Heptelidic acid
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| Category | Antibiotics |
| Catalog number | BBF-01815 |
| CAS | 57710-57-3 |
| Molecular Weight | 280.32 |
| Molecular Formula | C15H20O5 |
| Purity | ≥95% |
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Description
It is produced by the strain of Gliocladium virens, Chaetomium globosum, Trichoderma viride. It is a sesquiterpenoid antibiotic. It has antibacterial activity against anaerobes, especially has strong effect on fragile bacilli (MIC is 0.4 μg/mL). It has anti-plasmodium (IC80 is 0.01 μg/mL) and antitumor activity. It is also an inhibitor of glyceraldehyde 3-phosphate dehydrogenase (GAPDH) that acts by binding to the cysteine-149 residue.
Specification
| Synonyms | Koningic acid; (+)-Heptelidic Acid; (5aS,6R,9S,9aS)-6-isopropyl-1-oxo-1,5a,6,7,8,9a-hexahydro-3H-spiro[benzo[c]oxepine-9,2'-oxirane]-4-carboxylic acid; Spiro[2-benzoxepin-9(3H),2'-oxirane]-4-carboxylicacid,1,5a,6,7,8,9a-hexahydro-6-(1-methylethyl)-1-oxo-, (2'S,5aS,6R,9aS)-; Avocettin |
| IUPAC 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 |
| Canonical SMILES | CC(C)C1CCC2(CO2)C3C1C=C(COC3=O)C(=O)O |
| InChI | 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 |
| InChI Key | JESMSCGUTIEROV-RTWAVKEYSA-N |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Parasites |
| Boiling Point | 501.1±50.0 °C (Predicted) |
| Melting Point | 95 °C |
| Density | 1.27±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Two glyceraldehyde-3-phosphate dehydrogenase isozymes from the koningic acid (heptelidic acid) producer Trichoderma koningii
K Sakai, A Endo, K Hasumi Eur J Biochem . 1990 Oct 5;193(1):195-202. doi: 10.1111/j.1432-1033.1990.tb19323.x.
The sesquiterpene lactone koningic acid (heptelidic acid) irreversibly inactivated glyceraldehyde-3-phosphate dehydrogenase [D-glyceraldehyde 3-phosphate: NAD+ oxidoreductase (phosphorylating)] (EC 1.2.1.12) (GAPDH) and thus inhibits glycolysis. The koningic-acid-producing strain of Trichoderma koningii M3947 was shown to contain the koningic-acid-resistant GAPDH isozyme (GAPDH I) under conditions of koningic acid production. In peptone-rich medium, however, no koningic acid production was observed, and the koningic-acid-sensitive GAPDH isozyme (GAPDH II), in addition to the resistant enzyme, was produced. Both enzymes were tetramer with a molecular mass of 152 kDa (4 x 38 kDa) and lost enzyme activity when two of the four cysteine residues reacted with koningic acid. The apparent Km values of GAPDH I and II for glyceraldehyde 3-phosphate were 0.54 mM and 0.33 mM, respectively. The former isozyme was inhibited 50% by 1 mM koningic acid but not affected at 0.1 mM, while the latter isozyme was inhibited 50% at 0.01 mM. The immunochemical properties and partial amino acid sequences suggested that the two isozymes have different molecular structures. These results suggest that GAPDH I is responsible for the glycolysis in T. koningii when koningic acid is produced.
2. Furan, phenolic, and heptelidic acid derivatives produced by Aspergillus oryzae
Jeong-Yong Cho, Seong-Il Lim, Jae-Hak Moon, Minji Lee, Young-Do Nam, So-Young Lee, Hyoung Jae Lee, Yu Geon Lee Food Sci Biotechnol . 2016 Oct 31;25(5):1259-1264. doi: 10.1007/s10068-016-0199-z.
Eleven compounds, including a new sesquiterpene, were isolated from the culture medium ofAspergillus oryzaeincubated with capsaicin. The structure of the new compound was determined to be 1,3,5a,6,7,8,9,9a-octahydro-9-hydroxy-9-(hydroxymethyl)-6-isopropyl-1-oxobenzo[c]oxepine-4- carboxylic acid, a heptelidic acid derivative. In addition, 10 known compounds were identified, namely 5-(hydroxymethyl)-3-furancarboxylic acid (flufuran), 3-hydroxypropanoic acid, 5-(hydroxymethyl)-2- furancarboxylic acid, 2-(4-hydroxyphenyl)-ethanol, 4-hydroxybenzoic acid, vanillic acid, 3,4-dihydroxybenzoic acid, 2-furanol, hydroheptelidic acid, and trichoderonic acid A, using spectroscopic data from nuclear magnetic resonance and electrospray ionization-mass spectroscopy.
3. Deletion of the Trichoderma virens NRPS, Tex7, induces accumulation of the anti-cancer compound heptelidic acid
Tatyana I Igumenova, Lorraine S Puckhaber, Karuna Dixit, Charles M Kenerley, Prasun K Mukherjee, Benjamin A Horwitz, James T Taylor, Charles Suh Biochem Biophys Res Commun . 2020 Aug 27;529(3):672-677. doi: 10.1016/j.bbrc.2020.06.040.
The anticancer antibiotic heptelidic acid is a sesquiterpene lactone produced by the beneficial plant fungus Trichoderma virens. This species has been separated into two strains, referred to as P and Q, based on its biosynthesis of secondary metabolites; notably, only P-strains were reported to produce heptelidic acid. While characterizing a Q-strain of T. virens containing a directed mutation in the non-ribosomal peptide synthetase encoding gene Tex7, the appearance of an unknown compound in anomalously large quantities was visualized by TLC. Using a combination of HPLC, LC-MS/MS, and NMR spectroscopy, this compound was identified as heptelidic acid. This discovery alters the strain classification structure of T. virens. Additionally, the Tex7 mutants inhibited growth of maize seedlings, while retaining the ability to induce systemic resistance against the foliar fungal pathogen, Cochliobolus heterostrophus.
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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 ╳
