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

Essential Oils From Neotropical Myrtaceae: Chemical Diversity And Biological Properties

Myrtaceae family (121 genera, 3800-5800 spp.) is one of the most important families in tropical forests. They are aromatic trees or shrubs, which frequently produce edible fruits. In the neotropics, ca. 1000 species were found. Several members of this family are used in folk medicine, mainly as an antidiarrheal, antimicrobial, antioxidant, cleanser, antirheumatic, and anti-inflammatory agent and to decrease the blood cholesterol. In addition, some fruits are eaten fresh or used to make juices, liqueurs, and sweets very much appreciated by people. The flavor composition of some fruits belonging to the Myrtaceae family has been extensively studied due to their pleasant and intense aromas. Most of the essential oils of neotropical Myrtaceae analyzed so far are characterized by predominance of sesquiterpenes, some with important biological properties. In the present work, chemical and pharmacological studies carried out on neotropical Myrtaceae species are reviewed, based on original articles published since 1980. The uses in folk medicine and chemotaxonomic importance of secondary metabolites are also briefly discussed. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.817394Wilson, P.G., O'Brien, M.M., Gadek, P.A., Quinn, C.J., (2001) Am. J. Bot., 88, p. 2013Conti, E., Litt, A., Wilson, P.G., Graham, S.A., Briggs, B.G., Johnson, L.A.S., Sytsma, K.J., (1997) Syst. Bot., 22, p. 629Wilson, P.G., O'Brien, M.M., Heslewood, M.M., Quinn, C.J., (2005) Plant Syst. Evol., 251, p. 3Lucas, E.J., Belsham, S.R., Lughadha, E.M.N., Orlovich, D.A., Sakuragui, C.M., Chase, M.W., Wilson, P.G., (2005) Plant Syst. Evol., 251, p. 35Barroso, G.M., Perón, V., Myrtaceae (1994) Reserva Ecológica de Macaé de Cima, Nova Friburgo, RJ. Aspectos Florísticos das Espécies Vasculares, 1, pp. 261-302. , Eds. M. P. M. Lima, R. R. 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Antioxidant Capacity And Phenolic Content Of Four Myrtaceae Plants Of The South Of Brazil

Antioxidant compounds can be useful to prevent several degenerative diseases or as preservative in food and toiletries. Species of the Myrtaceae family are able to accumulate phenolic substances and those are closely related to the antioxidant activity due to their capacity to scavenge free radicals, protect against lipid peroxidation and quench reactive oxygen species. These facts prompted us to investigate the antioxidant capacity of the ethanolic extracts of the leaves of four Myrtaceae plants collected of the south of Brazil: Eugenia chlorophylla O. Berg., Eugenia pyriformis Cambess, Myrcia laruotteana Cambess and Myrcia obtecta (Berg) Kiacrsk. The antioxidant potential was performed using the DPPH (a single electron transfer reaction based assay) and ORAC (Oxygen Radical Absorbance Capacity, a hydrogen atom transfer reaction based assay) assays. Moreover, the total soluble phenolic content was also measured using the Folin-Ciocalteu reagent. A preliminary evaluation of the ethanolic extracts of these Myrtaceae plants revealed high levels of phenolic compounds (343.7-429.3 mg GAE) as well as high antioxidant activity according to both methods (1338 a 3785 μmol of TE/g of extract in ORAC and SC 50 in the range of 1.70 and 33.7 μg/mL in the DPPH). The highest antioxidant activity obtained by DPPH assay was exhibited by ethanol extract of the leaves of E. pyriformis (1.70 μg/mL), followed by extracts of M. laruotteana (3.38 μg/mL) and M. obtecta (6.66 μg/mL). In comparison with controls, in the DPPH assay, the extract of E. pyriformis was more active than trolox (SC 50 = 2.55 μg/mL), while the extracts of M. laruotteana and M. obtecta were more actives than quercetin (SC 50 = 7.80 μg/mL). In the ORAC assay, all species also show good antioxidant capacity (> 1000 μmol of TE/g). Initial HPLC-UV/DAD and ESI-MS confirmed the presence of phenolic acids constituents in the ethanol extracts. 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