SMQ-V047 N-002_ligas_size.pdf - Journal of the Mexican Chemical ...

More documents

Recommendations

Info

New Eremophilanoids from the Roots of Psacalium radulifolium. Hypoglycemic, antihyperglycemic and anti-oxidant evaluations 166 17. (a) Navarrete, A. Evaluación Farmacológica de Plantas Medicinales. En: Plantas Medicinales de México. Introducción a su Estudio. Editor: E. Estrada. Universidad Autónoma de Chapingo. México. 1996. pp. 255-268. (b) Sharma, S. R.; Dwivedi, S. K.; Swarup, D. J. Ethnopharmacol. 1997, 58, 39-44. (c) Fernando, M. R.; Wickramasinghe, S. M. D. N.; Thabrew, M. I.; Karunanyaka, E. H. J. Ethnopharmacol. 1989, 27, 7-14. (c) Trajanoski, Z.; Brunner, G. A.; Gferer, R. J.; Wach, P.; Pieber, T. R. Diabetes Care 1996, 19, 1412-1415. 18. Becker, M.; Newman, S.; Ismail-Beigi, F. Mol. Cell. Endocrinology 1996, 121, 165-170. 19. (a) Hennani, T.; Parihar, M. S. Ind. J. Phys. Pharm. 1998, 42, 440.452. (b) Anderson, S. M. Drug Develop. Res. 1999, 46, 67- 79. (c) Sies, H. Oxidative Stress. Introductory Remarks. In: Sies, H., Ed. Academic Press. Orlando, Florida. 1985. pp. 1-8. 20. Lotina-Hennsen, B.; Roque Reséndiz, J. L.; Jiménez, M.; Aguilar, M. Z. Naturforsch. 1991, 46c, 777-780. 21. Meckes, M.; Garduño-Ramírez, M. L.; Marquina, S.; Álvarez, L. Rev. Soc. Quím. Méx. 2001, 45, 195-199. 22. Bohlmann, F.; Zdero, Ch.; Grenz, M. Chem. Ber. 1977, 110, 474- 486. 23. (a) Joseph-Nathan, P.; Negrete M. C.; González, M. P. Phytochemistry 1970, 9, 1623-1628. (b) Bohlmann, F.; Zdero, Ch. Chem. Ber. 1970, 111, 3140-3145. 24. Bwititi, P.; Musabayane, C. T.; Nhachi, C. F. B. J. Ethnopharmacol. 2000, 69, 247-252. 25. Nicki, I.; Nicks, J. L.; Ashcroft, S. J. H. Biochem. J. 1990, 268, 713-718. 26. Cotelle, V.; Vernier, J. L.; Catteau, J. P.; Pommery, J.; Wallet, J. C.; Gaydou, E. M. Free Radical Biol. Med. 1996, 20, 35-43. 27. (a) Waffo, T. P.; Fauconneau, B.; Deffieux, G.; Huguet, F.; Vercauteren, J.; Merillon, J. M. J. Nat. Prod. 1998, 61, 655-657. (b) Rekka, E. A.; Kourounakis, A. P. Res. Comm. Mol. Pathol. Pharmacol. 1996, 92, 361-366.
Revista de la Sociedad Química de México, Vol. 47, Núm. 2 (2003) 167-172 Investigación Isolation and Chemical Transformations of Some Anti-inflammatory Triterpenes from Salvia mexicana L. var. minor Benth. Rosalba Argumedo Delira, Hortensia Parra-Delgado, Ma. Teresa Ramírez Apan, Antonio Nieto Camacho y Mariano Martínez-Vázquez* Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, México, D. F. Tel: +(52) 56224403; E-mail: marvaz@servidor.unam.mx Recibido el 6 de mayo del 2003; aceptado el 24 de junio del 2003 Dedicated to Dr. Alfonso Romo de Vivar Abstract. The acetone and methanol extracts of aerial parts of Salvia mexicana L. var. minor showed anti-inflammatory and antioxidant properties in the TPA y DPPH models respectively. The chromatography of these extracts led the isolation of β-sitosterol, betulinol, betulinic acid, ursolic acid and arbutin. The presence of these triterpenes is in agreement with previos phytochemical studies of Salvia, however this is the first time that arbutin is isolated from a species of this genus. On the other hand, since none or the isolated compound showed antioxidant properties in the DPPH model, it can be inferred that minor compounds not isolated or synergism effects could account for the antioxidant properties of the extracts. It is known that some pentacyclic triterpene derivatives with an α,β-unsaturated carbonyl in the ring A showed a better nitric oxide synthase inhibition activity that the natural triterpenes. It was decided to synthesize the methyl ester of 2-formyl-3-oxo-urs-28-oic and 2-formil-3-oxo-urs-1- en-28-oic acids from ursolic acid and evaluate them using the DPPH and TPA models. The results showed that both compounds have antiinflammatory activity, but only the 2-formyl-3-oxo-ursol-28-oic acid methyl ester was active in DPPH assay, which is in agreement with the proposed mechanism of this test. This is the first chemical study of Salvia mexicana L. var. minor (Benth). Keywords: Triterpenos, Salvia mexicana var. minor, antiinflamatory activity, chemical transformations. Resumen. Los extractos acetónico y metanólico de las partes aéreas de Salvia mexicana L. var. minor, mostraron poseer propiedades antiinflamatorias y antioxidantes en los modelos de TPA y DPPH, respectivamente. La cromatografía de estos extractos permitió el aislamiento de β-sitosterol, betulinol, ácido betulínico, ácido ursólico y arbutina. La presencia de estos triterpenos está de acuerdo con estudios previos de Salvia, sin embargo, es la primera vez que se aísla arbutina de una especie de éste género. Posiblemente las propiedades antiinflamatorias de los extractos se deban a la presencia del β-sitosterol y ácido ursólico, compuestos con probadas actividades antiinflamatorias. Por otro lado, es probable que las propiedades antioxidantes de estos extractos, se deban a la presencia de compuestos minoritarios o a efectos sinérgicos, ya que ninguno de los compuestos aislados fue activo en el modelo de DPPH. Datos recientes en la literatura señalan que algunos derivados de triterpenos pentacíclicos con una cetona α,β-insaturada en el anillo A, presentan una mayor inhibición de la enzima óxido nítrico sintetasa que los triterpenos naturales, por lo que se decidió obtener los ésteres metílicos de los ácidos 2- formil-3-oxo-urs-28-oico y 2-formil-3-oxo-urs-1-en-28-oico a partir del ácido ursólico, y evaluarlos en los modelos de DPPH y TPA. Los resultados muestran que ambos tienen propiedades antiinflamatorias, pero solo el éster metílico del ácido 2-formil-3-oxo-ursol-28-oico fue activo en el modelo de DPPH, resultado que está de acuerdo con el mecanismo asociado a esta prueba. Este es el primer estudio químico de la especie Salvia mexicana L. var. minor (Benth). Palabras clave: Triterpenos, Salvia mexicana var. minor, actividad anti-inflamatoria, transformaciones químicas. Introduction Salvia is an important genus consisting of ca 900 species in the family Lamiaceae (formerly Labiatae). Some species of Salvia have been cultivated worldwide to be used in folk medicine and for culinary purposes [1]. The dried leaves of S. officinalis (sage) L., for example, is well known for their antioxidative properties used in the food processing industry but applicable also to the area of human health [2]. Studies on the chemical constituents of Salvia have been mainly confined to the diterpenoids and the tanshinones [3,4], and several reviews of these components have already been published [5, 6]. In addition, there are several reports on the biological activities of some species of this genus [7-9]. Most of the 500 species of Salvia found in Mexico, Central and South America belong to the Subgenus Jungia (formerly Calosphace) [10]. The species Salvia mexicana has been divide in two varieties: S. mexicana var. major Benth. and S. mexicana L. var. minor Benth. Acetone extract of the aerial parts from the former afforded narigenine and a cis-languidulane diterpenoid named salvimexicanolide [10]. In addition, from the chloroform extract of the aerial parts of this species β-sitosterol, betulinic acid and a triterpenic lactone called salviolide were isolated [11]. As a part of our ongoing systematic studies looking for bioactive compounds from Mexican species [12], we report in this paper the chemical study, the free radical scavenging and the anti-inflammatory activities of some extracts and isolates from S. mexicana L.
Page 5 and 6:
REVISTA de la SOCIEDAD QUÍMICA d e
Page 7 and 8:
Editorial La investigación cientí
Page 9 and 10:
Editorial 103 Jacobo Gómez Lara (1
Page 11 and 12:
Revista de la Sociedad Química de
Page 13 and 14:
Revista de la Sociedad Química de
Page 15 and 16:
Synthesis, Structural, and Theoreti
Page 17 and 18:
Page 19 and 20:
Page 21 and 22: Synthesis, Structural, and Theoreti
Page 23 and 24: Revista de la Sociedad Química de
Page 25 and 26: 2D 1 H and 13 C NMR from the adduct
Page 31 and 32: Reactivity of IrH 2 {C 6 H 3 -2,6-(
Page 35 and 36: The Use of N,N’-Di[α-phenylethyl
Page 37 and 38: Reactivity of IrH 2 {C 6 H 3 -2,6-(
Page 39 and 40: Preparation of 11-Hydroxylated 11,1
Page 47 and 48: Chemical Composition and Antimicrob
Page 51 and 52: Sesquiterpene Lactone Sequestration
Page 53 and 54: Mechanism of Glutamate Neurochemist
Page 55 and 56: Mechanism of Glutamate Neurochemist
Page 59 and 60: Cumarinas presentes en especies del
Page 63 and 64: Preparación de materiales mesoporo
Page 65 and 66: Preparación de materiales mesoporo
Page 67 and 68: New Eremophilanoids from the Roots
Page 69 and 70: New Eremophilanoids from the Roots
Page 71: 165 Rev. Soc. Quím. Méx. Vol. 47,
Page 75 and 76: Isolation and Chemical Transformati
Page 77 and 78: Isolation and Chemical Transformati
Page 81 and 82: Two New Oleanolic Acid Saponins fro
Page 83 and 84: Two New Oleanolic Acid Saponins fro
Page 85 and 86: Análisis isobolográfico de la int
Page 91 and 92: 185 Rev. Soc. Quím. Méx. Vol. 47,
Page 93 and 94: Cytotoxic Evaluation of a Series of
Page 95 and 96: Cytotoxic Evaluation of a Series of
Page 97 and 98: El análisis conformacional a la lu
Page 109 and 110: Synthesis and properties of 2-Diazo
Page 111 and 112: Synthesis and properties of 2-Diazo
Page 115: Estudio fitoquímico de Salvia urua
show all

SMQ-V047 N-002_ligas_size.pdf - Journal of the Mexican Chemical ...

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?