83785-07-3
Chemical Structure
Iturin A-2
- CAS No.: 83785-07-3
- Formula:C48H74N12O14
- Molecular Weight:1043.17
InChIKey: HNAPWDKFUSLFFE-HRADWJPASA-N
SMILES: O=C1N2[C@](CCC2)([H])C(N[C@@H](C(N[C@H](C(N[C@@H](CC(N[C@H](C(N[C@@H](C(N[C@@H](C(N[C@H]1CCC(N)=O)=O)CC(N)=O)=O)CC3=CC=C(C=C3)O)=O)CC(N)=O)=O)CCCCCCCCCCC)=O)CO)=O)CC(N)=O)=O
Biological Activity: Iturin A-2 is a cyclic lipopeptide discovered in B. subtilis and exhibits inhibitory activity against the plant pathogenic fungus P. expansum (MIC = 8 µg/disk). Iturin A-2 is cytotoxic to MCF-7 and BT474 breast cancer cells, as well as HeLa cervical cancer cells, with IC50 values of 66.81, 95.04, and 77.5 µg/mL, respectively. In greenhouse studies, Iturin A-2 at concentrations of 100 and 300 mg/kg Iturin A-2 reduces the lesion area of southern corn leaf blight caused by B. maydis, and in field studies, concentrations of 300 and 500 mg/kg Iturin A-2 reduce the incidence of the disease. Iturin A-2 (12.5 µg/mL) inhibits cell division, but not nuclear division, in isolated fertilized starfish eggs[1][2][3][4].
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Iturin A-2 | Iturin A-2 is a cyclic lipopeptide discovered in B. subtilis and exhibits inhibitory activity against the plant pathogenic fungus P. expansum (MIC = 8 µg/disk). Iturin A-2 is cytotoxic to MCF-7 and BT474 breast cancer cells, as well as HeLa cervical cancer cells, with IC50 values of 66.81, 95.04, and 77.5 µg/mL, respectively. In greenhouse studies, Iturin A-2 at concentrations of 100 and 300 mg/kg Iturin A-2 reduces the lesion area of southern corn leaf blight caused by B. maydis, and in field studies, concentrations of 300 and 500 mg/kg Iturin A-2 reduce the incidence of the disease. Iturin A-2 (12.5 µg/mL) inhibits cell division, but not nuclear division, in isolated fertilized starfish eggs. | |||||||||||||||||||||
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References
- [1]. Bland J M. The first synthesis of a member of the iturin family, the antifungal cyclic lipopeptide, iturin-A2[J]. The Journal of Organic Chemistry, 1996, 61(16): 5663-5664.
- [2]. Jiang J, et al. Production, purification and characterization of ‘Iturin A-2’a lipopeptide with antitumor activity from Chinese Sauerkraut Bacterium Bacillus velezensis T701[J]. International Journal of Peptide Research and Therapeutics, 2021, 27(3): 2135-2147.
- [3]. YE Y, et al. Identification of antifungal substance (Iturin A2) produced by Bacillus subtilis B47 and its effect on southern corn leaf blight[J]. Journal of Integrative Agriculture, 2012, 11(1): 90-99.
- [4]. Miyashiro S, et al. Isolation of iturin A-2 as an inhibitor of cytokinesis of starfish embryos[J]. Comparative Biochemistry and Physiology Part C: Comparative Pharmacology, 1986, 84: 381-384.
