Contribuição ao estudo químico de plantas do nordeste brasileiro: Protium heptaphyllum March. e Protium tenuifolium Engl.

Abstract

This work describes the phytochemistry analysis of Protium heptaphyllum March ( 3 irseraceae ) popularly known in Brazil as "almecegueira", "breu-branco verdadeiro" _Amazônia ), "almecegueira cheirosa", "almecegueira de cheiro", "almecegeiro vermelho" , -almecegeiro bravo" and Protium tenuifolium Engl. ( Burseraceae ) popularly known as ~~ "copal", "cope , copal , copá and chutra» . "chutra". Chromatographic analysis of the resin of Protium heptaphyllum led to the isolation of the following substances: monoterpene; p-menth-3-ene-1,2,8-triol (25), triterpenes: [ 3 j3- hidroxy-urs-12-ene (5) e 313-hidroxy-olean-12-ene (6) ] and the 30,160-dihydroxy-urs-12-ene !'). From the ethanol extract of trunks was isolated a cumarin 6-methoxy-7-hidroxycumarin E 17), from hydrolate of mature and green fruits were isolated; a flavonoid: quercetin-3-Orha.mnosyl (26) and a catequin: (-)-epicatequin (27) and from ethanol extract of leaves a flavonoid quercetin (28). Substances 26, 27 and 28 are being reported for the first time in this genus, where as compound (25) are being reported for the first time as natural product. Successive fractionations were used by column in chromatography , exclusion of chromatography and flash chromatography of the ethanol extract of leaves of Protium tem4folium allowed isolation of 1-0-ethylglucose (29) and the flavonoid kaempferol-3-Orhamnosyl (30) and from the ethanol extract of barks 13 - sitosterol glucosideo (31). Essential oils obtained from different plant parts of the two species were characterized CG-MS and evaluated for their antimicrobial activities against several bacteria and fungi and showed significant antimicrobial activities. Were realized test for inhibition of acetylcolinesterase. The mixture of a,13-amyrin was examined for their anti-inflammatory and antinociceptive activities and present a potent anti-inflammatory activity. In virtue of activities presented by a, j3-amirin, some derivatives were prepared, through classic reactions, such as: foi inflation, acetylation, oxidation and sterefication, with objective of evaluated possible activities. It was done also quantitative determination of the mixture of a, j3-amyrin present in the resin, by High performance liquid chromatography iHPLC). Structural determination of the compounds and derivatives was stablished by analysis spectroscopic and spectrometric as: IV, MS, 'H and 13C, NMR including 2D NMR :echniques, and comparison with literature date.