Subscribe to RSS
DOI: 10.1055/s-0029-1186030
© Georg Thieme Verlag KG Stuttgart · New York
Flavonol Glycosides from the South African Medicinal Plant Sutherlandia frutescens
Publication History
received April 24, 2009
revised June 14, 2009
accepted July 9, 2009
Publication Date:
10 August 2009 (online)
Abstract
Phytochemical investigation of the leaves of Sutherlandia frutescens led to the isolation of four new 3-hydroxy-3-methylglutaroyl−containing flavonol glycosides, sutherlandins A–D (1−4). Their structures were elucidated by chemical and spectroscopic methods as quercetin 3-O-β-D-xylopyranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (1), quercetin 3-O-β-D-apiofuranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (2), kaempferol 3-O-β-D-xylopyranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (3), and kaempferol 3-O-β-D-apiofuranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (4).
Key words
Sutherlandia frutescens - Fabaceae - sutherlandins A–D - flavonoids
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Fu X, Li X C, Smillie T J, Carvalho P, Mabusela W, Syce J, Johnson Q, Folk W, Avery M A, Khan I A. Cycloartane glycosides from Sutherlandia frutescens. J Nat Prod. 2008; 71 1749-1753
- 2 van Wyk B E, Albrecht C. A review of the taxonomy, ethnobotany, chemistry and pharmacology of Sutherlandia frutescens (Fabaceae). J Ethnopharmacol. 2008; 119 620-629
- 3 Prevoo D, Swart P, Swart A C. The influence of Sutherlandia frutescens on adrenal steroidogenic cytochrome P450 enzymes. J Ethnopharmacol. 2008; 118 118-126
- 4 Ojewole J A O. Anticonvulsant property of Sutherlandia frutescens R. BR. (variety Incana E. MEY.) [Fabaceae] shoot aqueous extract. Brain Res Bull. 2008; 75 126-132
- 5 Mabry T J, Markham K R, Thomas M B. The systematic identification of flavonoids. Berlin; Springer 1970
- 6 Hübner G, Wray V, Nahrstedt A. Flavonol oligosaccharides from the seeds of Aesculus hippocastanum. Planta Med. 1999; 65 636-642
- 7 Kazuma K, Noda N, Suzuki M. Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry. 2003; 62 229-237
- 8 Lee V S, Chen C R, Liao Y W, Tzen J T, Chang C I. Structural determination and DPPH radical-scavenging activity of two acylated flavonoid tetraglycosides in oolong tea (Camellia sinensis). Chem Pharm Bull. 2008; 56 851-853
- 9 Semmar N, Fenet B, Gluchoff-Fiasson K, Hasan A, Jay M. Four new flavonol glycosides from the leaves of Astragalus caprinus. J Nat Prod. 2002; 65 576-579
- 10 Hara S, Okabe H, Mihashi K. Gas-liquid-chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem Pharm Bull. 1987; 35 501-506
- 11 Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull. 2007; 55 899-901
- 12 Kinjo J, Araki K, Fukui K, Higuchi H, Ikeda T, Nohara T, Ida Y, Takemoto N, Miyakoshi M, Shoji J. Six new triterpenoidal glycosides including two new sapogenols from Albizziae Cortex. V. Chem Pharm Bull. 1992; 40 3269-3273
- 13 Bergot B J, Baker F C, Lee E, Schooley D A. Absolute configuration of homomevalonate and 3-hydroxy-3-ethylglutaryl- and 3-hydroxy-3-methylglutaryl CoA, produced by cell-free extracts of insect corpora allata; cautionary note on prediction of absolute stereochemistry based on liquid chromatographic elution order of diastereomeric derivatives. J Am Chem Soc. 1979; 101 7432-7434
- 14 Fujimoto H, Nakamura E, Kim Y P, Okuyama E, Ishibashi M, Sassa T. Immunomodulatory constituents from an Ascomycete, Eupenicillium crustaceum, and revised absolute structure of macrophorin D. J Nat Prod. 2001; 64 1234-1237
- 15 Kamo T, Hirai N, Matsumoto C, Ohigashi H, Hirota M. Revised chirality of the acyl group of 8′-O-(3-hydroxy-3-methylglutaryl)-8′-hydroxyabscisic acid. Phytochemistry. 2004; 65 2517-2520
- 16 Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J. Saponin and sapogenol. XLIX. On the constituents of the roots of Glycyrrhiza inflata Batalin from Xinjiang, China. Characterization of two sweet oleanane-type triterpene oligoglycosides, apioglycyrrhizin and araboglycyrrhizin. Chem Pharm Bull. 1993; 41 1350-1357
Ikhlas A. Khan
National Center for Natural Products Research
The University of Mississippi
Mississippi, MS 38677
USA
Phone: + 1 66 29 15 78 21,
Fax: + 1 66 29 15 79 89
Email: ikhan@olemiss.edu
- www.thieme-connect.de/ejournals/toc/plantamedica