Annomolin and Annocherimolin, New Cytotoxic Annonaceous Acetogenins from Annona cherimolia Seeds

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2001-04, Vol.64 (4), p.502-506
• Main Authors: Kim, Dal Hwan, Ma, Eun Sook, Suk, Kui Duk, Son, Jong Keun, Lee, Jong Soon, Woo, Mi Hee
• Format: Article
• Language: English
• Subjects: Adenocarcinoma - pathology; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; Drug Screening Assays, Antitumor; Furans - chemistry; Furans - isolation & purification; Furans - pharmacology; General pharmacology; Humans; Lactones - chemistry; Lactones - isolation & purification; Lactones - pharmacology; Magnoliopsida - chemistry; Male; Medical sciences; Molecular Structure; Pancreatic Neoplasms - pathology; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Prostatic Neoplasms - pathology; Spectrum Analysis; Tumor Cells, Cultured
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np000335u

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.