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Isolation and Chemical Transformations of Some Anti-inflammatory Triterpenes from Salvia mexicana... 172 15. Martínez-Vázquez, M.; Ramírez A., T. O.; Lazcano, M. E.; Bye, R. Rev. Soc. Quím. Mex. 1999, 43, 103-105. 16. Recio, M. C.; Giner, R.; Terencio, M. C.; Sanz, M. J.; Ríos, J. L. Planta Med. 1991, 57, A56-57. 17. De Young, L. M.; Kheifets, J. B.; Ballaron, S. L.; Young, J. M. Agents Actions. 1989, 26, 335-341. 18. Fuerstenberg, G.; Richter, H.; Fusening, N. E.; Marks, F. Cancer Lett. 1981, 11, 191-204. 19. Carlson, R. P.; O´Neil-Davis, L.; Chang, J.; Lewis, A. J. Agents Actions. 1985, 17, 197-204. 20. Najid, A.; Simon, A.; Cook, J.; Chable-Rabinovitch, H.; Delage, C.; Chulia, A. J.; Rigaud, M. FEBS. 1992, 213-217. 21. You, H. J.; Chul, Y. C.; Ji, Y. K.; Park, S. J. Hahm, K.; Jeong, H. G. FEBS Lett. 2001, 509, 156-160. 22. Cottele, N.; Bernier, J. L.; Catteau, J. P.; Pommery, P.; Wallet, J. C.; Gaydou, E. M. Free Radical Biology & Medicine. 1996, 20, 35-43.
Revista de la Sociedad Química de México, Vol. 47, Núm. 2 (2003) 173-177 Investigación Two New Oleanolic Acid Saponins from the Roots of Viguiera hypargyrea Laura Alvarez, 1* Alejandro Zamilpa, 2 Silvia Marquina, 1 and Manasés González 1 1 Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Chamilpa, 62210, Cuernavaca, Morelos, México. Tel/Fax: (+52) (01 77) 7329 7997; E-mail: lalvarez@intermor.net.mx 2 Centro de Investigación Biomédica del Sur, Instituto Mexicano del Seguro Social, Argentina No. 1, Centro, 62790 Xochitepec, Morelos, México Recibido el 20 de mayo del 2003; aceptado el 24 de junio del 2003 Dedicated to Professor Alfonso Romo de Vivar Abstract. Two new triterpene saponins whose aglycons are based on the oleanane skeleton (1-2), were isolated from the roots of Viguiera hypargyrea, together with two known triterpene saponins (3 and 4) as well as the triterpenes friedelin, friedelan 3β-ol and oleanolic acid. The structures of the new compounds were established mainly by 2D NMR techniques of their peracetylated derivatives as 3-O-[α-Lrhamnopyranosyl (1 → 3)-β-D-xylopyranosyl (1 → 4)]-β-D-glucopyranosyl-oleanolic acid-28-O-β-D-glucopyranoside and 3-O-[α-Lrhamnopyranosyl (1 → 3)-β-D-xylopyranosyl (1 → 4)]-β-D-glucopyranosyl oleanolic acid respectively. Keywords: Viguiera hypargyrea, Asteraceae, roots, oleanolic acid saponins, bisdesmosides. Resumen. De las raíces de Viguiera hypargyrea se aislaron dos nuevas saponinas triterpénicas (1-2), cuyas agliconas corresponden al esqueleto del oleanano, junto con dos saponinas triterpénicas conocidas (3 y 4), así como los triterpenos friedelina, friedelan-3β-ol y ácido oleanólico. Las estructuras de los compuestos novedosos fueron establecidas principalmente por medio de técnicas de RMN 2D de sus derivados peracetilados como 3-O-[α-L-rhamnopiranosil (1 → 3)-β-D-xilopiranosil (1 → 4)]-β-D-glucopiranosil-ácido oleanólico-28-O-β-D-glucopiranósido y ácido 3-O-[α-L-ramnopiranosil (1 → 3)-β-D-xilopiranosil (1 → 4)]-β-D-glucopiranosil oleanólico respectivamente. Palabras clave: Viguiera hypargyrea, Asteraceae, raíces, saponinas del ácido olanólico, bisdesmósidos. Introduction Viguiera hypargyrea Blake (Asteraceae) is a perennial herb distributed on Northern Mexico [1]. The roots of this plant are used for gastrointestinal disorders in Mexican traditional medicine and it is commonly known as “plateada” [2]. Diterpenic acids and sesquiterpene lactones have been reported from the leaves [3]. We have recently reported that the n-hexane and ethyl acetate-soluble portions and their principal diterpenic acid components ent-beyer-15-en-19-oic and ent-kaur-16-en- 19-oic acids showed antispasmodic and antimicrobial effects [4]. Although the methanol-soluble portion did not exhibit apparent antispasmodic and antimicrobial activity at a sample concentration of 25 µg/mL and 10 mg/mL respectively, we had interest in the chemical constituents of this fraction, and here we report the results. Results and discussion Chromatographic separations of the methanol soluble fraction have resulted in the isolation of the known triterpenes friedelin, friedelan-3-β-ol and oleanolic acid, which were identified by direct comparison with authentic samples. Two new triterpene saponins based on the oleanane skeleton (1,2), which were characterized as their peracetate derivatives (1a,2a) were also isolated, together with the known saponins β-D-glucopyranosyl olean-12-en-28-oate (3) and 3-O-[methyl-β-D-glucuronopyranosiduronoate]-28-O-β-D-glucopyranosyl oleanolate (4), which were identified by comparison of their spectroscopic data with those previously described [5, 6]. In this paper, we report the structural determination of the new saponins on the basis of spectroscopic analysis and acidcatalyzed hydrolysis. Compound 1a was obtained as an oil after acetylation of the natural product 1. In the positive-ion FABMS of 1a, quasimolecular ion peaks were observed at m/z 1600 [M + K + H] + , 1584 [M + Na + H] + , and 1561 [M + H] + , and HRFABMS analysis revealed the molecular formula to be C 77 H 108 O 33 . Other significant peaks visible at m / z 1254 [M + K – C 14 H 19 O 10 ] + , 1068 [M – C 12 H 17 O 7 – C 11 H 15 O 7 ] + , and 777 [M – C 33 H 45 O 21 ] + , indicated the successive loss of one hexosyl, one deoxyhexosyl, one pentosyl and one hexosyl moieties. Another fragment ion at m/z 437 corresponded to the pseudomolecular ion of the aglycon. On acid hydrolysis, 1a liberated oleanolic acid as the genin, and glucose, rhamnose and xylose, which were identified by comparison with authentic samples by co-TLC, IR and NMR. On alkaline hydrolysis, only glucose was detected by co-TLC with an authentic sample, indicating that the glucose was bound to the genin by a glycosidic ester linkage at C-28 [7]. The 1 H and 13 C NMR spectra of 1a, which are presented in Table 1, showed that most of the signals of the aglycon were in good agreement with literature data for oleanolic acid [8]. Glycosylation shifts were observed
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Editorial La investigación cientí
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Editorial 103 Jacobo Gómez Lara (1
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