A cyclic lipopeptide with diverse biological activities
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Iturin A-2

Item No. 38911

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[(3R)-3-aminotetradecanoyl-L-asparaginyl-D-tyrosyl-D-asparaginyl-L-glutaminyl-L-prolyl-D-asparaginyl-L-seryl]
CAS Number
83785-07-3
Synonyms
  • C14 Iturin
Molecular Formula
C48H74N12O14
Formula Weight
1043.2
Purity
≥90%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleMethanol: Soluble
SMILES
O=C([C@@H](NC([C@H](NC([C@H](NC([C@@H](N1)CC(N)=O)=O)CC(C=C2)=CC=C2O)=O)CC(N)=O)=O)CCC(N)=O)N3CCC[C@@]3([H])C(N[C@@H](C(N[C@H](C(N[C@@H](CC1=O)CCCCCCCCCCC)=O)CO)=O)CC(N)=O)=O
InChi Code
InChI=1S/C48H74N12O14/c1-2-3-4-5-6-7-8-9-10-12-28-22-41(67)54-32(23-38(50)64)43(69)56-31(21-27-14-16-29(62)17-15-27)42(68)57-33(24-39(51)65)44(70)55-30(18-19-37(49)63)48(74)60-20-11-13-36(60)47(73)58-34(25-40(52)66)45(71)59-35(26-61)46(72)53-28/h14-17,28,30-36,61-62H,2-13,18-26H2,1H3,(H2,49,63)(H2,50,64)(H2,51,65)(H2,52,66)(H,53,72)(H,54,67)(H,55,70)(H,56,69)(H,57,68)(H,58,73)(H,59,71)/t28-,30+,31-,32+,33-,34-,35+,36+/m1/s1
InChi Key
HNAPWDKFUSLFFE-HRADWJPASA-N
Origin
Bacterium/Bacillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $482

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    Product Description

    Iturin A-2 is a cyclic lipopeptide that has been found in B. subtilis and has diverse biological activities.1,2,3,4 It is active against the plant pathogenic fungus P. expansum (MIC = 8 µg/disk).1 Iturin A-2 induces cytotoxicity in MCF-7 and BT474 breast cancer and HeLa cervical cancer cells (IC50s = 66.81, 95.04, and 77.5 µg/ml, respectively).2 It reduces southern corn leaf blight lesion area induced by B. maydis in greenhouse studies and reduces the incidence of southern corn leaf blight in field studies.3 Iturin A-2 (12.5 µg/ml) inhibits cell division, but not nuclear division, in isolated fertilized starfish eggs.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bland, J.M. The first synthesis of a member of the iturin family, the antifungal cyclic lipopeptide, iturin-A2. The Journal of Organic Chemistry 61(16), (1996).

    2. Jiang, J., Zhang, H., Zhang, C., et al. Production, purifcation and characterization of ‘iturin A‑2’ a lipopeptide with antitumor activity from Chinese sauerkraut bacterium Bacillus velezensis T701. Int. J. Pept. Res. Ther. 27, 2135-2147 (2007).

    3. Ye, Y.F., Li, Q.-Q., Fu, G., et al. Identification of antifungal substance (iturin A2) produced by Bacillus subtilis B47 and its effect on southern corn leaf blight. J. Integr. Agric. 11(1), 90-99 (2012).

    4. Tsuchimori, N., Ikegami, S., Miyashiro, S., et al. Isolation of iturin A-2 as an inhibitor of cytokinesis of starfish embryos. Comp. Biochem. Physiol. Part C 84(2), 381-384 (1986).