Artículo
de los A. Mesurado, M.; Arias Cassará, M.L.; Misico, R.; Bardón, A.; Ybarra, M.I.; Cartagena, E. "A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis" (2017) Chemistry and Biodiversity. 14(5)
Estamos trabajando para incorporar este artículo al repositorio
Consulte la política de Acceso Abierto del editor
Abstract:
The new methylated grindelane diterpenoid, 7β-hydroxy-8(17)-dehydrogrindelic acid (1b), together with the known 7α-hydroxy-8(17)-dehydrogrindelic acid (2a), 6-oxogrindelic acid (3a), 4β-hydroxy-6-oxo-19-norgrindelic (4a), 19-hydroxygrindelic acid (5a), 18-hydroxygrindelic acid (6a), 4α-carboxygrindelic acid (7a), 17-hydroxygrindelic acid (8a), 6α-hydroxygrindelic acid (9a), 8,17-bisnor-8-oxagrindelic acid (10a), 7α,8α-epoxygrindelic acid (11a), and strictanonic acid (12a) as methyl esters were obtained from an Argentine collection of Grindelia chiloensis (Cornel.) Cabrera. Their structures and relative configurations were established on the basis of spectroscopic analysis. CHCl3 extract from the aerial parts and their pure compounds were evaluated for their antifungal and depigmenting effects. Methyl ester derivative of 10a (10b) exhibited a remarkable mycelial growth inhibition against Botritis cinerea with an IC50 of 13.5 μg ml−1. While the new grindelane 1b exerted a clear color reduction of the yellow-orange pigment developed by Fusarium oxysporum against UV-induced damage. © 2017 Wiley-VHCA AG, Zurich, Switzerland
Registro:
| Documento: | Artículo |
| Título: | A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| Autor: | de los A. Mesurado, M.; Arias Cassará, M.L.; Misico, R.; Bardón, A.; Ybarra, M.I.; Cartagena, E. |
| Filiación: | Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho, 471, Tucumán, 4000, Argentina Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad de Buenos Aires, C1428EGA, Argentina |
| Palabras clave: | Antifungal and depigmenting effects; Botrytis cinerea; Fusarium oxysporum; Grindelane diterpenoids and derivatives; Grindelia chiloensis; 6 oxogrindelic acid; 7alpha,8alpha epoxygrindelic acid; antifungal agent; azoxystrobin; depigmenting agent; diterpenoid; enilconazole; ester derivative; methyl 17 hydroxygrindelate; methyl 17alpha hydroxy 8(17) dehydrogrindelate; methyl 18 hydroxygrindelate; methyl 19 hydroxygrindelate; methyl 4 beta hydroxy 6 oxo 19 norgrindelate; methyl 4alpha carbomethoxigrindelate; methyl 6alpha ydroxygrindelate; methyl 7beta hydroxy 8(17) dehydrogrindelate; methyl 8,17 bisnor 8 oxagrindelate; methyl strictanoate; unclassified drug; antifungal agent; depigmenting agent; diterpene; ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one; plant extract; antifungal activity; Argentina; Article; Botrytis cinerea; carbon nuclear magnetic resonance; controlled study; dose response; Fusarium oxysporum; Grindelia; Grindelia chiloensis; growth inhibition; heteronuclear multiple bond correlation; heteronuclear multiple quantum coherence; IC50; methylation; mycelial growth; nonhuman; pigmentation; proton nuclear magnetic resonance; ultraviolet radiation; chemical structure; chemistry; drug effects; Fusarium; Grindelia; isolation and purification; nuclear magnetic resonance spectroscopy; Antifungal Agents; Diterpenes; Fusarium; Grindelia; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Skin Lightening Preparations |
| Año: | 2017 |
| Volumen: | 14 |
| Número: | 5 |
| DOI: | http://dx.doi.org/10.1002/cbdv.201600426 |
| Título revista: | Chemistry and Biodiversity |
| Título revista abreviado: | Chem. Biodiversity |
| ISSN: | 16121872 |
| CODEN: | CBHIA |
| CAS: | enilconazole, 35554-44-0; Antifungal Agents; Diterpenes; ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one; Plant Extracts; Skin Lightening Preparations |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16121872_v14_n5_p_delosAMesurado |
Referencias:
- Hoffmann, J.J., Kingsolver, B.E., McLaughlin, S.P., Timmermann, B.N., (1984) Rec. Adv. Phytochem., 18, p. 251
- Del Vitto, L.A., Petenatti, E.M., Petenatti, M.E., (1997) Multequina, 6, p. 49
- Zhou, L., Fuentes, E.R., Hoffmann, J.J., Timmermann, B.N., (1995) Phytochemistry, 40, p. 1201
- Hernández, X.E., Orden, A.A., Giordano, O.S., Kurina, M., (2005) Electron. J. Biotechnol., 8, p. 277
- Lin, S.C., Chein, R.J., (2016) J. Org. Chem., , http://pubs.acs.org/doi/pdfplus/10.1021/acs.joc.6b02766, just accepted manuscript
- Wassner, D., Ravetta, D., (2000) Ind. Crops Prod., 11, p. 7
- Zavala, J.A., Ravetta, D.A., (2002) Plant Ecol., 161, p. 185
- Hoffman, J.J., Kingsolver, B.E., McLaughlin, S.P., Timmermann, B.N., Production of resins by arid-adapted Asteraceae (1984) Phytochemical adaptation to stress, p. 251. , ’, in ‘, ’, Eds., B. N. Timmermann, C. Steelink, F. Loewus, Plenum Publishing Co., New York, NY, p
- Bohlmann, F., Ahmed, M., Borthakur, N., Wallmeyer, M., Jakupovic, J., King, R.M., Robinson, H., (1982) Phytochemistry, 21, p. 167
- Timmermann, B.N., Luzbetak, D.J., Hoffmann, J.J., Jolad, S.D., Schram, K.H., Bates, R.B., Klenck, R.E., (1983) Phytochemistry, 22, p. 523
- Williamson, B., Tudzynski, B., Tudzynski, P., van Kan, J.A., (2007) Mol. Plant Pathol., 8, p. 561
- Joshi, M., Kamat, S.D., Kamat, D.V., (2014) Bionano. Frontier, 7, p. 34
- Arias Cassará, M.L., Borkosky, S.A., González Sierra, M., Bardón, A., Ybarra, M.I., (2010) Chem. Biodiversity, 7, p. 1745
- Guerreiro, E., Kavka, J., Saad, J.R., Oriental, M.A., Giordano, O.S., (1981) Rev. Latinoam. Quím., 12, p. 77
- Timmermann, B.N., Hoffmann, J.J., Jolad, S.D., Schram, K.H., (1985) Phytochemistry, 24, p. 1031
- Timmermann, B.N., Hoffmann, J.J., Jolad, S.D., Bates, R.B., Siahaan, T.J., (1987) Phytochemistry, 26, p. 467
- Mahmoud, A.A., Ahmed, A.A., Tanaka, T., Inuma, M., (2000) J. Nat. Prod., 63, p. 378
- Ahmed, A.A., Mahmoud, A.A., Ahmed, U.M., El-Bassuony, A.A., El-Rask, M.H., Pare, P.W., Kaechesy, J., (2001) J. Nat. Prod., 64, p. 1365
- Holme, D., Sorensen, N.A., (1954) Acta Chem. Scand., 8, p. 34
- Jakupovic, J., Baruah, R.N., Zdero, C., Eid, F., Eid, V.P., Pathak, V.P., Chau-Thi, V., Robinson, H., (1986) Phytochemistry, 25, p. 1873
- Rose, A.F., Jones, K.C., Haddon, W.F., Dreyer, D.L., (1981) Phytochemistry, 20, p. 2249
- Mangoni, L., Belardini, M., (1962) Gazz. Chim. Ital., 92, p. 983
- Hoffmann, P.J., Jolad, S.D., Timmermann, B.N., Bates, R.B., Camou, F.A., (1988) Phytochemistry, 27, p. 493
- Viswanath, B., Rajesh, B., Janardhan, A., Kumar, A.P., Narasimha, G., (2014) Enzyme Res., , http://dx.doi.org/10.1155/2014/163242
- Kopeć, W., Telenius, J., Khandelia, H., (2013) FEBS J., 280, p. 2785
- Gilabert, M., Ramos, A.N., Schiavone, M.M., Arena, M.E., Bardón, A., (2011) J. Nat. Prod., 74, p. 574
- Amaya, S., Pereira, J.A., Borkosky, S.A., Valdez, J.C., Bardón, A., Arena, M.E., (2012) Phytomedicine, 19, p. 173
- Gershenzon, J., Dudareva, N., (2007) Nat. Chem. Biol., 3, p. 408
- Tatum, J.H., Baker, R.A., Berry, R.E., (1985) Phytochemistry, 24, p. 457
- Sánchez-Calvo, J.M., Barbero, G.R., Guerrero-Vásquez, G., Durán, A.G., Macías, M., Rodríguez-Iglesias, M.A., Molinillo, J.M.G., Macías, F.A., (2016) Med. Chem. Res., 25, p. 1274
- Valderrama, J.A., Leiva, H., Rodriguez, J.A., Theoduloz, C., Schmeda-Hirshmann, G., (2008) Bioorg. Med. Chem., 16, p. 3687
- Rohnert, U., Heiser, I., Nemec, S., Baker, R., Osswald, W., Elstner, E.F., (1998) J. Plant Physiol., 153, p. 684
- González-Sierra, M., Olivieri, A.C., Colombo, M.I., Rúveda, E.A., (1989) J. Chem. Soc., Perkin Trans., 1, p. 1393
- González Sierra, M., Colombo, M.I., Olivieri, A.C., Zudenigo, M.E., Ruveda, E.A., (1984) J. Org. Chem., 49, p. 4984
- Hoffmann, J., McLaughlin, S.P., Jolad, S.D., Schram, K., Tempesta, M.S., Bates, R.B., (1982) J. Org. Chem., 47, p. 1725
- Rose, A.F., (1980) Phytochemistry, 19, p. 2689
- Olivieri, A.C., González-Sierra, M., Rúveda, E.A., (1986) J. Org. Chem., 51, p. 2824
- González-Sierra, M., Colombo, M.I., Zudenigo, M.E., Rúveda, E.A., (1984) Phytochemistry, 23, p. 1685
Citas:
---------- APA ----------
de los A. Mesurado, M., Arias Cassará, M.L., Misico, R., Bardón, A., Ybarra, M.I. & Cartagena, E. (2017) . A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis. Chemistry and Biodiversity, 14(5).http://dx.doi.org/10.1002/cbdv.201600426
---------- CHICAGO ----------
de los A. Mesurado, M., Arias Cassará, M.L., Misico, R., Bardón, A., Ybarra, M.I., Cartagena, E. "A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis" . Chemistry and Biodiversity 14, no. 5 (2017).http://dx.doi.org/10.1002/cbdv.201600426
---------- MLA ----------
de los A. Mesurado, M., Arias Cassará, M.L., Misico, R., Bardón, A., Ybarra, M.I., Cartagena, E. "A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis" . Chemistry and Biodiversity, vol. 14, no. 5, 2017.http://dx.doi.org/10.1002/cbdv.201600426
---------- VANCOUVER ----------
de los A. Mesurado, M., Arias Cassará, M.L., Misico, R., Bardón, A., Ybarra, M.I., Cartagena, E. A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis. Chem. Biodiversity. 2017;14(5).http://dx.doi.org/10.1002/cbdv.201600426
