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Química Nova

Print version ISSN 0100-4042On-line version ISSN 1678-7064

Abstract

SOUZA, César A. S. de et al. ASARONE-DERIVED PHENYLPROPANOIDS AND ISOQUINOLINE-DERIVED ALKALOIDS FROM THE BARK OF Duguetia pycnastera (Annonaceae) AND THEIR CYTOTOXICITIES. Quím. Nova [online]. 2020, vol.43, n.10, pp.1397-1403.  Epub Feb 22, 2021. ISSN 1678-7064.  http://dx.doi.org/10.21577/0100-4042.20170617.

The phytochemical investigation of the hexane and methanol extracts from the bark of Duguetia pycnastera Sandwith (Annonaceae) afforded seven known compounds, two asarone-derived phenylpropanoids and five isoquinoline-derived alkaloids. The asarones, γ-asarone (1-allyl-2,4,5-trimethoxybenzene) and 2,4,5-trimethoxy-styrene were isolated of the hexane extract while the aporphine alkaloids, O-methylmoschatoline, lysicamine, nornuciferidine, and guatterine N-oxide, and the benzyltetrahydroisoquinoline alkaloid, (S)-reticuline were isolated of the alkaloid fraction of the methanol extract. This is the first report of these compounds in D. pycnastera. γ-Asarone is being reported for the first time in the Annonaceae. Nornuciferidine is described for the second time in the Annonaceae while guatterine N-oxide is the third register. The structures of the isolated compounds were established by extensive analyses using 1D and 2D NMR spectroscopy in combination with MS. The cytotoxic activity of the isolated compounds (except for nornuciferidine) was evaluated against cancer and non-cancerous cell lines, in which lysicamine was the most active compound, mainly against HL-60, HepG2, and K562 with IC50 values of 24.40, 28.86 and 38.75 µmol L-1, respectively.

Keywords : Duguetia pycnastera; asarones; aporphine alkaloids; benzyltetrahydroisoquinoline alkaloid; cytotoxic activity.

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