Estudo qu?mico de Luehea speciosa e Ocotea costulatum

• Author(s): Silva, Wilson Dias da
• Date: 2020
• Origin: Oasisbr
• Subject(s): Qu?mica; Qu?mica
• Document Type: Master thesis
• Language: Portuguese

Description

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Coordena??o e Aperfei?oamento de Pessoal de N?vel Superior - CAPES

The present thesis describes the chemical study of two plant species. The ethanolic extract from the wood of Luehea speciosa Willd (Tiliaceae), collected in the Amazon region was fractionated by chromatografic technique. This yielded friedelin (Ls-1w), a mixture of ?-sitosterol, stigmasterol and 24-methylcholesterol (Ls-2W), (1S, 5S, 2R, 6R)-2,6-di(3,4,5-trimethoxyphenyl)-3,7- dioxabicyclo |3,3,0| octane (Ls-3w) and 8-hydroxy-6,7-dimethoxy- 3-methyl-isocoumarin (Ls-4w). These compounds have already been described in the literature. The ethanolic extract from the trunk wood of Ocotea costulatum (Lauraceae), collected in the Amazon region was fractionated by chromatografic technique. This afforded a benzodioxanic neolignan: rel-(7R, 8R) - ?8'-5'-methoxy-3,4,5- trimethoxy-7.0.3',8.0.4' - lignan (oc-1w) and two bicyclo octanoid neolignans: rel-(1R, 3S, 4R, 5S, 6S, 7R)-1-allyl-4- h y d r o x y - 7 - m e t h y l - 3 , 5 - d i m e t h o x y - ( 3 ' , 4 ' - m e t h y l e n e d i o x y - 5 ' - methoxyphenyl) - 8 - oxobicyclo|3,2,1| octane (Oc-2w) and rel- (1S, 4R, 5S, 6S, 7R)-1-allyl-4-hydroxy-7-methyl-3,5-dimethoxy- 6(3',4'-methylenedioxy-5'-methoxyphenyl)-8-oxobicyclo |3,2,1| oct-2-ene (Oc-3w). The compound Oc-3w is a new one. The molecular structures of these compounds were determinea by usual spectrometric techniques (IR, MS, 1H NMR and 13NMR). The structural elucidations involved longrange coupling constant analysis in the 1H NMR spectra and chemical shifts in the 13C NMR spectra. The chemical profile of the families Tiliaceae and Elaeocarpaceae was made by the search in chemical literature

A presente tese versa sobre o estudo qu?mico de duas esp?cies vegetais. O extrato etan?lico da madeira do tronco de Luehea speciosa Willd (Tiliaceae), coletada na regi?o Amaz?nica, foi fracionado por m?todos cromatogr?ficos e forneceu fridelina (Ls-1W), uma mistura de ?-sitosterol, estigmasterol e 24-metilcolesterol (Ls-2W), rel-(1S 5S 2R, 6R)-2,6-di (3, 4 5-trimetoxifenil)-3,7-dioxabiciclo|3,3,0|octano (Ls-3W, e 8-hidroxi- 6,7-dimetoxi-3-metil-isocumarina (Ls-4W). Estas subst?ncias j? se encontram descritas na literatura. O extrato etan?lico da madeira do tronco de Ocotea costulatum Mez. (Lauraceae), coletada na regi?o Amaz?nica, submetido ao fracionamento por t?cnicas cromatogr?ficas forneceu uma subst?ncia pertencente ? classe das neolignanas benzodiox?nicas: rel-(7R, 8R)-?8' -5'-metoxi-3,4,5-trimetoxi-7.0.3',8.0. 4'-lignana (Oc-1w); e duas neolignanas biciclo 13,2,11 oct?nicas: rel-(1R, 3S, 4R, 5S, 6S, 7R)-1-alil-4-hidroxi-7-metil-3,5-dime- toxi-(3',4'-metilenodioxi-5'-metoxifenil)-8-oxobiciclo |3,2,1| octano (Oc-2w) e rel-(1S, 4R, 5S, 6S, 7R)-1-alil-4-hidroxi-7- metil-3,5-dimetoxi-6 (3', 4' -metilenodioxi, 5'-metoxifenil)- 8-oxobiciclo |3,2,1| oct-2-eno (Oc-3w). As subst?ncias Oc-1w e Oc-2W j? se encontram descritas na literatura. A Oc-3w ? in?dita. As estruturas moleculares destas subst?ncias foram determinadas atrav?s de t?cnicas espectrom?tricas usuais (IV, EM, RMN de 1H e RMN de 13C). O perfil qu?mico das fam?lias Tiliaceae e Elaeocarpaceae foi elaborado atrav?s de levantamento bibliogr?fico da literatura qu?mica