Thielavin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03505 |
| CAS | 71950-66-8 |
| Molecular Weight | 538.54 |
| Molecular Formula | C29H30O10 |
| Purity | >95% by HPLC |
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Description
Thielavin A is a glucose-6-phosphatase (G6Pase) inhibitor produced by Chaetomium carinthiacum.
Specification
| Storage | -20°C |
| IUPAC Name | 4-[4-(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy-2-hydroxy-3,5,6-trimethylbenzoyl]oxy-2-hydroxy-3,5,6-trimethylbenzoic acid |
| Canonical SMILES | CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2C)C)C(=O)OC3=C(C(=C(C(=C3C)C)C(=O)O)O)C)O)C)O)C)O |
| InChI | InChI=1S/C29H30O10/c1-10-9-18(30)15(6)22(31)19(10)28(36)38-26-14(5)12(3)21(24(33)17(26)8)29(37)39-25-13(4)11(2)20(27(34)35)23(32)16(25)7/h9,30-33H,1-8H3,(H,34,35) |
| InChI Key | MGGMNKJGDSNTKZ-UHFFFAOYSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | White Powder |
| Boiling Point | 850°C at 760 mmHg |
| Density | 1.371 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Thielavins as glucose-6-phosphatase (G6Pase) inhibitors: producing strain, fermentation, isolation, structural elucidation and biological activities
Shinichi Sakemi, Hiroko Tonai-Kachi, Janice C Parker, Maria A VanVolkenburg, Nobuji Yoshikawa, Hiroyuki Nishida, Nakao Kojima, Taisuke Inagaki, Yasuhiro Kojima, Toshiyuki Saito, Hideo Hirai, Toshio Ichiba, Yoshinao Kato J Antibiot (Tokyo) . 2002 Nov;55(11):941-51. doi: 10.7164/antibiotics.55.941.
High-throughput screening of microbial extracts using rat hepatic microsomal glucose-6-phosphatase (G6Pase) led us to find thielavin B as a G6Pase inhibitor with inhibition of glucose output from glucagon-stimulated hepatocytes. Further searching for more potent analogs identified 11 new thielavins F-P in addition to the known thielavins A and B from a fungus Chaetomium carinthiacum ATCC 46463. Thielavin G showed the strongest activity as a G6Pase inhibitor (IC50=0.33 microM), while the IC50 of thielavin B was 5.5 microM. According to the structure-activity relationship, including authentic thielavins C, D and 3 partial hydrolysates from thielavins A and B, 3 benzoic acid-units and carboxylic acid functions are essential for G6Pase inhibition.
2. Thielavin A and B, new inhibitors of prostaglandin biosynthesis produced by Thielavia terricola
A Endo, S Takahashi, N Kitahara, K Furuya J Antibiot (Tokyo) . 1981 Dec;34(12):1562-8. doi: 10.7164/antibiotics.34.1562.
Two potent inhibitors of prostaglandin biosynthesis, thielavin A (C31H34O10) and B (C29H30O10), were isolated from cultures of Thielavia terricola. Both of these compounds were shown to be structurally related to depsides, thus consisting of three hydroxybenzoic acid groups. Concentrations required for 50% inhibition of the conversion of 14C-arachidonic acid into prostaglandins F2 alpha plus E2 by microsomes of ram seminal vesicles were 12 microM for thielavin A and 9 microM for thielavin B, respectively. Of the enzymatic steps involved in prostaglandin synthesis, thielavin A specifically inhibited the conversion of arachidonic acid into prostaglandin H2, while prostaglandin E2 synthesis from the endoperoxide was the most sensitive to thielavin B. Thromboxane A2 synthesis from prostaglandin H2 in bovine platelet microsomes were inhibited by 50% at concentrations of 150 and 350 microM of thielavin A and B, respectively. Thielavin B was significantly effective on carrageenan-induced oedema of rats when administered intravenously but on on oral administration. The anti-inflammatory activity was not detectable with thielavin A either on intravenous injection or on oral administration.
3. Thielavins A, J and K: α-Glucosidase inhibitors from MEXU 27095, an endophytic fungus from Hintonia latiflora
Martín González-Andrade, José Rivera-Chávez, María del Carmen González, Rachel Mata, Anthony E Glenn Phytochemistry . 2013 Oct;94:198-205. doi: 10.1016/j.phytochem.2013.05.021.
Bioassay-guided fractionation of the bio-active organic extract obtained from solid-media culture of MEXU 27095, an endophytic fungus isolated from the Mexican medicinal plant Hintonia latiflora (Rubiaceae), led to separation of three tridepsides which were identified as thielavins A, J and K. All three compounds inhibited Saccharomyces cerevisieae α-glucosidase (αGHY) in a concentration-dependent manner with IC50 values of 23.8, 15.8, and 22.1μM, respectively. Their inhibitory action was higher than that of acarbose (IC50=545μM), used as a positive control. Kinetic analysis established that the three compounds acted as non-competitive inhibitors with ki values of 27.8, 66.2 and 55.4μM, respectively (α=1.0, 1.2, 0.7, respectively); acarbose behaved as competitive inhibitor with a ki value of 156.1μM. Thielavin J inhibited the activity of α-glucosidase from Bacillus stearothermophilus (αGHBs) with an IC50 of 30.5μM, being less active than acarbose (IC50=0. 015μM); in this case, compound (2) (ki=20.0μM and α=2.9) and acarbose (ki=0.008μM and α=1.9) behaved as non-competitive inhibitors. Docking analysis predicted that all three thielavins and acarbose bind to homologated αGHBs and to αGHY (PDB: 3A4A) in a pocket close to the catalytic site for maltose and isomaltose, respectively. The α-glucosidase inhibitory properties of thielavin K (3) were corroborated in vivo since it induced a noted antihyperglycemic action during an oral sucrose tolerance test (3.1, 10.0 and 31.6mg/kg) in normal and nicotinamide-streptozotocin diabetic mice. In addition, at a dose of 10mg/kg, it provoked a moderate hypoglycemic activity in diabetic mice.
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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 ╳
