Triterpenes From The Flowers Of Gochnatia Polymorpha Subsp. Floccose

Phytochemical study of the flowers of Gochnatia polymorpha subsp. floccosa, Asteraceae, yielded eleven known triterpenes identified as lupeol, lupeyl acetate, lupeyl palmitate, taraxasterol, taraxasteryl acetate, pseudotaraxasterol, pseudotaraxasterol acetate, α-amyrin, α-amyryl palmitate, β-amyrin and β-amyryl palmitate, along with sitosterol, stigmasterol, palmitic and stearic acids. These compounds are been reported for the first time in the species. The compounds were identified by analysis of NMR spectra (1H, 13C and DEPT), GC-MS and comparison with literature data. Previous work have reported the isolation of triterpenes, diterpenes, sesquiterpenes, flavonoids, coumarins and phenolic compounds from aerial parts and roots from G. polymorpha.213556559Adams, R.P., Identification of Essential Oils Components by Gas Chromatography/ Mass Spectrometry (2007) Allured Publ. Corp, , Carol Stream, ILBohlmann, F., Zdero, C., Schmeda-Hirschmann, G., Jakupovic, J., Dominguez, X.A., King, R.M., Robinson, H., Dimeric guainolides and other constituents from Gochnatia species (1986) Phytochemistry, 25, pp. 1175-1178Cabrera, A.L., Klein, R.M., Compostas - tribo mutisiae (1973) Itajaí: Herbário Barbosa-Rodrigues, pp. 29-35. , In: Reitz R (org.)Catalan, C.A.N., Borkosky, S.A., Joseph-Nathan, P., The secondary metabolite chemistry of the subtribe Gochnatiinae (tribe Mutisieae, family Compositae) (1996) Biochem Syst Ecol, 24, pp. 659-718Catalan, C.A.N., Vega, M.I., Lopez, M.E., Cuenca, M.R., Gedris, T.E., Herz, W., Coumarins and a kaurane from Gochnatia polymorpha ssp polymorpha from Paraguay (2003) Biochem Syst Ecol, 31, pp. 417-422Correia, S.J., David, J.M., Silva, E.P., David, J.P., Lopes, L.M.X., Guedes, M.L.S., Flavonóides, norisoprenoides e outros terpenos das folhas de Tapira guianensis (2008) Quim Nova, 3, pp. 2056-2059Diaz, G., Nogueira, M.A., Olguin, C.F.A., Somensi, A., Vidotti, G.J., Estudo fitoquímico e biológico de Vernonia tweediana Baker (Asteraceae) (2008) Lat Am J Pharm, 27, pp. 56-61Farias, A.C.M., Silva, A.J.R., Tomassini, T.C.B., Constituents of Mochinea polymorpha (1984) J Nat Prod, 47, pp. 363-364Gallegos, R.S., Roque, N.F., Análise de misturas de triterpenos por RMN 13C (1990) Quim Nova, 13, pp. 278-281Goulart, M.O.F., Santana, A.E.G., Lima, R.A., Cavalcante, S.H., Carvalho, M.G., Braz-Filho, R., Fitoconstituintes químicos de Jatropha elliptica. Atribuição dos deslocamentos químicos dos átomos de carbono e hidrogênio dos diterpenos jatrofolonas A e B (1993) Quim Nova, 16, pp. 95-100Lima, M.C.L., Lemos, T.L.G., Braz-Filho, R., Pessoa, O.D.L., Chemical constituents from the flowers of Gochnatia blanquetiana (DC) Cabrera (2003) Rev Latinoam Quim, 31, pp. 85-88Lima, S.R., Oliveira, G.S., Morais, S.A.L., Nascimento, E.A., Chang, R., Estudo dos constituintes macromoleculares, extrativos voláteis e compostos fenólicos da Madeira de candeia - Moquinia polymorpha (Less) DC (2007) Cien Florestal, 17, pp. 145-155Mahato, S.B., Kundu, A.P., 13C NMR spectra of pentacyclic triterpenoids - a compilation and some salient features (1994) Phytochemistry, 37, pp. 1517-1575Mendes, C.C., Cruz, F.G., David, J.M., Nascimento, I.P., David, J.P., Triterpenos esterificados com ácidos graxos e ácidos triterpênicos isolados de (1999) Byrsonima Microphylla. Quim Nova, 22, pp. 185-188Moreira, A.S., Spitzer, V., Schapoval, E.E.S., Schenkel, E.P., Antiinflammatory activity of extracts and fractions from the leaves of gochnatia polymorpha (2000) Phytother Res, 14, pp. 638-640Sacilotto, A.C.B., Vichnewski, W., Herz, W., Ent-kaurene diterpenes from Gochnatia polymorpha var (1997) Polymorpha. Phytochemistry, 44, pp. 659-661Silva, J.R.A., Rezende, C.M., Pinto, A.C., Pinheiro, M.L.B., Cordeiro, M.C., Young, C.M., Bolzani, V.S., Ésteres triterpênicos de Himatanthus sucuuba (Spruce) Woodson (1998) Quim Nova, 21, pp. 702-704Stefanello, M.E.A., Cervi, A.C., Wisniewski-Jr., A., Simionatto, E.L., Óleo essencial de Gochnatia polymorpha (Less) Cabr. ssp. floccosa Cabr (2006) Quim Nova, 29, pp. 999-1002Stefanello, M.E.A., Salvador, M.J., Ito, I.Y., Macari, P.A.T., Avaliação da atividade antimicrobiana e citotóxica de extratos de Gochnatia polymorpha ssp (2006) Floccosa. Rev Bras Farmacogn, 16, pp. 525-53

Bioactivity-guided Isolation Of Cytotoxic Sesquiterpene Lactones Of Gochnatia Polymorpha Ssp. Floccosa

Phytochemical study of Gochnatia polymorpha (Less) Cabr. ssp. floccosa Cabr. trunk bark, guided by antiproliferative assays on 10 human cancer cell lines and the VERO cell line, yielded six known compounds identified as the triterpene bauerenyl acetate, the guaianolide 11α,13-dihydrozaluzanin C and the dimeric guaianolides 10-desoxygochnatiolide A, gochnatiolide A, 8-hydroxi-10-desoxygochnatiolide A and 8-hydroxigochnatiolide A. Extracts, fractions of extracts and isolated compounds were tested in vitro against a panel of human cancer cell lines, including U251 (glioma, CNS), UACC-62 (melanoma), MCF-7 (breast), NCI-ADR/RES (drug-resistant ovarian), 786.0 (kidney), NCI-H460 (lung, no small cells), PC-3 (prostate), OVCAR-3 (ovarian), HT-29 (colon), K562 (leukemia) and against the VERO no cancer cell line. Bauerenyl acetate was inactive, while 11α,13-dihydrozaluzanin C showed weak activity against UACC62 and the VERO cell line. The most active compounds were 10-desoxygochnatiolide A and gochnatiolide A, which inhibited the growth of kidney, melanoma, ovarian-resistant and glioma cell lines with values of TGI (total growth inhibition) varying 0.21-1.09 μg/mL. This is the first report about cytotoxic activity of dimeric lactones against cell lines. Copyright © 2011 John Wiley & Sons, Ltd.26710531056Bohlmann, F., Ahmed, M., Jakupovic, J., King, R.M., Robinson, H., Dimeric sesquiterpene lactones and kolavane derivatives from Gochnatia paniculata (1983) Phytochemistry, 22, pp. 191-195Bohlmann, F., Chen, Z., Guaianolides from Ainsliaea fragrans (1982) Phytochemistry, 21, pp. 2120-2122Bohlmann, F., Zdero, C., Schmeda-Hirschmann, G., Dimeric guainolides and other constituents from Gochnatia species (1986) Phytochemistry, 44, pp. 1175-1178. , et alCatalan, C., Vega, M.I., Lopez, M.L., Cuenca, M.R., Gedris, T.E., Herz, W., Coumarins and a kaurane from Gochnatia polymorpha ssp. polymorpha from Paraguay (2003) Biochem Syst Ecol, 31, pp. 417-422Farias, A.C.M., Silva, A.J.R., Tomassini, T.C.B., Constituents of Mochinea polymorpha (1984) J Nat Prod, 47, pp. 363-364Katinas, L., Pruski, J., Sancho, G., Telleria, M.C., The subfamily Mutisioideae (Asteraceae) (2008) Bot Rev, 74, pp. 469-716Moreira, A.S., Spitzer, V., Schapoval, E.E., Schenkel, E.P., Anti-inflammatory activity of extracts and fractions from the leaves of Gochnatia polymorpha (2000) Phytother Res, 14, pp. 638-640Piornedo, R.R., Souza, P., Stefanello, M.E.A., Strapasson, R.L.B., Zampronio, A.R., Kassuya, C.A.L., Anti-inflammatory activity of extracts and 11,13-dihydrozaluzanin C from Gochnatia polymorpha ssp. floccosa trunk bark in mice (2011) J Ethnopharmacol, 133, pp. 1077-1084Sacilotto, A.C.B., Vichnewski, W., Herz, W., Ent-kaurane diterpenes from Gochnatia polymorpha var. polymorpha (1997) Phytochemistry, 44, pp. 659-661Schlemper, V., Freitas, S.A., Schlemper, S.E.M., Antispasmodic effects of hydroalcoholic extract from Gochnatia polymorpha ssp. floccosa in the guinea pig ileum (2011) Res J Med Plant, 5, pp. 288-294Skehan, P., Storeng, R., Scudiero, D., New colorimetric cytotoxicity assay for anticancer-drug screening (1990) J Natl Cancer Inst, 82, pp. 1107-1118Silva, L.B., Strapasson, R.L.B., Riva, D., Salvador, M.J., Stefanello, M.E.A., Triterpenes from the flowers of Gochnatia polymorpha ssp. floccosa (Asteraceae) (2011) Braz J Pharmacogn, , DOI: 10.1590/S0102-695X2011005000031Stefanello, M.E.A., Salvador, M.J., Ito, I.Y., MacAri, P.A.T., Evaluation of antimicrobial and cytotoxic acitivity of extracts from Gochnatia polymorpha ssp. floccosa (2006) Braz J Pharmacogn, 16, pp. 525-530Zhang, S., Won, Y., Ong, C., Shen, H., Anti-cancer potential of sesquiterpene lactones: Bioactivity and molecular mechanisms (2005) Curr Med Chem, 5, pp. 239-24