Planta Med 2012; 78(7): 703-710
DOI: 10.1055/s-0031-1298269
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Metabolite Profiling of the Leaves of the Brazilian Folk Medicine Sideroxylon obtusifolium

Adriana Passos Oliveira1 , 2 , Melanie Raith1 , Ricardo Machado Kuster2 , Leandro Machado Rocha3 , Matthias Hamburger1 , Olivier Potterat1
  • 1Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
  • 2Research Group of Natural Products, Federal University of Rio de Janeiro, Rio de Janeiro State, Brazil
  • 3School of Pharmacy, Fluminense Federal University, Rio de Janeiro State, Brazil
Further Information

Publication History

received October 6, 2011 revised January 24, 2012

accepted January 25, 2012

Publication Date:
09 February 2012 (online)

Abstract

Sideroxylon obtusifolium (Roem. & Schult.) T. D. Penn. (family Sapotaceae) is a tree native to Central and South America. Infusions of the bark and the leaves are used in Brazilian folk medicine as an anti-inflammatory remedy. However, information on the constituents of S. obtusifolium remains scarce, and only common pentacyclic triterpenoids have been previously reported. HPLC-DAD/MS analyses revealed that saponins and flavonoids were the main constituents of the leaves. From the butanol-soluble fraction of an ethanolic extract, a total of four saponins and ten flavonol glycosides were isolated by a combination of chromatographic methods including Sephadex LH-20, MPLC, and HPLC. Their structures were established by acid hydrolysis and spectroscopic methods, mainly MSn, 1D and 2D NMR experiments. The compounds include the new triterpene glycoside 3-O-(β-D-glucopyranosyl)-protobassic acid 28-O-β-D-apiofuranosyl-(1 → 3)-O-[O-β-D-apiofuranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (1), as well as the new flavonol glycosides, quercetin-3-O-(O-α-L-rhamnopyranosyl-(1→ 2)-O-[β-D-glucopyranosyl-(1 → 3)]-β-D-galactopyranoside) (6) and kaempferol-3-O-(O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-β-D-galactopyranoside) (8). In addition, catechin and a glycerogalactolipid, gingerglycolipid A, were obtained from the ethyl acetate-soluble fraction. The isolated compounds could be used in the future as chemical markers for quality control of this herbal drug.

Supporting Information

References

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PD Dr. Olivier Potterat

Division of Pharmaceutical Biology
Department of Pharmaceutical Sciences
University of Basel

Klingelbergstrasse 50

4056 Basel

Switzerland

Phone: +41 6 12 67 15 34

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Email: olivier.potterat@unibas.ch

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