Calphostin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00206 |
| CAS | 124986-26-1 |
| Molecular Weight | 550.55 |
| Molecular Formula | C30H30O10 |
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Description
Calphostin D is a protein kinase C inhibitor produced by cladosporium cladosporioides.
Specification
| Synonyms | Phleichrome |
| IUPAC Name | 4,9-dihydroxy-6,7-bis(2-hydroxypropyl)-1,5,8,12-tetramethoxyperylene-3,10-dione |
| Canonical SMILES | CC(CC1=C2C3=C(C(=C(C4=C3C(=C5C2=C(C(=O)C=C5OC)C(=C1OC)O)C(=CC4=O)OC)O)OC)CC(C)O)O |
| InChI | InChI=1S/C30H30O10/c1-11(31)7-13-19-20-14(8-12(2)32)30(40-6)28(36)22-16(34)10-18(38-4)24(26(20)22)23-17(37-3)9-15(33)21(25(19)23)27(35)29(13)39-5/h9-12,31-32,35-36H,7-8H2,1-6H3 |
| InChI Key | WJBHEYCJMSCKIP-UHFFFAOYSA-N |
Properties
| Boiling Point | 878.4°C at 760 mmHg |
| Density | 1.48 g/cm3 |
Reference Reading
1. Improved production of phleichrome from the phytopathogenic fungus Cladosporium phlei using synthetic inducers and photodynamic ROS production by phleichrome
Kum-Kang So, Ik-Su Jo, Min-Seon Chae, Jung-Mi Kim, Hea-Jong Chung, Moon-Sik Yang, Beom-Tae Kim, Jin-Kug Kim, Jong-Kyung Choi, Dae-Hyuk Kim J Biosci Bioeng. 2015 Mar;119(3):289-96. doi: 10.1016/j.jbiosc.2014.08.011. Epub 2014 Sep 16.
Two different diketopiperazines, cyclo-(L-Pro-L-Leu) and cyclo-(L-Pro-L-Phe), which were isolated from the culture filtrate of Epichloe typhina and found to be inducers of phleichrome production, were chemically synthesized and evaluated for use in the improved production of phleichrome from wild-type and UV-mutagenized strains (M0035) of Cladosporium phlei. When supplemented with PDA and V8 juice agar media, both inducers showed significant increases in the production of phleichrome. Phleichrome production was increased in a dose-dependent manner up to a concentration of maximum yield for both inducers. No further significant induction was observed by supplementing inducers over the concentration of maximum yield. Among the two inducers, cyclo-(L-Pro-L-Phe) showed better inducing capability than cyclo-(L-Pro-L-Leu). The maximum yield was observed from the M0035 strain grown on V8 juice media supplemented with 150 μM cyclo-(L-Pro-L-Phe), which was estimated to be 232.6 mg of phleichrome per gram of mycelia and 10.2 mg of secreted phleichrome per 20 agar-plugs. Interestingly, growth inhibition was observed on V8 juice agar media with 100, 150, and 200 μM cyclo-(L-Pro-L-Phe) but not on PDA with the same amount of inducer, which suggests that the inhibitory effect might be through the overproduction of phleichrome rather than the toxic effect of the inducer itself. Superoxide production by purified phleichrome was dramatically stimulated upon illumination, thus demonstrating photodynamic production of superoxide in vitro by phleichrome.
2. Characterization of a mutant strain of a filamentous fungus Cladosporium phlei for the mass production of the secondary metabolite phleichrome
Min-Hee Yi, Jung-Ae Kim, Jung-Mi Kim, Jin-Ah Park, Beom-Tae Kim, Seung-Moon Park, Moon-Sik Yang, Ki-Jun Hwang, Dae-Hyuk Kim J Microbiol. 2011 Aug;49(4):680-3. doi: 10.1007/s12275-011-1022-4. Epub 2011 Sep 2.
UV-mutagenesis was performed to obtain mutant strains that demonstrate altered production of phleichrome, a secondary metabolite of Cladosporium phlei. Among fifty mutants selected, based on the increased area and intensity of the purple pigment surrounding the colonies, the strain M0035 showed the highest production of phleichrome, more than seven fold over wild type. Plate cultures of the M0035 strain resulted in a total of 592 mg phleichrome consisting of 146 mg and 446 mg from the mycelia and agar media, respectively. The M0035 strain displayed a growth rate and a mycelial mass comparable to the parental strain but had significantly reduced asexual sporulation.
3. Identification of a Polyketide Synthase Gene in the Synthesis of Phleichrome of the Phytopathogenic Fungus Cladosporium phlei
Kum-Kang So, Yun-Jo Chung, Jung-Mi Kim, Beom-Tae Kim, Seung-Moon Park, Dae-Hyuk Kim Mol Cells. 2015 Dec;38(12):1105-10. doi: 10.14348/molcells.2015.0208. Epub 2015 Nov 25.
Phleichrome, a pigment produced by the phytopathogenic fungus Cladosporium phlei, is a fungal perylenequinone whose photodynamic activity has been studied intensively. To determine the biological function of phleichrome and to engineer a strain with enhanced production of phleichrome, we identified the gene responsible for the synthesis of phleichrome. Structural comparison of phleichrome with other fungal perylenequinones suggested that phleichrome is synthesized via polyketide pathway. We recently identified four different polyketide synthase (PKS) genes encompassing three major clades of fungal PKSs that differ with respect to reducing conditions for the polyketide product. Based on in silico analysis of cloned genes, we hypothesized that the non-reducing PKS gene, Cppks1, is involved in phleichrome biosynthesis. Increased accumulation of Cppks1 transcript was observed in response to supplementation with the application of synthetic inducer cyclo-(l-Pro-l-Phe). In addition, heterologous expression of the Cppks1 gene in Cryphonectria parasitica resulted in the production of phleichrome. These results provide convincing evidence that the Cppks1 gene is responsible for the biosynthesis of phleichrome.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
