Mono-THF ring annonaceous acetogenins from Annona squamosa

Phytochemistry
D C HoppJ L McLaughlin

Abstract

Continuing work on the bark of Annona squamosa Rich. (Annonaceae), directed by the brine shrimp lethality test (BST), has resulted in the isolation of three new Annonaceous acetogenins, 4-deoxyannoreticuin, cis-4-deoxyannoreticuin, and (2,4-cis and trans)-squamoxinone. The first two are additional examples of acetogenins isolated from this plant species which contain the unusual feature of an oxygen functionality at the C-9 position. They have a hydroxylated mono-THF ring with respective threo/trans/threo and threo/cis/threo relative stereochemistries. The latter compound is a ketolactone mixture which has the same relative stereochemistry around the THF ring and the same spatial relationship between the THF ring and the hydroxyl group along the aliphatic chain as 4-deoxyannoreticuin, but is two methylene units longer. Additionally, the isolated hydroxyl group is at C-11, while the THF ring starts at C-17, instead of at C-9 and C-15, respectively, as for the first two compounds. All three compounds showed moderate, but significant, cytotoxicities against a panel of six human tumor cell lines with (2,4 cis and trans)-squamoxinone showing promising selectivity against the pancreatic cell line (PACA-2).

Citations

Apr 5, 2005·Natural Product Reports·Almudena BermejoDiego Cortes
Aug 29, 2001·Journal of Asian Natural Products Research·W M ZhaoL G Lou
Jun 7, 2006·Natural Product Research·M J ChavanS A Nirmal
Apr 2, 2015·Journal of Food Science and Technology·V Cijo GeorgeR Ashok Kumar
Dec 10, 2020·Food Research International·Luis M Anaya-EsparzaEfigenia Montalvo-González

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