Oudenone
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| Category | Antibiotics |
| Catalog number | BBF-02325 |
| CAS | 31323-50-9 |
| Molecular Weight | 208.25 |
| Molecular Formula | C12H16O3 |
| Purity | ≥95% |
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Description
It is produced by the strain of Oudemansiella sp. 10F. It is an oxygen-containing heterocyclic antibiotic. It has weak antibacterial and fungal activity. Oudenone of more than 3.13 mg/kg has antihypertensive effect on spontaneous hypertension in rats by intraperitoneal injection or oral administration.
Specification
| Synonyms | 1,3-Cyclopentanedione, 2-(dihydro-5-propyl-2(3H)-furylidene)-, (S)-; 2-[(S)-Tetrahydro-5-propylfuran-2-ylidene]-1,3-cyclopentanedione |
| IUPAC Name | 2-[(5S)-5-propyloxolan-2-ylidene]cyclopentane-1,3-dione |
| Canonical SMILES | CCCC1CCC(=C2C(=O)CCC2=O)O1 |
| InChI | InChI=1S/C12H16O3/c1-2-3-8-4-7-11(15-8)12-9(13)5-6-10(12)14/h8H,2-7H2,1H3/t8-/m0/s1 |
| InChI Key | AFHDYMGMZUYZQT-QMMMGPOBSA-N |
Properties
| Appearance | White Flake Crystal |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 340.6°C at 760 mmHg |
| Melting Point | 77-79°C |
| Density | 1.166 g/cm3 |
| Solubility | Soluble in Methanol, Ethanol |
Reference Reading
1. Pharmacodynamic actions of (S)-2-[4,5-dihydro-5-propyl-2-(3H)-furylidene]-1,3-cyclopentanedione (oudenone)
H Ozawa, T Koide Jpn J Pharmacol. 1976 Oct;26(5):581-92. doi: 10.1254/jjp.26.581.
The pharmacodynamic actions of (S)-2-[4,5-dihydro-5-propyl-2(3H)-furylidene]-1,3-cyclopentanedione (oudenone) were studied in both anesthetized animals and isolated organs. Oudenone (10--40 mg/kg i.v.) induced an initial rise in blood pressure followed by a prolonged hypotension in the anesthetized rats. In unanesthetized spontaneously hypertensive rats (SHR), oudenone (5--200 mg/kg p.o.) caused a dose-related decrease in the systolic blood pressure. The initial pressor effect was diminished by pretreatments with phentolamine, guanethidine, hexamethonium and was abolished in the pithed rats. In addition, intracisternal administrations of oudenone (100--600 mug/kg) showed a marked increase in blood pressure in the anesthetized rats, suggesting that the pressor effect may be due to centrally mediated actions. Oudenone, given intra-arterially into the femoral artery (400--800 mug/kg), caused a long-lasting vasodilation in anesthetized dogs. At a relatively high dose (40 mg/kg i.v.), oudenone antagonized all pressor responses to autonomic agents and central vagus nerve stimulation in anesthetized rats and dogs, however, oudenone showed no anti-cholinergic,-histaminergic, beta-adrenergic and adrenergic neuron blocking properties.
2. Inhibition of phenylalanine hydroxylase, a pterin-requiring monooxygenase, by oudenone and its derivatives
S Koizumi, T Nagatsu, H Iinuma, M Ohno, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1982 Apr;35(4):458-62. doi: 10.7164/antibiotics.35.458.
Phenylalanine hydroxylase was shown to be inhibited by oudenone and its derivatives in vitro. At a concentration of 2.3 x 10(-3) M, oudenone inhibited phenylalanine hydroxylase by 50%, and some of the oudenone derivatives showed more potent inhibition. The kinetic data have shown that the inhibition by oudenone is competitive with a tetrahydropterin cofactor (6,7-dimethyltetrahydropterin, DMPH4) and noncompetitive with phenylalanine and oxygen. Among 12 oudenone derivatives, there was no parallel structure-activity relationship between the inhibitory effect for phenylalanine hydroxylase and that for tyrosine hydroxylase. A derivative of oudenone, [compound No. 142; 2-(3,4-dihydroxyphenyl)-1-oxopropyl)cyclohexan-1,3-dione] showed the most potent inhibition among the oudenone derivatives. It inhibited phenylalanine hydroxylase by 50% at a concentration of 1.8 x 10(-5) M. This inhibition was a mixed type with either a tetrahydropterin cofactor, DMPH4, or with the substrate phenylalanine, which was different from the inhibition by oudenone. However, the same noncompetitive inhibition was shown toward oxygen.
3. Studies on the Biosynthesis of the Fungal Metabolite Oudenone. 2. Synthesis and Enzymatic Cyclization of an alpha-Diketone, Open-Chain Precursor into Oudenone in Cultures of Oudemansiella radicata
Youla S. Tsantrizos, Xianshu Yang, Andrew McClory J Org Chem. 1999 Sep 3;64(18):6609-6614. doi: 10.1021/jo9901135.
The alpha-diketone 4 was shown to be the open-chain biosynthetic precursor of the fungal metabolite oudenone (1a and 1b). Intact incorporation of 4 into 1 was achieved upon incubation of a (2)H-labeled, N-acetylcysteamine thioester derivative of 4 with growing cultures of Oudemansiella radicata. A biosynthetic scheme for the formation of the hexaketide 4 and its enzymatic cyclization into oudenone (1), consistent with the experimental data, is described. The proposed mechanism for the cyclization of 4 to 1 is analogous to the "polyepoxide cascade" model, which has been previously implicated in the biosynthesis of polyether antibiotics.
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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 ╳
