Antibacterial Alkaloids fromZanthoxylum rhoifolium

Abstract

Two new dihydrobenzophenanthridine-type alkaloids, 6-methoxy dioxolo[4',5':4,5]benzo[c] dioxolo[4,5- j]phenanthridine (1) and 2,3,13-trimethoxy-5,11a-dihydro dioxolo[4',5':4,5]benzo[c]phenanthridine (2) were isolated from the stem bark of Zanthoxylum rhoifolium, together with four other previously known benzophenanthridine alkaloids, 6-acetonyldihydronitidine (3) [= 8-acetonyldihydronitidine], 6-acetonyldihydroavicine (4) [= 8-acetonyldihydroavicine], 6-acetonyldihydrochelerythrine (5) and xanthoxyline (6). The structures were elucidated mainly by spectroscopic methods, including 1D and 2D NMR spectroscopy. For alkaloids 1 and 2 we propose the trivial names rhoifolines A and B. The crude plant extracts and the alkaloids 3, 4 and 6 showed activity against Gram (+/-) bacteria, while the new alkaloids 1 and 2 were inactive.

Avaliação da atividade antimicrobiana de duas espécies de Rutaceae do Nordeste Brasileiro

“…Inúmeros estudos de atividade antimicrobiana de espécies do gênero Zanthoxylum têm apresentado atividade bactericida, a exemplo de Z. tetraspermun (Nissanka et al, 2001), Z. clava-herculi (Gibbons et al, 2003) e Z. rhoifolium (Gonzaga et al, 2003), nas quais foram encontrados alcaloides benzofenantrídinicos de estruturas similares à diidroqueleritrina. Outro alcaloide benzofenantridínico, a sanguinarina, encontrado nas raízes de Sanguinaria canadensis Linné, Papaveraceae, apresenta a capacidade de inibir a aderência de bactérias na formação da placa dental e é utilizado em dentifrícios e enxaguatórios bucais na prevenção de periodontite (Godowski, 1989;Robbers et al, 1997).…”

Potential medicinal use of forest species of the Deciduous Seasonal Forest from Atlantic Forest Biome, South Brazil

“…Antimicrobial activity (Gonzaga et al 2003), antitumor activity (Silva et al 2007) C. canjerana, C. sylvestris, P. myrtifolia and Z. rhoifolium distinguished themselves for presenting anti-tumor activity. (Felipe et al 2014;Santos et al 2005;Silva et al 2007).…”

Zanthoxylum Genus as Potential Source of Bioactive Compounds

“…Representatives of these alkaloids have exhibited antimalarial (Nyangulu et al, 2005;Ross et al, 2004), antileukemic (Dupont et al, 2005), antioxidant (Pérez et al, 2003), nematicide (Matsuhashi et al, 2002), HIV (Chang et al, 2003), antibacterial (Gonzaga et al, 2003), antimicrobial (Nissanka et al, 2001) and antifungal activities (Queiroz et al, 2006), among others. Their distribution is very limited in plants, and only they have been isolated from some genera belonging to the families Papaveraceae, Rutaceae and Fumiraceae mainly, where they are considered chemotaxonomic markers.…”