Citromycetin
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| Category | Antibiotics |
| Catalog number | BBF-00645 |
| CAS | 478-60-4 |
| Molecular Weight | 290.22 |
| Molecular Formula | C14H10O7 |
| Purity | >95% by HPLC |
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Description
Citromycetin is produced by the strain of Citromyces sp. and Penicillum frequentans. Independently isolated and named from a number of different fungal species during the 1930s to 1950s; active against gram positive bacteria.
Specification
| Synonyms | 4H,5H-Pyrano(3,2-c)(1)benzopyran-10-carboxylic acid, 8,9-dihydroxy-2-methyl-4-oxo- |
| Storage | -20°C |
| IUPAC Name | 8,9-dihydroxy-2-methyl-4-oxo-5H-pyrano[3,2-c]chromene-10-carboxylic acid |
| Canonical SMILES | CC1=CC(=O)C2=C(O1)C3=C(C=C(C(=C3C(=O)O)O)O)OC2 |
| InChI | InChI=1S/C14H10O7/c1-5-2-7(15)6-4-20-9-3-8(16)12(17)11(14(18)19)10(9)13(6)21-5/h2-3,16-17H,4H2,1H3,(H,18,19) |
| InChI Key | PKEPGKZPVDAVKI-UHFFFAOYSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | Lemon-Yellow Needle Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Citromycetins and bilains A-C: new aromatic polyketides and diketopiperazines from Australian marine-derived and terrestrial Penicillium spp
Ranjala Ratnayake, Jennifer H Gill, Robert J Capon, Ernest Lacey, Michael Stewart J Nat Prod . 2007 Nov;70(11):1746-52. doi: 10.1021/np0702483.
Chemical analysis of an Australian marine-derived isolate of Penicillium bilaii, collected from the Huon estuary, Port Huon, Tasmania, yielded the known fungal aromatic polyketides citromycetin (1) and citromycin (2) together with two dihydro analogues, (-)-2,3-dihydrocitromycetin (3) and (-)-2,3-dihydrocitromycin (4). An Australian terrestrial isolate of Penicillium striatisporum collected near Shalvey, New South Wales, also yielded citromycetin (1), citromycin (2), and the new dihydro analogue (-)-2,3-dihydrocitromycetin (3), together with fulvic acid (5), anhydrofulvic acid (6), and a selection of new methoxylated analogues, 12-methoxycitromycetin (7), 12-methoxycitromycin (8), (-)-12-methoxy-2,3-dihydrocitromycetin (9), and 12-methoxyanhydrofulvic acid (10). P. bilaii also yielded the rare siderophore pistillarin (11), the known diketopiperazines cyclo-(L-Phe -L-Pro) (12), cyclo-(L-Pro-L-Tyr) (13), cyclo-(L-Pro-L-Val) (14), and cis-bis(methylthio)silvatin (15), and three new diketopiperazines, bilains A-C (16-18). The structures for the Penicillium metabolites 1- 18 were assigned by a combination of detailed spectroscopic analysis, including correlation with relevant literature data, chemical derivatization, degradation, and biosynthetic considerations. The citromycin polyketides 2 and 4 and the diketopiperazine 15 were weakly cytotoxic.
2. Antimicrobial Polyketide Metabolites from Penicillium bissettii and P. glabrum
Shara J van de Pas, Siouxsie Wiles, Alex Grey, Melissa M Cadelis, Natasha S L Nipper, Brent R Copp, Bevan S Weir, Soeren Geese Molecules . 2021 Dec 31;27(1):240. doi: 10.3390/molecules27010240.
Screening of several fungi from the New Zealand International Collection of Microorganisms from Plants identified two strains ofPenicillium, P. bissettiiandP. glabrum, which exhibited antimicrobial activity againstEscherichia coli,Klebsiella pneumoniae, andStaphylococcus aureus.Further investigation into the natural products of the fungi, through extraction and fractionation, led to the isolation of five known polyketide metabolites, penicillic acid (1), citromycetin (2), penialdin A (3), penialdin F (4), and myxotrichin B (5). Semi-synthetic derivatization of1led to the discovery of a novel dihydro (1a) derivative that provided evidence for the existence of the much-speculated open-chained form of1. Upon investigation of the antimicrobial activities of the natural products and derivatives, both penicillic acid (1) and penialdin F (4) were found to inhibit the growth of Methicillin-resistantS. aureus. Penialdin F (4) was also found to have some inhibitory activity againstMycobacterium abscessusandM. marinumalong with citromycetin (2).
3. Anti-Inflammatory and Protein Tyrosine Phosphatase 1B Inhibitory Metabolites from the Antarctic Marine-Derived Fungal Strain Penicillium glabrum SF-7123
Jae Hak Sohn, Tran Minh Ha, Joung Han Yim, Dong-Cheol Kim, Hyuncheol Oh Mar Drugs . 2020 May 9;18(5):247. doi: 10.3390/md18050247.
A chemical investigation of the marine-derived fungal strainPenicillium glabrum(SF-7123) revealed a new citromycetin (polyketide) derivative (1) and four known secondary fungal metabolites, i.e, neuchromenin (2), asterric acid (3), myxotrichin C (4), and deoxyfunicone (5). The structures of these metabolites were identified primarily by extensive analysis of their spectroscopic data, including NMR and MS data. Results from the initial screening of anti-inflammatory effects showed that2,4, and5possessed inhibitory activity against the excessive production of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated BV2 microglial cells, with IC50values of 2.7 µM, 28.1 µM, and 10.6 µM, respectively. Compounds2,4, and5also inhibited the excessive production of NO, with IC50values of 4.7 µM, 41.5 µM, and 40.1 µM, respectively, in LPS-stimulated RAW264.7 macrophage cells. In addition, these compounds inhibited LPS-induced overproduction of prostaglandin E2in both cellular models. Further investigation of the most active compound (2) revealed that these anti-inflammatory effects were associated with a suppressive effect on the over-expression of inducible nitric oxide synthase and cyclooxygenase-2. Finally, we showed that the anti-inflammatory effects of compound2were mediated via the downregulation of inflammation-related pathways such as those dependent on nuclear factor kappa B and p38 mitogen-activated protein kinase in LPS-stimulated BV2 and RAW264.7 cells. In the evaluation of the inhibitory effects of the isolated compounds on protein tyrosine phosphate 1B (PTP1B) activity, compound4was identified as a noncompetitive inhibitor of PTP1B, with an IC50value of 19.2 µM, and compound5was shown to inhibit the activity of PTP1B, with an IC50value of 24.3 µM, by binding to the active site of the enzyme. Taken together, this study demonstrates the potential value of marine-derived fungal isolates as a bioresource for bioactive compounds.
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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 ╳
