Cytotoxic and antimicrobial aporphine alkaloids fromFissistigma poilanei(Annonaceae) collected in Vietnam

Abstract

Two new aporphine alkaloids: 8-hydroxy-9-methoxy-1,2-methylenedioxyaporphine (1) and 8-hydroxy-3,9-dimethoxy-1,2-methylenedioxyaporphine (2) were isolated from the ethyl acetate extract of Fissistigma poilanei along with five known compounds: oxocrebanine (3), kuafumine (4), (2R,3R)-3',4',5,7-tetrahydroxydihydroflavonol-3-O-α-L-rhamnopyranoside (5), (+)-catechin 3-O-α-L-rhamnopyranoside (6) and quercetine 3,7-dimethoxy-3'-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside (7). These two new aporphine alkaloids exhibited a moderate cytotoxic activity against four human cancer cell lines (KB, Hep-G2, MCF-7, LU) as well as antimicrobial activity against Lactobacillus fermentum, Enterococcus faecium, Staphylococcus aureus and Bacillus subtillis.

Enantioselective synthesis and anti-parasitic properties of aporphine natural products

“…The syntheses of (+)-norglaucine (1) and (+)-nordicentrine (2) were completed by deprotection of the Boc groups in 12a/c respectively using anhydrous ZnBr2 (Scheme 3); the use of Brønsted acids (e.g. trifluoroacetic acid) led to low yields due to degradation of the sensitive aporphine products.…”

“…The aporphines comprise a large group of plant-derived tetracyclic alkaloids featuring a 1,2,3,4-tetrahydroisoquinoline motif. Many members of the aporphine family display interesting biological activities, such as anti-inflammatory [1], antimicrobial [2], anticancer [3,4] and antiparasitic [5,6] properties. In the latter context, a handful of aporphines have been evaluated for bioactivity against protozoan parasites; for example dicentrine, isolated from Cassytha filiformis L., demonstrated antiparasitic activity against Trypanosoma T. brucei, potentially by acting as an intercalating agent with the parasite DNA (the kinetoplast) [7].…”

FLAVONOL GLYCOSIDES FROM THE LEAVES OF FISSISTIGMA PALLENS (FIN. & GAGN.) MERR.

“…The leaves of F. pallens have been used in traditional medicine for the treatment of abdominal pain, stomach pain, and diarrhea [1]. The chemical studies of Fissistigma genus indicated the presence of alcaloids, sesquiterpens, phenolics and flavonoids [2][3][4][5]. These compounds have shown the potential significant biological effects as cytotoxic and antimicrobial [5].…”

“…The chemical studies of Fissistigma genus indicated the presence of alcaloids, sesquiterpens, phenolics and flavonoids [2][3][4][5]. These compounds have shown the potential significant biological effects as cytotoxic and antimicrobial [5]. However, a few phytochemical investigations of Fissistigma pallens have been studied [6,7].…”

Bioactive Components of Fissistigma cupreonitens

“…The genus Fissistigma (Annonaceae), comprises 100 species, is widely distributed in Africa, Asia, and Oceania. The phytochemical content of certain species of this genus were investigated such as F. maclurei [22], F. poilanei [23], F. latifolium [24], F. bracteolatum [25], F. cavaleriei [26], F. petelotii [27], F. oldhamii [28], F. acuminatissima [29], F. pallens [30], F. capitatum [29], F. rubiginosum [30], F. glaucescens [31], F. balansae [32], F. polyanthoides [33], F. polyanthum [34], F. kwangsiense [35], F. chloroneurum [29] and F. lanuginosum [36]. Alkaloids, flavonoids, triterpenoids, furanones, cyclopentenones, and benzenoids were reported from this genus [28,29,37,38].…”