Ansatrienin A
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| Category | Antibiotics |
| Catalog number | BBF-00694 |
| CAS | 82189-03-5 |
| Molecular Weight | 636.77 |
| Molecular Formula | C36H48N2O8 |
| Purity | >99% by HPLC |
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Description
It is produced by the strain of Streptomyces collinus Tu 1892, Str. rishiriensis and Str. diastatochromogenes var. diastatochromogenes. Ansaltriene has anti-mold and yeast activity, and has killing effect on HeLa S3, PLC liver cancer and other tumor cells.
Specification
| Related CAS | 80111-47-3 86992-54-3 |
| Synonyms | Mycotrienin I; CHEBI:29516; (+)-mycotrienin I; D-Alanine,N-(cyclohexylcarbonyl)-,11-ester with ansatrienol A; D-Alanine, N-(cyclohexylcarbonyl)-, (5R,6E,8E,10E,13S,14R,15R,16Z)-15-hydroxy-5-methoxy-14,16-dimethyl-3,22,24-trioxo-2-azabicyclo[18.3.1]tetracosa-6,8,10,16,20,23-hexaen-13-yl ester; 2-Azabicyclo[18.3.1]tetracosane, D-alanine deriv.; Ansatrienine A |
| Storage | -20°C |
| IUPAC Name | [(6E,8E,10E,16Z)-15-hydroxy-5-methoxy-14,16-dimethyl-3,22,24-trioxo-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20-hexaen-13-yl] (2R)-2-(cyclohexanecarbonylamino)propanoate |
| Canonical SMILES | CC1C(CC=CC=CC=CC(CC(=O)NC2=CC(=O)C=C(C2=O)CCC=C(C1O)C)OC)OC(=O)C(C)NC(=O)C3CCCCC3 |
| InChI | InChI=1S/C36H48N2O8/c1-23-14-13-17-27-20-28(39)21-30(34(27)42)38-32(40)22-29(45-4)18-11-6-5-7-12-19-31(24(2)33(23)41)46-36(44)25(3)37-35(43)26-15-9-8-10-16-26/h5-7,11-12,14,18,20-21,24-26,29,31,33,41H,8-10,13,15-17,19,22H2,1-4H3,(H,37,43)(H,38,40)/b6-5+,12-7+,18-11+,23-14-/t24?,25-,29?,31?,33?/m1/s1 |
| InChI Key | WWUVMHRJRCRFSL-FQELAZPASA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor); fungi; yeast |
| Boiling Point | 845.6±65.0 °C |
| Melting Point | 170 °C (dec.) |
| Density | 1.200±0.10 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Mycotrienin II, a translation inhibitor that prevents ICAM-1 expression induced by pro-inflammatory cytokines
Etsu Tashiro, Yuriko Yamada, Shigeru Taketani, Takao Kataoka, Masaya Imoto J Antibiot (Tokyo) . 2011 May;64(5):361-6. doi: 10.1038/ja.2011.23.
Pro-inflammatory cytokines, such as tumor necrosis factor (TNF)-α and interleukin-1α (IL-1α), trigger the activation of the transcription factor nuclear factor-κB, a molecule that induces the expression of a variety of genes, including intercellular adhesion molecule-1 (ICAM-1). Here, we report that mycotrienin II, a member of the triene-ansamycin group, inhibited the cell-surface ICAM-1 expression induced by TNF-α more strongly than that induced by IL-1α in human lung carcinoma A549 cells. Mycotrienin II was found to inhibit protein synthesis in intact living cells, as well as in cell-free translation systems. Among translation inhibitors tested, acetoxycycloheximide and anisomycin, but neither puromycin nor emetine, inhibited the TNF-α-induced ICAM-1 expression at lower concentrations than the IL-1α-induced ICAM-1 expression. Several compounds of the triene-ansamycin group (that is, mycotrienin I, trienomycin A, trierixin, quinotrierixin and quinotrierixin HQ) also inhibited ICAM-1 expression, as well as cell-free translation in a manner similar to mycotrienin II. These results indicate that mycotrienin II is a direct inhibitor of translation, thereby inhibiting ICAM-1 expression induced by pro-inflammatory cytokines.
2. Mycotrienins. A new class of potent inhibitors of osteoclastic bone resorption
J H Feyen, T Fehr, D Feuerbach, R Waelchli J Biol Chem . 1995 Oct 27;270(43):25949-55. doi: 10.1074/jbc.270.43.25949.
Pharmacological intervention using selective tyrosine kinase inhibitors has been shown to be an effective approach to inhibit osteoclast function. Here, we report on the structure-activity relations of benzoquinone ansamycins isolated from Streptomyces rishirensis, which form a new class of potent inhibitors of osteoclast-mediated bone resorption. Parathyroid hormone-stimulated bone resorption was inhibited concentration dependently by both mycotrienin I and mycotrienin II, showing half-maximal inhibition in the low nanomolar range in fetal rat long bones in vitro. Structure-activity relation studies indicate that position 19 contained within the quinone/hydroquinone element and the double bonds in position 4, 6, and 8 are crucial for full bioactivity. In contrast, substitutions in position 22 are well tolerated. The lack of a similar effect of 2,6-dimethyl-p-benzoquinone and vitamin K signifies that the mechanism of action is not solely due to the oxygen scavenger capacity of the quinone/hydroquinone moiety. The inhibition of osteoclastic bone resorption is in line with the diminished activity of immunopurified pp60c-src from bone suggesting that pp60c-src is a possible target of mycotrienins in the organ culture. Thus, mycotrienins may be useful as pharmacologic inhibitors of osteoclastic bone resorption.
3. Purification and characterization of a novel enoyl coenzyme A reductase from Streptomyces collinus
K A Reynolds, M K Speedie, K M Fox, P Wang, Y Lam, H G Floss J Bacteriol . 1992 Jun;174(12):3850-4. doi: 10.1128/jb.174.12.3850-3854.1992.
A novel NADPH-dependent enoyl reductase, catalyzing the conversion of 1-cyclohexenylcarbonyl coenzyme A (1-cyclohexenylcarbonyl-CoA) to cyclohexylcarbonyl-CoA, was purified to homogeneity from Streptomyces collinus. This enzyme, a dimer with subunits of identical M(r) (36,000), exhibits a Km of 1.5 +/- 0.3 microM for NADPH and 25 +/- 3 microM for 1-cyclohexenylcarbonyl-CoA. It has a pH optimum of 7.5, is most active at 30 degrees C, and is inhibited by both divalent cations and thiol reagents. Two internal peptide sequences were obtained. Ansatrienin A (an antibiotic produced by S. collinus) contains a cyclohexanecarboxylic acid moiety, and it is suggested that the 1-cyclohexenylcarbonyl-CoA reductase described herein catalyzes the final reductive step in the conversion of shikimic acid into this moiety.
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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 ╳
