Terreic acid
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| Category | Antibiotics |
| Catalog number | BBF-03501 |
| CAS | 121-40-4 |
| Molecular Weight | 154.12 |
| Molecular Formula | C7H6O4 |
| Purity | >98% |
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Description
Terreic acid is an antibiotic produced by Asp.terreus 5378 and Asp. parvulus. It has weak antibacterial and fungal activity. It also acts as an inhibitor of Bruton's tyrosine kinase (BTK).
Specification
| Synonyms | (-)-Terreic Acid |
| Storage | Store at -20°C |
| IUPAC Name | (1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione |
| Canonical SMILES | CC1=C(C(=O)C2C(C1=O)O2)O |
| InChI | InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1 |
| InChI Key | ATFNSNUJZOYXFC-RQJHMYQMSA-N |
Properties
| Appearance | Light Yellow Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 333.6°C at 760 mmHg |
| Melting Point | 127-127.5°C |
| Density | 1.613 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Polyketides in Aspergillus terreus: biosynthesis pathway discovery and application.
Yin Y;Cai M;Zhou X;Li Z;Zhang Y Appl Microbiol Biotechnol. 2016 Sep;100(18):7787-98. doi: 10.1007/s00253-016-7733-z. Epub 2016 Jul 26.
The knowledge of biosynthesis gene clusters, production improving methods, and bioactivity mechanisms is very important for the development of filamentous fungi metabolites. Metabolic engineering and heterologous expression methods can be applied to improve desired metabolite production, when their biosynthesis pathways have been revealed. And, stable supplement is a necessary basis of bioactivity mechanism discovery and following clinical trial. Aspergillus terreus is an outstanding producer of many bioactive agents, and a large part of them are polyketides. In this review, we took polyketides from A. terreus as examples, focusing on 13 polyketide synthase (PKS) genes in A. terreus NIH 2624 genome. The biosynthesis pathways of nine PKS genes have been reported, and their downstream metabolites are lovastatin, terreic acid, terrein, geodin, terretonin, citreoviridin, and asperfuranone, respectively. Among them, lovastatin is a well-known hypolipidemic agent. Terreic acid, terrein, citreoviridin, and asperfuranone show good bioactivities, especially anticancer activities. On the other hand, geodin and terretonin are mycotoxins. So, biosynthesis gene cluster information is important for the production or elimination of them.
2.Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products.
Klitgaard A;Frandsen RJ;Holm DK;Knudsen PB;Frisvad JC;Nielsen KF J Nat Prod. 2015 Jul 24;78(7):1518-25. doi: 10.1021/np500979d. Epub 2015 Jul 1.
We present the results from stable isotope labeled precursor feeding studies combined with ultrahigh performance liquid chromatography-high resolution mass spectrometry for the identification of labeled polyketide (PK) end-products. Feeding experiments were performed with (13)C8-6-methylsalicylic acid (6-MSA) and (13)C14-YWA1, both produced in-house, as well as commercial (13)C7-benzoic acid and (2)H7-cinnamic acid, in species of Fusarium, Byssochlamys, Aspergillus, and Penicillium. Incorporation of 6-MSA into terreic acid or patulin was not observed in any of six evaluated species covering three genera, because the 6-MSA was shunted into (2Z,4E)-2-methyl-2,4-hexadienedioic acid. This indicates that patulin and terreic acid may be produced in a closed compartment of the cell and that (2Z,4E)-2-methyl-2,4-hexadienedioic acid is a detoxification product toward terreic acid and patulin. In Fusarium spp., YWA1 was shown to be incorporated into aurofusarin, rubrofusarin, and antibiotic Y. In A. niger, benzoic acid was shown to be incorporated into asperrubrol. Incorporation levels of 0.7-20% into the end-products were detected in wild-type strains. Thus, stable isotope labeling is a promising technique for investigation of polyketide biosynthesis and possible compartmentalization of toxic metabolites.
3.Stereochemistry of the epoxydon group antibiotic G7063-2 isolated from a Streptomyces species HPL Y-25711.
Reddy GC;Sood RS;Nadkarni SR;Reden J;Ganguli BN;Fehlhaber HW;Snatzke G J Antibiot (Tokyo). 1984 Dec;37(12):1596-9.
The absolute configuration of the ring system of the antibiotic G7063-2 has been established as being the same as that reported for terreic acid, based on circular dichroism data. During structure elucidation experiments, reaction with ethereal diazomethane gave an adduct whose structure is proposed.
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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 ╳
