Naphthomycin A

Naphthomycin A

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Naphthomycin A
Category Antibiotics
Catalog number BBF-01986
CAS 55557-40-9
Molecular Weight 720.25
Molecular Formula C40H46ClNO9

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Description

Naphthomycin A 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

Synonyms Naphthomycin
IUPAC Name (7E,9S,10S,11R,12E,14R,16Z,20S,21S,22Z,24Z,26E)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-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=C(C(=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)C
InChI InChI=1S/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9-,16-14+,21-13-,23-12+,25-17+/t20-,22+,24-,27+,29-,35-/m0/s1
InChI Key AXEGRHYJHHPVDH-DLRKXJALSA-N

Properties

Appearance Yellow Needle Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; fungi
Boiling Point 975.3±65.0°C at 760 mmHg
Melting Point >190°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. Cloning and functional analysis of the naphthomycin biosynthetic gene cluster in Streptomyces sp. CS
Yingying Wu, Qianjin Kang, Yuemao Shen, Wenjin Su, Linquan Bai Mol Biosyst. 2011 Aug;7(8):2459-69. doi: 10.1039/c1mb05036b. Epub 2011 May 26.
Naphthomycins (NATs) are 29-membered naphthalenic ansamacrolactam antibiotics with antimicrobial and antineoplastic activities. Their biosynthesis starts from 3-amino-5-hydroxy-benzoic acid (AHBA). By PCR amplification with primers for AHBA synthase and amino-dehydroquinate (aDHQ) synthase, a genomic region containing orthologs of these genes was identified in Streptomyces sp. CS. It was confirmed to be involved in naphthomycin biosynthesis by deletion of a large DNA fragment, resulting in abolishment of naphthomycin production. A 106 kb region was sequenced, and 32 complete ORFs were identified, including five polyketide synthase genes, eight genes for AHBA synthesis, and putative genes for modification, regulation, transport or resistance. Targeted inactivation and complementation experiments proved that the halogenase gene nat1 is responsible for the chlorination of C-30 of NATs. The nat1 mutant could also be complemented with asm12, the halogenase gene of ansamitocin biosynthesis. Likewise, an asm12 mutant could be complemented with nat1, suggesting a similar catalytic mechanism for both halogenases. A putative hydroxylase gene, nat2, was also inactivated, whereupon the biosynthesis of NATs was completely abolished with a tetraketide desacetyl-SY4b accumulated, indicating the participation of nat2 in the formation of the naphthalene ring. The information presented here expands our understanding of the biosynthesis of naphthalenic ansamycins, and may pave the way for engineering ansamacrolactams with improved pharmaceutical properties.
3. A novel ansamycin, naphthomycin K from Streptomyces sp
Chunhua Lu, Yuemao Shen J Antibiot (Tokyo). 2007 Oct;60(10):649-53. doi: 10.1038/ja.2007.84.
One novel ansamycin, namely naphthomycin K, together with two known naphthomycins A and E, were isolated from the commensal strain Streptomyces sp. CS of the medicinal plant Maytenus hookeri. Their structures were elucidated by the analysis of NMR and MS data. Naphthomycin K showed evident cytotoxicity against P388 and A-549 cell lines, but no inhibitory activities against Staphylococcus aureus and Mycobacterium tuberculosis.

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