Cochlioquinone A1
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-00383 |
| CAS | |
| Molecular Weight | 590.74 |
| Molecular Formula | C33H50O9 |
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Description
It is produced by the strain of Bipolaris zeicila. Cochlioquinone A1 inhibited DGAT with IC50 of 6.3 μg/mL.
Specification
| IUPAC Name | [(2S,4S)-2-[(3R,4aR,6aR,12S,12aS,12bR)-8,12-dihydroxy-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-11-oxo-8-(2-oxopropyl)-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(CC(=O)C)O)OC3(CCC4C(C3C2O)(CCC(O4)C(C)(C)O)C)C)OC(=O)C |
| InChI | InChI=1S/C33H50O9/c1-10-17(2)27(40-20(5)35)19(4)21-15-22(36)25-26(37)28-31(8)13-11-23(30(6,7)38)41-24(31)12-14-32(28,9)42-29(25)33(21,39)16-18(3)34/h15,17,19,23-24,26-28,37-39H,10-14,16H2,1-9H3/t17-,19-,23+,24+,26+,27?,28+,31-,32+,33?/m0/s1 |
| InChI Key | YJGGIEJHHZMGCM-KXDDQDPQSA-N |
Properties
| Appearance | Dark Yellow Colloidal Solid |
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. Cochlioquinone A1, a new anti-angiogenic agent from Bipolaris zeicola
Hye Jin Jung, Hyang Burm Lee, Chi Hwan Lim, Chang Jin Kim, Ho Jeong Kwon Bioorg Med Chem. 2003 Nov 3;11(22):4743-7. doi: 10.1016/s0968-0896(03)00523-6.
Cochlioquinone A1 (CoA1) was newly isolated from the culture extract of Bipolaris zeicola as a potent anti-angiogenic agent. CoA1 inhibited in vitro angiogenesis of bovine aortic endothelial cells (BAECs) such as bFGF-induced tube formation and invasion at the concentration (1 microg/mL) without cytotoxicity. Notably, CoA1 exhibited more potent inhibition activity for the growth of BAECs than that of normal and cancer cell lines investigated in this study. These results demonstrate that CoA1 is a new anti-angiogenic agent and can be developed as a new therapeutic agent for angiogenesis-related 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 ╳
