Estudo fitoquimico do epicarpo de Hymenaea courbaril var. altissima : sintese de derivados odoriferos do tipo ambar-gris e sesquiterpenos da classe drimano a partir do (-)-acido ozico

AUTOR(ES)

Rosana Aparecida Giacomini

DATA DE PUBLICAÇÃO

2002

RESUMO

Hexanic extract of the epicarp of Hymenaea courbaril var. altissima furnished, after esterification with diazomethane, methyl esters of ozic, isoozic, kolavenic e zanzibadc acids. These diterpene acids belong to the ent-labdanic series and were also isolated, in addition, the sesquiterpenes a-copaene, caryophyllene oxide and spatulenol. We have observed that the composition of the hexanic extract of epicarp for a period of four years, and we have demonstrated that resin is one of the most important source of ozic acid (36 at 46%). This ozic acid was used as starting material in all of our synthetic investigations. We have synthesised the ambergris-type odorants ent-Ambrox®, ent-isoambrox, ent-8-norisoambrox and ent-8-norisoambrox from ozic acid. The last two odorants have not been described yet in the enantiomeric series. Similarly, we wave investigated the synthesis of a marine nor-12-sesquiterpene of drimane class and accomplished the synthesis of three homologues of it. All synthesised compounds were submitted to biologic tests, nominally bioauthography and Artemia salina citotoxicity. The most active compounds were the three marine nor-12-sesquiterpene homologues, which shown moderate LC50.

ASSUNTO(S)

sesquiterpenos

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