| Identification | Back Directory | [Name]
thielavin A | [CAS]
71950-66-8 | [Synonyms]
thielavin A
4-[(2,4-Dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,5,6-trimethylbenzoic acid 4-carboxy-3-hydroxy-2,5,6-trimethylphenyl ester | [Molecular Formula]
C29H30O10 | [MDL Number]
MFCD11111622 | [MOL File]
71950-66-8.mol | [Molecular Weight]
538.54 |
| Chemical Properties | Back Directory | [Melting point ]
235-236 °C | [Boiling point ]
850.0±65.0 °C(Predicted) | [density ]
1.371±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: souble; DMSO: souble; Ethanol: soluble | [form ]
White to off-white powder. | [pka]
2.82±0.28(Predicted) |
| Hazard Information | Back Directory | [Description]
Thielavin A is a fungal metabolite originally isolated from T. terricola that is related to thielavin B . Thielavin A inhibits COX, blocking both the conversion of arachidonic acid to prostaglandin H2 (PGH2; ) and the conversion of PGH2 to PGE2 (; IC50s = 10 and 40 μM, respectively). Thielavin A also inhibits glucose-6-phosphatase in rat liver microsomes (IC50 = 4.6 μM). It is a non-competitive inhibitor of α-glucosidase from S. cerevisiae (IC50 = 23.8 μM; Ki = 27.8 μM). | [Uses]
The fungal metabolite, thielavin A, and its relatives are glucose-6-phosphatase inhibitors. The three benzoic acid units are essential for inhibition. Thielavin A was originally isolated as a inhibitor of prostaglandin biosynthesis. The closely related thielavin B is a telomerase and cell wall transglycosylation inhibitor. | [Uses]
Thielavin A acts as an inhibitor of prostagladins biosynthesis. | [References]
[1] N KITAHARA. The structures of thielavins A, B and C. Prostaglandin synthetase inhibitors from fungi.[J]. Journal of Antibiotics, 1983, 36 5: 599-600. DOI: 10.7164/antibiotics.36.599
[2] N KITAHARA. Thielavin A and B, new inhibitors of prostaglandin biosynthesis produced by Thielavia terricola.[J]. Journal of Antibiotics, 1981, 34 12: 1562-1568. DOI: 10.7164/antibiotics.34.1562
[3] SHINICHI SAKEMI et al. et al. Thielavins as Glucose-6-phosphatase (G6Pase) Inhibitors: Producing Strain, Fermentation, Isolation, Structural Elucidation and Biological Activities.[J]. ChemInform, 2003, 34 17. DOI: 10.1002/chin.200317215
[4] Y TAKE. Comparative studies of the inhibitory properties of antibiotics on human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases and cellular DNA polymerases.[J]. Journal of Antibiotics, 1989, 42 1: 107-115. DOI: 10.7164/antibiotics.42.107
[5] RIVERA-CHáVEZ J, GONZáLEZ-ANDRADE M, GONZáLEZ M C, et al. Thielavins A, J and K: α-Glucosidase Inhibitors from MEXU 27095, an Endophytic Fungus from Hintonia latiflora[C]. 2013: 0. DOI: 10.1055/s-0033-1348676 |
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