Evaluation of biological potential of natural piperolídeos of Piper malacophyllum (C. Presl) C. DC. and synthetic analogues / Avaliação do pontencial biológico de piperolídeos naturais de Piper malacophyllum (C. Presl) C. DC. e de análogos sintéticos

AUTOR(ES)
DATA DE PUBLICAÇÃO

2008

RESUMO

Based on the powerful antifungal activity of piperolides (1 e 2) isolated from Piper malacophyllum leaves extracts, several analogues were synthesized aiming at establishing preliminary structure-activity relationship against Cladosporium cladosporioides, C. sphaerospermum and against epimastigote form of Trypanosoma cruzi. Phytochemical studies carried out on methanolic extract from leaves indicated butenolides 1 e 2 as major compounds in addition to two sesquiterpenes [shizukaacoradienol acetate (4) (new compound) and shizuka-acoradienol (5)] and two alkenylphenyl compounds [5-[(3E)-oct-3-en-1-yl]-1,3-benzodioxole (3) (new compound) and gibbilimbol B (6)]. The last two were detected as major compounds in the root, stem and fruit extracts. The alkenylbenzene 3 was also found as the major product in the essential oil from leaves. One validated method based on micellar electrokinetic chromatography (MEKC) was developed to analyse and validated the amount of butenolides the in P. malcophyllum leaves extracts. The butenolides 7-20, 22 e 23 were prepared by condensation of 4-methoxyfuran-2(5H)-one (24) with several benzaldehydes. The natural and synthetic piperolides were found as a promissing antifungal class against C. sphaerospermum and C. cladosporioides, although no trypanocidal activity was observed.

ASSUNTO(S)

piperales (avaliação) capillary electrophoresis synthetic analogues piper malacophyllum piper malacophyllum eletroforese capilar natural products antifungal and trypanocidal produtos naturais (análise) análogos sintéticos antifúngico e tripanocida piperolídeos piperolides metabólitos secundários

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