Schizostatin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-02887 |
| CAS | 163564-55-4 |
| Molecular Weight | 334.45 |
| Molecular Formula | C20H30O4 |
Online Inquiry
Description
It is a squalene synthase inhibitor produced by the strain of Schizophyllum commune SANK 17785. It inhibits squalene synthase with IC50 of 0.84 μmol/L. 1000 μg/mL of Schizostatin has no antibacterial effect on the tested bacteria, mycobacteria, yeast and mycoplasma.
Specification
| Synonyms | schizostatin E; 2-Butenedioic acid, 2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2E)-; 2-Butenedioic acid, 2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, (E,E,E)- |
| IUPAC Name | (E)-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]but-2-enedioic acid |
| Canonical SMILES | CC(=CCCC(=CCCC(=CCCC(=CC(=O)O)C(=O)O)C)C)C |
| InChI | InChI=1S/C20H30O4/c1-15(2)8-5-9-16(3)10-6-11-17(4)12-7-13-18(20(23)24)14-19(21)22/h8,10,12,14H,5-7,9,11,13H2,1-4H3,(H,21,22)(H,23,24)/b16-10+,17-12+,18-14+ |
| InChI Key | XNZYMBLMYICBGE-ABTLALLYSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 119-122°C |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Mannonerolidol, a new nerolidol mannoside from culture broth of Schizophyllum commune
E-Eum Woo, Ji-Yul Kim, Jeong-Seon Kim, Soon-Wo Kwon, In-Kyoung Lee, Bong-Sik Yun J Antibiot (Tokyo). 2019 Mar;72(3):178-180. doi: 10.1038/s41429-018-0130-3. Epub 2018 Dec 12.
To discover antimicrobial agents from higher fungi, mannonerolidol (3), a new nerolidol mannoside, together with known schizostatin (1) and nerolidol (2) were isolated from an antimicrobial fraction of the culture broth of Schizophyllum commune. Structures of these compounds were determined through spectroscopic methods. Compounds 1 and 3 exhibited antimicrobial activities against plant pathogenic fungi Rhizoctonia solani, Diaporthe sp., Botrytis cinerea, and Alternaria solani and bacteria Bacillus subtilis and Staphylococcus aureus.
2. Synergistic Interactions of Schizostatin Identified from Schizophyllum commune with Demethylation Inhibitor Fungicides
Min Young Park, Byeong Jun Jeon, Ji Eun Kang, Beom Seok Kim Plant Pathol J. 2020 Dec 1;36(6):579-590. doi: 10.5423/PPJ.OA.07.2020.0141.
Botrytis cinerea, which causes gray mold disease in more than 200 plant species, is an economically important pathogen that is mainly controlled by synthetic fungicides. Synergistic fungicide mixtures can help reduce fungicide residues in the environment and mitigate the development of fungicide-resistant strains. In this study, we screened microbial culture extracts on Botrytis cinerea to identify an antifungal synergist for tebuconazole. Among the 4,006 microbial extracts screened in this study, the culture extract from Schizophyllum commune displayed the most enhanced activity with a sub-lethal dosage of tebuconazole, and the active ingredient was identified as schizostatin. In combination with 5 μg/ml tebuconazole, schizostatin (1 μg/ml) showed disease control efficacy against gray mold on tomato leaf similar to that achieved with 20 μg/ml tebuconazole treatment alone. Interestingly, schizostatin showed demethylation inhibitor (DMI)-specific synergistic interactions in the crossed-paper strip assay using commercial fungicides. In a checkerboard assay with schizostatin and DMIs, the fractional inhibitory concentration values were 0.0938-0.375. To assess the molecular mechanisms underlying this synergism, the transcription levels of the ergosterol biosynthetic genes were observed in response to DMIs, schizostatin, and their mixtures. Treatment with DMIs increased the erg11 (the target gene of DMI fungicides) expression level 15.4-56.6-fold. However, treatment with a mixture of schizostatin and DMIs evidently reverted erg11 transcription levels to the pre-DMI treatment levels. These results show the potential of schizostatin as a natural antifungal synergist that can reduce the dose of DMIs applied in the field without compromising the disease control efficacy of the fungicides.
3. Control of Anthracnose and Gray Mold in Pepper Plants Using Culture Extract of White-Rot Fungus and Active Compound Schizostatin
Swarnalee Dutta, E-Eum Woo, Sang-Mi Yu, Rajalingam Nagendran, Bong-Sik Yun, Yong Hoon Lee Mycobiology. 2019 Mar 23;47(1):87-96. doi: 10.1080/12298093.2018.1551833. eCollection 2019 Mar.
Fungi produce various secondary metabolites that have beneficial and harmful effects on other organisms. Those bioactive metabolites have been explored as potential medicinal and antimicrobial resources. However, the activities of the culture filtrate (CF) and metabolites of white-rot fungus (Schizophyllum commune) have been underexplored. In this study, we assayed the antimicrobial activities of CF obtained from white-rot fungus against various plant pathogens and evaluated its efficacy for controlling anthracnose and gray mold in pepper plants. The CF inhibited the mycelial growth of various fungal plant pathogens, but not of bacterial pathogens. Diluted concentrations of CF significantly suppressed the severity of anthracnose and gray mold in pepper fruits. Furthermore, the incidence of anthracnose in field conditions was reduced by treatment with a 12.5% dilution of CF. The active compound responsible for the antifungal and disease control activity was identified and verified as schizostatin. Our results indicate that the CF of white-rot fungus can be used as an eco-friendly natural product against fungal plant pathogens. Moreover, the compound, schizostatin could be used as a biochemical resource or precursor for development as a pesticide. To the best of our knowledge, this is the first report on the control of plant diseases using CF and active compound from white-rot fungus. We discussed the controversial antagonistic activity of schizostatin and believe that the CF of white-rot fungus or its active compound, schizostatin, could be used as a biochemical pesticide against fungal diseases such as anthracnose and gray mold in many vegetables.
Recommended Products
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
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 ╳
