Dioxamycin

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Dioxamycin
Dioxamycin.svg
Names
IUPAC name
(2S,4S,5S)-4-[(1E,3E,5E)-7-[(2R,6R)-6-[(2R,3S,4aR,12bS)-2,3,4a,8,12b-pentahydroxy-3-methyl-1,7,12-trioxo-2,4-dihydrobenzo[a]anthracen-9-yl]-2-methyloxan-3-yl]oxy-7-oxohepta-1,3,5-trienyl]-2,5-dimethyl-1,3-dioxolane-2-carboxylic acid [1]
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C38H40O15/c1-18-23(51-26(39)10-8-6-5-7-9-24-19(2)52-36(4,53-24)34(45)46)13-14-25(50-18)20-11-12-21-27(29(20)40)30(41)22-15-16-37(48)17-35(3,47)32(43)33(44)38(37,49)28(22)31(21)42/h5-12,15-16,18-19,23-25,32,40,43,47-49H,13-14,17H2,1-4H3,(H,45,46)/b6-5+,9-7+,10-8+/t18-,19+,23?,24+,25-,32+,35+,36+,37+,38-/m1/s1
    Key: HWMMBHOXHRVLCU-QOUANJGESA-N
  • C[C@H]1[C@@H](O[C@@](O1)(C)C(=O)O)/C=C/C=C/C=C/C(=O)OC2CC[C@@H](O[C@@H]2C)C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C=C[C@]6([C@@]5(C(=O)[C@@H]([C@@](C6)(C)O)O)O)O)O
Properties
C38H40O15
Molar mass 736.723 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dioxamycin is a benz[a] anthraquinone antibiotic and kinase inhibitor with the molecular formula C38H40O15. [1] [2] [3] Dioxamycin is produced by the bacterium Streptomyces cocklensis and Streptomyces xantholiticus . [2] [4]

Related Research Articles

<i>Streptomyces</i> Genus of bacteria

Streptomyces is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, and have genomes with high GC content. Found predominantly in soil and decaying vegetation, most streptomycetes produce spores, and are noted for their distinct "earthy" odor that results from production of a volatile metabolite, geosmin.

<span class="mw-page-title-main">Aquayamycin</span> Chemical compound

Aquayamycin is an anthraquinone derivative. It is an inhibitor of the enzyme tyrosine hydroxylase.

<i>Streptomyces griseus</i> Species of bacterium

Streptomyces griseus is a species of bacteria in the genus Streptomyces commonly found in soil. A few strains have been also reported from deep-sea sediments. It is a Gram-positive bacterium with high GC content. Along with most other streptomycetes, S. griseus strains are well known producers of antibiotics and other such commercially significant secondary metabolites. These strains are known to be producers of 32 different structural types of bioactive compounds. Streptomycin, the first antibiotic ever reported from a bacterium, comes from strains of S. griseus. Recently, the whole genome sequence of one of its strains had been completed.

<span class="mw-page-title-main">Antipain</span> Chemical compound

Antipain is an oligopeptide that is isolated from actinomycetes and used in biochemical research as a protease inhibitor of trypsin and papain. It was discovered in 1972 and was the first natural peptide found that contained an ureylene group. Antipain can aid in prevention of coagulation in blood. It is an inhibitor of serine and cysteine proteases.

Streptomyces nodosus is a bacterial species in the genus Streptomyces.

Streptomyces avermitilis is a species of bacteria in the genus Streptomyces. This bacterium was discovered by Satoshi Ōmura in Shizuoka Prefecture, Japan.

Streptomyces isolates have yielded the majority of human, animal, and agricultural antibiotics, as well as a number of fundamental chemotherapy medicines. Streptomyces is the largest antibiotic-producing genus of Actinomycetota, producing chemotherapy, antibacterial, antifungal, antiparasitic drugs, and immunosuppressants. Streptomyces isolates are typically initiated with the aerial hyphal formation from the mycelium.

Streptomyces albidoflavus is a bacterium species from the genus of Streptomyces which has been isolated from soil from Poland. Streptomyces albidoflavus produces dibutyl phthalate and streptothricins.

Streptomyces albospinus is a bacterium species from the genus of Streptomyces which has been isolated from soil from the Akita City in Japan. Streptomyces albospinus produces spinamycine, phenamide, phenelfamycin G and phenelfamycin H.

Streptomyces cocklensis is a bacterium species from the genus of Streptomyces which has been isolated from soil from the Cockle Park Experimental Farm in Northumberland in the United Kingdom. Streptomyces cocklensis produces dioxamycin.

Streptomyces coeruleorubidus is a bacterium species from the genus of Streptomyces which has been isolated from marine sediment. Streptomyces coeruleorubidus produces the following medications: pacidamycin 1, baumycin B1, baumycin B2, baumycin C1, feudomycin A, feudomycin B, feudomycin C, ficellomycin, feudomycinone A, and rubomycin.

Streptomyces griseoaurantiacus is a thermotolerant bacterium species from the genus of Streptomyces which was isolated from marine sediment. Streptomyces griseoaurantiacus produces the antibiotics manumycin, diperamycin and chinikomycin, and griseolic acid.

Streptomyces nitrosporeus is a bacterium species from the genus of Streptomyces which has been isolated from garden soil in Japan. Streptomyces nitrosporeus produces Benzastatin E, Benzastatin F, Benzastatin G Nitrosporeusine A and Nitrosporeusine B and the antibiotics nitrosporin and virantomycin and the inhibitor of angiotensin-converting enzyme foroxymithine. Streptomyces nitrosporeus can degrade cellulose.

Streptomyces phaeochromogenes is a bacterium species from the genus of Streptomyces. Streptomyces phaeochromogenes produces tyrosinate, bromoperoxidase, ditryptophenalin, phaeochromycin A, phaeochromycin B, phaeochromycin C, phaeochromycin D and phaeochromycin E. Streptomyces phaeochromogenes also produces moenomycin and bambermycin.

Streptomyces platensis is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces platensis produces oxytetracycline, platensimycin, migrastatin, isomigrastatin, platencin, dorrigocin A, dorrigocin B and terramycine.

Streptomyces rishiriensis is a bacterium species from the genus of Streptomyces which has been isolated from soil in Hokkaido in Japan. Streptomyces rishiriensis produces coumermycin A1, notomycin, 2-chloroadenosine, phosphophenylalanarginine and lactonamycin.

Streptomyces rochei is a bacterium species from the genus of Streptomyces which has been isolated from soil in Russia. Streptomyces rochei produces borrelidin, butyrolactol A, butyrolactol B, uricase and streptothricin. Streptomyces rochei has antifungal activity against Fusarium oxysporum f.sp. lycopersici and Aspergillus fumigatus. Streptomyces rochei produces moenomycin and bambermycin. Streptomyces rochei produces amicetin A, amicetin B, amicetin C and streptolin. Streptomyces rochei produces endo-β-N-acetylglucosaminidase mithramycin, amicetin, bamicetin, and plicacetin.

Streptomyces violaceus is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces violaceus produces rhodomycine, violamycin-B5 and violarin B.

Streptomyces virginiae is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces virginiae produces actithiazic acid, virginiamycins and cycloserine. Streptomyces virginiae also produces monensin A, monensin B, monensin C, monensin D, actithiazic acid.

Lydicamycin is an organic compound with the molecular formula C47H74N4O10. Lydicamycin is an antibiotic with activity against Gram-positive bacteria. The bacteria Streptomyces lydicamycinicus and Streptomyces platensis produces lydicamycin.

References

  1. 1 2 "Dioxamycin". Pubchem.ncbi.NLM.nih.gov.
  2. 1 2 Rahman, Atta-ur (20 January 2015). Studies in Natural Products Chemistry. Elsevier. p. 422. ISBN   978-0-444-63470-2.
  3. Sawa, Ryuichi; Matsuda, Naoko; Uchida, Takeshi; Ikeda, Takako; Sawa, Tsutomu; Naganawa, Hiroshi; Hamada, Masa; Takeuchi, Tomio (1991). "Dioxamycin, a new benz(a)anthraquinone antibiotic". The Journal of Antibiotics. 44 (4): 396–402. doi: 10.7164/antibiotics.44.396 . PMID   2032948.
  4. Kim, Byung-Yong; Zucchi, Tiago Domingues; Fiedler, Hans-Peter; Goodfellow, Michael (1 February 2012). "Streptomyces cocklensis sp. nov., a dioxamycin-producing actinomycete". International Journal of Systematic and Evolutionary Microbiology. 62 (2): 279–283. doi: 10.1099/ijs.0.029983-0 . PMID   21398501.

Further reading