Bisabosqual D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00156 |
| CAS | |
| Molecular Weight | 418.49 |
| Molecular Formula | C23H30O7 |
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Description
Bisabosqual D is a squalene synthase inhibitor produced by Stachybotry ruwenzoriensia.
Specification
| IUPAC Name | (7S,8R,11S,12R,13S)-7-[(3R)-3,4-dihydroxy-4-methylpentyl]-11-hydroxy-7,11-dimethyl-6,15-dioxatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14)-triene-2,3-dicarbaldehyde |
| Canonical SMILES | CC1(CCC2C3C1OC4=C(C(=CC(=C34)OC2(C)CCC(C(C)(C)O)O)C=O)C=O)O |
| InChI | InChI=1S/C23H30O7/c1-21(2,27)16(26)6-8-23(4)14-5-7-22(3,28)20-17(14)18-15(30-23)9-12(10-24)13(11-25)19(18)29-20/h9-11,14,16-17,20,26-28H,5-8H2,1-4H3/t14-,16-,17+,20-,22+,23+/m1/s1 |
| InChI Key | DWPUMDIAHUOAEN-PLOOWVJUSA-N |
Reference Reading
1. 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.
2. 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.
3. 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.
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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 ╳
