New diterpenoids from leaves of Guarea macrophylla (Meliaceae)

Abstract

A fase em hexano do extrato etanólico das folhas de Guarea macrophylla (Meliaceae) foi submetida a fracionamento cromatográfico. Esses procedimentos permitiram o isolamento de um novo diterpenóide: 7α-hidroperóxido-isopimara-8(14),15-dieno-2α,3β-diol, um novo norditerpenóide: 19-nor-isopimara-7,15,4(18)-trien-3-ona além de sete diterpenóides de estruturas conhecidas. As estruturas dos compostos isolados foram definidas através de análise dos dados espectrométricos e comparação com aqueles descritos na literatura.The hexane phase from the ethanol extract from leaves of Guarea macrophylla (Meliaceae) was submitted to chromatographic separation. These procedures allowed the isolation of one new diterpenoid: 7α-hydroperoxy-isopimara-8(14), 15-diene-2α,3β-diol, one new nor-diterpenoid: 19-nor-isopimara-7,15,4(18)-trien-3-one besides seven known diterpenoids. Their structures were deduced by analysis of spectrometric data and comparison of data described in the literature.

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

“…two coupled peaks at δ 3.71 (ddd, J = 11.7, 9.6 and 4.2 Hz) and 3.05 (d, J = 9.6 Hz), which could be assigned to H-3α and H-2β. Chemical shift values, splitting patterns, and coupling constants of these signals closely resembled those observed in isopirama-8(14),15-diene-7α-peroxy-2α,3β-diol, previously isolated from leaves of G. macrophylla[11], suggesting the same stereochemistry to C-2 and C-3 in both compounds 13. C and DEPT 135°NMR spectral data confirmed this proposal due to the peaks of sp 2 carbons at δ 150.2 (C-15), 109.3 (C-16), 121.3 (C-7), and 135.2 (C-8) as well as the oxymethine carbons at δ 68.4 (C-2) and 83.7 (C-3).…”

A Comparative Study on Chemical Composition, Antileishmanial and Cytotoxic Activities of the Essential Oils from Leaves of Guarea macrophylla (Meliaceae) from Two Different Regions of São Paulo State, Brazil, Using Multivariate Statistical Analysis

“…[1][2][3][4] Chemically, Meliaceae species produce different classes of secondary metabolites, including terpenoids, lactones, steroids, limonoids, etc., which display several biological activities. 2,4 Belonging to Meliaceae, Guarea macrophylla is composed of triterpenes, 5 diterpenes, 6,7 sesquiterpenes, 6 flavonoids, and lignoids. 8 The essential oils from fruits, 9 stem barks, 10 and leaves 11 were chemically analyzed and a predominance of sesquiterpenes and diterpenes was observed.…”