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Ansatrienin A

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Ansatrienin A
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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Fermentation Lab

4 R&D and scale-up labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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.
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
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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