Acetogenin from anonna species

Acetogenin and substances found in annona montana and other annona species. These acetogenins in graviola have anti cancer benefits.

Tucupentol, a novel mono-tetrahydrofuranic acetogenin from Annona montana, as a potent inhibitor of mitochondrial complex I.
Chem Biodivers. 2009 Mar; Alvarez Colom O, Neske A, Chahboune N, Zafra-Polo MC, Bardón A. Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Tucumán, Argentina.
Ten acetogenins, one of them new, were isolated from leaves and twigs of a Bolivian collection of Annona montana. The new compound that we named tucupentol is a mono-tetrahydrofuran-pentahydroxy-acetogenin. The inhibitory potency of tucupentol on the mitochondrial complex I was evaluated, and this activity was compared with that of the known acetogenins, annonacin-A, cis-annonacin-10-one, aromin, and gigantetronenin, also isolated from this plant material. The mentioned acetogenins acted as selective inhibitors of mitochondrial complex I in the 0.8-5.4-nM range.

Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.
Bioorg Med Chem Lett. 2009 Apr 15; Department of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China.
Twelve annonaceous acetogenins with different stereochemical structures and configuration were selected to test for their inhibitions on the growth of Hela, SMMC-7541, SGC-7901, MCF-7 and A-5408 tumor cell lines. This was the first to simultaneously investigate effects of structural factors of stereochemical structures and configuration on cytotoxicities with structure-activity relationship. The present study showed that cytotoxic selectivities of acetogenins with threo/trans/threo/trans/erythro stereochemical arrangement were gently more active than those with threo/trans/threo/trans/threo stereochemical arrangement, and ACGs with cis THF ring partly produced notable cytotoxic selectivities. Furthermore, acetogenins with S configuration at C-24 exhibited gently more cytotoxic selectivities potency than those with R configuration at C-24.

Apolar Annonaceous acetogenins from the fruit pulp of Annona muricata.
Molecules. 2009 Nov 2;14(11):4387-95. Melot A, Fall D, Gleye C, Champy P. CNRS UMR 8076 BioCIS, Faculté de Pharmacie Paris-Sud 11, Châtenay-Malabry, France.
A methylene chloride extract of the pulp of Annona muricata L. was fractionated in search for scarcely functionalized Annonaceous acetogenins (type E). Previously known C-35 and C-37 mono-epoxy unsaturated compounds, epomuricenins-A and -B (1+2) and epomusenins-A and -B (3+4), were obtained. Two new mono-epoxy saturated C-35 representatives, epomurinins-A and -B (5+6) were also isolated.