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Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae.
Phytochemistry. 2009 Apr; 70(6):785-94.P

Abstract

The dried fruits and seeds of Styphnolobium japonicum (L.) Schott (syn. Sophora japonica L.) are used in traditional Chinese medicine and known as Fructus Sophorae or Huai Jiao. The major flavonoids in these fruits and seeds were studied by LC-MS and other spectroscopic techniques to aid the chemical authentication of Fructus Sophorae. Among the flavonoids were two previously unreported kaempferol glycosides: kaempferol 3-O-beta-glucopyranosyl(1-->2)-beta-galactopyranoside-7-O-alpha-rhamnopyranoside and kaempferol 3-O-beta-xylopyranosyl(1-->3)-alpha-rhamnopyranosyl(1-->6)[beta-glucopyranosyl(1-->2)]-beta-glucopyranoside, the structures of which were determined by NMR. Two further tetraglycosides were identified for the first time in S. japonicum as kaempferol 3-O-beta-glucopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and kaempferol 3-O-beta-glucopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside-7-O-alpha-rhamnopyranoside; the latter was the main flavonoid in mature seeds. The chromatographic profiles of 27 recorded flavonoids were relatively consistent among fruits of similar ages collected from five trees of S. japonicum, and those of maturing unripe and ripe fruits were similar to a market sample of Fructus Sophorae, and thus provide useful markers for authentication of this herbal ingredient. The flower buds (Huai Mi) and flowers (Huai Hua) of S. japonicum (collectively Flos Sophorae) contained rutin as the main flavonoid and lacked the flavone glycosides that were present in flower buds and flowers of Sophora flavescens Ait., reported to be occasional substitutes for Flos Sophorae. The single major flavonoid in fruits of S. flavescens was determined as 3'-hydroxydaidzein.

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Authors+Show Affiliations

Kite GC
Royal Botanic Gardens, Kew, Richmond, Surrey, UK. g.kite@kew.org
Veitch NC
No affiliation info available
Boalch ME
No affiliation info available
Lewis GP
No affiliation info available
Leon CJ
No affiliation info available
Simmonds MS
No affiliation info available

MeSH

Chromatography, LiquidFabaceaeFlavonolsGlycosidesMagnetic Resonance SpectroscopySpectrometry, Mass, Electrospray IonizationTandem Mass Spectrometry

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19447452

Citation

Kite, Geoffrey C., et al. "Flavonol Tetraglycosides From Fruits of Styphnolobium Japonicum (Leguminosae) and the Authentication of Fructus Sophorae and Flos Sophorae." Phytochemistry, vol. 70, no. 6, 2009, pp. 785-94.
Kite GC, Veitch NC, Boalch ME, et al. Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae. Phytochemistry. 2009;70(6):785-94.
Kite, G. C., Veitch, N. C., Boalch, M. E., Lewis, G. P., Leon, C. J., & Simmonds, M. S. (2009). Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae. Phytochemistry, 70(6), 785-94. https://doi.org/10.1016/j.phytochem.2009.04.003
Kite GC, et al. Flavonol Tetraglycosides From Fruits of Styphnolobium Japonicum (Leguminosae) and the Authentication of Fructus Sophorae and Flos Sophorae. Phytochemistry. 2009;70(6):785-94. PubMed PMID: 19447452.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae. AU - Kite,Geoffrey C, AU - Veitch,Nigel C, AU - Boalch,Martha E, AU - Lewis,Gwilym P, AU - Leon,Christine J, AU - Simmonds,Monique S J, Y1 - 2009/05/15/ PY - 2009/01/28/received PY - 2009/04/01/revised PY - 2009/04/02/accepted PY - 2009/5/19/entrez PY - 2009/5/19/pubmed PY - 2009/6/27/medline SP - 785 EP - 94 JF - Phytochemistry JO - Phytochemistry VL - 70 IS - 6 N2 - The dried fruits and seeds of Styphnolobium japonicum (L.) Schott (syn. Sophora japonica L.) are used in traditional Chinese medicine and known as Fructus Sophorae or Huai Jiao. The major flavonoids in these fruits and seeds were studied by LC-MS and other spectroscopic techniques to aid the chemical authentication of Fructus Sophorae. Among the flavonoids were two previously unreported kaempferol glycosides: kaempferol 3-O-beta-glucopyranosyl(1-->2)-beta-galactopyranoside-7-O-alpha-rhamnopyranoside and kaempferol 3-O-beta-xylopyranosyl(1-->3)-alpha-rhamnopyranosyl(1-->6)[beta-glucopyranosyl(1-->2)]-beta-glucopyranoside, the structures of which were determined by NMR. Two further tetraglycosides were identified for the first time in S. japonicum as kaempferol 3-O-beta-glucopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and kaempferol 3-O-beta-glucopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside-7-O-alpha-rhamnopyranoside; the latter was the main flavonoid in mature seeds. The chromatographic profiles of 27 recorded flavonoids were relatively consistent among fruits of similar ages collected from five trees of S. japonicum, and those of maturing unripe and ripe fruits were similar to a market sample of Fructus Sophorae, and thus provide useful markers for authentication of this herbal ingredient. The flower buds (Huai Mi) and flowers (Huai Hua) of S. japonicum (collectively Flos Sophorae) contained rutin as the main flavonoid and lacked the flavone glycosides that were present in flower buds and flowers of Sophora flavescens Ait., reported to be occasional substitutes for Flos Sophorae. The single major flavonoid in fruits of S. flavescens was determined as 3'-hydroxydaidzein. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/19447452/Flavonol_tetraglycosides_from_fruits_of_Styphnolobium_japonicum__Leguminosae__and_the_authentication_of_Fructus_Sophorae_and_Flos_Sophorae_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(09)00140-X DB - PRIME DP - Unbound Medicine ER -