Constituintes bioorgânicos isolados de Annona cacans Warming (Annonaceae) e avaliações de bioatividades

Abstract

This work reports the phytochemical investigation of wood and leaves (hexane and ethanol) and fruits (ethyl acetate) of Annona cacans Warming (Annonaceae). The research was carried out with usual chromatographic techniques including High Performance Liquid Chromatography. This investigation led to the isolation and identification of 4-hydroxy-3-5-methoxybenzaldehyde; ethyl p-hydroxybenzoate; bornyl p-hydroxycinnamate; four steroids: b-sitosterol, stigmasterol, 3- O-b-D-glucopyranosyl-b-sitosterol and 3-O-b-D-glucopyranosylstigmasterol; four kauranoid diterpenes: ent-kaur-16-en-19-oic acid that was used to obtain methyl ent-kaur-16-en-19-ate and this derivative used to preparation of methyl ent-16a,17-dihydroxykauran-19-ate, ent-16b,17- dihydroxykauran-19-oic acid, methyl -ent-16b,17-dihydroxykauran-19-ate, ent-17-formylkauran- 19-oic acid which afforded the two derivatives ent-(16R,17R)-17-hydroxy-17-methoxykauran-19- oic acid and ent-(16R,17S)-17-hydroxy-17-methoxykauran-19-oic acid-; five aporphine alkaloids liriodenine (1,2-methylenedioxy-7-oxoaporphine), oxolaureline (10-methoxy-1,2- methylenedioxy-7-oxoaporphne), lanuginosine (9-methoxy-1,2-methylenedioxy-7-oxoaporphne), lisicamine and O-methylmoscatoline; and four monotetrahydrofuranic: acetogenins cis- Rbrazilinone-A, trans-Rbrazilinone-B that were also used to obtain the acetyl derivatives cis- Rbrazilinone-A1 and trans-Rbrazilinone-B1, respectively-, cacansin-9-one and annoreticuin-9-one. The structures were elucidated on the basis of their spectral data obtained of IR and mainly 1H and 13C (1 and 2D) NMR and high and low resolution EIMS spectra and comparison with literature values. The biological tests for insecticide activity were run with the ethanolic extracts of wood and leaves and with the ethyl acetate extract of fruits. A preliminary investigation of the moluscicide activity against Biomphararia glabrata was carried out with the ethyl acetate extract and methanol fractionation of fruits and also with the ethanol, hexane and chloroform extracts of leaves. Cytotoxicity against Artemia salina was investigated with the ethyl acetate extract of fruits, hexane and ethanol extracts of leaves, hexane and ethanol extracts of wood, methanol extract of fruits and chloroform extract of wood.