Thielavin B
目录号 : GC45034
A natural COX inhibitor
Cas No.:71950-67-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Thielavin B is a fungal metabolite that contains O-substituted salicylic acid. It inhibits cyclooxygenase, blocking both the conversion of arachidonic acid to Prostaglandin H2 (PGH2) and the conversion of PGH2 to PGE2 . Thielavin B also inhibits the reverse transcriptase of avian myeloblastosis virus, bacterial transglycosylases, and telomerase activity.
| Cas No. | 71950-67-9 | SDF | |
| Canonical SMILES | OC1=C(C)C(O)=C(C(OC2=C(C)C(C)=C(C(OC3=C(C)C(C)=C(C(O)=O)C(OC)=C3C)=O)C(OC)=C2C)=O)C(C)=C1 | ||
| 分子式 | C31H34O10 | 分子量 | 566.6 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.7649 mL | 8.8246 mL | 17.6491 mL |
| 5 mM | 0.353 mL | 1.7649 mL | 3.5298 mL |
| 10 mM | 0.1765 mL | 0.8825 mL | 1.7649 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Thielavin A and B, new inhibitors of prostaglandin biosynthesis produced by Thielavia terricola
J Antibiot (Tokyo) 1981 Dec;34(12):1562-8.PMID:7333968DOI: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.
Thielavin B methyl ester: a cytotoxic benzoate trimer from an unidentified fungus (MSX 55526) from the Order Sordariales
Tetrahedron Lett 2011 Nov 2;52(44):5733-5735.PMID:22566715DOI:10.1016/j.tetlet.2011.08.125.
As part of our ongoing investigation of filamentous fungi for anticancer leads, an active fungal extract was identified from the Mycosynthetix library (MSX 55526; from the Order Sordariales). Bioactivity-directed fractionation yielded the known ergosterol peroxide (2) and 5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol(3), and a new benzoate trimer, termed Thielavin B methyl ester (1). The structure elucidation of 1 was facilitated by the use of HRMS coupled to an APPI (atmospheric pressure photoionization) source. Compound 1 proved to be moderately active against a panel of three cancer cell lines.
Inhibition of telomerase activity by fungus metabolites, CRM646-A and Thielavin B
Biosci Biotechnol Biochem 2001 Mar;65(3):651-3.PMID:11330682DOI:10.1271/bbb.65.651.
We performed a screening program to identify telomerase inhibitors from our drug source obtained from fungus fermentations, and found that two compounds, CRM646-A and Thielavin B, inhibited telomerase activity at doses of 3.2 and 32 microM, respectively. These compounds also inhibited the activity of viral reverse transcriptase at almost the same dose levels which inhibited telomerase activity.
Thielavins as glucose-6-phosphatase (G6Pase) inhibitors: producing strain, fermentation, isolation, structural elucidation and biological activities
J Antibiot (Tokyo) 2002 Nov;55(11):941-51.PMID:12546415DOI: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.
Screening systems for detecting inhibitors of cell wall transglycosylation in Enterococcus. Cell wall transglycosylation inhibitors in Enterococcus
J Antibiot (Tokyo) 1998 May;51(5):471-9.PMID:9666175DOI:10.7164/antibiotics.51.471.
We devised two screening systems to detect cell wall transglycosylation inhibitors. One screen utilizes a mutant of Enterococcus faecalis strain A256 that is dependent on vancomycin or moenomycin for growth. In the absence of transglycosylation inhibitors the strain fails to grow, while in the presence of inhibitors, cells are rescued. A second screening organism E. faecalis strain MDD212 utilizes a translational fusion of the lacZ gene to the vanH promoter in a derivative of E. faecalis that contains a vancomycin resistance determinant. Induction of beta-galactosidase occurs when cells are exposed to inhibitors of transglycosylation. Our natural products drug source of fungal fermentations was tested with these screens. Several cultures that produced the same family of compounds, called the thielavins, were detected. Thielavin B inhibited the formation of peptidoglycan in an in vitro assay, suggesting that these screening systems can detect compounds that interfere with cell wall transglycosylation.