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| Names | |
|---|---|
| Preferred IUPAC name 6-(4,5-Dihydroxy-2-propylnaphthalen-1-yl)-4-hydroxy-2H-pyran-2-one | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
PubChem CID | |
| |
| |
| Properties | |
| C18H16O5 | |
| Molar mass | 312.321 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Phaeochromycin A is an anti-inflammatory polyketide isolated from Streptomyces . [1]
Oxytetracycline is a broad-spectrum tetracycline antibiotic, the second of the group to be discovered.
In organic chemistry, polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone and methylene groups: [−C(=O)−CH2−]n. First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity.
The avermectins are a series of drugs and pesticides used to treat parasitic worm infestations and to reduce insect pests. They are a group of 16-membered macrocyclic lactone derivatives with potent anthelmintic and insecticidal properties. These naturally occurring compounds are generated as fermentation products by Streptomyces avermitilis, a soil actinomycete. Eight different avermectins were isolated in four pairs of homologue compounds, with a major (a-component) and minor (b-component) component usually in ratios of 80:20 to 90:10. Avermectin B1, a mixture of B1a and B1b, is the drug and pesticide abamectin. Other anthelmintics derived from the avermectins include ivermectin, selamectin, doramectin, eprinomectin.
Doxorubicin (DXR) is a 14-hydroxylated version of daunorubicin, the immediate precursor of DXR in its biosynthetic pathway. Daunorubicin is more abundantly found as a natural product because it is produced by a number of different wild type strains of streptomyces. In contrast, only one known non-wild type species, streptomyces peucetius subspecies caesius ATCC 27952, was initially found to be capable of producing the more widely used doxorubicin. This strain was created by Arcamone et al. in 1969 by mutating a strain producing daunorubicin, but not DXR, at least in detectable quantities. Subsequently, Hutchinson's group showed that under special environmental conditions, or by the introduction of genetic modifications, other strains of streptomyces can produce doxorubicin. His group has also cloned many of the genes required for DXR production, although not all of them have been fully characterized. In 1996, Strohl's group discovered, isolated and characterized dox A, the gene encoding the enzyme that converts daunorubicin into DXR. By 1999, they produced recombinant Dox A, a Cytochrome P450 oxidase, and found that it catalyzes multiple steps in DXR biosynthesis, including steps leading to daunorubicin. This was significant because it became clear that all daunorubicin producing strains have the necessary genes to produce DXR, the much more therapeutically important of the two. Hutchinson's group went on to develop methods to improve the yield of DXR, from the fermentation process used in its commercial production, not only by introducing Dox A encoding plasmids, but also by introducing mutations to deactivate enzymes that shunt DXR precursors to less useful products, for example baumycin-like glycosides. Some triple mutants, that also over-expressed Dox A, were able to double the yield of DXR. This is of more than academic interest because at that time DXR cost about $1.37 million per kg and current production in 1999 was 225 kg per annum. More efficient production techniques have brought the price down to $1.1 million per kg for the non-liposomal formulation. Although DXR can be produced semi-synthetically from daunorubicin, the process involves electrophilic bromination and multiple steps and the yield is poor. Since daunorubicin is produced by fermentation, it would be ideal if the bacteria could complete DXR synthesis more effectively.
Pikromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated. Pikromycin is synthesized through a type I polyketide synthase system in Streptomyces venezuelae, a species of Gram-positive bacterium in the genus Streptomyces. Pikromycin is derived from narbonolide, a 14-membered ring macrolide. Along with the narbonolide backbone, pikromycin includes a desosamine sugar and a hydroxyl group. Although Pikromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as ertythromycins and new epothilones.
Streptomyces rimosus is a bacterium species in the genus Streptomyces.
Mayamycin is a cytotoxic polyketide isolated from a marine Streptomyces.
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.
Spectinabilin is a nitrophenyl-substituted polyketide metabolite. It was first isolated from crude streptovaricin complex produced by Streptomyces spectabilis and presented at the 13th Interscience Conference on Antimicrobial Agents and Chemotherapy in Washington, D.C. in September 1973. Spectinabilin is a biologically active compound, exhibiting both antimalarial and antiviral activity.
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 arenae is a bacterium species from the genus Streptomyces which has been isolated from soil from Illinois in the United States. Streptomyces arenae produces pentalenolactone, 2,5-dihydrophenylalanine, naphthocyclinone and arenaemycine.
Streptomyces glaucescens is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces glaucescens produces tetracenomycin C, tetracenomycin D and tetracenomycin E.
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 resistomycificus is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces resistomycificus produces the pentacyclic polyketide resistomycin.
Streptomyces spiroverticillatus is a bacterium species from the genus of Streptomyces which has been isolated from soil in Japan. Streptomyces spiroverticillatus produces tautomycin.
Streptomyces tsukubensis is a bacterium species from the genus of Streptomyces which has been isolated from soil in Ibaraki in Japan. Streptomyces tsukubensis produces the immunosuppressant tacrolimus.
Tsukamurella pulmonis is a Gram-positive and aerobic bacterium from the genus Tsukamurella which has been isolated from the sputum from a patient with lung tuberculosis in Germany.
A jadomycin is a natural product produced by Streptomyces venezuelae ISP5230 (ATCC10712), the organism which is most well known for making the antibiotic chloramphenicol. The name jadomycin is applied to a family of related angucyclines which are distinguished by the E ring, which is derived from an amino acid. The amino acid incorporation which forms the E-ring is a chemical reaction, rather than enzymatic, an uncommon occurrence in biosynthesis. As such a number of jadomycins incorporating different amino acids have been discovered. Jadomycin A was the first compound of this family to be isolated and constitutes the angucylic backbone with L-isoleucine incorporated into the E-ring. A related analog, jadomycin B, is modified by glycosylation with a 2,6-dideoxy sugar, L-digitoxose. Jadomycins have cytotoxic and antibacterial properties.
Ossamycin is a fermentation-derived natural product belonging to a family of 22- to 26-membered macrocyclic polyketides which is featured with a 6,6-spiroacetal (1,7-dioxaspiro[5,5]-undecanyl) moiety connected to one side of the macrocycle. Widely-studied 26-membered oligomycins/rutamycins, 24-membered dunaimycins, and 22-membered cytovaricin are also in this family.
Pladienolide B is a natural product produced by bacterial strain, Streptomyces platensis MER-11107, which is a gram-positive bacteria isolated from soil in Japan. Pladienolide B is a molecule of interest due to its potential anti-cancer properties. Its anti-cancer mode of action includes binding to the SF3B complex in the U2 snRNP in the human spliceosome.
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