Producción CyT
AAPS PharmSciTech - Phytochemical and pharmacological studies on total alkaloid fraction of Solanum pseudocapsicum species group (Solanaceae).
Congreso
Fecha:
2011Editorial y Lugar de Edición:
SpringerResumen *
Introduction The Solanum pseudocapsicum species group includes 7 Americans species (1). It is strongly promising as new potential natural resource. One of its worldwide species, S. pseudocapsicum, has antimicrobial (2), antifungal (3), antiviral (4), antispasmodic (5), cytotoxic (5), antihypertensive (5), hepatoprotective (6), anti-tumor and antioxidant properties (7,8) that have been proved with crude extracts or extracts enriched in alkaloids. From the phytochemical point of view, this species is peculiar by having an alkaloid of unusual structure, the solanocapsine (9,10), along with other minor alkaloids (11). The objectives in this work are: 1) to verify the presence of solanocapsine in the remaining native South American species in order to determine its chemotaxonomical value; 2) to test anticholinesterase and antiviral activities (against non endemic and Argentinean endemic viruses); 3) to check if solanocapsine is the principal responsible of the pharmacological activities proved. Material and methods The alkaloid extraction of four species was made from dry leaves. The identification of solanocapsine was performed by Nuclear Magnetic Resonance Spectroscopy of Carbon (13C NMR), through the presence of the unique and characteristics signal of the 18 carbon of solanocapsine (spectra of 13C RMN, ä= 96,77 ppm). 13C NMR spectra of extracts enriched in alkaloids were made for S. pseudocapsicum L., S. delicatulum L.B. Smith & Downs, S. argentinum Bitter & Lillo, and S. tucumanense Griseb. The anticholinesterase activity was proved by inhibiting the enzyme acetylcholinesterase, using the Ellman et al. (12) methodology. For the antiviral activity, the Herpes simplex virus type I (VSH-I, strain Kos p31), the virus of the Encephalitis Equina Venezolana (EEV, strain TC83), the virus of the Encephalitis of San Luis (VESL, strain 78V6507) and the virus Junin (VJ, strain XJ Cl3) were used. The activity was measured by the method of neutral red uptake (13). Results The presence of solanocapsine was detected in S. pseudocapsicum, S. argentinum and S. tucumanense. A high inhibition on the acetylcholinesterase was observed in extracts of S. pseudocapsicum while the inhibition was moderate for S. argentinum and S. tucumanense. Solanum delicatulum’s extracts did not show inhibition. Solanum pseudocapsicum showed high antiviral activity against VJ and EEV while S.delicatulum have low activity against EEV and VSH-I. The extracts of S. tucumanense were negative against these viruses. Conclusions Apparently, solanocapsine is a chemotaxonomic marker since it is present in most species of the S. pseudocapsicum species group. The solanocapsine is not responsible for the pharmacological activities tested due to anticholinesterase and antiviral activities were not evidenced in the species with solanocapsine. Solanum pseudocapsicum is the species pharmacologically more active. Finally, further studies are necessary to determine the compounds responsible of the pharmacological activity demonstrated. Reference 1. Knapp S. A revision of the Solanum havanense species group and new taxonomic additions to the Geminata clade (Solanum, Solanaceae). Ann Mo Bot Gard. 2008;95:405-85. 2. Mitscher L A, Juvarkar J V, Beal J L. Solacasine, a new steroidal alkaloid from Solanum pseudocapsicum possessing antimicrobial activity. Experientia. 1976;32:415-16. 3. Aliero AA, Grierson DS, Afolayan AJ. Antifungal Activiy of Solanum pseudocapsicum. Res J Bot. 2006;1(3):129-33. 4. Van Den Berghe DA, Ieven M, Mertens F, Vlietinck AJ, Lammens E. J Nat Prod. 1978;11:463-67. 5. Dhar ML, Dhar MM., Dhawan BN, Mehrotra BN, Srimal RC, Tandon J S. Indian J Exp Biol. 1973;1:43-5. 6. Vijayan P, Prashanth HC, Preethy Vijayaraj, Dhanaraj SA, Badami S, Suresh B. Hepatoprotective Effect of the Total Alkaloid Fracction of Solanum pseudocapsicum Leaves. Pharm Biol. 2003;41(6):443-48. 7. Vijayan P, Kumar SV, Dhanaraj S A, Badami S, Suresh B. In vitro citotoxity and anti-tumor properties of the total alkaloid fraction of unripe fruits of Solanum pseudocapsicum. Pharm Biol. 2002;40(6):456-60. 8. Vijayan P, Vijayaraj P, Setty P, et al. The cytotoxic activity of the total alkaloids isolated from different parts of Solanum pseudocapsicum. Biol Pharm Bull. 2004;27:528-30. 9. Schreiber K, Ripperger H. Justus Liebigs Ann Chem. 1962;655:114-35. 10. Schreiber K, Ripperger H. Z Naturforsch B. 1962;17:217-221. 11. Chakravarty AK, Das B, Ali E, Pakrashi S. Studies on Indian Medicinal Plants. Part 77. Structure and stereochemistry of some new steroidal alkaloids from Solanum pseudocapsicum and Solanum giganteum by nuclear magnetic resonance spectroscopy. J Chem Soc Pekin Trans. 1984;1:467-74. 12. Ellman GL, Courtney KD, Andres V Jr, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961;7:88-95. 13. Borenfreud E, Puerner JA. Toxicity determined in vitro by morphological alterations and neutral red absorption. Toxicol. Lett. 1985;24:119-24. Información suministrada por el agente en SIGEVAPalabras Clave
PHYTOCHEMICALSOLANUM PSEUDOCAPSICUMALKALOIDPHARMACOLOGICAL