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...

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Bibliographic Details
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
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np000335u