Annomocherin, annonacin and annomontacin: A novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds

A novel and two known bioactive mono-tetrahydrofuran (THF) annonaceous acet ogenins, annomocherin (1), annonacin (2) and annomontacin (3), have been is olated from the fractionated ethanolic extracts of the seeds of Annona cher imolia, guided by the brine shrimp lethality test (BST). Their structures w ere elucidated on the basis of spectroscopic and chemical methods. All comp ounds have a relative stereochemistry of threo/trans/threo for the mono-THF ring with two flanking hydroxyls. Compound 1 has a double bond at C-23/24 of aliphatic chain. Compound 1 was isolated from natural sources for the fi rst time, and was named annomocherin. Two known Compounds 2 and 3 which hav e never been isolated from this species before, were obtained. Compound 1 e xhibited potent and selective cytotoxicities against the breast carcinoma ( MCF-7) and kidney carcinoma (A-498) cell lines with 100 to 1,000 times the potency of adriamycin. In brine shrimp lethality test (BST), 1-3 exhibited cytotoxicity.