Naphthomycin B
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| Category | Antibiotics |
| Catalog number | BBF-02571 |
| CAS | 86825-88-9 |
| Molecular Weight | 706.22 |
| Molecular Formula | C39H44ClNO9 |
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Description
Naphthomycin B is a macrolide (Ansa family) antibiotic produced by strains such as Str.collinus Tv105, Str.galbus subsp. griseosporeus Tv 353, Str. diastatochromogene, Str. sp. Y83 40369. It has activity against gram-positive bacteria and fungi.
Specification
| IUPAC Name | 31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21-hexamethyl-29-azatricyclo[28.3.1.05,33]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone |
| Canonical SMILES | CC1C=CC=CC=CC(=O)NC2=C(C(=O)C3=C(C2=O)C=C(C(=C3C(=O)C(=CC(C(C(C=CC(CC=C(C(=O)CC1O)C)O)C)O)C)C)O)C)Cl |
| InChI | InChI=1S/C39H44ClNO9/c1-20-11-9-7-8-10-12-30(45)41-34-33(40)39(50)31-27(38(34)49)18-25(6)37(48)32(31)36(47)24(5)17-23(4)35(46)22(3)14-16-26(42)15-13-21(2)29(44)19-28(20)43/h7-14,16-18,20,22-23,26,28,35,42-43,46,48H,15,19H2,1-6H3,(H,41,45) |
| InChI Key | PGLCKEFYXCGUGA-UHFFFAOYSA-N |
Properties
| Appearance | Orange Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 974.3±65.0°C at 760 mmHg |
| Melting Point | 155-160°C (dec.) |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species
Sangkeun Son, Sung-Kyun Ko, Mina Jang, Jae Kyoung Lee, Min Cheol Kwon, Dong Hyo Kang, In-Ja Ryoo, Jung-Sook Lee, Young-Soo Hong, Bo Yeon Kim, Jae-Hyuk Jang, Jong Seog Ahn J Nat Prod. 2017 May 26;80(5):1378-1386. doi: 10.1021/acs.jnatprod.6b01059. Epub 2017 Apr 13.
A bioassay-guided investigation in conjunction with chemical screening led to the isolation of three new glycosides, ulleungoside (1), 2-methylaminobenzoyl 6-deoxy-α-l-talopyranoside (2), and naphthomycinoside (3), along with three known secondary metabolites (5-7) from Streptomyces sp. KCB13F030. Their structures were elucidated by detailed NMR and MS spectroscopic analyses. Absolute configurational analysis of the sugar units based on the magnitudes of the coupling constants, NOESY correlations, chemical derivatization, and optical rotation measurements revealed that compounds 1-3 and 5 incorporate the rare deoxyhexose 6-deoxy-α-l-talopyranose. The absolute configuration of a polyketide extender unit of 3 was determined by applying the J-based configuration analysis and modified Mosher's method. Ulleungoside (1) and naphthomycin A (7) showed in vitro inhibitory effects against indoleamine 2,3-dioxygenase activity. Further bioevaluation revealed that compounds 1 and 7 had moderate antiproliferative activities against several cancer cell lines, and compounds 5 and 6, which are members of the piericidin family, induced autophagosome accumulation.
2. The complete genome sequence of Streptomyces autolyticus CGMCC 0516, the producer of geldanamycin, autolytimycin, reblastatin and elaiophylin
Min Yin, Mingxing Jiang, Zhen Ren, Yilong Dong, Tao Lu J Biotechnol. 2017 Jun 20;252:27-31. doi: 10.1016/j.jbiotec.2017.04.037. Epub 2017 May 2.
Streptomyces autolyticus CGMCC 0516 produces the anti-tumor benzoquinone ansamycins geldanamycin, autolytimycin, and reblastatin and the 16-membered macrodiolide elaiophylin. Here, we report the complete genome sequence of S. autolyticus CGMCC 0516, which consists of a 10,029,028bp linear chromosome and seven circular plasmids. Fifty-seven putative biosynthetic gene clusters for secondary metabolites were found. The geldanamycin, autolytimycin, and reblastatin biosynthetic gene clusters were located on the left arm (2.06-2.15Mb) of the chromosome, and the elaiophylin gene cluster was located on the right arm (9.45-9.53Mb). Twenty-one putative gene clusters with high or moderate similarity to important antibiotic biosynthetic gene clusters were found, including the antitumor agents echoside, bafilomycin, hygrocin, and toxoflavin; the antibacterial/antifungal agents nigericin, skyllamycin, kanamycin, naphthomycin, eco-02301, and bottromycin A2; the immunosuppressants meridamycin and brasilicardin A; the anti-inflammatory agent cyclooctatin; and the acute iron poisoning medication desferrioxamine B. The genome sequence reported here will enable us to study the biosynthetic mechanism of these important antibiotics and will facilitate the discovery of novel secondary metabolites with potential applications to human health.
3. Naphthomycins L-N, ansamycin antibiotics from Streptomyces sp. CS
Yin-He Yang, Xiao-Li Fu, Liang-Qun Li, Ying Zeng, Cheng-Yun Li, Yi-Neng He, Pei-Ji Zhao J Nat Prod. 2012 Jul 27;75(7):1409-13. doi: 10.1021/np300109s. Epub 2012 Jun 28.
Previous analyses of the naphthomycin biosynthetic gene cluster and a comparison with known naphthomycin-type products from Streptomyces sp. CS have suggested that new products can be found from this strain. In this study, screening by LC-MS of Streptomyces sp. CS products formed under different culture conditions revealed several unknown peaks in the product spectra of extracts derived from oatmeal medium cultures. Three new naphthomycins, naphthomycins L (1), M (2), and N (3), and the known naphthomycins A (4), E (5), and D (6) were obtained. The structures were elucidated using spectroscopic data from 1D and 2D NMR and HRESIMS experiments.
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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 ╳
