Cyathin A3
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| Category | Antibiotics |
| Catalog number | BBF-01101 |
| CAS | 38598-35-5 |
| Molecular Weight | 318.45 |
| Molecular Formula | C20H30O3 |
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Description
It is produced by the strain of Cyathus helenae, C. africanus. It has weak activity against gram-positive bacteria, negative bacteria, actinomycetes and dermatophytes, and has anti-ischemia effect (improving cerebral ischemia in rat model).
Specification
| IUPAC Name | (3aR,5aR,9R,10aR)-9-hydroxy-8-(hydroxymethyl)-3a,5a-dimethyl-1-propan-2-yl-3,4,5,9,10,10a-hexahydro-2H-cyclohepta[e]inden-6-one |
| Canonical SMILES | CC(C)C1=C2C3CC(C(=CC(=O)C3(CCC2(CC1)C)C)CO)O |
| InChI | InChI=1S/C20H30O3/c1-12(2)14-5-6-19(3)7-8-20(4)15(18(14)19)10-16(22)13(11-21)9-17(20)23/h9,12,15-16,21-22H,5-8,10-11H2,1-4H3/t15-,16-,19-,20-/m1/s1 |
| InChI Key | RGROGZCBGZBCAG-XNFNUYLZSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi |
| Melting Point | 148-150 °C |
| Solubility | Soluble in Methanol, Acetone |
Reference Reading
1. Bacteria-induced static batch fungal fermentation of the diterpenoid cyathin A(3), a small-molecule inducer of nerve growth factor
Emma Dixon, Tatiana Schweibenz, Alison Hight, Brian Kang, Allyson Dailey, Sarah Kim, Meng-Yang Chen, Yura Kim, Sarah Neale, Ashley Groth, Trish Ike, Sarah Khan, Brandon Schweibenz, David Lieu, David Stone, Tania Orellana, Robin D Couch J Ind Microbiol Biotechnol. 2011 May;38(5):607-15. doi: 10.1007/s10295-010-0805-7. Epub 2010 Aug 17.
Cyathin A(3), produced by the fungus Cyathus helenae, is a member of the cyathane family of diterpene natural products. While many of the cyathanes display antibacterial/antimicrobial activity or have cytotoxic activity against human cancer cell lines, their most exciting therapeutic potential is derived from their ability to induce nerve growth factor (NGF) release from glial cells, making the cyathanes attractive lead molecules for the development of neuroprotective therapeutics to prevent/treat Alzheimer's disease. To investigate if cyathin A(3) has NGF-inducing activity, we set out to obtain it using published C. helenae bench-scale fungal fermentations. However, to overcome nonproducing fermentations, we developed an alternative, bacteria-induced static batch fermentation approach to the production of cyathin A(3), as described in this report. HPLC, UV absorption spectra, and mass spectrometry identify cyathin A(3) in fungal fermentations induced by the timely addition of Escherichia coli K12 or Bacillus megabacterium. Pre-filtration of the bacterial culture abolishes cyathin A(3) induction, suggesting that bacteria-associated media changes or physical interaction between the fungus and bacteria underlie the induction mechanism. Through alteration of incubation conditions, including agitation, the timing of induction, and media composition, we optimized the fermentation to yield nearly 1 mg cyathin A(3)/ml media, a sixfold increase over previously described yields. Additionally, by comparison of fermentation profiles, we reveal that cyathin A(3) biosynthesis is regulated by carbon catabolite repression. We have used an enzyme-linked immunosorbent assay to illustrate that cyathin A(3) induces NGF release from cultured glial cells, and therefore cyathin A(3) warrants further examination in the development of neuroprotective therapeutics.
2. Enantioselective total synthesis of cyathin A3
Dale E Ward, Jianheng Shen Org Lett. 2007 Jul 19;9(15):2843-6. doi: 10.1021/ol070994z. Epub 2007 Jun 20.
The total synthesis of (-)-cyathin A3 is described. The key step involves an unusual enantioselective Diels-Alder reaction of 2,5-dimethyl-1,4-benzoquinone with 2,4-bis(trimethylsilyloxy)-1,3-pentadiene, using Mikami's catalyst [(R)-BINOL + Cl2Ti(OiPr)2 + 4 A mol sieves] modified by addition of Mg and SiO2. Because cyathin A3 is easily transformed into allocyathin B3, cyathin B3, cyathin C3, and neoallocyathin A4, this route also constitutes formal syntheses of these natural products.
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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 ╳
