Napyradiomycin B3
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| Category | Antibiotics |
| Catalog number | BBF-01994 |
| CAS | |
| Molecular Weight | 560.3 |
| Molecular Formula | C25H29BrCl2O5 |
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Description
Napyradiomycin B3 is an antibiotic produced by Chainia rubra MG802-AF1. It has anti-gram-positive bacteria and mycobacterial activity.
Specification
| Synonyms | Antibiotic MG 802AFB3 |
| IUPAC Name | (3R,4aR,10aS)-10a-[[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione |
| Canonical SMILES | CC1(C(CCC(=C)C1CC23C(=O)C4=C(C(=CC(=C4)O)O)C(=O)C2(CC(C(O3)(C)C)Cl)Cl)Br)C |
| InChI | InChI=1S/C25H29BrCl2O5/c1-12-6-7-17(26)22(2,3)15(12)10-25-20(31)14-8-13(29)9-16(30)19(14)21(32)24(25,28)11-18(27)23(4,5)33-25/h8-9,15,17-18,29-30H,1,6-7,10-11H2,2-5H3/t15-,17+,18-,24+,25+/m1/s1 |
| InChI Key | PVEFIGXLPBGZAX-RVRKADHMSA-N |
Properties
| Appearance | Yellow Brown Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 674.1±55.0°C at 760 mmHg |
| Melting Point | 105-115°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Structures of new antibiotics napyradiomycins
K Shiomi, H Nakamura, H Iinuma, H Naganawa, K Isshiki, T Takeuchi, H Umezawa, Y Iitaka J Antibiot (Tokyo). 1986 Apr;39(4):494-501. doi: 10.7164/antibiotics.39.494.
Structures of novel antibiotics, napyradiomycins A, B1, B2, B3, C1 and C2 were determined. By X-ray crystallography, napyradiomycin B2 was determined to be (3R,10aR)-3-chloro-10a-[[(1R,3S)-3-chloro-2, 2-dimethyl-6-methylenecyclohexyl]methyl]-3,10a-dihydro-6,8-dihydro xy-2, 2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione. The structures of other napyradiomycins were elucidated by NMR studies. Napyradiomycins C1 and C2 have unique structures which contain 14-membered ring cyclized by carbon-carbon bond.
2. Novel antibiotics napyradiomycins. Production, isolation, physico-chemical properties and biological activity
K Shiomi, H Iinuma, M Hamada, H Naganawa, M Manabe, C Matsuki, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1986 Apr;39(4):487-93. doi: 10.7164/antibiotics.39.487.
Novel antibacterial antibiotics napyradiomycins A, B1, B2, B3, C1 and C2 have been isolated from the culture broth of Chainia rubra MG802-AF1. In this paper, taxonomy of the producer, and production, isolation, physico-chemical properties and biological activities of napyradiomycins are reported. They contain the naphtopyran chromophore and halogens, and inhibit the growth of Gram-positive bacteria including drug-resistant strains.
3. Antibacterial and cytotoxic new napyradiomycins from the marine-derived Streptomyces sp. SCSIO 10428
Zhengchao Wu, Sumei Li, Jie Li, Yuchan Chen, Kumar Saurav, Qingbo Zhang, Haibo Zhang, Wenjun Zhang, Weimin Zhang, Si Zhang, Changsheng Zhang Mar Drugs. 2013 Jun 14;11(6):2113-25. doi: 10.3390/md11062113.
Three new napyradiomycins (1-3) were isolated from the culture broth of a marine-derived actinomycete strain SCSIO 10428, together with six known related analogues napyradiomycin A1 (4), 18-oxonapyradiomycin A1 (5), napyradiomycin B1 (6), napyradiomycin B3 (7), naphthomevalin (8), and napyradiomycin SR (9). The strain SCSIO 10428 was identified as a Streptomyces species by the sequence analysis of its 16S rRNA gene. The structures of new compounds 1-3, designated 4-dehydro-4a-dechlorona pyradiomycin A1 (1), 3-dechloro-3-bromonapyradiomycin A1 (2), and 3-chloro-6, 8-dihydroxy-8-α-lapachone (3), respectively, were elucidated by comparing their 1D and 2D NMR spectroscopic data with known congeners. None of the napyradiomycins 1-9 showed antioxidative activities. Napyradiomycins 1-8 displayed antibacterial activities against three Gram-positive bacteria Staphylococcus and Bacillus strains with MIC values ranging from 0.25 to 32 μg mL⁻¹, with the exception that compound 3 had a MIC value of above 128 μg mL⁻¹ against Staphylococcus aureus ATCC 29213. Napyradiomycins 2, 4, 6, and 7 exhibited moderate cytotoxicities against four human cancer cell lines SF-268, MCF-7, NCI-H460, and HepG-2 with IC₅₀ values below 20 μM, while the IC₅₀ values for other five napyradiomycins 1, 3, 5, 8 and 9 were above 20 μM.
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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 ╳
