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
Dec 26, 2001·Chemical Reviews·J DuusK Bock
Nov 8, 2003·Journal of Asian Natural Products Research·Yu-Ping TangBiao Yu
Jan 13, 2006·Carbohydrate Research·Bent O PetersenOle W Sørensen
Apr 28, 2007·Phytochemistry·Geoffrey C KiteNigel C Veitch
Jun 15, 2007·Journal of Agricultural and Food Chemistry·Wesley G TaylorDaniel H Sutherland
May 24, 2008·Natural Product Reports·Nigel C Veitch, Renée J Grayer
Aug 30, 2008·Journal of Agricultural and Food Chemistry·Pilar TruchadoFrancisco A Tomás-Barberán
May 19, 2009·Phytochemistry·Geoffrey C KiteMonique S J Simmonds
Aug 29, 2009·Rapid Communications in Mass Spectrometry : RCM·Geoffrey C Kite, Nigel C Veitch
Citations
Oct 5, 2013·Chinese Journal of Integrative Medicine·Kanika PatelDinesh Kumar Patel
Aug 9, 2012·Archives of Pharmacal Research·Hyun Ah JungJae Sue Choi
Jan 18, 2013·Archives of Pharmacal Research·Agung NugrohoHee-Juhn Park
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
Apr 10, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jayanta Kumar PatraKwang-Hyun Baek
Feb 11, 2018·Journal of the Science of Food and Agriculture·Angelo GismondiAntonella Canini
Dec 12, 2017·Natural Product Research·Agung NugrohoHee-Juhn Park
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
Jul 6, 2019·Tree Physiology·Xinye WangGehong Wei
Jul 31, 2019·Antioxidants·Ivana Savic GajicDragoljub Gajic
Jan 9, 2021·Ecotoxicology and Environmental Safety·Chunyan ZhangZiwei Wang
Feb 19, 2021·Natural Product Research·Anna Budzianowska, Jaromir Budzianowski
Feb 26, 2021·Molecular Plant-microbe Interactions : MPMI·Dongying LiuGehong Wei
Jul 3, 2021·Antibiotics·Diana ObistioiuErsilia Alexa