Malformin A
(Synonyms: Malformin A1) 目录号 : GC40007
A cyclopentapeptide fungal metabolite with diverse biological activities
Cas No.:3022-92-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Malformin A is a cyclopentapeptide fungal metabolite that has been found in A. niger and has diverse biological activities. It is a plant growth regulator that induces malformations in plant structure. 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). 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. Malformin A also increases the accumulation of reactive oxygen species, decreases the mitochondrial membrane potential, and induces autophagy in PC3 and LNCaP cells. It is toxic to mice when administered intraperitoneally (LD50 = 3.1 mg/kg) but not orally up to doses of 50 mg/kg.
| Cas No. | 3022-92-2 | SDF | |
| 别名 | Malformin A1 | ||
| Canonical 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 | ||
| 分子式 | C23H39N5O5S2 | 分子量 | 529.7 |
| 溶解度 | DMSO: 1 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.8879 mL | 9.4393 mL | 18.8786 mL |
| 5 mM | 0.3776 mL | 1.8879 mL | 3.7757 mL |
| 10 mM | 0.1888 mL | 0.9439 mL | 1.8879 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The structure and synthesis of Malformin A
Proc Natl Acad Sci U S A 1974 Jul;71(7):2791-4.PMID:4528068DOI:10.1073/pnas.71.7.2791.
A structure (the disulfide form of cyclo-D-cysteinyl-L-valyl-D-cysteinyl-D-leucyl-L-isoleucyl), previously proposed for Malformin A, was reexamined. On the basis of chemical degradations, a different structure (the disulfide form of cyclo-D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-isoleucyl) was established. Accordingly, a compound with this structure was synthesized and was found to be identical with Malformin A. The synthetic product causes curvatures on corn roots; maximum effect was seen at a concentration of 0.1 mug/ml, the optimal concentration for Malformin A.
Structure of Malformin A, a Phytotoxic Metabolite Produced by Aspergillus niger
Biosci Biotechnol Biochem 1993 Jan;57(2):240-3.PMID:27314776DOI:10.1271/bbb.57.240.
Malformins-produced by Aspergillus niger were separated by HPLC and subjected to structural determination. Amino acid analyses and mass spectra suggested that all of them structurally resembled cyclic pentapeptide malformin A1. Two-dimensional NMR experiments and MS/MS experiments led us to deduce cyclo-D-cysteinyl-D-cysteinyl-L-amino acid-D-amino acid-L-amino acid as being the essential structure of malformins.
Fibrinolytic activation promoted by the cyclopentapeptide malformin: involvement of cytoskeletal reorganization
Biol Pharm Bull 2011;34(9):1426-31.PMID:21881228DOI:10.1248/bpb.34.1426.
Malformin A?, a cyclopentapeptide of fungal origin, enhances cellular fibrinolytic activity depending on the existence of a cofactor in blood plasma. However, the nature of this cofactor remains unknown. Here, we report that vitronectin acts as a plasma cofactor of Malformin A?. We purified the cofactor from bovine plasma by activity-based fractionation, and confirmed that vitronectin in conjunction with plasminogen supports the activity of Malformin A? to promote the fibrinolytic activity of U937 cells. Malformin A? action was abolished by Arg-Gly-Asp peptide (a competitor of vitronectin-integrin binding), wortmannin (an inhibitor of signaling kinases), and cytochalasin B (an inhibitor of actin polymerization). Changes in actin organization and a decrease in filopodia were observed in cells treated with Malformin A? and plasma. A focal localization of plasminogen on the cell surface was augmented by Malformin A?, whereas the amount of cell-surface-bound plasminogen was minimally altered by the treatment. Our results suggest the involvement of cytoskeletal reorganization via vitronectin signaling in the cellular fibrinolytic activity-enhancing action of Malformin A?.
Allomalformin
Int J Pept Protein Res 1982 Jul;20(1):16-25.PMID:7118425doi
In an attempt to find explanation for the initial erroneous sequence assignment for malformin, a sequence-isomer of the natural product, 3-isoleucine-5-valine malformin or briefly "allomalformin" that on partial acid hydrolysis could have given rise to misleading fragments, was synthesized and compared with both natural and synthetic preparations of malformin. Allomalformin is identical to the parent microbial peptide (Malformin A, or briefly malformin) with respect to biological activity and conformation (ORD and CD spectra) and is indistinguishable from it by high pressure liquid chromatography. Yet, the two isomers have slightly different Rf values on thin-layer chromatograms and by this method no allomalformin could be detected in samples of the natural product. On the other hand both high pressure liquid chromatography and thin-layer chromatography demonstrated the presence of the lower homolog, 5-valine malformin, in the samples examined. On partial acid hydrolysis this natural analog should liberate Val-Cys, while Cys-Val forms from malformin itself. Similarly, the corresponding desthio cyclopentapeptides should give rise to Val-Ala and Ala-Val respectively; the former being more resistant to further hydrolysis persists in the partial hydrolysates. The presence of Val-Cys in partial hydrolysates of malformin and of Val-Ala in the partial hydrolysates of desthiomalformin, both originating from the accompanying lower homolog rather than from malformin itself, is likely to have led to the postulation of the erroneous Cys-Val-Cys partial sequence.
Proteome analysis of Aspergillus niger: lactate added in starch-containing medium can increase production of the mycotoxin fumonisin B2 by modifying acetyl-CoA metabolism
BMC Microbiol 2009 Dec 10;9:255.PMID:20003296DOI:10.1186/1471-2180-9-255.
Background: Aspergillus niger is a filamentous fungus found in the environment, on foods and feeds and is used as host for production of organic acids, enzymes and proteins. The mycotoxin fumonisin B2 was recently found to be produced by A. niger and hence very little is known about production and regulation of this metabolite. Proteome analysis was used with the purpose to reveal how fumonisin B2 production by A. niger is influenced by starch and lactate in the medium. Results: Fumonisin B2 production by A. niger was significantly increased when lactate and starch were combined in the medium. Production of a few other A. niger secondary metabolites was affected similarly by lactate and starch (fumonisin B4, orlandin, desmethylkotanin and pyranonigrin A), while production of others was not (ochratoxin A, ochratoxin alpha, Malformin A, malformin C, kotanin, aurasperone B and tensidol B). The proteome of A. niger was clearly different during growth on media containing 3% starch, 3% starch + 3% lactate or 3% lactate. The identity of 59 spots was obtained, mainly those showing higher or lower expression levels on medium with starch and lactate. Many of them were enzymes in primary metabolism and other processes that affect the intracellular level of acetyl-CoA or NADPH. This included enzymes in the pentose phosphate pathway, pyruvate metabolism, the tricarboxylic acid cycle, ammonium assimilation, fatty acid biosynthesis and oxidative stress protection. Conclusions: Lactate added in a medium containing nitrate and starch can increase fumonisin B2 production by A. niger as well as production of some other secondary metabolites. Changes in the balance of intracellular metabolites towards a higher level of carbon passing through acetyl-CoA and a high capacity to regenerate NADPH during growth on medium with starch and lactate were found to be the likely cause of this effect. The results lead to the hypothesis that fumonisin production by A. niger is regulated by acetyl-CoA.