Monoglycerides and Fatty acids from Ibervillea sonorae Root: Isolation and Hypoglycemic Activity

Abstract

Eleven monoglycerides (MG), 1-monopalmitin (1), glyceryl 1-monomargarate (2), 1-monostearin (3), glyceryl 1-monononadecylate (4), glyceryl 1-monoarachidate (5), glyceryl 1-monobehenate (6), glyceryl 1-monotricosanoate (7), glyceryl 1-monotetracosanoate (8), glyceryl 1-monopentacosanoate (9), glyceryl 1-monohexacosanoate (10) and glyceryl 1-monooctacosanoate (11), together with five fatty acids (FA), lauric acid (12), myristic acid (13), pentadecanoic acid (14), palmitic acid (15) and stearic acid (16) were isolated of the root of Ibervillea sonorae Greene (Cucurbitaceae). Their structures were determined by spectroscopic and chemical methods as well as GC-MS analysis. The hypoglycemic activity of the dichloromethane (DCM) extract, of fractions (F1 - F10 and SF1 - SF5), of monoglycerides (MG) and of fatty acids (FA) mixtures obtained of the root from I. sonorae was evaluated in normoglycemic and alloxan-induced diabetic mice. The results showed that by intraperitoneal administration the DCM extract (300 mg/kg), F9 (300 mg/kg) and SF1 (150 mg/kg) significantly reduced glucose levels in both models. For fraction SF1, the hypoglycemic activity was more pronounced than that of tolbutamide (150 mg/kg) used as control. However, neither MG (75 mg/kg) nor FA (75 mg/kg) mixtures isolated from SF1 exhibited a significant hypoglycemic effect. However, when MG and FA were combined in equal proportions (75 mg: 75 mg/kg), their effect was comparable to that of SF1. The observed activity for the DCM extract, F9, SF1 and the MG-FA mixture provides additional support for the popular use of this plant in the treatment of diabetes mellitus in Mexican traditional medicine.

Key words

Ibervillea sonorae - Cucurbitaceae - dichloromethane extract - monoglycerides - fatty acids - hypoglycemic activity

References

• 1 Aguilar C A, Xolalpa M S. La herbolaria mexicana en el tratamiento de la diabetes.  Ciencia. 2002;  53 24-35.
• 2 Achenbach H, Horn K, Domínguez A, Rombold C, Gomez L. Cucurbitanes and cucurbitane-type glycosides from Ibervillea sonorae .  Phytochemistry. 1993;  33 437-45.
• 3 Xolalpa M S. A tu Salud.  Rev Med Prev. 2006;  26 69-71.
• 4 Alarcon-Aguilar F J, Campos-Sepulveda A E, Xolalpa-Molina S, Hernandez-Galicia E, Roman-Ramos R. Hypoglycemic activity of Ibervillea sonorae roots in healthy and diabetic mice and rats.  Pharm Biol. 2002;  40 570-5.
• 5 Alarcon-Aguilar F J, Calzada-Bermejo F, Hernandez-Galicia E, Ruiz-Angeles C, Roman-Ramos R. Acute and chronic hypoglycemic effect of Ibervillea sonorae extracts-II.  J Ethnopharmacol. 2005;  97 447-52.
• 6 Weckert E, Hummer K, Domínguez A, Horn K, Achenbach H. The absolute configuration of kinoin C.  Phytochemistry. 1993;  133 447-8.
• 7 NOM-062-ZOO-1999 (revised in 2001 Norma Oficial Mexicana. Especificaciones técnicas para la producción, cuidado y uso de los animales de laboratorio. Mexico; Diario Oficial de la Federación 6 de Diciembre de 1999: 2001.
• 8 Steel R, Torrie J. Bioestadística, principios y procedimientos.  México:. McGraw-Hill;  1989 662.
• 9 Kawagishi H, Miyazawa T, Kume H, Arimoto Y, Inakuma T. Aldehyde dehydrogenase inhibitors from the mushroom Clitocybe clavipes .  J Nat Prod. 2002;  65 1712-4.
• 10 Konishi T, Satsu H, Hatsugai Y, Aizawa K, Inakuma T, Nagata S. et al . Inhibitory effect of a bitter melon extract on the P-glycoprotein activity in intestinal Caco-2 cells.  Br J Pharmacol. 2004;  143 379-87.
• 11 Marles R J, Fansworth N R. Antidiabetic plants and their active constituents.  Phytomedicine. 1995;  2 137-89.
• 12 Bergsson G, Steingrimsson O, Thormar H. Bactericidal effects of fatty acids and monoglycerides on Helicobacter pylory .  Int J Antimicrob Agents. 2002;  20 258-62.
• 13 Song-Lee W, Jeong K M, Beck Y, Park Y D, Jeong T S. Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots.  Bioorg Med Chem Lett. 2005;  15 3573-5.
• 14 Shimada H, Tyler V E, McLaughlin J L. Biologically active acylglycerides from the berries of Saw-Palmetto (Serenoa repens).  J Nat Prod. 1997;  60 417-8.

1 Part of this work was taken from the Ph.D. thesis of Erica Hernandez.