Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

Abstract

O presente trabalho descreve o isolamento, a partir do caule de Annona amazonica, do ácido acantóico, um diterpeno do tipo pimaradieno que possui várias e importantes atividades biológicas descritas na literatura. Neste estudo foi verificado que este composto apresenta significante atividade tripanocida contra as formas epimastigotas de Trypanosoma cruzi. Também foi constatado que este diterpeno é o constituinte majoritário da planta, encontrado em cerca de 65% do extrato hexânico, demonstrando que A. amazonica é uma nova fonte natural renovável desta substância. Além do ácido acantóico, a investigação química resultou no isolamento dos alcalóides liriodenina e cassiticina, entre outros compostos, tais como terpenos, esteróides e ácidos graxos. Adicionalmente, é descrita a completa e inequívoca atribuição dos deslocamentos químicos de RMN de 1 H e 13 C da cassiticina.The present work reports the isolation of acanthoic acid, a promising pimaradiene-type diterpene with several important biological activities described in the literature, from the stems of Annona amazonica. We found that acanthoic acid has significant trypanocidal activity against the epimastigote forms of Trypanosoma cruzi. This diterpene is the major constituent of the plant, comprising at least 65% of the hexane extract, demonstrating that A. amazonica is a new renewable natural source for this compound. The chemical investigation also resulted in the isolation of the alkaloids liriodenine and cassythicine, and other compounds including terpenes, sterols, and fatty acids. Additionally, the complete and unequivocal 1 H and 13 C NMR chemical shift assignments for cassythicine are provided. Keywords: Annona amazonica, Annonaceae, acanthoic acid, cassythicine, trypanocidal activity IntroductionThe family Annonaceae, comprised of tropical and subtropical species with about 135 genera and more than 2500 species and widely distributed in South and Central America, Africa, Asia, and Australia, 1 is known for its edible fruits and the medicinal properties of several species. 2 In Brazil, there are 26 genera with about 260 species, including the genus Annona, which contains approximately 120 species. 3 Chemical investigations of species of Annonaceae have revealed their high chemical diversity in terms of secondary metabolites, such as alkaloids, acetogenins, terpenoids and lactones. These compounds have shown important biological activities, including antiparasitic, in particular against Leishmania sp., Plasmodium falciparum, and Trypanosoma cruzi. [4][5][6][7][8][9][10][11][12] Annona amazonica R.E. Fries is a tropical tree that grows up to 20-25 m tall and 35-60 cm in diameter, and is found from Panama to South America. In Brazil this species commonly occurs in the Amazon, mainly in the states of Amazonas and Pará. 13 To the best of our knowledge, only one previous phytochemical study has described the isolation and identification of cyanogenic constituents from this species. 14 Here we describe the isolation and structural identification of the chemica...

Antileishmanial Activity of a New ent-Kaurene Diterpene Glucoside Isolated from Leaves of Xylopia excellens R.E.Fr. (Annonaceae)

“…Beyond this, the number of commercially available drugs for the treatment of chronic diseases still is below a satisfactory number [6]. In our continuous search for new biologically active compounds from Amazonian plants [7][8][9], this work reports a new ent-kaurene diterpene glucoside from Xylopia excellens R.E.Fr. and its evaluation against promastigote forms of Leishmania amazonensis.…”

Alkaloids from leaves of Annona salzmannii and Annona vepretorum (Annonaceae)

“…However, anonaine, asimilobine and liriodenine were described in the stem bark of A. salzmannii (Da Cruz et al, 2011). These compounds are very common in Annonaceae species, mainly in the genus Annona (Guinaudeau et al, 1975, 1979Leboeuf et al, 1982;Chang et al, 2000;Pinheiro et al, 2009;Costa et al, 2009Costa et al, , 2010Costa et al, , 2011b. Anonaine have been described in Annona glabra L. and Annona montana Macfad.…”

FIRST RECORD OF Xanthopastis timais IN AMARYLLIS AND EFFECT OF SOURSOP EXTRACT ON LARVAL MORTALITY

“…Accordingly, the search for plant extracts with insecticidal action becomes an interesting alternative for pest control. For instance, plants belonging to the Annonaceae group have been cited as an important group, since they have several secondary metabolites with biological activity in their composition, which, in turn, would decrease selection of resistant insect species (PINHEIRO et al, 2009;GOMES, 2013;LIMA et al, 2014). Within this botanical family, soursop (Annona muricata L.) should be highlighted for its scientifically proven insecticidal, nematicidal, acaricidal and bactericidal action; on top of that, its seeds, which are disposed during fruit processing, make a promising source of material to produce insecticidal extracts (HERNANDÉZ; ANGEL, 1997;BROGLIO-MICHELETTI et al, 2009;TRINDADE et al, 2011;KRINSKI;MASSAROLI;MACHADO, 2014;MACIEL et al, 2015).…”