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Aflastatin A
Aflastatin A
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Product Name Aflastatin A
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CAS No.: 179729-59-0
Catalog No.: CFN00102
Molecular Formula: C62H115NO24
Molecular Weight: 1258.57 g/mol
Purity: >=98%
Type of Compound: Alkaloids
Physical Desc.: Powder
Source: From Streptomyces sp.
Solvent: DMSO, Pyridine, Methanol, Ethanol, etc.
Download: COA    MSDS
Similar structural: Comparison (Web)  (SDF)
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Related Screening Libraries
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10 mM * 1 mL in DMSO / Inquiry / In-stock
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Biological Activity
Description: Aflastatin A exhibits antimicrobial activity against some bacteria, yeasts and fungi, it is a specific inhibitor of aflatoxin production by Aspergillus parasiticus, inhibits a very early step in aflatoxin biosynthesis prior to the transcription of aflR and can influence glucose metabolism in the fungus. Aflastatin A has antitumor activity. Aflastatin A inhibits an early step in melanin production, which suppresses the expression of PKS1.
Targets: Antifection | PKS1
In vitro:
J Antibiot (Tokyo). 2001 Aug;54(8):650-7.
Effects of aflastatin A, an inhibitor of aflatoxin production, on aflatoxin biosynthetic pathway and glucose metabolism in Aspergillus parasiticus.[Pubmed: 11592501]
Aflastatin A inhibits aflatoxin production by Aspergillus parasiticus via an unknown mechanism.
METHODS AND RESULTS:
We found that Aflastatin A clearly inhibited production of norsolorinic acid, an early biosynthetic intermediate of aflatoxin, at a concentration of 0.25 microg/ml. Reverse-transcriptase polymerase chain reaction (RT-PCR), and real-time quantitative PCR (TaqMan PCR) experiments indicated that the transcription of genes encoding aflatoxin biosynthetic enzymes (pksA, ver-1, and omtA) and a gene encoding a regulatory protein for expression of the biosynthetic enzymes (aflR) were significantly reduced by the addition of Aflastatin A. We also found that Aflastatin A elevated the glucose consumption and ethanol accumulation by A. parasiticus, and repressed transcription of genes involved in ethanol utilization.
CONCLUSIONS:
These results suggest that Aflastatin A inhibits a very early step in aflatoxin biosynthesis prior to the transcription of aflR and can influence glucose metabolism in the fungus.
J Antibiot (Tokyo). 1997 Feb;50(2):111-8.
Aflastatin A, a novel inhibitor of aflatoxin production by aflatoxigenic fungi.[Pubmed: 9099219]
Aflastatin A, a novel inhibitor of the production of aflatoxin by aflatoxigenic fungi, has been isolated from the solvent extract of mycelial cake of Streptomyces sp. and its molecular formula was determined as C62H115NO24.
METHODS AND RESULTS:
Aflastatin A completely inhibited aflatoxin production by Aspergillus parasiticus NRRL 2999 in liquid medium or on agar plate at a concentration of 0.5 microgram/ml. The mycelial growth of this fungus was not affected in the liquid medium at the same concentration, while the hyphal extension rate was reduced on the plate together with some morphological changes. The growth of the fungus was not completely inhibited even at a concentration of 100 micrograms/ml.
CONCLUSIONS:
Aflastatin A exhibits antimicrobial activity against some bacteria, yeasts and fungi as well as antitumor activity.
Microbiology. 2001 Sep;147(Pt 9):2623-8.
Inhibitory effect of aflastatin A on melanin biosynthesis by Colletotrichum lagenarium.[Pubmed: 11535802]
Aflastatin A, a novel inhibitor of the production of aflatoxin by aflatoxigenic fungi, has been isolated from the solvent extract of mycelial cake of Streptomyces sp. and its molecular formula was determined as C62H115NO24.
METHODS AND RESULTS:
Aflastatin A completely inhibited aflatoxin production by Aspergillus parasiticus NRRL 2999 in liquid medium or on agar plate at a concentration of 0.5 microgram/ml. The mycelial growth of this fungus was not affected in the liquid medium at the same concentration, while the hyphal extension rate was reduced on the plate together with some morphological changes. The growth of the fungus was not completely inhibited even at a concentration of 100 micrograms/ml.
CONCLUSIONS:
Aflastatin A exhibits antimicrobial activity against some bacteria, yeasts and fungi as well as antitumor activity.
Aflastatin A Description
Source: From Streptomyces sp.
Solvent: DMSO, Pyridine, Methanol, Ethanol, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.7946 mL 3.9728 mL 7.9455 mL 15.8911 mL 19.8638 mL
5 mM 0.1589 mL 0.7946 mL 1.5891 mL 3.1782 mL 3.9728 mL
10 mM 0.0795 mL 0.3973 mL 0.7946 mL 1.5891 mL 1.9864 mL
50 mM 0.0159 mL 0.0795 mL 0.1589 mL 0.3178 mL 0.3973 mL
100 mM 0.0079 mL 0.0397 mL 0.0795 mL 0.1589 mL 0.1986 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Structure Identification:
J Org Chem. 2000 Jan 28;65(2):438-44.
Absolute configuration of aflastatin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus.[Pubmed: 10813953]
Aflastatin A (1) is a specific inhibitor of aflatoxin production by Aspergillus parasiticus. It has the novel structure of a tetramic acid derivative with a long alkyl side chain. The absolute configurations of 29 chiral centers contained in Aflastatin A were chemically elucidated in this study.
METHODS AND RESULTS:
First, four small fragment molecules were prepared from Aflastatin A or its methyl ether (2), and their absolute structures were assigned as N-methyl-D-alanine, (2S,4R)-2, 4-dimethyl-1,6-hexanediol dibenzoate, (R)-3-hydroxydodecanoic acid, and (R)-1,2,4-butanetriol tribenzoate. Next, an acyclic fragment molecule 3 with 13 chiral centers was obtained from Aflastatin A by NaIO(4) oxidation, and its relative stereochemistry was elucidated by J-based configuration analysis. Finally, by further J-based configuration analysis using a fragment molecule 7 prepared from 2 with 28 chiral carbons, all relative configurations in the alkyl side chain of Aflastatin A were clarified.
CONCLUSIONS:
By connecting these relative configurations with the absolute configurations of first four fragment molecules, the absolute stereochemistry of Aflastatin A was fully determined.
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