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Redalyc.New Prenylated Flavanones from Esenbeckia Berlandieri Ssp

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Redalyc.New Prenylated Flavanones from Esenbeckia Berlandieri Ssp Journal of the Mexican Chemical Society ISSN: 1870-249X [email protected] Sociedad Química de México México Cano, Arturo; Espinoza, Marina; Ramos, Clara H.; Delgado, Guillermo New Prenylated Flavanones from Esenbeckia berlandieri ssp. acapulcensis Journal of the Mexican Chemical Society, vol. 50, núm. 2, 2006, pp. 71-75 Sociedad Química de México Distrito Federal, México Available in: http://www.redalyc.org/articulo.oa?id=47550204 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative J. Mex. Chem. Soc. 2006, 50(2), 71-75 Article © 2006, Sociedad Química de México ISSN 1870-249X New Prenylated Flavanones from Esenbeckia berlandieri ssp. acapulcensis Arturo Cano,1* Marina Espinoza,1 Clara H. Ramos2 and Guillermo Delgado3* 1 Facultad de Estudios Superiores Zaragoza, Universidad Nacional Autónoma de México. Av. Guelatao No. 66 (Eje 7 Oriente). Col. Ejército de Oriente. Iztapalapa 09230. México D. F. Email: [email protected] 2 Instituto de Biología, Universidad Nacional Autónoma de México. Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, México D. F. 3 Instituto de Química, Universidad Nacional Autónoma de México. Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, México D. F. Email: [email protected] Recibido el 12 de enero del 2006; aceptado el 29 de junio del 2006 Abstract. Three new (1-3) and four known prenylated flavanones as Resumen. Tres flavanonas preniladas novedosas (1-3), cuatro cono- well as friedelin were isolated from the aerial parts of Esenbeckia cidas así como friedelina fueron aisladas de las partes aéreas de berlandieri ssp acapulcensis (Rutaceae). The structures of the new Esenbeckia berlandieri ssp acapulcensis (Rutaceae). Las estructuras compounds were elucidated as 5,7-dihydroxy-8-(2,3-epoxy-3-methyl- de los compuestos nuevos fueron determinadas como 5,7-dihidroxi-8- butyl)flavanone (1), 5,4´-dihydroxy-7-methoxy-8-(2,3-dihydroxy-3- (2,3-epoxi-3-metilbutil)flavanona (1), 5,4´-dihidroxi-7-metoxi-8-(2,3- methylbutyl)flavanone (2), and 5,7,4´-trihydroxy-8-(2,3-dihydroxy-3- dihidroxi-3-metilbutil)flavanona (10) y 5,7,4´-trihidroxi-8-(2,3- methylbutyl)flavanone (3). The isolated flavanones possess diferen- dihidroxi-3-metilbutil)flavanona (11). Las flavanonas aisladas poseen tially functionalized isoprene units at C-8, and this is the first report isoprenilos con diferente funcionalidad unidos a C-8, y este es el of flavanones isolated from Esenbeckia species. primer reporte de flavanonas aisladas de especies de Esenbeckia Keywords: Esenbeckia berlandieri ssp. acapulcensis, Rutaceae, Palabras clave: Esenbeckia berlandieri ssp. acapulcensis, Rutaceae, prenylflavanones. prenilflavanonas. The genus Esenbeckia (family Rutaceae, subfamily Rutoideae) and 2.82) and between the aromatic protons H-2´ through H-6´ δ is known to be a source of metabolites such as limonoids [1- ( H 7.43 – 7.47) revealed the presence of a 2,8-disubstituted 3], coumarins [2,4-10], phenylpropanoids [5], polyprenols, 5,7-dihydroxychroman-4-one ring. Because ten of eleven phloroglucinols [11], alkaloids [2,6-10,12-14], triterpenoids unsaturations were accounted for a flavanone nucleus, it was [3,15], and flavonoids [16]. In our research on the chemical concluded the presence of an isoprenyl group. The presence of constituents of this group of plants, new prenylated flavanones an epoxide in this fragment was confirmed by the 13C NMR δ δ were isolated from Esenbeckia berlandieri ssp. acapulcensis resonances at C 79.1 and 71.8 and by the signal at H 4.71 in and this is the first report of prenylated flavanones from the 1H NMR spectrum. These results indicated that 1 is 5,7- Esenbeckia species. In this paper the isolation, structural deter- dihydroxy-8-(2,3-epoxy-3-methylbutyl)flavanone (2´,3´´- mination and some biological evaluations of these compounds epoxy-glabranin). Compound 2 had a molecular formula + 1 13 are described. C21H24O7 as deduced from EIMS m/z 370 (M -H2O), H, C NMR and DEPT spectral data. The IR spectrum of 2 indicated the presence of the carbonyl group of a γ-pyrone (1643 cm-1) Results and Discussion and hydroxyl groups (3585-3055 cm-1). The flavanone nucleus was determined by the presence of the AMX system for H-2 δ δ The ethanolic extract of the leaves of E. berlandieri ssp. aca- ( H 5.38, dd, J = 12.7, 3.1) and H-3a ( H 3.09, J = 17.1, 12.7), δ pulcensis was chromatographed on a silica gel column eluted H-3b ( H 2.79, J = 17.1, 3.1), and the hydroxyl at C-4´ was with a n-hexane-EtOAc gradient to give 1-3, together with the evident by the presence of an AA´BB´ proton doublets cen- δ δ known compounds 7-methylglabranin (4) [17], glabranin (5), tered at H 7.37 (2H, d, J = 9 Hz, H-2´, H-6´) and H 6.94 (2H, [18-20], 8-prenylnaringenin (6) [21,22], and 7-methyl-8- d, J = 9 Hz, H-3´, H-5´) in the 1H NMR spectrum, and by the prenylnaringenin (7) [23]. result of the methylation of 3 (vide infra). The 13C NMR sig- 13 δ The totally decoupled C NMR spectrum of 1 (Tables 1 nals at C 90.5, 71.9, 29.7, 25.9 and 23.9 revealed the presence and 2) showed 20 resonances, sorted by DEPT experiments in of a 2,3-dihydroxy-3-methylbutyl group at C-8. Thus, the two methyls, two methylenes, eight methines (six sp2 and two structure of 2 was determined to be 5,4´-dihydroxy-7- sp3 carbon bearing an oxygen atom) and eight quaternary car- methoxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (7- bons (including one carbonyl and one sp3 carbon bearing oxy- methyl-8-(2´´,3´´-dihydroxyprenyl)-naringenin). The IR, 1H and 13C NMR spectra of 3 were similar to gen), deducing a molecular formula of C20H20O5, in agreement with the 1H NMR and the EIMS (M+ 340). The IR spectrum those of 2 except for the absence of a methyl group at C-7, in -1 established the presence of hydroxyl groups (3591-3066 cm ) agreement with the molecular formula C20H22O7 registered by and the carbonyl group of a γ-pyrone (1642 cm-1), 1H-1H NMR EIMS (M+ m/z 374). Reaction of 3 with diazomethane afforded δ δ 2, identical by direct comparison with the natural product, con- COSY correlations between H-2 ( H 5.44) and H-3 ( H 3.07 72 J. Mex. Chem. Soc. 2006, 50(2) Arturo Cano et al. 1 Table 1. H NMR Data (200 MHz, CDCl3) for Compounds 1-3 H 12 3 H-2 5.44 5.38 5.36 (dd, 12.7, 3.2) (dd, 12.9, 3.3) (dd, 12.7, 3.3) H-3eq 2.82 2.79 2.78 (dd, 17.1, 3.2) (dd, 17.1, 3.3) (dd, 17.1, 3.3) H-3ax 3.07 3.09 3.05 (dd, 17.1, 12.7) (dd, 17.1, 12.9) (dd, 17.1, 12.7) H-6 6.04 6.03 6.03 (s) (s) (s) H-1´´ 3.06-2.99 3.09-2.98 3.11-2.99 (m) (m) (m) H-2´´ 4.71 4.69 4.70 (t, 8.9) (dd, 10.2, 2.7) (tq, 8.1, 2.4) H-4´´ 1.21 1.20 1.21 (s) (d, 1.8) (d, 1.8) H-5´´ 1.19 1.33 1.19 (s) (d, 2.4) (d, 1.5) C5-OH 12.10 12.00 12.31 (s) (s) (s)s C7-OCH3 3.86 (s) H-2´, H-6´ 7.47-7.43 ´ H-3´, H-5´ (m) H-4´ H-2´, H-6´ 7.37 7.31 (d, 9.0) (d, 8.4) H-3´, H-5´ 6.94 6.89 (d, 9.0) (d, 8.4) 13 Table 2. C NMR Data (50 MHz, CDCl3) for Compounds 1-3. firming the structure 3. This result was similar to that of the methylation of 6 to afford 7 (vide infra). C1 2 3 The S- configuration at C(2) for compounds 1-3 was assigned following previous observations of the enantiodiffer- 2 79.1 79.0 79.2 entiated biotransformation of chalcones to flavanones by the 3 43.6 43.2 43.5 corresponding enzyme [24,25], establishing that optically 4 195.1 195.4 196.2 active flavanones in higher plants possess S- configuration. 5 165.1 165.2 162.2 Regarding the configuration at C-2´´, it has been previ- 6 91.7 91.6 96.6 7 168.6 168.6 163.6 ously discussed the epoxidation of the prenyl residue proceeds 8 104.8 104.7 106.0 with high stereoselectivity for quinoline alkaloids and 9 157.1 160.1 159.2 coumarins in a given species of the Rutaceae and Umbelliferae 10 103.1 103.1 103.7 [26], and the opening of the epoxide occurs through an acid 1´ 138.0 130.6 130.6 catalyzed reaction not involving the chiral center. However, 2´ 126.1 127.7 127.7 since this is only a working hypothesis, additional arguments 3´ 128.9 114.2 115.4 are necessary to determine the stereochemistry of the chiral 4´ 126.1 157.3 155.8 carbon at the prenyl fragment. 5´ 128.9 114.2 115.4 Methylation of 5 and 6 with diazomethane afforded 4 and 6´ 126.1 127.7 127.5 7, respectively, which were identified by their physicochemi- 1´´ 26.8 29.7 29.5 cal properties.
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