Scytalol D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02894 |
| CAS | 208183-24-8 |
| Molecular Weight | 264.27 |
| Molecular Formula | C14H16O5 |
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Description
It is produced by the strain of Scytalidium sp. 36-93. It selectively inhibits biosynthesis of dihydroxynaphthalene melanin in Lachnellula sp. A32-89, but does not inhibit the growth of the strain.
Specification
| Synonyms | 1(2H)-Naphthalenone, 3,4-dihydro-4,8-dihydroxy-6-methoxy-3-(2-oxopropyl)-, (3R,4R)-rel-(+)- |
| IUPAC Name | (3R,4R)-4,8-dihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2H-naphthalen-1-one |
| Canonical SMILES | CC(=O)CC1CC(=O)C2=C(C1O)C=C(C=C2O)OC |
| InChI | InChI=1S/C14H16O5/c1-7(15)3-8-4-11(16)13-10(14(8)18)5-9(19-2)6-12(13)17/h5-6,8,14,17-18H,3-4H2,1-2H3/t8-,14-/m1/s1 |
| InChI Key | YYYQERYXAQFNMH-XLKFXECMSA-N |
Properties
| Appearance | Colorless Oily Matter |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Changes in Fungicide Resistance Frequency and Population Structure of Pyricularia oryzae after Discontinuance of MBI-D Fungicides
F Suzuki, J Yamaguchi, A Koba, T Nakajima, M Arai Plant Dis. 2010 Mar;94(3):329-334. doi: 10.1094/PDIS-94-3-0329.
The changes in fungicide resistance frequency and population structure of the rice blast fungus Pyricularia oryzae were monitored after the discontinuance of melanin biosynthesis inhibitor targeting scytalone dehydratase (MBI-D) fungicides use in Saga Prefecture, Japan. After discontinuance in 2003, the frequency of resistant isolates decreased from 71.8% in 2002 to 25% in 2003, and became undetectable in 2007. The initial marked decrease was due to a decline of isolates possessing the predominant haplotype, although the haplotypic diversity among resistant isolates remained high from 2003 to 2005. These results revealed that resistant isolates were less fit in comparison with sensitive isolates in the absence of MBI-D fungicide pressure under field conditions. Pairwise FST values indicated that the change in population structure after MBI-D discontinuance was explainable by a rapid change in the proportions of resistant and sensitive subpopulations. Depending upon the existence of fitness cost and rapid changes in population structure, it may be possible to reintroduce MBI-D fungicides in areas where resistance has already developed, although we speculate that fitness cost related to MBI-D resistance may be small based on our present results and previous findings.
2. Proteomic analysis of the inhibitory effect of oligochitosan on the fungal pathogen, Botrytis cinerea
Yuan Sui, Zengxin Ma, Xianghong Meng J Sci Food Agric. 2019 Mar 30;99(5):2622-2628. doi: 10.1002/jsfa.9480. Epub 2018 Dec 24.
Background: The fungal pathogen Botrytis cinerea infects a broad range of horticultural plants worldwide, resulting in significant economic losses. A derivative of chitosan, oligochitosan, has been reported to be an eco-friendly alternative to synthetic fungicides. Results: Oligochitosan can greatly inhibit B. cinerea spore germination and induce protein carbonylation. To further investigate the molecular mechanism underlying the inhibitory effect, a comparative proteome analysis was conducted of oligochitosan-treated versus non-treated B. cinerea spores. The cellular proteins were obtained from B. cinerea spore samples and subjected to two-dimensional gel electrophoresis. In total, 21 differentially expressed proteins (DEPs) were identified. Three DEPs were up-regulated in the oligochitosan-treated versus the untreated spores, including scytalone dehydratase and a serine carboxypeptidase III precursor. By contrast, seven DEPs, including Hsp 88 and cell division cycle protein 48, were down-regulated by oligochitosan treatment. Notably, 10 DEPs, including phosphatidylserine decarboxylase proenzyme and ATP-dependent molecular chaperone HSC82, were only detected in the control spores, whereas one DEP, a non-annotated predicted protein, was only detected in the oligochitosan-treated spores. Conclusion: Oligochitosan may affect the spore germination of B. cinerea by impairing protein function. These findings have practical implications with respect to the use of oligochitosan for controlling fungal pathogens. © 2018 Society of Chemical Industry.
3. Identification of Scytalone Dehydratase Inhibitors Effective against Melanin Biosynthesis Dehydratase Inhibitor-Resistant Pyricularia oryzae
Takayuki Motoyama, Yasumitsu Kondoh, Takeshi Shimizu, Teruo Hayashi, Kaori Honda, Motoko Uchida, Hiroyuki Osada J Agric Food Chem. 2022 Mar 16;70(10):3109-3116. doi: 10.1021/acs.jafc.1c04984. Epub 2022 Mar 2.
Melanin is a secondary metabolite required for the infection of the rice blast fungus Pyricularia oryzae. Melanin biosynthesis enzymes are targets for controlling rice blast disease, and three types of commercial melanin biosynthesis inhibitors (MBIs) including MBI-R, MBI-D, and MBI-P have been developed. However, the occurrence of MBI-D-resistant strains containing scytalone dehydratase (SDH1/RSY1) with V75M mutations has been recently reported. In this study, we aimed to identify inhibitors of SDH1-V75M. We screened the RIKEN Natural Products Depository chemical library using chemical array technology and evaluated the inhibition of SDH1-V75M by candidate compounds. NPD13731 strongly inhibited the activity of wild-type and mutant SDH1. The structure-activity relationship data were used to create a more potent inhibitor 16, which controlled rice blast disease in rice plants infected with MBI-D-resistant P. oryzae. Compound 16, which we named melabiostin, may be used to develop fungicides for controlling rice blast infections.
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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 ╳
