WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H333098
CAS#: 37248-47-8
Description: Validamycin A, also known as Validacin, is an antifungal agent used to protect rice plants against sheath blight caused by the pathogenic fungus, R. solani, due to its ability to inhibit trehalase, a trehalose-hydrolizing enzyme (Ki = 1.9 nM; IC50 = 0.7 μM). Validamycin A Induces Broad-Spectrum Resistance Involving Salicylic Acid and Jasmonic Acid/Ethylene Signaling Pathways.
Hodoodo Cat#: H333098
Name: Validamycin A
CAS#: 37248-47-8
Chemical Formula: C20H35NO13
Exact Mass: 497.21
Molecular Weight: 497.494
Elemental Analysis: C, 48.29; H, 7.09; N, 2.82; O, 41.81
Synonym: Validamycin A,
IUPAC/Chemical Name: (2R,3R,4S,5S,6R)-2-(((1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
InChi Key: JARYYMUOCXVXNK-CSLFJTBJSA-N
InChi Code: InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1
SMILES Code: O[C@H]([C@H]1O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@H]2[C@H](O)[C@@H](O)[C@@H](N[C@@]3([H])C=C(CO)[C@@H](O)[C@H](O)[C@H]3O)C[C@@H]2CO
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 497.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Ren L, Hou YP, Zhu YY, Zhao FF, Duan YB, Wu LY, Duan XX, Zhang J, Zhou MG. Validamycin A Enhances the Interaction Between Neutral Trehalase and 14-3-3 Protein Bmh1 in Fusarium graminearum. Phytopathology. 2022 Feb;112(2):290-298. doi: 10.1094/PHYTO-05-21-0214-R. Epub 2022 Feb 1. PMID: 34156266.
2: Yu J, Xu Z, Zhang C, Chen L, Hu X, Yu R, Zhao X. Residue behavior and risk assessment of validamycin a in grape under field conditions. J Environ Sci Health B. 2021;56(6):587-593. doi: 10.1080/03601234.2021.1926179. Epub 2021 Jun 8. PMID: 34102954.
3: Bian C, Duan Y, Xiu Q, Wang J, Tao X, Zhou M. Mechanism of validamycin A inhibiting DON biosynthesis and synergizing with DMI fungicides against Fusarium graminearum. Mol Plant Pathol. 2021 Jul;22(7):769-785. doi: 10.1111/mpp.13060. Epub 2021 May 2. PMID: 33934484; PMCID: PMC8232029.
4: García MD, Argüelles JC. Trehalase inhibition by validamycin A may be a promising target to design new fungicides and insecticides. Pest Manag Sci. 2021 Sep;77(9):3832-3835. doi: 10.1002/ps.6382. Epub 2021 Apr 10. PMID: 33786994.
5: Li W, Dai X, Pu E, Bian H, Chen Z, Zhang X, Guo Z, Li P, Li H, Yong Y, Wang C, Zhang Y, Han L. HLB-MCX-Based Solid-Phase Extraction Combined with Liquid Chromatography-Tandem Mass Spectrometry for the Simultaneous Determination of Four Agricultural Antibiotics (Kasugamycin, Validamycin A, Ningnanmycin, and Polyoxin B) Residues in Plant-Origin Foods. J Agric Food Chem. 2020 Nov 25;68(47):14025-14037. doi: 10.1021/acs.jafc.0c04620. Epub 2020 Nov 15. PMID: 33190501.
6: Bian C, Duan Y, Wang J, Xiu Q, Wang J, Hou Y, Song X, Zhou M. Validamycin A Induces Broad-Spectrum Resistance Involving Salicylic Acid and Jasmonic Acid/Ethylene Signaling Pathways. Mol Plant Microbe Interact. 2020 Dec;33(12):1424-1437. doi: 10.1094/MPMI-08-20-0211-R. Epub 2020 Oct 22. PMID: 32815479.
7: Plabutong N, Ekronarongchai S, Niwetbowornchai N, Edwards SW, Virakul S, Chiewchengchol D, Thammahong A. The Inhibitory Effect of Validamycin A on Aspergillus flavus. Int J Microbiol. 2020 Jun 27;2020:3972415. doi: 10.1155/2020/3972415. PMID: 32676114; PMCID: PMC7336217.
8: Marten AD, Stothard AI, Kalera K, Swarts BM, Conway MJ. Validamycin A Delays Development and Prevents Flight in Aedes aegypti (Diptera: Culicidae). J Med Entomol. 2020 Jul 4;57(4):1096-1103. doi: 10.1093/jme/tjaa004. PMID: 31982917; PMCID: PMC7334893.
9: Adhav AS, Kokane SR, Joshi RS. Functional characterization of Helicoverpa armigera trehalase and investigation of physiological effects caused due to its inhibition by Validamycin A formulation. Int J Biol Macromol. 2018 Jun;112:638-647. doi: 10.1016/j.ijbiomac.2018.01.221. Epub 2018 Feb 26. PMID: 29412176.
10: Zhang H, Wang C, Li H, Nie Y, Fang L, Chen Z. Simultaneous determination of kasugamycin and validamycin-A residues in cereals by consecutive solid-phase extraction combined with liquid chromatography-tandem mass spectrometry. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Mar;35(3):487-497. doi: 10.1080/19440049.2017.1411615. Epub 2017 Dec 28. PMID: 29210618.
11: Jiang J, Sun YF, Tang X, He CN, Shao YL, Tang YJ, Zhou WW. Alkaline pH shock enhanced production of validamycin A in fermentation of Streptomyces hygroscopicus. Bioresour Technol. 2018 Feb;249:234-240. doi: 10.1016/j.biortech.2017.10.012. Epub 2017 Oct 6. PMID: 29045927.
12: Lu C, Wu H, Su X, Bai L. Elimination of indigenous linear plasmids in Streptomyces hygroscopicus var. jinggangensis and Streptomyces sp. FR008 to increase validamycin A and candicidin productivities. Appl Microbiol Biotechnol. 2017 May;101(10):4247-4257. doi: 10.1007/s00253-017-8165-0. Epub 2017 Feb 25. PMID: 28238083.
13: Wu Q, Zhang L, Xia H, Yu C, Dou K, Li Y, Chen J. Omics for understanding synergistic action of validamycin A and Trichoderma asperellum GDFS1009 against maize sheath blight pathogen. Sci Rep. 2017 Jan 6;7:40140. doi: 10.1038/srep40140. PMID: 28057927; PMCID: PMC5216365.
14: Peng Y, Lu C, Bai L. [Effects of pigment gene deletions on validamycin A production in Streptomyces hygroscopicus var. jinggangensis]. Wei Sheng Wu Xue Bao. 2016 Nov 4;56(11):1719-29. Chinese. PMID: 29741834.
15: Feng J, Jiang J, Liu Y, Li W, Azat R, Zheng X, Zhou WW. Significance of oxygen carriers and role of liquid paraffin in improving validamycin A production. J Ind Microbiol Biotechnol. 2016 Oct;43(10):1365-72. doi: 10.1007/s10295-016-1822-y. Epub 2016 Aug 11. PMID: 27514663.
16: Li W, Feng J, Liu Y, Jiang J, Zheng X, Zhou WW. Novel spectrophotometric approach for determination of validamycin A in fermentation of Streptomyces hygroscopicus. J Biosci Bioeng. 2016 Dec;122(6):736-739. doi: 10.1016/j.jbiosc.2016.05.007. Epub 2016 Jun 11. PMID: 27296090.
17: Qu S, Kang Q, Wu H, Wang L, Bai L. Positive and negative regulation of GlnR in validamycin A biosynthesis by binding to different loci in promoter region. Appl Microbiol Biotechnol. 2015 Jun;99(11):4771-83. doi: 10.1007/s00253-015-6437-0. Epub 2015 Feb 12. PMID: 25672849.
18: Zhou TC, Zhong JJ. Production of validamycin A from hemicellulose hydrolysate by Streptomyces hygroscopicus 5008. Bioresour Technol. 2015 Jan;175:160-6. doi: 10.1016/j.biortech.2014.10.051. Epub 2014 Oct 20. PMID: 25459817.
19: Wang C, Zhang Z, Shen Y, Tian Z, Xu D, Han C. Determination of validamycin A in agricultural food samples by solid-phase extraction combined with liquid chromatography-atmospheric pressure chemical ionisation-tandem mass spectrometry. Food Chem. 2015 Feb 15;169:150-5. doi: 10.1016/j.foodchem.2014.07.145. Epub 2014 Aug 7. PMID: 25236210.
20: Zhou TC, Kim BG, Zhong JJ. Enhanced production of validamycin A in Streptomyces hygroscopicus 5008 by engineering validamycin biosynthetic gene cluster. Appl Microbiol Biotechnol. 2014 Sep;98(18):7911-22. doi: 10.1007/s00253-014-5943-9. Epub 2014 Jul 25. PMID: 25060680.
