Abstract:
A detailed chemical study of the aerial parts and rhizomes of Hyalis argentea var. latisquama yielded a variety of sesqui- and diterpenes. In total, 26 compounds were isolated and identified, of which four are new, namely, two ent-kaurenes (1 and 2), a diterpene lactone (3), and a lindenanolide (4). The previously reported compounds included a series of lindenanolides, guaianolides, elemanolides, and additional diterpenes. The antifungal activity of the isolated compounds was tested against Cryptococcus neoformans and Candida albicans. Among the isolated compounds, the lindenanolides were the only structural class that showed strong antifungal activity, and onoseriolide acetate (5) was the most active. On the other hand, the isolated guaianolides were only moderately active, while the diterpenes did not show significant antifungal activity. © 2014 The American Chemical Society and American Society of Pharmacognosy.
Registro:
Documento: |
Artículo
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Título: | Antifungal terpenoids from Hyalis argentea var. latisquama |
Autor: | Fernández, L.R.; Butassi, E.; Svetaz, L.; Zacchino, S.A.; Palermo, J.A.; Sánchez, M. |
Filiación: | UMYMFOR, Departamento de Química Orgánica, Universidad de Buenos Aires, CP1428, Buenos Aires, Argentina Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, CP2000, Rosario, Argentina
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Palabras clave: | 8alpha,9alpha exposyonoseriolide acetate; amphotericin B; ent 7alpha hydroxy 15 oxokauran 19 beta dextro glucopyranosyl ester; ent 7alpha,15beta dihydroxykaur 16 ene 19 beta dextro glucopyranosyl ester; hyalic acid beta dextro glucopyranosyl ester; terpenoid derivative; unclassified drug; antifungal activity; article; Candida albicans; controlled study; Cryptococcus neoformans; drug identification; drug isolation; fungus growth; growth inhibition; Hyalis latisquama; medicinal plant; nonhuman; rhizome; Antifungal Agents; Asteraceae; Candida albicans; Cryptococcus neoformans; Diterpenes, Kaurane; Molecular Structure; Sesquiterpenes; Sesquiterpenes, Guaiane |
Año: | 2014
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Volumen: | 77
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Número: | 7
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Página de inicio: | 1579
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Página de fin: | 1585
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DOI: |
http://dx.doi.org/10.1021/np500032u |
Título revista: | Journal of Natural Products
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Título revista abreviado: | J. Nat. Prod.
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ISSN: | 01633864
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CODEN: | JNPRD
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CAS: | amphotericin B, 1397-89-3, 30652-87-0
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v77_n7_p1579_Fernandez |
Referencias:
- (2013), http://www.catalogueoflife.org/col/details/species/id/14577840, Catalogue of Life Home Page. (accessed Dec 1); Panero, J.L., Funk, V.A., (2008) Mol. Phylogenet. Evol., 47, pp. 757-782
- Ybarra, M.I., Borkosky, S.A., Catalán, C.A.N., Cerda-García-Rojas, C.M., Joseph-Nathan, P., (1997) Phytochemistry, 44, pp. 479-483
- Bohlmann, F., Zdero, C., King, R.M., Robinson, H., (1980) Phytochemistry, 19, pp. 689-691
- Bittner, M., Jakupovic, J., Bohlmann, F., Silva, M., (1989) Phytochemistry, 28, pp. 271-273
- Bohlmann, F., Zdero, C., Robinson, H., King, R.M., (1981) Phytochemistry, 20, pp. 1631-1634
- Bohlmann, F., Jakupovic, J., Hartono, L., King, R.M., Robinson, H., (1985) Phytochemistry, 24, pp. 1100-1101
- Hikino, H., Meguro, K., Kusano, G., Takemoto, T., (1964) Chem. Pharm. Bull., 12, pp. 632-634
- Romo De Vivar, A., Cabrera, A., Ortega, A., Romo, J., (1967) Tetrahedron, 23, pp. 3903-3907
- Bohlmann, F., Chen, Z.-L., (1982) Phytochemistry, 21, pp. 2120-2122
- Singhal, A.K., Chowdhury, P.K., Sharma, R.P., Baruah, J.N., Herz, W., (1982) Phytochemistry, 21, pp. 462-463
- Miyase, T., Kuroyanagi, M., Noro, T., Ueno, A., Fukushima, S., (1985) Chem. Pharm. Bull., 33, pp. 4445-4450
- Li, X., Liu, J., Cai, J., Cai, P., (2008) Magn. Reson. Chem., 46, pp. 1070-1073
- Nishimura, K., Miyase, T., Ueno, A., Noro, T., Kuroyanagi, M., Fukushima, S., (1986) Phytochemistry, 25, pp. 2375-2379
- Herz, W., Sharma, R.P., (1976) J. Org. Chem., 41, pp. 1021-1026
- Yamasaki, K., Kohda, H., Kobayashi, T., Kasai, R., Tanaka, O., (1976) Tetrahedron Lett., 13, pp. 1005-1008
- Hu, X.-Y., Luo, Y.-G., Chen, X.-Z., Zhuo, L., Zhang, G.-L., (2008) J. Asian Nat. Prod. Res., 10, pp. 125-131
- Yamasaki, K., Kohda, H., Kobayashi, T., Kaneda, N., Kasai, R., Tanaka, O., Kosaburo, N., (1977) Chem. Pharm. Bull., 25, pp. 2895-2899
- Batista, R., Garcia, P.A., Castro, M.A., Del Corral, J.M., Feliciano, A.S., De Oliveira, A.B., (2010) An. Acad. Bras. Cienc., 82, pp. 823-831
- Sartori, M., Pretto, J., Cruz, A., Bresciani, F., Yunes, R., Sortino, M., Zacchino, S., Cechinel Filho, V., (2003) Pharmazie, 58, pp. 567-569
- Jurd, L., King Jr., A.D., Mihara, K., (1971) Phytochemistry, 10, pp. 2965-2970
- (2008) Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Approved Standard, 28, pp. 1-25. , Clinical and Laboratory Standards Institute. (CLSI document M27-A3), 3 rd ed. Clinical and Laboratory Standards Institute; NCCLS: Wayne, PA, Vol
- Pfaller, M.A., Diekema, D., (2007) Clin. Microbiol. Rev., 20, pp. 133-163
- Espinel Ingroff, A., (2008) Rev. Iberoamer. Micol., 25, pp. 101-106
- Calugi, C., Trabocchi, A., Guarna, A., (2011) Expert Opin. Ther. Pat., 21, pp. 381-397
- Butts, A., Krysan, D.J., (2012) PLoS Pathog., 8, p. 1002870
- Rahalison, L., Hamburger, M., Hostettmann, K., Monod, M., Frenk, E., (1991) Phytochem. Anal., 2, pp. 199-203
- Orabi, K.Y., Walker, L.A., Clark, A.M., Hufford, C.D., (2000) J. Nat. Prod., 63, pp. 685-687
- Castelli, M.V., Butassi, E., Monteiro, M.C., Svetaz, L., Vicente, F., Zacchino, S., (2014) Expert Opin. Ther. Pat., 24, pp. 323-338
- Cosenza, V.A., Navarro, D.A., Fissore, E.N., Rojas, A.M., Stortz, C.A., (2014) Carbohydr. Polym., 102, pp. 780-789
Citas:
---------- APA ----------
Fernández, L.R., Butassi, E., Svetaz, L., Zacchino, S.A., Palermo, J.A. & Sánchez, M.
(2014)
. Antifungal terpenoids from Hyalis argentea var. latisquama. Journal of Natural Products, 77(7), 1579-1585.
http://dx.doi.org/10.1021/np500032u---------- CHICAGO ----------
Fernández, L.R., Butassi, E., Svetaz, L., Zacchino, S.A., Palermo, J.A., Sánchez, M.
"Antifungal terpenoids from Hyalis argentea var. latisquama"
. Journal of Natural Products 77, no. 7
(2014) : 1579-1585.
http://dx.doi.org/10.1021/np500032u---------- MLA ----------
Fernández, L.R., Butassi, E., Svetaz, L., Zacchino, S.A., Palermo, J.A., Sánchez, M.
"Antifungal terpenoids from Hyalis argentea var. latisquama"
. Journal of Natural Products, vol. 77, no. 7, 2014, pp. 1579-1585.
http://dx.doi.org/10.1021/np500032u---------- VANCOUVER ----------
Fernández, L.R., Butassi, E., Svetaz, L., Zacchino, S.A., Palermo, J.A., Sánchez, M. Antifungal terpenoids from Hyalis argentea var. latisquama. J. Nat. Prod. 2014;77(7):1579-1585.
http://dx.doi.org/10.1021/np500032u