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Quercetin and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranosides from Anthyllis hermanniae: structure determination and conformational studies.
J Nat Prod. 2011 Sep 23; 74(9):1939-45.JN

Abstract

The study reports the isolation and structural identification of two new flavonol triglycosides from the methanolic extract of Anthyllis hermanniae, exhibiting the same glycosylation pattern: quercetin 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranoside (1) and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranoside (2). A conformational study related to the central arabinoside moiety was carried out including the analysis of the contribution of NOE effects and acetylation to the elucidation of the 2-O-linked arabinoside configuration of the anomeric carbon. We also report the total synthesis of a model compound, quercetin 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (3), which verifies the structures of the isolated compounds.

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Authors+Show Affiliations

Halabalaki M
Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, University of Athens, Panepistimioupolis-Zografou, Athens, 15771, Greece.
Urbain A
No affiliation info available
Paschali A
No affiliation info available
Mitakou S
No affiliation info available
Tillequin F
No affiliation info available
Skaltsounis AL
No affiliation info available

MeSH

FabaceaeGlycosidesGlycosylationGreeceKaempferolsMolecular StructureQuercetinStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

21861458

Citation

Halabalaki, Maria, et al. "Quercetin and Kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranosides From Anthyllis Hermanniae: Structure Determination and Conformational Studies." Journal of Natural Products, vol. 74, no. 9, 2011, pp. 1939-45.
Halabalaki M, Urbain A, Paschali A, et al. Quercetin and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranosides from Anthyllis hermanniae: structure determination and conformational studies. J Nat Prod. 2011;74(9):1939-45.
Halabalaki, M., Urbain, A., Paschali, A., Mitakou, S., Tillequin, F., & Skaltsounis, A. L. (2011). Quercetin and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranosides from Anthyllis hermanniae: structure determination and conformational studies. Journal of Natural Products, 74(9), 1939-45. https://doi.org/10.1021/np200444n
Halabalaki M, et al. Quercetin and Kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranosides From Anthyllis Hermanniae: Structure Determination and Conformational Studies. J Nat Prod. 2011 Sep 23;74(9):1939-45. PubMed PMID: 21861458.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Quercetin and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranosides from Anthyllis hermanniae: structure determination and conformational studies. AU - Halabalaki,Maria, AU - Urbain,Aurélie, AU - Paschali,Aristea, AU - Mitakou,Sofia, AU - Tillequin,François, AU - Skaltsounis,Alexios-Leandros, Y1 - 2011/08/23/ PY - 2011/8/25/entrez PY - 2011/8/25/pubmed PY - 2011/12/13/medline SP - 1939 EP - 45 JF - Journal of natural products JO - J Nat Prod VL - 74 IS - 9 N2 - The study reports the isolation and structural identification of two new flavonol triglycosides from the methanolic extract of Anthyllis hermanniae, exhibiting the same glycosylation pattern: quercetin 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranoside (1) and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]-7-O-α-L-rhamnopyranoside (2). A conformational study related to the central arabinoside moiety was carried out including the analysis of the contribution of NOE effects and acetylation to the elucidation of the 2-O-linked arabinoside configuration of the anomeric carbon. We also report the total synthesis of a model compound, quercetin 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (3), which verifies the structures of the isolated compounds. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/21861458/Quercetin_and_kaempferol_3_O_[α_L_rhamnopyranosyl__1→2__α_L_arabinopyranoside]_7_O_α_L_rhamnopyranosides_from_Anthyllis_hermanniae:_structure_determination_and_conformational_studies_ L2 - https://doi.org/10.1021/np200444n DB - PRIME DP - Unbound Medicine ER -