Bisabosqual B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00154 |
| CAS | |
| Molecular Weight | 386.48 |
| Molecular Formula | C23H30O5 |
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Description
Bisabosqual B is a squalene synthase inhibitor produced by Stachybotry ruwenzoriensia. Bisabosqual B Antifungal activity is weak.
Specification
| Synonyms | (3S,3aR,9S,9aR,9bS)-2,3,3a,9,9a,9b-Hexahydro-3-hydroxy-6-(hydroxymethyl)-3,9-dimethyl-9-(4-methyl-3-pentenyl)-1H-benzofuro[4,3,2-cde][1]benzopyran-5-carbaldehyde |
| IUPAC Name | (7S,8R,11S,12R,13S)-11-hydroxy-3-(hydroxymethyl)-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-carbaldehyde |
| Canonical SMILES | CC(=CCCC1(C2CCC(C3C2C4=C(O1)C=C(C(=C4O3)C=O)CO)(C)O)C)C |
| InChI | InChI=1S/C23H30O5/c1-13(2)6-5-8-23(4)16-7-9-22(3,26)21-18(16)19-17(28-23)10-14(11-24)15(12-25)20(19)27-21/h6,10,12,16,18,21,24,26H,5,7-9,11H2,1-4H3/t16-,18+,21-,22+,23+/m1/s1 |
| InChI Key | PJUNMTHNNQPMQB-MQRVUQIVSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Stachybisbins A and B, the first cases of seco-bisabosquals from Stachybotrys bisbyi
Yan-Ru Bao, Guo-Dong Chen, Yue-Hua Wu, Xiao-Xia Li, Dan Hu, Xing-Zhong Liu, Yan Li, Xin-Sheng Yao, Hao Gao Fitoterapia. 2015 Sep;105:151-5. doi: 10.1016/j.fitote.2015.06.022. Epub 2015 Jul 3.
Stachybisbins A (1) and B (2), two new meroterpenoids with unprecedented seco-bisabosqual skeleton, together with three biogenetically related metabolites (3-5), were isolated from a wetland fungal strain of Stachybotrys bisbyi. The structures of the new compounds were determined by spectroscopic analyses, modified Mosher's method, and quantum chemical CD method. The cytotoxic activities of all compounds were tested against HL-60, SMMC-7721, A-549, MCF-7, and SW480 human cancer cell lines.
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. New Bisabosquals from Stachybotrys sp. PH30583 Elicited on Solid Media
Bao-Hui Ruan, Shu-Quan Li, Xue-Qiong Yang, Ya-Bin Yang, Ya-Mei Wu, Li-Jiao Shi, Hai-Yue Yin, Hao Zhou, Zhong-Tao Ding Molecules. 2018 Jun 29;23(7):1577. doi: 10.3390/molecules23071577.
Stachybotrys sp. PH30583 cultured in liquid medium only led to one structure type of novel isochroman dimers. Using the one strain-many compounds strategy, the reinvestigation of the metabolites from Stachybotrys sp. PH30583 cultured in rice solid medium led to the isolation of four triprenyl phenols, including two new bisabosquals and two known phenylspirodrimanes. Nitrobisabosquals A and B (1 and 2) are the first case of pyrrolidone-bisabosquals reported in literature. Totally different compounds were isolated using rice solid medium, compared with those isolated using liquid medium, so that rice solid medium presents a key factor in the production of triprenyl phenols. Compound 1 exhibited cytotoxicity against tumor cells, A-549, HL-60, MCF-7 SMMC-7721, and SW480, as well as weak anticoagulant activity with activated partial thromboplastin time (APTT) of 32.1 ± 0.17 s (p < 0.05 vs. Con.) at a concentration of 5 mM. Triprenyl phenol metabolites could be used as chemotaxonomic markers for Stachybotrys.
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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 ╳
