Viridin
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| Category | Antibiotics |
| Catalog number | BBF-02969 |
| CAS | 3306-52-3 |
| Molecular Weight | 352.34 |
| Molecular Formula | C20H16O6 |
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Description
It is a steroidal antibiotic produced by the strain of Gliocladium virens. It has anti-fungal and gram-positive bacterial effects.
Specification
| Synonyms | (1S-(1alpha,2alpha,11balpha))-1,7,8,11b-Tetrahydro-1-hydroxy-2-methoxy-11b-methylcyclopenta(7,8)phenanthro(10,1-bc)furan-3,6,9(2H)-trione; 18-Norandrosta-5,8,11,13-tetraeno(6,5,4-bc)furan-3,7,17-trione, 1-hydroxy-2-methoxy-, (1beta,2beta)-; Cyclopenta(7,8)phenanthro(10,1-bc)furan-3,6,9(2H)-trione, 1,7,8,11b-tetrahydro-1-hydroxy-2-methoxy-11b-methyl-, (1S,2R,11bS)- |
| IUPAC Name | (1R,17S,18S)-18-hydroxy-17-methoxy-1-methyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11,16-trione |
| Canonical SMILES | CC12C(C(C(=O)C3=COC(=C31)C(=O)C4=C2C=CC5=C4CCC5=O)OC)O |
| InChI | InChI=1S/C20H16O6/c1-20-11-5-3-8-9(4-6-12(8)21)13(11)16(23)17-14(20)10(7-26-17)15(22)18(25-2)19(20)24/h3,5,7,18-19,24H,4,6H2,1-2H3/t18-,19-,20-/m1/s1 |
| InChI Key | YEIGUXGHHKAURB-VAMGGRTRSA-N |
Properties
| Appearance | Prismatic Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi |
| Boiling Point | 611.3±55.0°C (Predicted) |
| Melting Point | 245°C (dec.) |
| Density | 1.51±0.1 g/cm3 (Predicted) |
Reference Reading
1. Enantioselective Chemical Syntheses of the Furanosteroids (-)-Viridin and (-)-Viridiol
Matthew Del Bel, Alexander R Abela, Jeffrey D Ng, Carlos A Guerrero J Am Chem Soc. 2017 May 24;139(20):6819-6822. doi: 10.1021/jacs.7b02829. Epub 2017 May 12.
Herein we describe concise enantioselective chemical syntheses of (-)-viridin and (-)-viridiol. Our convergent approach couples two achiral fragments of similar complexity and employs an enantioselective intramolecular Heck reaction to set the absolute stereochemical configuration of an all-carbon quaternary stereocenter. To complete the syntheses of these base- and nucleophile-sensitive natural products, we conduct carefully orchestrated site- and diastereoselective oxidations and other transformations. Our work is the first to generate these targets as single enantiomers.
2. Total Synthesis of Viridin and Viridiol
Yang Ji, Zhengyuan Xin, Haibing He, Shuanhu Gao J Am Chem Soc. 2019 Oct 16;141(41):16208-16212. doi: 10.1021/jacs.9b08577. Epub 2019 Oct 3.
The asymmetric total synthesis of (-)-viridin and (-)-viridiol, antifungal metabolites, was achieved in 17 and 18 steps from a commercially available starting material. An intramolecular [3+2] cycloaddition was applied to an easily available l-ribose derivative in order to construct the highly substituted D ring containing the key chiral cis-triol fragment. Co-catalyzed metal-hydride H atom transfer (MHAT) radical cyclization was utilized to form the C-ring and the all-carbon quaternary center at C-10. This convergent strategy provides a scalable approach to prepare viridin and viridiol for biological studies.
3. Bioconversion of antifungal viridin to phytotoxin viridiol by environmental non-viridin producing microorganisms
Gilles-Alex Pakora, Stéphane Mann, Daouda Kone, Didier Buisson Bioorg Chem. 2021 Jul;112:104959. doi: 10.1016/j.bioorg.2021.104959. Epub 2021 May 1.
Biotransformation of viridin, an antifungal produced by biocontrol agent, with non-viridin producing microorganisms is studied. The results show that some environmental non-targeted microorganisms are able to reduce it in the known phytotoxin viridiol, and its 3-epimer. Consequently, this reduction, which happens in some cases by detoxification mechanism, could be disastrous for the plant in a biocontrol of plant disease. However, a process fermentation/biotransformation could be an efficient approach for the preparation of this phytotoxin.
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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 ╳
