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

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.

Key words

Sideroxylon obtusifolium - Sapotaceae - HPLC-PDA-MS profiling - saponins - flavonoids

References

• 1 Lorenzi H. Plantas medicinais no Brasil: Nativas e exóticas. Nova Odessa: Instituto Plantarum; 2002: 183-184
• 2 Santos M G, Fevereiro P C A, Reis G L. Recursos vegetais da Restinga de Carapebus, Rio de Janeiro, Brasil.  Rev Biol Neotrop. 2009;  6 35-54
• 3 Araújo T A S, Alencar N L, Amorim E L C, Albuquerque U P. A new approach to study medicinal plants with tannins and flavonoids contents from the local knowledge.  J Ethnopharmacol. 2008;  120 72-80
• 4 Albuquerque U P, Oliveira R F. Is the use-impact on native caatinga species in Brazil reduced by the high species richness of medicinal plants?.  J Ethnopharmacol. 2007;  113 156-170
• 5 Albuquerque U P. Re-examining hypotheses concerning the use and knowledge of medicinal plants: a study in the Caatinga vegetation of NE Brazil.  J Ethnobiol Ethnomed. 2006;  2 30
• 6 Albuquerque U P, Monteiro J M, Ramos M A, Amorim E L C. Medicinal and magic plants from a public market in northeastern Brazil.  J Ethnopharmacol. 2007;  110 76-91
• 7 Melo J G, Amorim E L C, Albuquerque U P. Native medicinal plants commercialized in Brazil – priorities for conservation.  Environ Monit Assess. 2009;  156 567-580
• 8 Monteiro J M, Ramos M A, Araújo E L, Amorim E L C, Albuquerque U P. Dynamics of medicinal plants knowledge and commerce in an urban ecosystem (Pernambuco, Northeast Brazil).  Environ Monit Assess. 2011;  178 179-202
• 9 Nascimento V T, Moura N P, Vasconcelos M A S, Maciel M I S, Albuquerque U P. Chemical characterization of native wild plants of dry seasonal forests of the semi-arid region of northeastern Brazil.  Food Res Int. 2011;  44 2112-2119
• 10 Araujo-Neto V, Bomfim R R, Oliveira V O B, Passos A M P R, Oliveira J P R, Lima C A, Mendes S S, Estevam C S, Thomazzi S M. Therapeutic benefits of Sideroxylon obtusifolium (Humb. ex Roem. & Schult.) T.D. Penn., Sapotaceae, in experimental models of pain and inflammation.  Rev Bras Farmacog. 2010;  20 933-938
• 11 Desmarchelier C, Romão R L, Coussio J, Ciccia G. Antioxidant and free radical scavenging activities in extracts from medicinal trees used in the ‘Caatinga region in northeastern Brazil.  J Ethnopharmacol. 1999;  67 69-77
• 12 Desmarchelier C J, Moraes Barros S B. Pharmacological activity of South American plants: effects on spontaneous in vivo lipid peroxidation.  Phytother Res. 2003;  17 80-82
• 13 Jiang Y, Ali A O, Guillaume D, Weniger B, Anton R. Triterpenoid saponins from the root of Sideroxylon cubense.  Phytochemistry. 1994;  35 1013-1015
• 14 Nicolas G, Oulad-Ali A, Guillaume D, Lobstein A, Weniger B, Anton R. Triterpenoid saponins from the root of Sideroxylon foetidissimum.  Phytochemistry. 1995;  38 225-228
• 15 Sánchez-Medina A, Stevenson P C, Habtemariam S, Peña-Rodríguez L M, Corcoran O, Mallet A I, Veitch N C. Triterpenoid saponins from a cytotoxic root extract of Sideroxylon foetidissimum subsp. gaumeri.  Phytochemistry. 2009;  70 765-772
• 16 Momtaz S, Mapunya B M, Houghton P J, Edgerly C, Hussein A, Naidoo S, Lall N. Tyrosinase inhibition by extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening.  J Ethnopharmacol. 2008;  119 507-512
• 17 Erosa-Rejón G, Peña-Rodríguez L M, Sterner O. Isolation of kaempferol-3-rutinoside from the leaf of Sideroxylon foetidissimum subsp. Gaumeri.  Rev Latinoam Quím. 2010;  38 7-11
• 18 Nakano T, Hasegawa M. Isolation of erythrodiol 3-palmitate from Bumelia obtusifolia.  Planta Med. 1975;  27 89-92
• 19 Eskander J, Lavau C, Abdel-khalik S M, Soliman H S M, Mahmoud I I, Long C. Saponins from the leaves of Mimusops laurifolia.  J Nat Prod. 2005;  68 832-841
• 20 Abbet C, Neuburger M, Wagner T, Quitschau M, Hamburger M, Potterat O. Phyteumosides A and B: new saponins with unique triterpenoid aglycons from Phyteuma orbiculare. L.  Org Lett. 2011;  13 1354-1357
• 21 Tabopda T K, Miatine-Offer A C, Miyamoto T, Tanaka C, Ngadjui B T, Mirjolet J F, Duchamp O, Lacaille-Dubois M A. Three new medicagenic acid saponins from Polygala micrantha Guill. & Perr.  Helv Chim Acta. 2011;  94 914-922
• 22 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
• 23 Verotta L, Caldiroli S, Gariboldi P, Tatò M. 600 MHz ¹H and ¹³C NMR full assignments of two saponins from Nothapodytes foetida.  Phytochem Anal. 1996;  7 245-252
• 24 Kitagawa I, Inada A, Yosioka I. Saponin and sapogenol. XII. Mi-saponin A and Mi-saponin B, two major bisdesmosides from the seed kernels of Madhuca longifolia.  Chem Pharm Bull. 1975;  23 2268-2278
• 25 Toyota M, Msonthi J D, Hostettmann K. A molluscicidal and antifungal triterpenoid saponin from the roots of Clerodendrum wildii.  Phytochemistry. 1990;  29 2849-2851
• 26 Burger I, Burger B V, Albrecht C F, Spies H S C, Sándor P. Triterpenoid saponins from Becium grandiflorum var. obovatum.  Phytochemistry. 1998;  49 2087-2095
• 27 Yasukawa K, Sekine H, Takido M. Two flavonol glycosides from Lysimachia fortunei.  Phytochemistry. 1989;  28 2215-2216
• 28 Yasukawa K, Takido M. A flavonol glycoside from Lysimachia mauritiana.  Phytochemistry. 1987;  26 1224-1226
• 29 Fijkumoto H, Ishigijro K, Murashima T, Yamaki M, Isor K. Structure determination of a kaempferol 3-rhamnosyldiglucoside from Impatiens balsamina.  Phytochemistry. 1994;  37 1486-1488
• 30 Yasukawa K, Sekine H, Takido M. Two flavonol glycosides from Lysimachia fortunei.  Phytochemistry. 1989;  28 2215-2216
• 31 Zhou X, Peng J, Fan G, Wu Y. Isolation and purification of flavonoid glycosides from Trollius ledebouri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase.  J Chromatogr A. 2005;  1092 216-221
• 32 Barrios J, Cordero C P, Aristizabal F, Heredia F J, Morales A L, Osorio C. Chemical analysis and screening as anticancer agent of anthocyanin-rich extract from uva caimarona (Pourouma cecropiifolia Mart.) fruit.  J Agric Food Chem. 2010;  58 2100-2110
• 33 Liu C D, Chen J, Wang J H. A novel kaempferol triglycoside from flower buds of Panax quinquefolium.  Chem Nat Compd. 2009;  45 808-810
• 34 Shen C C, Chang Y S, Ho L K. Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids.  Phytochemistry. 1993;  34 843-845
• 35 Yoshikawa M, Yamaguchi S, Kunimi K, Matsuda H, Okuno Y, Yamahara J, Murakami N. Stomachic principles in Ginger. III. An anti-ulcer principle, 6-gingesulfonic acid, and three monoacyldigalactosylglycerols, gingerglycolipids A, B, and C, from Zingiberis rhizoma originating in Taiwan.  Chem Pharm Bull. 1994;  42 1226-1230
• 36 Narod F B, Gurib-Fakim A, Subratty A H. Flavonoids from endemic Sideroxylon species (Sapotaceae) of Mauritius.  Res J Chem Environ. 2003;  7 53-58