Aranorosinol B
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| Category | Antibiotics |
| Catalog number | BBF-00070 |
| CAS | 145147-05-3 |
| Molecular Weight | 477.59 |
| Molecular Formula | C26H39NO7 |
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Description
Aranorosinol B is an antibiotic produced by Pseudoarachniotus roseus. It has only weak antibacterial and antifungal activity.
Specification
| IUPAC Name | (2E,4E)-N-[2',6-dihydroxy-6-(2-oxopropyl)spiro[4,8-dioxatricyclo[5.1.0.03,5]octane-2,5'-oxolane]-3'-yl]-4,6-dimethyldodeca-2,4-dienamide |
| Canonical SMILES | CCCCCCC(C)C=C(C)C=CC(=O)NC1CC2(C3C(O3)C(C4C2O4)(CC(=O)C)O)OC1O |
| InChI | InChI=1S/C26H39NO7/c1-5-6-7-8-9-15(2)12-16(3)10-11-19(29)27-18-14-26(34-24(18)30)22-20(32-22)25(31,13-17(4)28)21-23(26)33-21/h10-12,15,18,20-24,30-31H,5-9,13-14H2,1-4H3,(H,27,29)/b11-10+,16-12+ |
| InChI Key | YFJWRMZGLWVCSQ-NJLIKGMNSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 684.6°C at 760 mmHg |
| Melting Point | 84-85°C |
| Density | 1.26 g/cm3 |
Reference Reading
1. Total Synthesis and Structural Reassignment of Aranorosinol A, Aranorosinol B, and EI-2128-1
Haiyong Yu, Yingyuan Tian, Yan Zong, Jianyu Zhang, Tao Xu J Org Chem. 2020 Mar 20;85(6):4335-4343. doi: 10.1021/acs.joc.0c00028. Epub 2020 Mar 6.
Herein, we report a concise and collective total synthesis of three natural products aranorosinol A, aranorosinol B, and EI-2128-1 and also the known penicimutanolone. A unified strategy was conceived, which divergently accessed all four congeners within 9-11 steps (LLS) from a common intermediate. Bisoxirane-directed 1,2-addition was utilized as a key step to generate the desired configuration of the C8 stereocenter of aranorosinol A and B, 28 years after their first isolation, and these were both assigned as S configurations, while the C4' and C6' configurations of EI-2128-1 were both determined to be R,R-configurations.
2. Aranorosinol A and aranorosinol B, two new metabolites from Pseudoarachniotus roseus: production, isolation, structure elucidation and biological properties
K Roy, E K Vijayakumar, T Mukhopadhyay, S Chatterjee, R G Bhat, J Blumbach, B N Ganguli J Antibiot (Tokyo). 1992 Oct;45(10):1592-8. doi: 10.7164/antibiotics.45.1592.
Two new secondary metabolites, aranorosinol A (1) and aranorosinol B (2), were isolated from a strain of Pseudoarachniotus roseus. Their structures were elucidated on the basis of their spectral properties and chemical transformations and were found to be similar to aranorosin (3) isolated from the same strain.
3. Isolation and characterization of inhibitors of the essential histidine kinase, YycG in Bacillus subtilis and Staphylococcus aureus
Takafumi Watanabe, Yoshiki Hashimoto, Kaneyoshi Yamamoto, Kiyo Hirao, Akira Ishihama, Motohiro Hino, Ryutaro Utsumi J Antibiot (Tokyo). 2003 Dec;56(12):1045-52. doi: 10.7164/antibiotics.56.1045.
The set of sensor kinase YycG and response regulator YycF is the only essential two-component system (TCS) in Bacillus subtilis and Staphylococcus aureus. We have developed a screening method for antibacterial agents that inhibit YycG, the essential histidine kinase (HK). To increase screening sensitivity, a temperature-sensitive yycF mutant (CNM2000) of B. subtilis with super-sensitivity to HK inhibitors was constructed, which was used for the screening of acetone extracts from 4000 microbes. A total of 11 samples showed higher sensitivity to CNM2000 than to wild-type parent 168, and seven of those were characterized to be potent inhibitors against autophosphorylation of YycG. One sample compound was purified and identified as aranorosinol B, a known antibacterial agent against Gram-positive bacteria including B. subtilis and S. aureus. Aranorosinol B inhibited YycG from both B. subtilis and S. aureus with a half-maximum inhibitory concentration (IC50) of 223 and 211 microM, respectively.
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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 ╳
