Aranorosinol A
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| Category | Antibiotics |
| Catalog number | BBF-00069 |
| CAS | 145147-04-2 |
| Molecular Weight | 421.53 |
| Molecular Formula | C23H35NO6 |
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Description
Aranorosinol A is an antibiotic produced by Pseudoarachniotus roseus. It has only weak antibacterial and antifungal activity.
Specification
| IUPAC Name | (2E,4E,6R)-N-[(1S,2'R,3R,3'S,5R,7S)-2',6-dihydroxyspiro[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)O)OC1O |
| InChI | InChI=1S/C23H35NO6/c1-4-5-6-7-8-13(2)11-14(3)9-10-16(25)24-15-12-23(30-22(15)27)20-18(28-20)17(26)19-21(23)29-19/h9-11,13,15,17-22,26-27H,4-8,12H2,1-3H3,(H,24,25)/b10-9+,14-11+ |
| InChI Key | NDLASBSIMFTZFG-QDCWQMMGSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 638.6°C at 760 mmHg |
| Melting Point | 133-135°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. Production of antioomycete compounds active against the phytopathogens Phytophthora sojae and Aphanomyces cochlioides by clavicipitoid entomopathogenic fungi
Sastia Prama Putri, Kei-Ichi Ishido, Hiroshi Kinoshita, Shigeru Kitani, Fumio Ihara, Yasuko Sakihama, Yasuhiro Igarashi, Takuya Nihira J Biosci Bioeng. 2014 May;117(5):557-62. doi: 10.1016/j.jbiosc.2013.10.014. Epub 2013 Nov 21.
A total of 412 strains belonging to 14 genera of clavicipitoid entomopathogenic fungi (EPF) were screened for activities against two economically important plant pathogenic oomycetes, Phytophthora sojae and Aphanomyces cochlioides. To identify the antioomycete compounds produced by EPF, the extracts of 13 highly active EPF strains were characterized in detail by high performance liquid chromatography with diode array detection and high-resolution mass spectrometric detection and antioomycete assay. The antioomycete activity of several Metarhizium extracts was associated with previously isolated aurovertins, fungerin, N-(methyl-3-oxodec-6-enoyl)-2-pyrroline, and N-(methyl-3-oxodecanoyl)-2-pyrroline. The depsipeptide beauvericin was confirmed to be one of the active principles of three strains of Isaria tenuipes, which strongly inhibited mycelial growth of both P. sojae and A. cochlioides. Two known bioactive metabolites, paecilosetin and aranorosinol A, together with a novel and potent antioomycete compound, farinomalein, were isolated from the extracts of Isaria farinosa and all compounds were confirmed to have antioomycete activity. Identification of 8 antioomycete compounds from 13 clavicipitioid EPF demonstrated a new potential use of EPF as a source of compounds for the control of soil-borne plant pathogenic oomycetes.
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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 ╳
