Hydroxymycotrienin A
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| Category | Antibiotics |
| Catalog number | BBF-01014 |
| CAS | 178550-61-3 |
| Molecular Weight | 652.77 |
| Molecular Formula | C36H48N2O9 |
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Description
Hydroxymycotrienin A is an Ansa antibiotic produced by Bacillus sp. BMJ958-62F4. It has the activity of inhibiting human neck tumor cell line, and its inhibitory effect on human papillomavirus (HPV) gene positive neck tumor cells (such as HeLa, CaSki, SiHa, etc.) is stronger than HPV gene negative cells.
Specification
| IUPAC Name | [(6Z,8Z,10Z,16Z)-15,24-dihydroxy-5-methoxy-14,16-dimethyl-3,21,22-trioxo-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24)-hexaen-13-yl] (2R)-2-(cyclohexanecarbonylamino)propanoate |
| Canonical SMILES | CC1C(CC=CC=CC=CC(CC(=O)NC2=CC(=O)C(=O)C(=C2O)CCC=C(C1O)C)OC)OC(=O)C(C)NC(=O)C3CCCCC3 |
| InChI | InChI=1S/C36H48N2O9/c1-22-14-13-18-27-33(42)28(21-29(39)34(27)43)38-31(40)20-26(46-4)17-11-6-5-7-12-19-30(23(2)32(22)41)47-36(45)24(3)37-35(44)25-15-9-8-10-16-25/h5-7,11-12,14,17,21,23-26,30,32,41-42H,8-10,13,15-16,18-20H2,1-4H3,(H,37,44)(H,38,40)/b6-5-,12-7-,17-11-,22-14-/t23?,24-,26?,30?,32?/m1/s1 |
| InChI Key | HYWXXXJZXNFLKQ-VMVMLMRHSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 823.1±65.0 °C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Hydroxymycotrienins A and B, new ansamycin group antibiotics
N Hosokawa, H Naganawa, M Hamada, T Takeuchi, S Ikeno, M Hori J Antibiot (Tokyo). 1996 May;49(5):425-31. doi: 10.7164/antibiotics.49.425.
New ansamycins designated hydroxymycotrienins A and B were isolated from culture broths of Bacillus sp. BMJ958-62F4. The two antibiotics inhibited more strongly the growth of human cervical cancer cell lines of human papilloma virus (HPV) positive than that of HPV negative cell lines. The structures, some biological and biochemical properties are reported.
2. Identification of AstG1, A LAL family regulator that positively controls ansatrienins production in Streptomyces sp. XZQH13
Chao Xie, Jing-Jing Deng, Hao-Xin Wang Curr Microbiol. 2015 Jun;70(6):859-64. doi: 10.1007/s00284-015-0798-6. Epub 2015 Mar 18.
Ansamycins is a group of type I polyketides characterized by the unique starter unit 3-amino-5-hydroxybenzoic acid. This family of secondary metabolites shows diverse biological activities, well-known members of which include rifamycin, geldanamycin, and maytansine. Previously, we isolated an AHBA synthase gene-positive strain Streptomyces sp. XZQH13 containing a "silent" ansamycin biosynthetic gene cluster ast. The constitutive expression of the Large-ATP-binding regulators of the LuxR family regulator gene astG1 located within the cluster triggered the expression of the biosynthetic genes. Reverse transcription-PCR experiments showed that the expression of the key biosynthetic genes, astB4, astD1, and astF1, was induced in the astG1 overexpression mutant compared to the wild type. This led to the isolation of two known ansatrienins, hydroxymycotrienin A (1) and thiazinotrienomycin G (2), which were identified by analysis of the mass spectral and NMR spectral data, from the mutant. These observations suggest that astG1 is probably a pathway-specific positive regulator for the biosynthesis of ansatrienin.
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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 ╳
