Hatomarubigin B
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| Category | Antibiotics |
| Catalog number | BBF-01326 |
| CAS | 139501-91-0 |
| Molecular Weight | 336.34 |
| Molecular Formula | C20H16O5 |
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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-1,7,12(2H)-trione,3,4-dihydro-11-hydroxy-8-methoxy-3-methyl-, (S)- |
| IUPAC Name | (3S)-11-hydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1CC2=C(C(=O)C1)C3=C(C=C2)C(=O)C4=C(C=CC(=C4C3=O)O)OC |
| InChI | InChI=1S/C20H16O5/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/h3-6,9,21H,7-8H2,1-2H3/t9-/m0/s1 |
| InChI Key | IAWMODONDSIOEK-VIFPVBQESA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 594.8 °C at 760 mmHg |
| Melting Point | 254-256 °C |
| Density | 1.373 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. 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.
2. Total synthesis of (+)-hatomarubigin B
G B Caygill, D S Larsen, S Brooker J Org Chem. 2001 Nov 2;66(22):7427-31. doi: 10.1021/jo015839r.
The first total synthesis of (+)-hatomarubigin 3 is described. The tetra-O-acetyl diborate promoted Diels-Alder reaction of 5-hydroxy-8-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1,4-naphthoquinone 8 and (E, 1R*,5R*)-3-(2'-methoxyvinyl)cyclohex-2-enol (+/-)-7 gave a mixture of four cycloadducts from which (1S,3S,6S,6aR,12aR,12bS)-1,8-dihydroxy-6-dimethoxy-1-hydroxy-3-methyl-11-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1,2,3,4,6,6a,12a,12b-octahydrobenz[a]anthracene-7,12-dione 12 was isolated in 51% yield. Selective methylation and acetylation of 12 gave (1S,3S,6S,6aR,12aR,12bS)-1-acetoxy-6,8-dimethoxy-3-methyl-11-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyloxy)-1,2,3,4,6,6a,12a,12b-octahydrobenz[a]anthracene-7,12-dione 10a. Sequential aromatization, photooxidation and hydrolysis of the glucosyl unit gave (+)-3 (98% ee) in an 8% overall yield from 8.
3. 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.
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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 ╳
