Flavonoid glycosides of the black locust tree, Robinia pseudoacacia (Leguminosae).

Phytochemistry
Nigel C VeitchGwilym P Lewis

Abstract

Four flavone glycosides isolated from extracts of the leaves of Robinia pseudoacacia (Leguminosae) were characterised by spectroscopic and chemical methods as the 7-O-beta-d-glucuronopyranosyl-(1-->2)[alpha-l-rhamnopyranosyl-(1-->6)]-beta-d-glucopyranosides of acacetin (5,7-dihydroxy-4'-methoxyflavone), apigenin (5,7,4'-trihydroxyflavone), diosmetin (5,7,3'-trihydroxy-4'-methoxyflavone) and luteolin (5,7,3',4'-tetrahydroxyflavone). Assignment of glycosidic (1)H and (13)C resonances in their NMR spectra was facilitated by (2)J(HC) correlations detected using the H2BC (heteronuclear two-bond correlation) pulse sequence. Spectroscopic analysis of two known triglycosides, acacetin 7-O-beta-d-glucopyranosyl-(1-->2)[alpha-l-rhamnopyranosyl-(1-->6)]-beta-d-glucopyranoside (previously unrecorded from this species) and acacetin 7-O-beta-d-xylopyranosyl-(1-->2)[alpha-l-rhamnopyranosyl-(1-->6)]-beta-d-glucopyranoside ('acacetin trioside'), enabled inconsistencies in the literature relating to these structures to be resolved. Comparison of the flavonoid chemistry of leaves and flowers of R. pseudoacacia using LC-UV and LC-MS showed that flavone 7-O-glycosides, particularly of acacetin, predominated in the former, whereas the latter compris...Continue Reading

References

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Citations

Oct 5, 2013·Chinese Journal of Integrative Medicine·Kanika PatelDinesh Kumar Patel
Jan 30, 2013·Journal of Natural Products·Erdenechimeg SelengeFumihiko Yoshizaki
Dec 14, 2011·Fitoterapia·Ludmila YarmolinskyShimon Ben-Shabat
Sep 30, 2011·Rapid Communications in Mass Spectrometry : RCM·Geoffrey C Kite, Nigel C Veitch
May 7, 2013·Bioorganic & Medicinal Chemistry Letters·Jong Hoon AhnMi Kyeong Lee
Feb 11, 2018·Journal of the Science of Food and Agriculture·Angelo GismondiAntonella Canini
Nov 15, 2018·Medicines·William N Setzer
Oct 4, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Larissa Marina Pereira SilvaSilvana Maria Zucolotto
Feb 26, 2021·Molecular Plant-microbe Interactions : MPMI·Dongying LiuGehong Wei

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