Hatomarubigin D
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| Category | Antibiotics |
| Catalog number | BBF-01328 |
| CAS | 139501-93-2 |
| Molecular Weight | 688.72 |
| Molecular Formula | C41H36O10 |
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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,10,10'-methylenebis(1,2,3,4-tetrahydro-1,11-dihydroxy-8-methoxy-3-methyl-, (1S-(1alpha,3alpha,10(1'R*,3'R*)))- |
| IUPAC Name | (1S,3S)-10-[[(1S,3S)-1,11-dihydroxy-8-methoxy-3-methyl-7,12-dioxo-1,2,3,4-tetrahydrobenzo[a]anthracen-10-yl]methyl]-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)CC5=CC(=C6C(=C5O)C(=O)C7=C(C6=O)C=CC8=C7C(CC(C8)C)O)OC)O)O |
| InChI | InChI=1S/C41H36O10/c1-16-9-18-5-7-22-30(28(18)24(42)11-16)40(48)34-32(38(22)46)26(50-3)14-20(36(34)44)13-21-15-27(51-4)33-35(37(21)45)41(49)31-23(39(33)47)8-6-19-10-17(2)12-25(43)29(19)31/h5-8,14-17,24-25,42-45H,9-13H2,1-4H3/t16-,17-,24-,25-/m0/s1 |
| InChI Key | AASPEXAITKEFPE-SEMUBUJISA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 982.0 °C at 760 mmHg |
| Melting Point | 286-288 °C |
| Density | 1.433 g/cm3 |
| Solubility | Soluble in Dioxane |
Reference Reading
1. Functional analysis of hatomarubigin biosynthesis genes and production of a new hatomarubigin using a heterologous expression system
Masumi Izawa, Shoko Kimata, Ayumi Maeda, Takashi Kawasaki, Yoichi Hayakawa J Antibiot (Tokyo). 2014 Feb;67(2):159-62. doi: 10.1038/ja.2013.96. Epub 2013 Oct 16.
The function of hatomarubigin biosynthesis genes was analyzed by heterologous expression of the hrb gene cluster. Streptomyces lividans carrying a gene cluster consisting of 25 genes (hrbR1-hrbX) with hrbY was found to produce all the known hatomarubigins including hatomarubigin D, which has a unique dimeric angucycline with a methylene linkage. Gene disruption was used in this heterologous expression system to analyze the function of hrbF, a gene with no homology to any known angucycline biosynthesis genes. A new metabolite was detected in the fermented broth of S. lividans expressing the hrb genes lacking hrbF and was designated hatomarubigin F. This compound was identified as 5-hydroxyhatomarubigin E by NMR spectroscopic analysis, suggesting that HrbF regulates the regiospecificity of oxygenation enzymes.
2. 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.
3. 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.
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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 ╳
