Epi-cochlioquinone A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01241 |
| CAS | 147384-57-4 |
| Molecular Weight | 532.67 |
| Molecular Formula | C30H44O8 |
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Description
It is produced by the strain of Stachybitrys bisbyi. It can inhibit rat liver microsomal ACAT with IC50 of 1.7 μmol/L, inhibit plasma lecithin cholesterol acyltransferase (LCAT) with IC50 of 15.8 μmol/L, and inhibit cholesterol absorption in rats by 50% at 75 mg/kg.
Specification
| Synonyms | Epicochlioquinone A; (8-alpha)-Cochlioquinone A; Cochlioquinone A, (8-alpha)- |
| IUPAC Name | [(2S,3R,4S)-2-[(3R,4aR,6aS,12S,12aS,12bR)-12-hydroxy-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-8,11-dioxo-1,2,3,4a,5,6,12,12a-octahydropyrano[3,2-a]xanthen-9-yl]-4-methylhexan-3-yl] acetate |
| Canonical SMILES | CCC(C)C(C(C)C1=CC(=O)C2=C(C1=O)OC3(CCC4C(C3C2O)(CCC(O4)C(C)(C)O)C)C)OC(=O)C |
| InChI | InChI=1S/C30H44O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,34-35H,9-13H2,1-8H3/t15-,16-,20+,21+,24+,25+,27+,29-,30-/m0/s1 |
| InChI Key | UWSYUCZPPVXEKW-UDLMDNSSSA-N |
Properties
| Appearance | Yellow Crystal |
| Boiling Point | 638.8±55.0 °C (Predicted) |
| Melting Point | 158-161 °C |
| Density | 1.21±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol |
Reference Reading
1. Genome-based mining of new antimicrobial meroterpenoids from the phytopathogenic fungus Bipolaris sorokiniana strain 11134
Jianying Han, Jingyu Zhang, Zhijun Song, Guoliang Zhu, Miaomiao Liu, Huanqin Dai, Tom Hsiang, Xueting Liu, Lixin Zhang, Ronald J Quinn, Yunjiang Feng Appl Microbiol Biotechnol. 2020 May;104(9):3835-3846. doi: 10.1007/s00253-020-10522-1. Epub 2020 Mar 26.
Polyketide-terpenoid hybrid compounds are one of the largest families of meroterpenoids, with great potential for drug development for resistant pathogens. Genome sequence analysis of secondary metabolite gene clusters of a phytopathogenic fungus, Bipolaris sorokiniana 11134, revealed a type I polyketide gene cluster, consisting of highly reducing polyketide synthase, non-reducing polyketide synthase, and adjacent prenyltransferase. MS- and UV-guided isolations led to the isolation of ten meroterpenoids, including two new compounds: 19-dehydroxyl-3-epi-arthripenoid A (1) and 12-keto-cochlioquinone A (2). The structures of 1-10 were elucidated by the analysis of NMR and high-resolution electrospray ionization mass spectroscopy data. Compounds 5-8 and 10 showed moderate activity against common Staphylococcus aureus and methicillin-resistant S. aureus, with minimum inhibitory concentration (MIC) values of 12.5-100 μg/mL. Compound 5 also exhibited activity against four clinical resistant S. aureus strains and synergistic antifungal activity against Candida albicans with MIC values of 12.5-25 μg/mL. The biosynthetic gene cluster of the isolated compounds and their putative biosynthetic pathway are also proposed. KEY POINTS: · Ten meroterpenoids were identified from B. sorokiniana, including two new compounds. · Cochlioquinone B (5) showed activity against MRSA and synergistic activity against C. albicans. · The biosynthetic gene cluster and biosynthetic pathway of meroterpenoids are proposed. · Genome mining provided a new direction to uncover the diversity of meroterpenoids.
2. Identification of meroterpenoids from Bipolaris victoriae S27 and their potential activity against tumor metastasis and inhibition of the NF-κB signaling pathway
Li Feng, Xin-Jia Wang, Ling Li, An-Xin Zhang, Ran-Ran Shang, Ning-Hua Tan, Zhe Wang Phytochemistry. 2022 Aug;200:113180. doi: 10.1016/j.phytochem.2022.113180. Epub 2022 Apr 12.
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.
3. A Novel Cochlioquinone Derivative, CoB1, Regulates Autophagy in Pseudomonas aeruginosa Infection through the PAK1/Akt1/mTOR Signaling Pathway
Pengcheng Zhu, Huimin Bu, Shirui Tan, Jinjuan Liu, Bo Yuan, Guokai Dong, Meng Wang, Yuji Jiang, Hong Zhu, Hui Li, Zhenjun Li, Jihong Jiang, Min Wu, Rongpeng Li J Immunol. 2020 Sep 1;205(5):1293-1305. doi: 10.4049/jimmunol.1901346. Epub 2020 Aug 3.
Owing to multiple antibiotic resistance, Pseudomonas aeruginosa causes the most intractable infections to human beings worldwide, thus exploring novel drugs to defend against this bacterium remains of great importance. In this study, we purified a novel cochlioquinone B derivative (CoB1) from Salvia miltiorrhiza endophytic Bipolaris sorokiniana and reveal its role in host defense against P. aeruginosa infection by activating cytoprotective autophagy in alveolar macrophages (AMs) both in vivo and in vitro. Using a P. aeruginosa infection model, we observed that CoB1-treated mice manifest weakened lung injury, reduced bacterial systemic dissemination, decreased mortality, and dampened inflammatory responses, compared with the wild type littermates. We demonstrate that CoB1-induced autophagy in mouse AMs is associated with decreased PAK1 expression via the ubiquitination-mediated degradation pathway. The inhibition of PAK1 decreases the phosphorylation level of Akt, blocks the Akt/mTOR signaling pathway, and promotes the release of ULK1/2-Atg13-FIP200 complex from mTOR to initiate autophagosome formation, resulting in increased bacterial clearance capacity. Together, our results provide a molecular basis for the use of CoB1 to regulate host immune responses against P. aeruginosa infection and indicate that CoB1 is a potential option for the treatment of infection diseases.
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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 ╳
