A cyclopentapeptide fungal metabolite with diverse biological activities
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Malformin A

Item No. 27510

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo(D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-isoleucyl), cyclic (1→2)-disulfide
CAS Number
3022-92-2
Synonyms
  • Malformin A1
Molecular Formula
C23H39N5O5S2
Formula Weight
529.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/ml
SMILES
O=C1[C@@]([C@@H](C)CC)([H])NC([C@@H](CC(C)C)NC([C@H](C(C)C)NC([C@@H]2NC([C@@H](CSSC2)N1)=O)=O)=O)=O
InChi Code
InChI=1S/C23H39N5O5S2/c1-7-13(6)18-23(33)26-15-9-34-35-10-16(25-20(15)30)21(31)27-17(12(4)5)22(32)24-14(8-11(2)3)19(29)28-18/h11-18H,7-10H2,1-6H3,(H,24,32)(H,25,30)(H,26,33)(H,27,31)(H,28,29)/t13-,14+,15+,16+,17-,18-/m0/s1
InChi Key
RNCGDQLZIATDOU-ZDRBWGSPSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $358

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    Product Description

    Malformin A is a cyclopentapeptide fungal metabolite that has been found in A. niger and has diverse biological activities.1,2,3,4,5,6 It is a plant growth regulator that induces malformations in plant structure.2 Malformin A inhibits replication of tobacco mosaic virus (TMV) in local lesion and leaf-disc assays (IC50s = 19.7 and 45.4 µg/ml, respectively).3 It is cytotoxic to NCI-H460, MIA PaCa-2, MCF-7, SF-268, and WI-38 cancer cells (IC50s = 70, 50, 100, 70, and 100 nM, respectively), inhibits proliferation of PC3 and LNCaP cells (IC50s = 130 and 90 nM, respectively), and induces apoptosis and necrosis in PC3 and LNCaP cells.4,5 Malformin A also increases the accumulation of reactive oxygen species, decreases the mitochondrial membrane potential, and induces autophagy in PC3 and LNCaP cells.5 It is toxic to mice when administered intraperitoneally (LD50 = 3.1 mg/kg) but not orally up to doses of 50 mg/kg.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, K.-W., Sugawara, F., Yoshida, S., et al. Structure of malformin A, a phytotoxic metabolite produced by Aspergillus niger. Biosci. Biotechnol. Biochem. 57(2), 240-243 (1993).

    2. Curtis, R.W., and Buckhout, T.J. Effect of malformin on the growth, development, and behavior of Phaseolus vulgaris L. Bot. Gaz. 138(2), 153-158 (1977).

    3. Tan, Q.-W., Gao, F.-L., Wang, F.-R., et al. Anti-TMV activity of malformin A1, a cyclic penta-peptide produced by an endophytic fungus Aspergillus tubingensis FJBJ11. Int. J. Mol. Sci. 16(3), 5750-5761 (2015).

    4. Zhan, J., Gunaherath, G.M.K.B., Wijeratne, E.M.K., et al. Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis. Phytochemistry 68(3), 368-372 (2007).

    5. Liu, Y., Wang, M., Wang, D., et al. Malformin A1 promotes cell death through induction of apoptosis, necrosis and autophagy in prostate cancer cells. Cancer Chemother. Pharmacol. 77(1), 63-75 (2016).

    6. Yoshizawa, T., Tsuchiya, Y., Morooka, N., et al. Malformin A1 as a mammalian toxicant from Aspergillus niger. Agr. Biol. Chem. 39(6), 1325-1326 (1975).