| Identification | Back Directory | [Name]
bullatacin | [CAS]
102989-24-2 | [Synonyms]
bullatacin
2(5H)-Furanone, 3-[(2R,13R)-2,13-dihydroxy-13-[(2R,2'R,5R,5'R)-octahydro-5'-[(1R)-1-hydroxyundecyl][2,2'-bifuran]-5-yl]tridecyl]-5-methyl-, (5S)- | [Molecular Formula]
C37H66O7 | [MDL Number]
MFCD03427326 | [MOL File]
102989-24-2.mol | [Molecular Weight]
622.92 |
| Chemical Properties | Back Directory | [Melting point ]
45-48 °C(Solv: methanol (67-56-1); water (7732-18-5)) | [Boiling point ]
745.5±40.0 °C(Predicted) | [density ]
1.054±0.06 g/cm3(Predicted) | [pka]
14.46±0.20(Predicted) |
| Hazard Information | Back Directory | [Uses]
Asimicin (Bullatacin) is antitumor acetogenin that can be isolated from the bark and seeds of the pawpaw tree, Asimina trilobal Dunal. Asimicin inhibits mitochondrial respiration through the inhibition of complex I. Asimicin shows toxicity to Aphis gossypii, mosquito larvae and mammalian[1][2][3][4]. | [Anticancer Research]
Bullatacin is a bis(tetrahydrofuranoid) fatty acid lactone found in some fruits fromAnnonaceae family. It is a member of acetogenin class of phytochemicals. It fightsagainst the MDR phenotype of human mammary adenocarcinoma. It has showsantitumor properties by induction of chromatin migration and tumor cellcondensation followed by apoptosis (Oberlies et al. 1997; Desai et al. 2008). | [References]
[1] Kawamata T, et al. Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization. Chemistry. 2018 Dec 17;24(71):18907-18912. DOI:10.1002/chem.201805317
[2] Zhao GX, et al. Asimin, asiminacin, and asiminecin: novel highly cytotoxic asimicin isomers from Asimina triloba. J Med Chem. 1994 Jun 24;37(13):1971-6. DOI:10.1021/jm00039a009
[3] Ligang Zhou, et al. Secondary Metabolites with Antinematodal Activity from Higher Plants. Studies in Natural Products Chemistry. Volume 37, 2012, Pages 67-114.
[4] E. David Morgan and Ian D. Wilson. Insect Hormones and Insect Chemical Ecology. Comprehensive Natural Products Chemistry. Volume 8, 1999, Pages 263-375. |
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