Cyclo(L-Ala-L-Pro) | CAS:36357-32-1 | Manufacturer ChemFaces

Cyclo(L-Ala-L-Pro)

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Description:

Cyclo(L-Ala-L-Pro) and cyclo(L-Val-L-Pro) inhibit aflatoxin production of Aspergillus parasiticus and Aspergillus flavus in liquid medium at concentrations of several hundred uM without affecting fungal growth.

Targets:

Antifection

In vitro:

Microbiology. 2013 May;159(Pt 5):902-12.

Prevention of aflatoxin contamination by a soil bacterium of Stenotrophomonas sp. that produces aflatoxin production inhibitors.[Pubmed: 23449921]

A soil bacterium, designated strain no. 27, was found to produce aflatoxin-production inhibitors. The strain was identified as a species of the genus Stenotrophomonas, and was found to be closely related to Stenotrophomonas rhizophila.
METHODS AND RESULTS:
Two diketopiperazines, Cyclo(L-Ala-L-Pro) and cyclo(L-Val-L-Pro), were isolated from the bacterial culture filtrate as main active components. These compounds inhibited aflatoxin production of Aspergillus parasiticus and Aspergillus flavus in liquid medium at concentrations of several hundred μM without affecting fungal growth. Both inhibitors inhibited production of norsorolinic acid, a biosynthetic intermediate involved in an early step of the aflatoxin biosynthetic pathway, and reduced the mRNA level of aflR, which is a gene encoding a key regulatory protein necessary for the expression of aflatoxin-biosynthetic enzymes. These results indicated that the inhibitors targets are present in early regulatory steps leading to AflR expression. Co-culture of strain no. 27 with aflatoxigenic fungi in liquid medium effectively suppressed aflatoxin production of the fungus without affecting fungal growth. Furthermore, application of the bacterial cells to peanuts in laboratory experiments and at a farmer's warehouse in Thailand by dipping peanuts in the bacterial cell suspension strongly inhibited aflatoxin accumulation. The inhibitory effect was dependent on bacterial cell numbers.
CONCLUSIONS:
These results indicated that strain no. 27 may be a practically effective biocontrol agent for aflatoxin control.

Cyclo(L-Ala-L-Pro) Description

Source:	From Phellinus igniarius.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, 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. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
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.

Kinase Assay:

Toxins (Basel). 2017 Jul 12;9(7).

The Mode of Action of Cyclo(l-Ala-l-Pro) in Inhibiting Aflatoxin Production of Aspergillus flavus.[Pubmed: 28704973 ]

Cyclo(L-Ala-L-Pro) inhibits aflatoxin production in aflatoxigenic fungi without affecting fungal growth. The mode of action of Cyclo(L-Ala-L-Pro) in inhibiting aflatoxin production of Aspergillus flavus was investigated.
METHODS AND RESULTS:
A glutathione S-transferase (GST) of the fungus, designated AfGST, was identified as a binding protein of Cyclo(L-Ala-L-Pro) in an experiment performed using Cyclo(L-Ala-L-Pro)-immobilized Sepharose beads. Cyclo(L-Ala-L-Pro) specifically bound to recombinant AfGST and inhibited its GST activity. Ethacrynic acid, a known GST inhibitor, inhibited the GST activity of recombinant AfGST and aflatoxin production of the fungus. Ethacrynic acid reduced the expression level of AflR, a key regulatory protein for aflatoxin production, similar to Cyclo(L-Ala-L-Pro).
CONCLUSIONS:
These results suggest that Cyclo(L-Ala-L-Pro) inhibits aflatoxin production by affecting GST function in A. flavus, and that AfGST inhibitors are possible candidates as selective aflatoxin production inhibitors.

Product Name	Cyclo(L-Ala-L-Pro)
Price:	$238 / 10mg
CAS No.:	36357-32-1
Catalog No.:	CFN96111
Molecular Formula:	C₈H₁₂N₂O₂
Molecular Weight:	168.2 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	From Phellinus igniarius.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Alkaloids Compound Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.9453 mL	29.7265 mL	59.453 mL	118.9061 mL	148.6326 mL
5 mM	1.1891 mL	5.9453 mL	11.8906 mL	23.7812 mL	29.7265 mL
10 mM	0.5945 mL	2.9727 mL	5.9453 mL	11.8906 mL	14.8633 mL
50 mM	0.1189 mL	0.5945 mL	1.1891 mL	2.3781 mL	2.9727 mL
100 mM	0.0595 mL	0.2973 mL	0.5945 mL	1.1891 mL	1.4863 mL

CFN90275	Cyclo(Pro-Val)	5654-87-5	196.25	C₁₀H₁₆N₂O₂
CFN96114	Cyclo(D-Val-L-Pro)	27483-18-7	196.3	C₁₀H₁₆N₂O₂
CFN91062	Cyclo(Hyp-Val)	1425501-89-8	212.2	C₁₀H₁₆N₂O₃
CFN90281	Cyclo(Pro-Leu)	5654-86-4	210.27	C₁₁H₁₈N₂O₂
CFN96128	Cyclo(D-Leu-L-Pro)	36238-67-2	210.3	C₁₁H₁₈N₂O₂
CFN90285	Cyclo(Hpro-Leu)	1016899-93-6	226.27	C₁₁H₁₈N₂O₃
CFN96088	Cyclo(L-Leu-trans-4-hydroxy-L-Pro)	115006-86-5	226.3	C₁₁H₁₈N₂O₃
CFN90270	Cyclo(Pro-Pro)	6708-06-1	194.23	C₁₀H₁₄N₂O₂
CFN96160	Cyclo(Gly-L-Pro)	3705-27-9	154.2	C₇H₁₀N₂O₂
CFN90282	Cyclo(Pro-Ala)	65556-33-4	168.20	C₈H₁₂N₂O₂