Five Novel Mono-tetrahydrofuran Ring Acetogenins from the Seeds of Annona muricata
| Autor: | Matthew J. Rieser, Zhe-Ming Gu, Xin-ping Fang, Karl V. Wood, Lu Zeng, Jerry L. McLaughlin |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
Lung Neoplasms
Stereochemistry Annonacin Pharmaceutical Science Breast Neoplasms Pharmacognosy Analytical Chemistry chemistry.chemical_compound 4-Butyrolactone Plant Tumors Drug Discovery Tumor Cells Cultured Humans Annona muricata Pharmacology chemistry.chemical_classification Plants Medicinal biology Organic Chemistry Absolute configuration biology.organism_classification Antineoplastic Agents Phytogenic Complementary and alternative medicine chemistry Annonaceae Seeds Molecular Medicine Drug Screening Assays Antitumor Artemia salina Aliphatic compound HT29 Cells Lactone |
| Zdroj: | Journal of Natural Products. 59:100-108 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np960037q |
| Popis: | Bioactivity-directed fractionation of the seeds of Annona muricata L. (Annonaceae) resulted in the isolation of five new compounds: cis-annonacin (1), cis-annonacin-10-one (2), cis-goniothalamicin (3), arianacin (4), and javoricin (5). Three of these (1-3) are among the first cis mono-tetrahydrofuran ring acetogenins to be reported. NMR analyses of published model synthetic compounds, prepared cyclized formal acetals, and prepared Mosher ester derivatives permitted the determinations of absolute stereochemistries. Bioassays of the pure compounds, in the brine shrimp test, for the inhibition of crown gall tumors, and in a panel of human solid tumor cell lines for cytotoxicity, evaluated relative potencies. Compound 1 was selectively cytotoxic to colon adenocarcinoma cells (HT-29) in which it was 10,000 times the potency of adriamycin. |
| Databáze: | OpenAIRE |
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