquercetin with methyl(tri-O-aCetyl-a-D-glUCOpy~dnOsyl bromide)-uronate, followed by total acetylation of the product and subsequent removal of the protecting groups.
Synthesis of Glucuronides in the Flavonoid-Series, II11s2)
Isolation of Apigenin-7-P-~-glucuronide from Ruelliu tuherosa L. and its SynthesisFroin the yellow buds of Ruelliae tuberosa L. (Acmtlzaceae) a flavone-glycoside was isolated which could be identihed as S.7.4'-trihydroxyflavone(apigen1n)-7-~-~-gluc~ironide (3) Its structure was confirmed by coupling 4'-O-benzylapigenin with methyl(tri-O-acetyl-cc-~-glucopyranosyl bromide)uronate, followed by total acetylation, debenzylation and saponification to 3.
Kondensation von Apigenin (I) mit dem Glucuronsäure‐Derivat (II) und nachfolgende Acetylierung liefern die Acetate (IIIa) und (IIIb) (chromatographisch trennbar); aus (IIIa) wird durch Verseifung das Diglucuronid (IV) erhalten, das früher aus Antirrhinum majus isoliert worden ist.
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