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Heptelidic acid (Koningic acid) is a naturally occurring sesquiterpene lactone-based antibiotic isolated from Trichoderma koningii, acting as a specific GAPDH inhibitor (IC50 = 90 μM) with anticancer activity. It inhibits Etoposide-induced apoptosis via downregulation of caspases.
| ln Vitro |
The culture filtrate of three distinct fungal strains that were recovered from soil samples contained the sesquiterpene antibiotic heptelidic acid. Characterization, fermentation, isolation, and organism production are all produced by heptelidic acid[1]. For human leukemia U937 cells, heptelidic acid prevents apoptosis triggered by etoposide[2]. Heptelidic acid, administered 8 hours after etoposide therapy, inhibits caspase-3 activation in U937 cells with an IC50 value of 40 μM[2]. Human GAPDH's active site can be directly bound by heptelidic acid (Koningic acid; KA), a naturally occurring substance derived from the Trichoderma fungus. Cell viability in human cells treated with heptelidic acid was successfully restored by the expression of T. koningii KAr-GAPDH. Following treatment with Heptelidic acid at a concentration of 0-200 μM (IC50=5 μM), HEK293T cells expressing T. koningii KAr-GAPDH demonstrated full cell viability[3].
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| ln Vivo |
Bioavailable heptelidic acid (Koningic acid; KA) dynamically alters glycolysis in vivo[3].
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| Cell Assay |
Cell Viability Assay[3]
Cell Types: HEK293T cells expressing KAr-GAPDH or EV (top left) Tested Concentrations: 0.1, 1, 10, 100, 1000 μM Incubation Duration: 24 hrs (hours) Experimental Results: IC50=5 μM. |
| Animal Protocol |
Animal/Disease Models: 6-week old female Foxn1nu (nude) mice bearing BT-474 tumor[3]
Doses: 1, 2.5, 5, and 10 mg/kg Route of Administration: Daily intraperitoneal (ip)injections, 24 hrs (hours) Experimental Results: 1 mg/kg was determined to be the maximum tolerated dose (MTD) based upon behavioral monitoring and adverse events at higher doses (hemolysis, hematuria, and anemia). |
| References |
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| Additional Infomation |
Heptelidic acid is a terpene lactone.
Heptelidic acid has been reported in Trichoderma virens, Phyllosticta, and Trichoderma koningii with data available. |
| Molecular Formula |
C15H20O5
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|---|---|
| Molecular Weight |
280.32
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| Exact Mass |
280.131
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| CAS # |
57710-57-3
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| PubChem CID |
10945834
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| Appearance |
Colorless to off-white solid powder
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| LogP |
1.621
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
20
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| Complexity |
481
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| Defined Atom Stereocenter Count |
4
|
| SMILES |
CC(C)[C@H]1CC[C@@]2(CO2)[C@@H]3[C@@H]1C=C(COC3=O)C(=O)O
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| InChi Key |
JESMSCGUTIEROV-RTWAVKEYSA-N
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| InChi Code |
InChI=1S/C15H20O5/c1-8(2)10-3-4-15(7-20-15)12-11(10)5-9(13(16)17)6-19-14(12)18/h5,8,10-12H,3-4,6-7H2,1-2H3,(H,16,17)/t10-,11-,12-,15-/m1/s1
|
| Chemical Name |
(5aS,6R,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
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| Synonyms |
Avocettin Koningic acid Heptelidic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5674 mL | 17.8368 mL | 35.6735 mL | |
| 5 mM | 0.7135 mL | 3.5674 mL | 7.1347 mL | |
| 10 mM | 0.3567 mL | 1.7837 mL | 3.5674 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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