Annojahnin from Annona jahnii: a possible precursor of mono-tetrahydrofuran acetogenins

• Published in: Phytochemistry (Oxford) Vol. 49; no. 6; pp. 1609 - 1616
• Main Authors: Colman-Saizarbitoria, T, Johnson, H.A, Alali, F.Q, Hopp, D.C, Rogers, L.L, McLaughlin, J.L
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01-11-1998; Elsevier
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemistry; 4-Butyrolactone - isolation & purification; 4-Butyrolactone - pharmacology; acetogenin; annojahnin; Annona jahnii; Annonaceae; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; brine shrimp; cytotoxicity; Drug Screening Assays, Antitumor; Fatty Alcohols - chemistry; Fatty Alcohols - isolation & purification; Fatty Alcohols - pharmacology; Fundamental and applied biological sciences. Psychology; Furans - chemistry; General pharmacology; Humans; Lactones - chemistry; Mass Spectrometry - methods; Medical sciences; Metabolism; Metabolism. Physicochemical requirements; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development; Plants - chemistry; Tumor Cells, Cultured; annojahnin; Annonaceae; brine shrimp; Annona jahnii; acetogenin; cytotoxicity; Antineoplastic agent; Human; Bioassay; Molecular structure; Aliphatic compound; Pharmacognosy; Furan derivatives; Cytotoxicity; In vitro; Biological activity; Medicinal plant; Cell line; Structure activity relation; Dicotyledones; Branch; Angiospermae; Absolute configuration; Plant origin; Isolation; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(98)00316-1

A new cytotoxic Annonaceous acetogenin, annojahnin (
1), was isolated from the twigs of
Annona jahnii (Annonaceae) by bioactivity-directed fractionation using lethality to brine shrimp. Compound
1 represents an unusual type of C–37 Annonaceous acetogenin, lacking either tetrahydrofuran (THF) or epoxide rings, bearing a keto group at C–10, and possessing a double bond located two methylenes away from a vicinal diol. The structure and absolute configuration of
1 were elucidated by
1H and
13C NMR, COSY, and single-relayed COSY and from chemical derivatives. 4-Deoxy-18/21-
trans-annomontacin 10-one (
4) and 4-deoxy-18/21-
cis-annomontacin-10-one (
5), two semisynthetic mono-THF acetogenins, were prepared from
1 by reactions that mimic the biogenetic pathways. These acetogenins showed selective cytotoxicities, comparable or superior to adriamycin, among six human solid tumor cell lines. Reduction of the 10-keto of
1, to the racemic 10-OH derivative (
3), retained the bioactivities as did the conversion of
1 to
4 and
5.