Hatomarubigin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01325 |
| CAS | 139562-86-0 |
| Molecular Weight | 336.34 |
| Molecular Formula | C20H16O5 |
Online Inquiry
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-6-hydroxy-8-methoxy-3-methyl-, (S)- |
| IUPAC Name | (3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1CC2=CC(=C3C(=C2C(=O)C1)C(=O)C4=C(C3=O)C(=CC=C4)OC)O |
| InChI | InChI=1S/C20H16O5/c1-9-6-10-8-13(22)17-18(15(10)12(21)7-9)19(23)11-4-3-5-14(25-2)16(11)20(17)24/h3-5,8-9,22H,6-7H2,1-2H3/t9-/m0/s1 |
| InChI Key | INDHOTAYTXVPSZ-VIFPVBQESA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 594.8 °C at 760 mmHg |
| Melting Point | 236-238 °C |
| Density | 1.373 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis
Madan K Kharel, Pallab Pahari, Micah D Shepherd, Nidhi Tibrewal, S Eric Nybo, Khaled A Shaaban, Jürgen Rohr Nat Prod Rep. 2012 Feb;29(2):264-325. doi: 10.1039/c1np00068c. Epub 2011 Dec 21.
Covering: 1997 to 2010. The angucycline group is the largest group of type II PKS-engineered natural products, rich in biological activities and chemical scaffolds. This stimulated synthetic creativity and biosynthetic inquisitiveness. The synthetic studies used five different strategies, involving Diels-Alder reactions, nucleophilic additions, electrophilic additions, transition-metal mediated cross-couplings and intramolecular cyclizations to generate the angucycline frames. Biosynthetic studies were particularly intriguing when unusual framework rearrangements by post-PKS tailoring oxidoreductases occurred, or when unusual glycosylation reactions were involved in decorating the benz[a]anthracene-derived cores. This review follows our previous reviews, which were published in 1992 and 1997, and covers new angucycline group antibiotics published between 1997 and 2010. However, in contrast to the previous reviews, the main focus of this article is on new synthetic approaches and biosynthetic investigations, most of which were published between 1997 and 2010, but go beyond, e.g. for some biosyntheses all the way back to the 1980s, to provide the necessary context of information.
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. 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.
Recommended Products
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
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 ╳
