Xanthones from Vismia latifolia

Abstract

Este trabalho relata o isolamento e a identificação de uma nova xantona, 1,4,8-triidroxixantona (1,4,8-triidroxi-9H-xanten-9-ona), isolada das raízes de Vismia latifolia (Guttiferae). Quatro outras xantonas conhecidas também foram isoladas: 1,5-diidroxi-8-metoxixantona, 1,7-diidroxixantona, 1,6-diidroxi-7-metoxixantona e 1,3,5,6-tetraidroxixantona, sendo as duas últimas inéditas no gênero Vismia. As estruturas foram estabelecidas através das técnicas de espectroscópicas de UV, IV, EM e RMN (1D e 2D).A new xanthone,1,4,8-trihydroxyxanthone (1,4,8-trihydroxy-9H-xanthen-9-one), was isolated from the roots of Vismia latifolia (Guttiferae). Four other known xanthones were isolated: 1,5-dihydroxy-8-methoxyxanthone, 1,7-dihydroxyxanthone, 1,6-dihydroxy-7-methoxyxanthone and 1,3,5,6-tetrahydroxyxanthone. The last two compounds were isolated for the first time from a Vismia species. The structures were established by UV, IR, MS, 1D and 2D NMR spectroscopic techniques.

Bioactive compounds and scavenging capacity of extracts from different parts ofVismia caulifloraagainst reactive oxygen and nitrogen species

“…The glycosylation position of each sugar moiety was not assigned in this study, since, in principle, any of the hydroxyl groups in phenolic compounds can be glycosylated, but certain positions are favored: for example, the 7-hydroxyl group in flavones, flavanones, and isoflavones; the 3-and 7-hydroxyls in flavonols and flavanols; and the 3-and 5-hydroxyls in anthocyanidins are common glycosylation sites (Cuyckens & Claeys, 2004) À , corresponding to a loss of catechin or epicatechin, and these patterns match those previously reported (Dou et al, 2007). Peaks 28 and 29 presented [M-H] À at m/z 287 and 257, respectively, with UV-Vis and fragmentation pattern similar to those already reported for xanthones (dos Santos et al, 2000;Du et al, 2012), and were assigned as xanthone derivative compounds. Peaks 30 and 31 were tentatively identified as apigenin derivatives due to similar UV-Vis and MS spectra acquired for apigenin standard and, in both peaks, the ion at m/z 269 was present, as well as the well-known losses of small neutral molecules, such as H 2 O (-18 u) and CO 2 (-44 u) (Cuyckens & Claeys, 2004).…”

Antimicrobial activities of methanol extract and compounds from stem bark of Vismia rubescens

“…Comparison of the data with those reported in the literature led to the identification of the compounds as 1,4,8-trihydroxyxanthone (1) (Dos Santos et al, 2000), 1,7-dihydroxyxanthone (2) , physcion (3) , friedelin (4) and friedelanol (5) (Gunusekara and Sultanbawa, 1997) (Fig. 1).…”

“…1). Many triterpenoids, anthraquinones, xanthones have been reported from Vismia species (Araújo et al, 1990;Nagem and Faria De Jesus, 1990;Nagem and Alves, 1995;Nagem and De Olivera, 1997;Bilia et al, 2000;Dos Santos et al, 2000;Nguemeving et al, 2006;Tala et al, 2007;Wabo et al, 2007).…”

“…The decoction extract of the bark and roots is used in the Western Province of Cameroon as febrifugal and in the treatment of various microbial infections (skin diseases, diarrhoea and venereal diseases). Previous studies have reported the presence of triterpenoids, prenylated anthrones, anthraquinones, bianthraquinones, benzophenones, xanthones and lignans from Vismia species (Araújo et al, 1990;Nagem and Alves, 1995;Nagem and De Olivera, 1997;Bilia et al, 2000;Dos Santos et al, 2000;Nguemeving et al, 2006;Tala et al, 2007;Wabo et al, 2007). Antimicrobial, cytotoxic and antifeedant activities have been reported for various Vismia constituents (Cassinelli et al, 1986;Seo et al, 2000;Tala et al, 2007;Wabo et al, 2007).…”

Chemistry and biology of genusVismia

“…), commonly known as "pau-desangue", as a mixture of two enantiomers (Dos Santos et al, 2000a). Photochemical investigation of V. latifolia yielded subelliptenone G (35), 1,3,5,6-tetrahydroxyxanthone(36), 1,5-dihydroxy-8-methoxyxanthone (37), 1,6-dihydroxy-7-methoxyxanthone (38) (Dos Santos et al, 2000b).…”