Thielavin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03124 |
| CAS | |
| Molecular Weight | 552.57 |
| Molecular Formula | C30H32O10 |
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Description
Thielavin D is a glucose-6-phosphatase (G6Pase) inhibitor produced by Chaetomium carinthiacum.
Specification
| IUPAC Name | 4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-methoxy-3,5,6-trimethylbenzoyl]oxy-2-methoxy-3,5,6-trimethylbenzoic acid |
| Canonical SMILES | CC1=CC(=CC(=C1C(=O)OC2=C(C(=C(C(=C2C)C)C(=O)OC3=C(C(=C(C(=C3C)C)C(=O)O)OC)C)OC)C)O)O |
| InChI | InChI=1S/C30H32O10/c1-12-10-19(31)11-20(32)21(12)29(35)39-25-16(5)14(3)23(27(38-9)18(25)7)30(36)40-24-15(4)13(2)22(28(33)34)26(37-8)17(24)6/h10-11,31-32H,1-9H3,(H,33,34) |
| InChI Key | FZXHJXWRAYWGLP-UHFFFAOYSA-N |
Properties
| Appearance | Powder |
| Boiling Point | 795.8±60.0°C at 760 mmHg |
| Melting Point | 235-238°C |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Dereplication-guided isolation of depsides thielavins S-T and lecanorins D-F from the endophytic fungus Setophoma sp
Lívia S de Medeiros, Lucas M Abreu, Anita Nielsen, Hanne Ingmer, Thomas O Larsen, Kristian F Nielsen, Edson Rodrigues-Filho Phytochemistry. 2015 Mar;111:154-62. doi: 10.1016/j.phytochem.2014.12.020. Epub 2015 Jan 10.
Dereplication methodology using UHPLC-DAD-QTOFMS was applied during the metabolic profiling investigation of the endophyte Setophoma sp., a fungus isolated from symptomless guava fruits. The approach performed allowed a fast analysis of the microbial secondary metabolites. From this fungus, seven highly C-alkylated depsides were isolated and identified as polyketides thielavins S, T, U and V and lecanorins D, E and F. Their structures were elucidated through spectroscopic methods including NMR, HRMS and especially with assistance of HRMS/MS experiments. The compounds were tested for quorum sensing regulation activity in the virulence gene expression of Staphylococcus aureus, but no inhibitory effect was detected. Nevertheless, moderate antibacterial activity was encountered in three of tested depsides, particularly with thielavin T, whose MIC was 6.25 μg/mL against S. aureus.
2. Thielavins as glucose-6-phosphatase (G6Pase) inhibitors: producing strain, fermentation, isolation, structural elucidation and biological activities
Shinichi Sakemi, Hideo Hirai, Toshio Ichiba, Taisuke Inagaki, Yoshinao Kato, Nakao Kojima, Hiroyuki Nishida, Janice C Parker, Toshiyuki Saito, Hiroko Tonai-Kachi, Maria A VanVolkenburg, Nobuji Yoshikawa, Yasuhiro Kojima 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.
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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 ╳
