Harzianic acidCAS# 157148-06-6 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 157148-06-6 | SDF | Download SDF |
| PubChem ID | 54691490 | Appearance | Powder |
| Formula | C19H27NO6 | M.Wt | 365.42 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-hydroxy-2-[[(4E)-4-[(2E,4E)-1-hydroxyocta-2,4-dienylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl]-3-methylbutanoic acid | ||
| SMILES | CCCC=CC=CC(=C1C(=O)C(N(C1=O)C)CC(C(C)C)(C(=O)O)O)O | ||
| Standard InChIKey | FQSWTHMMNDRFAI-RFJZBCCMSA-N | ||
| Standard InChI | InChI=1S/C19H27NO6/c1-5-6-7-8-9-10-14(21)15-16(22)13(20(4)17(15)23)11-19(26,12(2)3)18(24)25/h7-10,12-13,21,26H,5-6,11H2,1-4H3,(H,24,25)/b8-7+,10-9+,15-14+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Harzianic acid is a Trichoderma secondary metabolite. 2. Harzianic acid shows plant growth promotion activity. 3. Harzianic acid has antifungal activity and antibiotic activity against Pythium irregulare, Sclerotinia sclerotiorum, and Rhizoctonia solani. |
| Targets | Antifection |
Harzianic acid Dilution Calculator
Harzianic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7366 mL | 13.6829 mL | 27.3658 mL | 54.7315 mL | 68.4144 mL |
| 5 mM | 0.5473 mL | 2.7366 mL | 5.4732 mL | 10.9463 mL | 13.6829 mL |
| 10 mM | 0.2737 mL | 1.3683 mL | 2.7366 mL | 5.4732 mL | 6.8414 mL |
| 50 mM | 0.0547 mL | 0.2737 mL | 0.5473 mL | 1.0946 mL | 1.3683 mL |
| 100 mM | 0.0274 mL | 0.1368 mL | 0.2737 mL | 0.5473 mL | 0.6841 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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A novel fungal metabolite with beneficial properties for agricultural applications.[Pubmed:25006784]
Molecules. 2014 Jul 8;19(7):9760-72.
Trichoderma are ubiquitous soil fungi that include species widely used as biocontrol agents in agriculture. Many isolates are known to secrete several secondary metabolites with different biological activities towards plants and other microbes. Harzianic acid (HA) is a T. harzianum metabolite able to promote plant growth and strongly bind iron. In this work, we isolated from the culture filtrate of a T. harzianum strain a new metabolite, named isoHarzianic acid (iso-HA), a stereoisomer of HA. The structure and absolute configuration of this compound has been determined by spectroscopic methods, including UV-Vis, MS, 1D and 2D NMR analyses. In vitro applications of iso-HA inhibited the mycelium radial growth of Sclerotinia sclerotiorum and Rhizoctonia solani. Moreover, iso HA improved the germination of tomato seeds and induced disease resistance. HPLC-DAD experiments showed that the production of HA and iso HA was affected by the presence of plant tissue in the liquid medium. In particular, tomato tissue elicited the production of HA but negatively modulated the biosynthesis of its analogue iso-HA, suggesting that different forms of the same Trichoderma secondary metabolite have specific roles in the molecular mechanism regulating the Trichoderma plant interaction.
Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers.[Pubmed:25629709]
Org Lett. 2015 Feb 6;17(3):692-5.
The bioactive natural product Harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of Harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of Harzianic acid.
Harzianic acid, an antifungal and plant growth promoting metabolite from Trichoderma harzianum.[Pubmed:19894739]
J Nat Prod. 2009 Nov;72(11):2032-5.
A Trichoderma harzianum strain, isolated from composted hardwood bark in Western Australia, was found to produce a metabolite with antifungal and plant growth promoting activity. The structure and absolute configuration of the fungal compound, Harzianic acid (1), were determined by X-ray diffraction studies. Harzianic acid showed antibiotic activity against Pythium irregulare, Sclerotinia sclerotiorum, and Rhizoctonia solani. A plant growth promotion effect was observed at low concentrations of 1.
Harzianic acid: a novel siderophore from Trichoderma harzianum.[Pubmed:23909277]
FEMS Microbiol Lett. 2013 Oct;347(2):123-9.
Agriculture-relevant microorganisms are considered to produce secondary metabolites during processes of competition with other micro- and macro-organisms, symbiosis, parasitism or pathogenesis. Many different strains of the genus Trichoderma, in addition to a direct activity against phytopathogens, are well-known producers of secondary metabolites and compounds that substantially affect the metabolism of the host plant. Harzianic acid is a Trichoderma secondary metabolite, showing antifungal and plant growth promotion activities. This report demonstrates the ability of this tetramic acid to bind with a good affinity essential metals such as Fe(3+) , which may represent a mechanism of iron solubilisation that significantly alters nutrient availability in the soil environment for other microorganisms and the host plant.
