Annomolin and annocherimolin, new cytotoxic annonaceous acetogenins from Annona cherimolia seeds.
Two new cytotoxic annonaceous acetogenins, annomolin (1) and annocherimolin (2), were isolated from an ethanolic extract of the seeds of Annona cherimolia. Annomolin has a mono-THF ring with one flanking hydroxyl and possesses a 1,2-diol at C-7/8 of the aliphatic chain. Annocherimolin has a mono-THF ring with two flanking hydroxyls and possesses a double bond at C-21/22. Their structures were elucidated by spectral data and chemical derivatization. Compound 1 showed cytotoxic selectivity for the human prostate tumor cell line (PC-3), with a potency of over 10,000 times that of adriamycin. Compound 2 showed cytotoxic potencies about 10,000 times those of adriamycin in the breast (MCF-7) and colon (HT-29) cancer cell lines.
Kim
D H
DH
Department of Pharmacy, College of Pharmacy, Catholic University of Daegu, Gyeongsan, 712-702, Korea.
Ma
E S
ES
Suk
K D
KD
Son
J K
JK
Lee
J S
JS
Woo
M H
MH
D000230:Adenocarcinoma / Q000473:pathology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019684:Magnoliopsida / Q000737:chemistry*; D008297:Male; D015394:Molecular Structure; D010190:Pancreatic Neoplasms / Q000473:pathology; D011471:Prostatic Neoplasms / Q000473:pathology; D013057:Spectrum Analysis; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C430169:annocherimolin; C430168:annomolin