Phellinsin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02385 |
| CAS | |
| Molecular Weight | 358.30 |
| Molecular Formula | C18H14O8 |
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Description
It is produced by the strain of Phellinus sp. PL3. It selectively inhibits the activity of the chitin synthase I and II with IC50 (μg/mL) of 76 and 28, respectively. It has the antifungal activity on Colletotrichum lagenarium, Pyricularia oryzae, aspergillus fumigatus and Trichophyton mentagrophytes and so on (MIC is 12.5-50 μg/mL).
Specification
| Synonyms | Phellinsin A |
| IUPAC Name | (2R,3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid |
| Canonical SMILES | C1=CC(=C(C=C1C=C2C(C(OC2=O)C3=CC(=C(C=C3)O)O)C(=O)O)O)O |
| InChI | InChI=1S/C18H14O8/c19-11-3-1-8(6-13(11)21)5-10-15(17(23)24)16(26-18(10)25)9-2-4-12(20)14(22)7-9/h1-7,15-16,19-22H,(H,23,24)/b10-5+/t15-,16+/m1/s1 |
| InChI Key | OIVDIVRTEKNHDH-HYWCFLMXSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Fungi |
| Solubility | Soluble in Methanol |
Reference Reading
1. Enzymatic transformation of caffeic acid with enhanced cyclooxygenase-2 inhibitory activity
Jong-Sup Bae, Tae Hoon Kim Bioorg Med Chem Lett. 2012 Jan 15;22(2):793-6. doi: 10.1016/j.bmcl.2011.12.072. Epub 2011 Dec 21.
Convenient enzymatic transformation of the phenylpropanoid caffeic acid (1) with polyphenol oxidase originating from pear afforded three new oxidized metabolites, caffeoxynic acid (2), caffeicinic acid (3), and isocaffeicinic acid (4), along with, 7,8-erythro-caffeicin (5) and phellinsin A (6). The structures of the three new caffeic acid oxidation products were elucidated on the basis of spectroscopic methods. The new products 2 and 3 exhibited significantly enhanced inhibitory activity against cyclooxygenase-2 (COX-2) when compared to parent caffeic acid.
2. Phellinsin A from Phellinus sp. PL3 exhibits antioxidant activities
Eui Il Hwang, Ju-Ryoung Kim, Tae-Sook Jeong, Sangku Lee, Mun-Chual Rho, Sung Uk Kim Planta Med. 2006 May;72(6):572-5. doi: 10.1055/s-2006-931533.
Phellinsin A, which was isolated from the culture broth of Phellinus sp. PL3, exhibited significant low-density lipoproteins (LDL)-antioxidant activity. It inhibited the Cu2+-mediated oxidation of LDL (IC50: 5.3 microM) and 2,2'-azobis(2-methylpropionamidine) dihydrochloride (AAPH)-mediated oxidation of LDL (IC50: 2.8 microM) in the thiobarbituric acid-reactive substances (TBARS) assay as well as the macrophage-mediated LDL oxidation (73% inhibition at 5 microM). In addition, it delayed LDL oxidation with a prolonged lag time (192 min at 2 microM, control: 44 min). This compound also showed a 10-fold more potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (IC50: 1.7 microM) than trolox (IC50: 18.6 microM), a known DPPH inhibitor. In addition, phellinsin A inhibited xanthine oxidase activity with an IC50 value of 31.0 microM, whereas allopurinol, a xanthine oxidase inhibitor, showed an IC50 value of 40.7 microM.
3. Phellinsin A, a novel chitin synthases inhibitor produced by Phellinus sp. PL3
E I Hwang, B S Yun, Y K Kim, B M Kwon, H G Kim, H B Lee, W J Jeong, S U Kim J Antibiot (Tokyo). 2000 Sep;53(9):903-11. doi: 10.7164/antibiotics.53.903.
Phellinsin A, a novel chitin synthases inhibitor was isolated from the cultured broth of fungus PL3, which was identified as Phellinus sp. PL3. Phellinsin A was purified by solvent partition, silica gel, ODS column chromatographies, and preparative HPLC, consecutively. The structure of phellinsin A was assigned as a phenolic compound on the basis of various spectroscopic analyses including UV, IR, Mass, and NMR. Its molecular weight and formula were found to be 358 and C18H14O8, respectively. Phellinsin A selectively inhibited chitin synthase I and II of Saccharomyces cerevisiae with an IC50 value of 76 and 28 microg/ml, respectively, in our cell free assay system. This compound showed antifungal activity against Colletotrichum lagenarium, Pyricularia oryzae, Rhizoctonia solani, Aspergillus fumigatus, and Trichophyton mentagrophytes.
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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 ╳
