ISOLATION AND CHARACTERIZATION OF SECONDARY METABOLITES FROM PITHECELLOBIUM DULCE BENTH FRUIT PEEL
Keywords:Pithecellobium dulce, Pinitol, Sterols, Quercetin
Objective: The present study describes the isolation and characterization of valuable secondary metabolites from the fruit peel of Pithecellobium dulce.
Methods: Solvent extraction of the plant material using methanol followed by column chromatographic separation of the extract with solvents (Petroleum ether, ethyl acetate and methanol) of increasing polarity using silica gel yields four compounds (1-4).
Results: The structures of the compounds stigmasterol (1), Î²-sitosterol (2), quercetin (3) and pinitol (4) were established on the basis of FTIR, 1H and 13C NMR; and mass spectra and in comparison with their literature values.
Conclusion: Two sterols namely stigmasterol (1) and Î²-sitosterol (2), along with a flavonoid quercetin (3) and a cyclitol pinitol (4) have been isolated from the methanol extract of fruit peel of Pithecellobium dulce for the first time.
Nigam SK, Gupta RK, Mitra CR. Pithecellobium dulce. I. Isolation and characterization of the constituents of the legume. J Pharm Sci 1962;52:459-62.
Nigam SK, Mitra CR. Pithecellobium dulce. IV. Constituents of flowers, heartwood, and root bark. Planta Med 1968;163:335-7.
Nigam SK, Mitra CR. Pithecellobium dulce. V. Chemistry of the seed saponin and constituents of the leaves. Planta Med 1970;18:44-50.
Adinarayana D, Ramachandraiahchetty P. Chemical investigation of some medicinal plants occurring in southern India. Indian J Chem 1985;24B:453.
Zapesochnaya GG, Yarosh EA, Syanidze NV, Yarosh GI. Flavanoids of the leaves of Pithecellobium dulce. Khim Prir Soedin 1980;2:252-3.
Sahu NP, Mahato SB. Anti-inflammatory triterpene saponins of Pithecellobium dulce: Characterization of echinocystic acid bisdesmoside. Phytochemistry 1994;375:1425-7.
Nigam SK, Misra G, Uddin R, Yoshikawa K, Kawamoto M, Arihara S. Pithedulosides A-G, Oleanane glycosides from Pithecellobium dulce. Phytochemistry 1997;44:1329-34.
Yoshikawa K, Suzaki Y, Tanaka M, Arihara S, Nigam SK. Three acylated saponins and a related compound from Pithecellobium dulce. J Nat Prod 1997;6012:1269-74.
Saxena VK, Singal M. Geinstein 4'-O-alpha-LÂ¬ rhamnopyranoside from Pithecellobium dulce. Fitoterapia 1998;694:305-6.
Niranjan PS, Kazuo K, Zhonghua J, Sukdeb B, Basudeb A, Tamotsu N. A minor acylated triterpenoid saponin from the seeds of Pithecellobium dulce. J Chem Res 1999;32:558-9.
Banerjee A. Studies on alkylated resin from Pithecellobium dulce. J Indian Chem Soc 2005;82:186-7.
Shanmugakumaran SD, Amerjothy S, Balakrishna K. Pharmacognostical, Antibacterial and antifungal potentials of the leaf extracts of Pithecellobium dulce Benth. Pharmacogn Mag 2006;72:163-7.
Chandran PGR, Balaji S. Phytochemical investigation and pharmocological studies of the flowers of Pithecellobium dulce. Ethnobotanical Leaflets 2008;12:245-53.
Sugumaran M, Vetrichelvan T, Darline Quine S. Anti-diabetic potential of aqueous and alcoholic leaf extracts of Pithecellobium dulce. Asian J Res Chem 2009;2:83-5.
Nagmoti DM, Kothavade PS, Bulani VD, Gawali NB, Juvekar AR. Antidiabetic and antihyperlipidemic activity of Pithecellobium dulce (Roxb.) Benth seeds extract in streptozotocin-induced diabetic rats. Eur J Integrative Med 2015;7:263â€“73.
Katekhaye DS, Nagmoti DM. Î±-Glucosidase and Î±-amylase inhibitory activities of Pithecellobium dulce bark and leaves. Phytopharmacology 2013;4:123-30.
Sukantha TA, Subashini KS, Ravindran NT, Balashanmugam P. Evaluation of in vitro antioxidant and antibacterial activity of Pithecellobium dulce Benth fruit peel. Int J Curr Res 2011;3:378-82.
Sukantha TA, Subashini KS, Ravindran NT. Antibacterial activity of selected medicinal plant in traditional treatment of wound infection in Southeast India. Int J Pharm Pharm Sci 2014;6:511-3.
Kim MJ, Yoo KH, Kim JH, Seo YT, Ha BW, Kho JH, et al. Effect of pinitol on glucose metabolism and adipocytokines in uncontrolled type 2 diabetes. Diabetes Res Clin Pract 2007;77 Suppl 1:S247-51.
Panda S, Jafri M, Kar A, Meheta BK. Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma. Fitoterapia 2009;80:123-6.
Thamaraiselvan R, Natarajan Nandakumar, Maruthaiveeran PB. D-pinitol a low-molecular cyclitol prevents 7,12-Dimethylbenza. anthracene induced experimental breast cancer through regulating anti-apoptotic protein Bcl-2, mitochondrial and carbohydrate key metabolism enzymes. Biomed Nutr 2012;2:25-30.
Singh RK, Pandey BL, Tripathi M, Pandey VB. Anti-inflammatory effect of (+)pinitol. Fitoterapia 2001;72:168-70.
Kim JI, Kim JC, Kang MJ, Lee MS, Kim JJ, Cha IJ. Effects of pinitol isolated from soybeans on glycaemic control and cardiovascular risk factors in Korean patients with type II diabetes mellitus: a randomised controlled study. Eur J Clin Nutr 2005;56:456-8.
Alma MS, Chopra N, Ali M, Niwa M. Oleanen and sitgmasterol derivatives from Ambroma augusta. Phytochem 1996;414:1197-200.
Kamboj A, Saluja AK. Isolation of Stigmasterol and Î²-sitosterol from petroleum ether extract of aerial parts of Ageratum conyzoides (Asteraceae). Int J Pharm Pharm Sci 2011;3:94-6.
Wagner H, Chari VM, Sonnenbichler J. C-13 NMR spectra of natural flavonoids, Tetrahedron Lett 1976;21:1799-802.
Narda Blanco, Yonny Flores, Giovanna R Almanza. Secondary metabolites from Senna versicolor. Rev Boliv Quim 2008;25:36-42.
Narayanan CR, Joshi DD, Mujumdar AM, Dhekne VV. Pinitol-a new anti-diabetic compound from the leaves of Bougainvillea spectabilis. Curr Sci 1987;563:139-41.
Singh RK, Pandey BL, Tripathi M, Pandey VB. Anti-inflammatory effect of (+)-pinitol. Fitoterapia 2001;72:168-70.
Lee JS, Jung ID, Jeong YI. D-Pinitol inhibits Th1 Polarization via the suppression of dendritic cells. Int Immunopharmacol 2007;7:791-804.