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 acetogenins, annomocherin (1), annonacin (2) and annomontacin (3), have been isolated from the fractionated ethanolic extracts of the seeds of Annona cherimolia, guided by the brine shrimp lethality test (BST). Their structures were elucidated on the basis of spectroscopic and chemical methods. All compounds 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 first time, and was named annomocherin. Two known Compounds 2 and 3 which have never been isolated from this species before, were obtained. Compound 1 exhibited 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.
Kim
D H
DH
Department of Pharmacy, College of Pharmacy, Catholic University of Daegu, Gyeongsan, Korea.
Son
J K
JK
Woo
M H
MH
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology*; D029061:Annonaceae / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology*; D005233:Fatty Alcohols / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology*; D005663:Furans / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D007202:Indicators and Reagents; D007783:Lactones / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D012639:Seeds / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005233:Fatty Alcohols; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; C445664:annomocherin; C073066:annomontacin; C053442:annonacin; D015107:4-Butyrolactone