Cochlioquinone A
目录号 : GC43288An inhibitor of diacylglycerol kinase and diacylglycerol acyltransferase
Cas No.:32450-25-2
Sample solution is provided at 25 µL, 10mM.
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Cochlioquinone A, a bioactive compound isolated from D. sacchari and Bipolaris sp., is an inhibitor of diacylglycerol kinase (DGK; Ki = 3.1 µM) and diacylglycerol acyltransferase (DGAT; IC50 = 5.6 µM). It has been shown to reduce the concentration of phosphatidic acid in T cell lymphoma with an IC50 value of 3 µM. It is also reported to compete with macrophage inflammatory protein-1α for binding to human CCR5 chemokine receptors with an IC50 value of 11 µM.
Cas No. | 32450-25-2 | SDF | |
Canonical SMILES | C[C@]12[C@@](O[C@@H](C(C)(O)C)CC2)([H])CC[C@@]([C@]1([H])[C@@H]3O)(C)OC4=C3C(C=C([C@H](C)[C@H](OC(C)=O)[C@@H](C)CC)C4=O)=O | ||
分子式 | C30H44O8 | 分子量 | 532.7 |
溶解度 | DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.8772 mL | 9.3861 mL | 18.7723 mL |
5 mM | 0.3754 mL | 1.8772 mL | 3.7545 mL |
10 mM | 0.1877 mL | 0.9386 mL | 1.8772 mL |
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Cochlioquinone A, a nematocidal agent which competes for specific [3H]ivermectin binding sites
J Antibiot (Tokyo) 1990 Sep;43(9):1179-82.PMID:2211380DOI:10.7164/antibiotics.43.1179.
Cochlioquinone A, isolated from the fungus Helminthosporium sativum, was found to have nematocidal activity. Cochlioquinone A is a competitive inhibitor of specific [3H]ivermectin binding suggesting that Cochlioquinone A and ivermectin interact with the same membrane receptor.
Cochlioquinone A, an inhibitor of diacylglycerol kinase
J Antibiot (Tokyo) 1995 Oct;48(10):1076-80.PMID:7490210DOI:10.7164/antibiotics.48.1076.
The effects of Cochlioquinone A, isolated from Drechslera sacchari, were studied in vitro and in vivo. This compound specifically inhibited diacylglycerol kinase activity with Ki = 3.1 microM. The kinetics revealed that Cochlioquinone A inhibited diacylglycerol kinase in competition with ATP, and non-competitively with diacylglycerol. The compound inhibited neither protein kinase C, epidermal growth factor receptor-associated protein tyrosine kinase, nor phospholipase C. Cochlioquinone A reduced the concentration of phosphatidic acid in T cell lymphoma with a half maximal concentration of 3 microM, and simultaneously augmented the phosphorylation of 80 kDa protein, a known substrate of protein kinase C. The degree of the phosphorylation of 80 kDa protein in the presence of Cochlioquinone A was similar to that in the presence of phorbol myristate acetate (0.1 microgram/ml). These results demonstrate that Cochlioquinone A is a specific inhibitor of diacylglycerol kinase, which regulates the activity of protein kinase C.
Epi-cochlioquinone A, a novel acyl-CoA : cholesterol acyltransferase inhibitor produced by Stachybotrys bisbyi
J Antibiot (Tokyo) 1996 May;49(5):409-13.PMID:8682715DOI:10.7164/antibiotics.49.409.
A novel acyl-CoA : cholesterol acyltransferase (ACAT) inhibitor, designated epi-cochlioquinone A has been isolated from the fermentation broth of Stachybotrys bisbyi SANK 17777. The molecular formula, physicochemical properties, NMR spectroscopic analysis and X-ray crystallographic analysis revealed that this compound was a stereoisomer of Cochlioquinone A, which has been previously reported as a nematocidal agent. It inhibited ACAT activity in an enzyme assay using rat liver microsomes with an IC50 value of 1.7 microM. However, it showed about 10-fold less potent inhibitory effect on plasma lecithin cholesterol acyltransferase (LCAT) than on ACAT. In addition, it inhibited in vivo cholesterol absorption in rats by 50% at 75 mg/kg.
Identification of meroterpenoids from Bipolaris victoriae S27 and their potential activity against tumor metastasis and inhibition of the NF-κB signaling pathway
Phytochemistry 2022 Aug;200:113180.PMID:35427653DOI:10.1016/j.phytochem.2022.113180.
Three undescribed meroterpenoids, named bipolacochlioquinones A-C, together with seven known compounds, were isolated from the plant endophytic fungus Bipolaris victoriae S27 derived from the fresh stems of Rubia podantha Diels. Their structures were mainly determined by extensive spectroscopic analysis. The relative configurations of bipolacochlioquinones A-C were assigned using the ROESY spectrum, comparison of their spectral data with that reported in the literatures, and NMR calculations. Moreover, their complete absolute configurations were further established by electronic circular dichroism calculations using density functional theory. Among them, bipolacochlioquinone A is found to represent the first example of previously undescribed 6/6/6/6/6 pentacyclic dioxane-containing cochlioquinones, and bipolacochlioquinone B possesses a rare 6/6/6/6/5 pentacyclic system bearing a tetrahydrofuran ring fused to a polyketide and a sesquiterpenoid subunit. All compounds were evaluated for their inhibitory effects on tumor growth, metastasis, and the NF-κB signaling pathway. Among them, bipolacochlioquinone C and Cochlioquinone A show the most potent cytotoxicities and NF-κB inhibitory activities. The effects of bipolacochlioquinone C and Cochlioquinone A on the expression of NF-κB-associated proteins were also evaluated using western blotting. These results indicate that bipolacochlioquinone C and Cochlioquinone A can inhibit the growth and metastasis of HCT116 and MDA-MB-231 cells by suppressing the NF-κB signaling pathway.
Antileishmanial activity of compounds produced by endophytic fungi derived from medicinal plant Vernonia polyanthes and their potential as source of bioactive substances
World J Microbiol Biotechnol 2015 Nov;31(11):1793-800.PMID:26318306DOI:10.1007/s11274-015-1932-0.
The purpose of this work was to evaluate the antileishmanial activity of endophytic fungi isolated from leaves of Vernonia polyanthes plant and their prospective use in the discovery of bioactive compounds. Sixteen endophytes were isolated by using potato dextrose agar medium and submitted to cultivation in rice medium. The fungal cultures were extracted with ethanol and used as crude extracts for testing their antileishmanial activity. The most active ethanol extract was obtained from P2-F3 strain, which was identified as Cochliobolus sativus by ITS rRNA gene sequence data. Followed by a bioassay-guided fractionation, the Cochlioquinone A, isocochlioquinone A and anhydrocochlioquinone A compounds were isolated from the crude extracts and demonstrated to inhibit the parasites. From the present work, it is possible to conclude that endophytic fungi derived from medicinal plant V. polyanthes may be considered promising source for the discovery of bioactive compounds.