Metabolite profiling of the leaves of the Brazilian folk medicine Sideroxylon obtusifolium.
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 MS (n), 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.
Division of Pharmaceutical Biology, University of Basel, Klingelbergstrasse 50, Basel, Switzerland.
Adriana
A
Passos Oliveira
Melanie
M
Raith
Ricardo Machado
RM
Kuster
Leandro Machado
LM
Rocha
Matthias
M
Hamburger
Olivier
O
Potterat
D001938:Brazil; D005419:Flavonoids / Q000302:isolation & purification*; D055442:Metabolome; D018515:Plant Leaves / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000302:isolation & purification*; D029632:Sapotaceae / Q000737:chemistry*
D005419:Flavonoids; D012503:Saponins