Hatomarubigin C
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| Category | Antibiotics |
| Catalog number | BBF-01327 |
| CAS | 139501-92-1 |
| Molecular Weight | 338.35 |
| Molecular Formula | C20H18O5 |
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Description
It is produced by the strain of Streptomyces sp. 2238-SVT4. It can enhance the effect of Colchicines against multidrug resistance (MDR) tumor cells.
Specification
| Synonyms | Benz(a)anthracene-7,12-dione,1,2,3,4-tetrahydro-1,11-dihydroxy-8-methoxy-3-methyl-, (1S-cis)-; (1S)-1β,11-Dihydroxy-3β-methyl-8-methoxy-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione |
| IUPAC Name | (1S,3S)-1,11-dihydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydrobenzo[a]anthracene-7,12-dione |
| Canonical SMILES | CC1CC(C2=C(C1)C=CC3=C2C(=O)C4=C(C=CC(=C4C3=O)OC)O)O |
| InChI | InChI=1S/C20H18O5/c1-9-7-10-3-4-11-16(15(10)13(22)8-9)20(24)17-12(21)5-6-14(25-2)18(17)19(11)23/h3-6,9,13,21-22H,7-8H2,1-2H3/t9-,13-/m0/s1 |
| InChI Key | CAEGIOZCLWNLAP-ZANVPECISA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 613.0 °C at 760 mmHg |
| Melting Point | 174-176 °C |
| Density | 1.379 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Studies on the isotetracenone antibiotics. IV. Hatomarubigins A, B, C and D, new isotetracenone antibiotics effective against multidrug-resistant tumor cells
Y Hayakawa, S C Ha, Y J Kim, K Furihata, H Seto J Antibiot (Tokyo). 1991 Nov;44(11):1179-86. doi: 10.7164/antibiotics.44.1179.
A complex of new isotetracenone group antibiotics was isolated from the cultured broth of Streptomyces sp. 2238-SVT4. It consisted of four related compounds, designated hatomarubigins A, B, C and D, whose structures were elucidated by NMR spectral analysis including a variety of 2D techniques. They enhanced the cytotoxicity of colchicine against multidrug-resistant tumor cells.
2. Cloning and characterization of a gene cluster for hatomarubigin biosynthesis in Streptomyces sp. strain 2238-SVT4
Takashi Kawasaki, Reiko Hirashima, Tomoka Maruta, Haruka Sato, Ayumi Maeda, Yuki Yamada, Maho Takeda, Yoichi Hayakawa Appl Environ Microbiol. 2010 Jul;76(13):4201-6. doi: 10.1128/AEM.00668-10. Epub 2010 May 7.
Streptomyces sp. strain 2238-SVT4 produces hatomarubigins A, B, C, and D, which belong to the angucycline family. Among them, hatomarubigin D has a unique dimeric structure with a methylene linkage. PCR using aromatase and cyclase gene-specific primers identified the hrb gene cluster for angucycline biosynthesis in Streptomyces sp. 2238-SVT4. The cluster consisted of 30 open reading frames, including those for the minimal polyketide synthase, ketoreductase, aromatase, cyclase, O-methyltransferase, oxidoreductase, and oxygenase genes. Expression of a part of the gene cluster containing hrbR1 to hrbX in Streptomyces lividans TK23 resulted in the production of hatomarubigins A, B, and C. Hatomarubigin D was obtained from the conversion of hatomarubigin C by a purified enzyme encoded by hrbY, among the remaining genes.
3. Seitomycin: isolation, structure elucidation and biological activity of a new angucycline antibiotic from a terrestrial Streptomycete
Mohamed Abdelfattah, Rajendra P Maskey, Ratnakar N Asolkar, Iris Grün-Wollny, Hartmut Laatsch J Antibiot (Tokyo). 2003 Jun;56(6):539-42. doi: 10.7164/antibiotics.56.539.
A new antibiotic, named seitomycin (1c), and the known microbial metabolite tetrangulol methyl ether (2) were found in the ethyl acetate extract of two terrestrial Streptomyces sp. isolates. The structure of the new antibiotic was elucidated by spectroscopic studies and by comparison of the NMR data with the structurally related hatomarubigin C (1a) and SM-196 B (1b). Seitomycin (1c) showed moderate antimicrobial and weak phytotoxic activity, similar to tetrangulol methyl ether (2).
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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 ╳
