This present work addresses research on the discovery of new compounds from natural sources. It is based on a study of Mangifera indica leaf metabolism by the Tropidacris collaris grasshopper. We found that the grasshopper hydrolyzed the flavonoid isoquercitrin to quercetin when the O- glycosidic bond was broken and sugar released as a probable energy source for the insect. There was not, however, hydrolysis of the major compound in the leaves, mangiferin, which contains the C- glycosidic bond. All compounds were isolated and their chemical structure determined by UV, IR, MS, 1H and 13C NMR.
(a) RatesS.M. (2001) Plants as source of drugs. Toxicon, 39, 603–613; (b) Hartmann T. (2007) From waste products to ecochemicals: fifty years research of plant secondary metabolism. Phytochemistry, 68, 2831-2846; (c) Vogt MJ. (2009) Biological activity of amides and analogs from Piper species and synthetic analogs. Ph.D thesis, University of São Paulo, p 39; (d) Bajaj VK, Gupta RS. (2013) Review on research of suppression of male fertility and male contraceptive drug development by natural products. Natural Product Communications, 8, 1183-1193.
2.
(a) RamosC.S., SouzaL.J., KatoM.J., BatistaR. (2012) Biotransformation of 4-nerolidylcatechol by Heraclides brasiliensis (Lepidoptera: Papilionidae) reduces the toxicity of Piper umbellata (Piperaceae). Chemoecology, 19, 73–80; (b) Ramos CS, Paz AJLN, Silva TMG, Silva TMS. (2012) Potentialization of antioxidant activity of Piper umbellata (Piperaceae) leaves after their metabolism in Heraclides brasiliensis larvae (Lepidoptera: Papilionidae). African Journal of Pharmacy and Pharmacology, 48, 3299-3301; (c) Barbosa QPS, Almeida AV, Ramos CS. (2014) Metabolism of safrole by Heraclides thoas brasiliensis (Papilionidae). Journal of the Lepidopterists'Society, 68, 283-285.
3.
(a) MenesesM.A., CaputoG., ScognamiglioM., ReverchonE., AdamiR. (2015) Antioxidant phenolic compounds recovery from Mangifera indica L. by-products by supercritical antisolvent extraction. Journal of Food Engineering, 163, 45–53; (b) Ajila CM, Prasada Rao, UJS. (2013) Mango peel dietary fibre: Composition and associated bound phenolics. Journal of Functional Foods, 5, 444-450; (c) Schieber A, Ullrich W, Carle R. (2000) Characterization of polyphenols in mango puree concentrate by HPLC with diode array and mass spectrometric detection. Innovative Food Science & Emerging Technologies, 1, 161-166; (d) Sanugul K, Akao T, LI Y, Kakiuchi N, Nakamura N, Hattori M. (2005) Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosylbond. Biological and Pharmaceutical Bulletin, 28, 1672-1678; (e) Awaad AS, Mohamed NH, Maitland DJ, Soliman GA. (2008) Anti-ulcerogenic activity of extract and some isolated flavonoids from Desmostachia bipinnata (L.) Stapf. Records of Natural Products, 2 76-82; (f) Tallini LR, Pedrazza GPR, Bordignon SAL, Costa ACO, Steppe M, Fuentefria A, Zuanazzi JAS. (2015) Analysis of flavonoids in Rubus erythrocladus and Morus nigra leaves extracts by liquid chromatography and capillary electrophoresis. Revista Brasileira de Farmacognosia, 25, 219-227; (g) Gomez-Zaleta B, Ramírez-Silva MT, Gutierrez A, Gonzalez-Vergara E, Guizado-Rodríguez M, Rojas-Hernandez A. (2006) UV/vis, 1H, and 13C NMR spectroscopic studies to determine mangiferin pKa values. Spectrochimica Acta Part A, 64, 1002-1009.
4.
AgrawalP.K. (1989) Studies in Organic Chemistry. 39. Carbon-13 NMR of flavonoids. Elsevier, Amsterdam, 564 pp.
