Estudo fitoquímico da madeira de Guarea macrophylla (Meliaceae)

Abstract

Recebido em 2/12/08; aceito em 26/5/09; publicado na web em 30/10/09 PHYTOCHEMICAL STUDY OF THE WOOD FROM Guarea macrophylla (MELIACEAE). In the present work, the crude ethanol extract from wood of G. macrophylla was submitted to liquid/liquid partition between hexane, CH 2 Cl 2 , EtOAc and n-BuOH. Each phase was individually chromatographed over silica gel, Sephadex LH-20 or Amberlite XAD-2 to give eight terpene derivatives, such as five sesquiterpenoids (caryophyllene oxide, guai-6-en-10b-ol, spathulenol, aromadendrane-4b,10a-diol and aloaromadendrane-4a,10b-diol) as well as three triterpenoids (cicloart-24-ene-3b,23(R*)-diol, cicloart-24-ene-3b,23(S*)-diol, and cicloart-23E-ene-3b,25-diol). Additionally, were isolated three fatty acids (linolenic, linoleic and stearic), two steroids (sitosterol and stigmasterol) and sacarose. The structures of all these compounds were characterized by spectrometric analysis, mainly mass spectrometry and NMR and comparison of these data described in the literature.

Terpenoids from Leaves of Guarea macrophylla Display In Vitro Cytotoxic Activity and Induce Apoptosis In Melanoma Cells

“…The structures of the isolated compounds (▶ Fig. 1) were fully characterized by NMR and MS data analysis as well as by comparison with those reported in the literature [3,6].…”

Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)

“…8 Previous phytochemical investigations have shown the presence of sesqui-, di-and triterpenes in its leaves and barks, besides the chemical composition of volatile oil. 9 Despite the large number of chemical studies conducted on the Meliaceae family, there are few reports concerning the identification of phenolic compounds in this family and no reports on this type of secondary metabolites in Guarea are available. 10 Therefore, in order to contribute to the study of the phenolic composition in the Meliaceae family, we report the phytochemical analysis of the n-BuOH extract from leaves of G. macrophylla and the identification of flavonoids glycosides (quercetin 3-O-b-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-b-Dglucopyranoside) for the first time in the genus Guarea plus a neolignan glucoside (dehydrodiconiferyl alcohol 4-b-D-glucoside) for the first time in the Meliaceae family.…”

Drimanes from Drimys brasiliensis with leishmanicidal and antimalarial activity

“…The fractionation of the chloroform extract of the stem bark led to the isolation of five compounds, which were identified as spathulenol ( Figure, compound 1), which is an aromadendrane sesquiterpene and the drimanes polygodial ( Figure, The column chromatography of the chloroform extracts yielded the isolation of principally fatty alcohols and acids from the branches and fatty alcohols and acids and a mixture of the lignans α and β-cubebin from the leaves. The compounds were characterised by H 1 and C 13 NmR and comparison of the NmR spectra with previously reported data , Lago & Roque 2009.…”