Matthew J. Rieser

Muricatacin: A simple biologically active acetogenin derivative from the seeds of annona muricata (annonaceae)

A biologically active constituent, bearing similarities to the annonacin group of Annonaceous acetogenins, has been isolated from the seeds of Annona muricata. The absolute configuration about the tetrahydrofuran ring of annonacin, which was also isolated, is proposed.

New cytotoxic annonaceous acetogenins: Bullatanocin and cis- and trans-Bullatanocinone, from Annona bullata (Annonaceae)

Abstract Further bioactivity-directed fractionation of the ethanol extract of the bark of Annona bullata Rich. (Annonaceae) has led to the isolation of the new nonadjacent bis-tetrahydrofuran acetogenins, bullatanocin ( 1 ), cis- bullatanocinone ( 2 ) and trans-bullatanocinone ( 3 ). A known adjacent bis-tetrahydrofuran acetogenin, desacetyluvaricin ( 4 ), which is new to this species, was also isolated. Brine shrimp lethality test (BST) data and cytotoxicities against human solid tumor cell lines of 1–4 were compared with those of the diastereoisomers, bullatalicin ( 5 ), cis- and trans-bullatalicinone ( 6 and 7 ) and 4-deoxyasimicin ( 8 ). 1 shows cytotoxic potencies 10,000 times those of adriamycin in the lung and colon cancer cell lines.

Biologically active acetogenins from stem bark of Asimina triloba.

In continuing our research with cytotoxic and pesticidal components from the stem bark of the North American paw paw, Asimina triloba, the novel cytotoxic monotetrahydrofuran Annonaceous acetogenins, cis- and trans-annonacin-A-one, cis- and trans-gigantetrocinone and cis-isoannonacin, in addition to the known compounds, trans-isoannonacin and squamolone, have been identified. Brine shrimp lethality testing was used to direct the fractionation. The structures were elucidated by spectral analysis and/or chemical synthesis. These acetogenins have potent cytotoxicities against the human tumour cell lines of A-549 (lung carcinoma), MCF-7 (breast carcinoma) and HT-29 (colon adenocarcinoma).

The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba.

A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba. By spectral and chemical methods, 1 was identified as (30S)-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, asiminacin, bullatin, (30S)-bullanin, and (30R) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.

A new type of cytotoxic annonaceous acetogenin: Giganin from goniothalamus giganteus

A new cytotoxic Annonaceous acetogenin, giganin (1), was isolated from the bark of Goniothalamus giganteus (Annonaceae). This compound represents a new type of Annonaceous acetogenin lacking tetrahydrofuran or epoxide rings along the aliphatic chain, and its structure was elucidated by 1H and 13C NMR, MS, COSY, and single-relayed COSY.