Bisabosqual C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00155 |
| CAS | |
| Molecular Weight | 400.46 |
| Molecular Formula | C23H28O6 |
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Description
Bisabosqual C is a squalene synthase inhibitor produced by Stachybotry ruwenzoriensia.
Specification
| Synonyms | (3S,3aS,9S,9aR,9bR)-2,3,3a,9,9a,9b-Hexahydro-3,9b-dihydroxy-3,9-dimethyl-9-(4-methyl-3-pentenyl)-1H-benzofuro[4,3,2-cde][1]benzopyran-5,6-dicarbaldehyde |
| IUPAC Name | (7S,8R,11S,12S,13R)-11,13-dihydroxy-7,11-dimethyl-7-(4-methylpent-3-enyl)-6,15-dioxatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14)-triene-2,3-dicarbaldehyde |
| Canonical SMILES | CC(=CCCC1(C2CCC(C3C2(C4=C(O1)C=C(C(=C4O3)C=O)C=O)O)(C)O)C)C |
| InChI | InChI=1S/C23H28O6/c1-13(2)6-5-8-22(4)17-7-9-21(3,26)20-23(17,27)18-16(29-22)10-14(11-24)15(12-25)19(18)28-20/h6,10-12,17,20,26-27H,5,7-9H2,1-4H3/t17-,20-,21-,22-,23+/m0/s1 |
| InChI Key | FGBBGDWEXFKAKY-DIMAQAOGSA-N |
Reference Reading
1. Bisabosquals, novel squalene synthase inhibitors. I. Taxonomy, fermentation, isolation and biological activities
K Minagawa, S Kouzuki, K Nomura, T Yamaguchi, Y Kawamura, K Matsushima, H Tani, K Ishii, T Tanimoto, T Kamigauchi J Antibiot (Tokyo). 2001 Nov;54(11):890-5. doi: 10.7164/antibiotics.54.890.
In the course of screening for yeast squalene synthase inhibitors, bisabosqual A was isolated from the culture broth of Stachybotrys sp. RF-7260. The related compounds bisabosquals B, C and D were also isolated from Stachybotrys ruwenzoriensis RF-6853. Bisabosquals inhibited squalene synthases. IC50 values of bisabosqual A against the microsomal squalene synthases from Saccharomyces cerevisiae, Candida albicans, HepG2 cell and rat liver were 0.43, 0.25, 0.95 and 2.5 microg/ml, respectively. Bisabosqual C exhibited inhibitory activities similar to bisabosqual A. Bisabosqual A showed broad spectrum antifungal activity in vitro.
2. Bisabosquals, novel squalene synthase inhibitors. II. Physico-chemical properties and structure elucidation
K Minagawa, S Kouzuki, K Nomura, Y Kawamura, H Tani, Y Terui, H Nakai, T Kamigauchi J Antibiot (Tokyo). 2001 Nov;54(11):896-903. doi: 10.7164/antibiotics.54.896.
The squalene synthase inhibitor bisabosqual A was isolated from the culture broth of Stachybotrys sp. RF-7260, and its structure was determined on the basis of spectroscopic methods including detailed 2D NMR analyses. The structures of bisabosquals B, C and D isolated from Stachybotrys ruwenzoriensis RF-6853 were determined by spectroscopic methods and chemical reactions. The absolute stereochemistry of bisabosquals A, B and D was determined by X-ray crystallographic analysis. They have novel cis-fused tetracyclic structures with a bisabolane-type sesquiterpene and phenol moieties.
3. Seven new cytotoxic phenylspirodrimane derivatives from the endophytic fungus Stachybotrys chartarum
Hong Zhang, Ming-Hua Yang, Fang-Fang Zhuo, Na Gao, Xiao-Bei Cheng, Xiao-Bing Wang, Yue-Hu Pei, Ling-Yi Kong RSC Adv. 2019 Jan 25;9(7):3520-3531. doi: 10.1039/c8ra10195g.
Seven undescribed phenylspirodrimane derivatives, stachybochartins A-G (1-7), and four known analogues (8-11) were isolated from the endophytic fungus Stachybotrys chartarum obtained from Pinellia ternata. Stachybochartins A-D are four rare C-C-coupled dimeric derivatives and stachybochartin G features a seco-bisabosqual skeleton. Their structures and configurations were elucidated via spectroscopic analysis, electronic circular dichroism (ECD) calculations, the ECD exciton chirality method and the modified Mosher's method. Stachybochartins A-D and G displayed cytotoxic activities against MDA-MB-231 breast cancer cells and U-2OS osteosarcoma cells, with IC50 values ranging from 4.5 to 21.7 μM. Stachybochartins C and G exerted strong anti-proliferative activities against U-2OS cells in concentration- and time-dependent manners and induced apoptosis.
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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 ╳
