6beta-hydroxymaslinic acid, a triterpene from Vochysia ferruginea

Abstract

Um novo ácido triterpenóide pentacíclico foi isolado a partir de folhas e frutos de Vochysia ferruginea. A estrutura do novo composto foi elucidada por espectroscopia de RMN como sendo o ácido 2α,3β,6β-triidroxiolean-12-en-28-óico (ácido 6β-hidroximaslínico, 1). Além do novo triterpenóide, foram isolados das folhas e frutos o glicosídeo de β-sitosterol e três misturas contendo os triterpenóides conhecidos uvaol e eritrodiol, ácidos ursólico e oleanólico e os ácidos 2α,3β-diidroxiurs-12-en-28-óico e o respectivo isômero oleanólico (ácido maslínico ou cratególico). Nos frutos, a bellericagenina A e o seu éster (28 → 1) β-D-glicopiranosílico (bellericasídeo A) estão presentes em elevados teores.A novel oleane acid was isolated from the leaves and the fruits of Vochysia ferruginea. The structure of the new triterpenoid was elucidated by NMR spectroscopy as 2α,3β,6β-trihydroxyolean-12-en-28-oic acid (6β-hydroxymaslinic acid, 1). In addition, β-sitosterol-glucoside and three mixtures containing known triterpenoids, uvaol and erythrodiol, ursolic and oleanolic acids, 2α,3β-dihydroxyurs-12-en-28-oic acid and its respective oleanolic isomer (maslinic or crategolic acid), were isolated from the leaves and the fruits of Vochysia ferruginea. In the fruits, bellericagenin A and its (28 → 1)β-D-glucopyranosyl ester (bellericaside A) were present in high amount.

Chemical constituents from Terminalia glabrescens

“…These were characterized as n-alkanes in the range between C 18 and C 33 , with a large predominance of chains with odd numbers of carbon atoms, where C 29 and C 31 were found as the main homologues. The isolation of squalene and of the triterpene 2 in the 13 C NMR resonances were in accordance with reported data. 9,11 The alkane composition was determined on the basis of GC-FID retention times and by comparison with authentic standards.…”

“…Compound 1 was obtained as an amorphous solid and its HBBD 13 C NMR spectrum displayed signals for 30 carbon atoms. With the aid of information afforded by the DEPT spectra these signals could be attributed to seven quaternary, six methine, eleven methylene and six methyl carbon atoms.…”

The good and the bad: Alkaloid screening and brineshrimp bioassays of aqueous extracts of 31 medicinal plants of eastern Nicaragua

“…Vochysia ferruginea Mart. (Vochysiaceae) contains fatty acids such as lauric acid, myristic acid, tannins, triterpene such as 6β-hydroxymaslinic acid, polyphenols such as β-sitosterol-glucoside, uvaol, erythrodiol, urosolic acid, oleanolic acid, crategolic acid, bellericagenin A, bellericaside A, betulinic acid (Gibbs, 1974;Zucaro et al, 2000). It is clear, in particular, that V. ferruginea contains a number of cytotoxic compounds, and, thus, not surprisingly, showed bioactivity (e.g., anaesthetic, analgesic, antifungal, antiseptic, bactericide, and anti-inflammatory activities) in many other assays (Gibbs, 1974;Cambie & Ash, 1994;Hess et al, 1995;Calderon et al, 2000Calderon et al, , 2001Zucaro et al, 2000).…”

“…In addition to alkaloids, the four cytotoxic species have been tested in other contexts, and apparently contain other secondary metabolites such as fatty acids, flavanoids, glycosides, phenols, saponins, tannins, and terpenoids (Gibbs, 1974;Cambie & Ash, 1994;Hess et al, 1995;Calderon et al, 2000Calderon et al, , 2001Zucaro et al, 2000). Obviously, these other compounds might have been the source of the cytotoxicity as well as, or instead, of the alkaloids.…”

Análise da variação genética de populações de Vochysia pyramidalis e V. tucanorum por AFLP e da composição de ácidos graxos de sementes

“…Investigações fitoquímicas da fração butanólica identificaram diferentes triterpenóides pentacíclicos como ácido betulínico, eritrodiol, ácido epi-betulínico, e derivados do ácido ursólico e ácido oleanólico, os quais provavelmente conferem a essa planta medicinal a potente ação gastroprotetora. Outros autores (Hess et al, 1995;Hess & Delle Monache, 1999;;Zucaro et al, 2000;Calderón et al, 2001;Weniger et al, 2005;Gaspi, et al, 2006;Hiruma-Lima et al, 2006) já haviam detectado na casca do caule de algumas espécies de Vochysia, terpenóides (ácidos betulínico, serícico e divergióico), esteróides (  sitosterol), saponinas, componentes fenólicos e taninos que, acredita-se, sejam os responsáveis por seu efeito analgésico, por sua ação no sistema nervoso central, apresentando também propriedades anti-inflamatórias, anti-bacterianas e anticonvulsivantes.…”