Hyaluromycin

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Hyaluromycin
Hyaluromycin Structure.png
Names
Systematic IUPAC name
(2S)-4,9,10'-Trihydroxy-N-(2-hydroxy-5-oxo-1-cyclopenten-1-yl)-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[4,3-g]chromene]-7'-carboxamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C30H21NO13/c1-41-16-8-15(34)19-20(23(16)36)25(38)27-12(22(19)35)9-30(44-27)5-4-10-6-11-7-17(28(39)31-21-13(32)2-3-14(21)33)42-29(40)18(11)24(37)26(10)43-30/h6-8,32,35,37-38H,2-5,9H2,1H3,(H,31,39)/t30-/m0/s1
    Key: SVUGCIHLYMYXQP-PMERELPUSA-N
  • InChI=1S/C30H21NO13/c1-41-16-8-15(34)19-20(23(16)36)25(38)27-12(22(19)35)9-30(44-27)5-4-10-6-11-7-17(28(39)31-21-13(32)2-3-14(21)33)42-29(40)18(11)24(37)26(10)43-30/h6-8,32,34,36-37H,2-5,9H2,1H3,(H,31,39)/t30-/m0/s1
    Key: LBCHZWBDBFDLQH-PMERELPUSA-N
  • O=C1OC(=Cc2cc3CC[C@]4(Cc5c(O4)c(O)c4C(=O)C(=CC(=O)c4c5O)OC)Oc3c(O)c12)C(=O)NC=1C(=O)CCC=1O
  • COC1=C(C2=C(C(=C1)O)C(=O)C3=C(C2=O)O[C@]4(C3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)NC7=C(CCC7=O)O)O)O
Properties
C30H21NO13
Molar mass 603.492 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hyaluromycin is a member of the rubromycin family of antibiotics that inhibits the hydrolysis of hyaluronic acid by hyaluronidase. [1] It has been isolated from cultures of Streptomyces hyaluromycini . [2]

Related Research Articles

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<i>Streptomyces</i> Genus of bacteria

Streptomyces is the largest genus of Actinomycetota, and the type genus of the family Streptomycetaceae. Over 700 species of Streptomyces bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, and have very large 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. Different strains of the same species may colonize very diverse environments.

<span class="mw-page-title-main">Hyaluronidase</span> Class of enzymes

Hyaluronidases are a family of enzymes that catalyse the degradation of hyaluronic acid. Karl Meyer classified these enzymes in 1971, into three distinct groups, a scheme based on the enzyme reaction products. The three main types of hyaluronidases are two classes of eukaryotic endoglycosidase hydrolases and a prokaryotic lyase-type of glycosidase.

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

Novobiocin, also known as albamycin, is an aminocoumarin antibiotic that is produced by the actinomycete Streptomyces niveus, which has recently been identified as a subjective synonym for S. spheroides a member of the class Actinomycetia. Other aminocoumarin antibiotics include clorobiocin and coumermycin A1. Novobiocin was first reported in the mid-1950s.

Triacsin C is an inhibitor of long fatty acyl CoA synthetase that has been isolated from Streptomyces aureofaciens. It blocks β-cell apoptosis, induced by fatty acids (lipoapoptosis) in a rat model of obesity. In addition, it blocks the de novo synthesis of triglycerides, diglycerides, and cholesterol esters, thus interfering with lipid metabolism.

<span class="mw-page-title-main">Squalene monooxygenase</span> Mammalian protein found in Homo sapiens

Squalene monooxygenase is a eukaryotic enzyme that uses NADPH and diatomic oxygen to oxidize squalene to 2,3-oxidosqualene. Squalene epoxidase catalyzes the first oxygenation step in sterol biosynthesis and is thought to be one of the rate-limiting enzymes in this pathway. In humans, squalene epoxidase is encoded by the SQLE gene. Several eukaryote genomes lack a squalene monooxygenase encoding gene, but instead encode an alternative squalene epoxidase that performs the same task.

<span class="mw-page-title-main">Aminocoumarin</span> Class of antibiotic chemical compounds

Aminocoumarin is a class of antibiotics that act by an inhibition of the DNA gyrase enzyme involved in the cell division in bacteria. They are derived from Streptomyces species, whose best-known representative – Streptomyces coelicolor – was completely sequenced in 2002. The aminocoumarin antibiotics include:

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<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

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

Ubenimex (INN), also known more commonly as bestatin, is a competitive, reversible protease inhibitor. It is an inhibitor of arginyl aminopeptidase (aminopeptidase B), leukotriene A4 hydrolase (a zinc metalloprotease that displays both epoxide hydrolase and aminopeptidase activities), alanyl aminopeptidase (aminopeptidase M/N), leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase), and membrane dipeptidase (leukotriene D4 hydrolase). It is being studied for use in the treatment of acute myelocytic leukemia and lymphedema. It is derived from Streptomyces olivoreticuli. Ubenimex has been found to inhibit the enzymatic degradation of oxytocin, vasopressin, enkephalins, and various other peptides and compounds.

<span class="mw-page-title-main">SSI protease inhibitor</span>

In molecular biology the protein SSI is a Subtilisin inhibitor-like which stands for Streptomyces subtilisin inhibitor. This is a protease inhibitor. These are often synthesised as part of a larger precursor protein, either as a prepropeptide. The function of this protein domain is to prevent access of the substrate to the active site. It is found only in bacteria.

<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.

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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 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 mobaraensis is a spore forming bacterium species from the genus of Streptomyces. Streptomyces mobaraensis produces bleomycin, detoxin, piericidin A, piericidin B, reticulol and transglutaminase. Streptomyces mobaraensis is used in the food industry to produce transglutaminase to texture meat and fish products.

Streptomyces hyaluromycini is a Gram-positive bacterium species from the genus of Streptomyces which has been isolated from the tunicate Molgula manhattensis from the Tokyo Bay on Japan. This species produces hyaluromycin which is a Hyaluronidase inhibitor.

Butyrolactol A is an organic chemical compound of interest for its potential use as an antifungal antibiotic.

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

Hyaluromycin is a member of the rubromycin family of antibiotics that inhibits the hydrolysis of hyaluronic acid by hyaluronidase. It has been isolated from cultures of Streptomyces hyaluromycini.

References

  1. Harunari E, Imada C, Igarashi Y, Fukuda T, Terahara T, Kobayashi T (January 2014). "Hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine Streptomyces sp". Marine Drugs. 12 (1): 491–507. doi: 10.3390/md12010491 . PMC   3917283 . PMID   24451191.
  2. Harunari E, Komaki H, Ichikawa N, Hosoyama A, Kimura A, Hamada M, Igarashi Y (January 2018). "Draft genome sequence of Streptomyces hyaluromycini MB-PO13T, a hyaluromycin producer". Standards in Genomic Sciences. 13 (2): 2. doi: 10.1186/s40793-017-0286-7 . PMC   5765640 . PMID   29371910.