Topopyrone A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02700 |
| CAS | |
| Molecular Weight | 372.71 |
| Molecular Formula | C18H9ClO7 |
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Description
It is produced by the strain of Phoma sp. BAUA 2861 and Penicillum sp. BAUA 4206. Topopyrone A selectively inhibits topoisomerase I with the IC50 of 1.22 ng/mL. It also has anti-Gram-positive bacteria activity.
Specification
| IUPAC Name | 10-chloro-5,9,11-trihydroxy-2-methylnaphtho[2,3-h]chromene-4,7,12-trione |
| Canonical SMILES | CC1=CC(=O)C2=C(C=C3C(=C2O1)C(=O)C4=C(C(=C(C=C4C3=O)O)Cl)O)O |
| InChI | InChI=1S/C18H9ClO7/c1-5-2-8(20)13-9(21)3-7-12(18(13)26-5)16(24)11-6(15(7)23)4-10(22)14(19)17(11)25/h2-4,21-22,25H,1H3 |
| InChI Key | KUCMIJRMIDNZCP-UHFFFAOYSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >280°C |
Reference Reading
1. Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. II. Structure elucidation
D Ishiyama, Y Kanai, H Senda, W Iwatani, W Iwatani, H Konno, S Kanazawa J Antibiot (Tokyo). 2000 Sep;53(9):873-8. doi: 10.7164/antibiotics.53.873.
The structures of novel topoisomerase I inhibitors, topopyrones A, B, C and D were elucidated by spectral analysis of the chemical derivatives. These compounds are an anthraquinone type containing a fused 1,4-pyrone moiety. Topopyrones A and B contain a chlorine atom, however C and D do not. It was suggested that topopyrones B and D are converted from topopyrones A and C, respectively by Wessely-Moser type rearrangement.
2. Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. I. Producing strain, fermentation, isolation, physico-chemical properties and biological activity
Y Kanai, D Ishiyama, H Senda, W Iwatani, H Takahashi, H Konno, S Tokumasu, S Kanazawa J Antibiot (Tokyo). 2000 Sep;53(9):863-72. doi: 10.7164/antibiotics.53.863.
In the course of a screening program for specific inhibitors of human topoisomerase I using a recombinant yeast, we have discovered four new active compounds. All four compounds were isolated from the culture broth of a fungus, Phoma sp. BAUA2861, and two of them were isolated from the culture broth of a fungus, Penicillium sp. BAUA4206. We designated these compounds as topopyrones A, B, C and D. Topopyrones A, B, C and D selectively inhibited recombinant yeast growth dependent on expression of human topoisomerase I with IC50 values of 1.22, 0.15, 4.88 and 19.63 ng/ml, respectively. The activity and selectivity of topopyrone B were comparable to those of camptothecin. The relaxation of supercoiled pBR322 DNA by human DNA topoisomerase I was inhibited by these compounds, however they did not inhibit human DNA topoisomerase II. Topopyrones A, B, C and D were cytotoxic to all tumor cell lines when tested in vitro. Topopyrone B has potent inhibitory activity against herpesvirus, especially varicella zoster virus (VZV). It inhibited VZV growth with EC50 value of 0.038 microg/ml, which is 24-fold stronger than that of acyclovir (0.9 microg/ml). Topopyrones A, B, and C were inhibitory to Gram-positive bacteria.
3. Identification and Heterologous Expression of the Topopyrone Nonaketide Synthase Gene from Phoma sp
Nobuyuki Kashiwa, Yutaka Ebizuka, Isao Fujii Chem Pharm Bull (Tokyo). 2016;64(7):947-51. doi: 10.1248/cpb.c16-00172.
Non-reducing iterative type I polyketide synthase genes, pnk1 and pnk2, were cloned from the fungus Phoma sp. BAUA2861, which produces the topoisomerase I inhibitors, topopyrones A to D. Heterologous expression of these polyketide synthase genes under the α-amylase promoter in Aspergillus oryzae was carried out to identify their functions. The pnk2 transformant produced topopyrones C, D, and haematommone. Therefore, the pnk2 gene was found to encode for the topopyrone nonaketide synthase.
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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 ╳
