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Cytotoxic Acetogenins from the Roots of Annona purpurea

1
Facultad de Ciencias Químicas, Universidad de Colima, Carretera Colima-Coquimatlán km 9, 28400 Coquimatlán, Colima, Mexico
2
Dipartimento di Scienze del Farmaco, Università degli Studi di Padova, Via F. Marzolo 5, 35131 Padova, Italy
3
Fondazione per la Biologia e la Medicina della Rigenerazione T.E.S.-Tissue Engineering and Signalling Onlus, Via F. Marzolo, 13, 35131 Padova, Italy
4
Facultad de Medicina, Universidad de Colima, Av. Universidad 333, Las Víboras, 28040 Colima, Mexico
5
Dipartimento di Scienze Biomediche, Università degli Studi di Padova, Via G. Colombo 3, 35121, Padova, Italy
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(8), 1870; https://doi.org/10.3390/ijms20081870
Received: 23 March 2019 / Revised: 5 April 2019 / Accepted: 6 April 2019 / Published: 16 April 2019
(This article belongs to the Special Issue Traditional Medicine – Unraveling Its Molecular Mechanism, Volume 2)
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Abstract

Annona purpurea, known in Mexico as “cabeza de negro” or “ilama”, belongs to the Annonaceae family. Its roots are employed in folk medicine in several regions of Mexico. Taking that information into account, a chemical and biological analysis of the components present in the roots of this species was proposed. Our results demonstrated that the dichloromethane (DCM) extract was exclusively constituted by a mixture of five new acetogenins named annopurpuricins A–E (15). These compounds have an aliphatic chain of 37 carbons with a terminal α,β unsaturated γ-lactone. Compounds 1 and 2 belong to the adjacent bis-THF (tetrahydrofuran) α-monohydroxylated type, while compounds 3 and 4 belong to the adjacent bis-THF α,α’-dihydroxylated type; only compound 5 possesses a bis-epoxide system. Complete structure analysis was carried out by spectroscopy and chemical methods. All compounds were evaluated for their antiproliferative activity on three human tumor cell lines (MSTO-211H, HeLa and HepG2). Compounds 14 inhibited significantly the growth of HeLa and HepG2 cells, showing GI50 values in the low/subnanomolar range, while 5 was completely ineffective under the tested conditions. The investigation of the mechanism of action responsible for cytotoxicity revealed for the most interesting compound 1 the ability to block the complex I activity on isolated rat liver mitochondria (RLM). View Full-Text
Keywords: Annona purpurea; Annonaceae; acetogenins; annopurpuricins; cytotoxicity; mitochondria Annona purpurea; Annonaceae; acetogenins; annopurpuricins; cytotoxicity; mitochondria
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Hernández-Fuentes, G.A.; García-Argáez, A.N.; Peraza Campos, A.L.; Delgado-Enciso, I.; Muñiz-Valencia, R.; Martínez-Martínez, F.J.; Toninello, A.; Gómez-Sandoval, Z.; Mojica-Sánchez, J.P.; Dalla Via, L.; Parra-Delgado, H. Cytotoxic Acetogenins from the Roots of Annona purpurea. Int. J. Mol. Sci. 2019, 20, 1870.

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