Cuevaene A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Bioactive by-products |
| Catalog number | BBF-01089 |
| CAS | 1246172-08-6 |
| Molecular Weight | 354.40 |
| Molecular Formula | C21H22O5 |
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Description
It is produced by the strain of Streptomyces sp. HKI 0180. It has a moderate level of activity against gram-positive bacteria, Its MIC against Staphylococcus aureus and Bacillus subtilis is greater than 50 μg/mL.
Specification
| Synonyms | (2E,4Z,6E)-7-(8-hydroxy-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-yl)-4-methoxy-6-methylhepta-2,4,6-trienoic acid |
| IUPAC Name | (2E,4Z,6E)-7-(8-hydroxy-1,2,3,4-tetrahydrodibenzofuran-1-yl)-4-methoxy-6-methylhepta-2,4,6-trienoic acid |
| Canonical SMILES | CC(=CC1CCCC2=C1C3=C(O2)C=CC(=C3)O)C=C(C=CC(=O)O)OC |
| InChI | InChI=1S/C21H22O5/c1-13(11-16(25-2)7-9-20(23)24)10-14-4-3-5-19-21(14)17-12-15(22)6-8-18(17)26-19/h6-12,14,22H,3-5H2,1-2H3,(H,23,24)/b9-7+,13-10+,16-11- |
| InChI Key | LWPQRRAIIWETLD-LUGDWHTQSA-N |
Properties
| Appearance | Waxy Matter |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Methanol |
Reference Reading
1. Increased perception-action binding in Tourette syndrome
Maximilian Kleimaker, Adam Takacs, Giulia Conte, Rebecca Onken, Julius Verrel, Tobias Bäumer, Alexander Münchau, Christian Beste Brain. 2020 Jun 1;143(6):1934-1945. doi: 10.1093/brain/awaa111.
Gilles de la Tourette syndrome is a multifaceted neurodevelopmental disorder characterized by multiple motor and vocal tics. Research in Tourette syndrome has traditionally focused on the motor system. However, there is increasing evidence that perceptual and cognitive processes play a crucial role as well. Against this background it has been reasoned that processes linking perception and action might be particularly affected in these patients with the strength of perception-action binding being increased. However, this has not yet been studied experimentally. Here, we investigated adult Tourette patients within the framework of the 'Theory of Event Coding' using an experimental approach allowing us to directly test the strength of perception-action binding. We included 24 adult patients with Tourette syndrome and n = 24 healthy control subjects using a previously established visual-motor event file task with four levels of feature overlap requiring repeating or alternating responses. Concomitant to behavioural testing, EEG was recorded and analysed using temporal signal decomposition and source localization methods. On a behavioural level, perception-action binding was increased in Tourette patients. Tic frequency correlated with performance in conditions where unbinding processes of previously established perception-action bindings were required with higher tic frequency being associated with stronger perception-action binding. This suggests that perception-action binding is intimately related to the occurrence of tics. Analysis of EEG data showed that behavioural changes cannot be explained based on simple perceptual or motor processes. Instead, cognitive processes linking perception to action in inferior parietal cortices are crucial. Our findings suggest that motor or sensory processes alone are less relevant for the understanding of Tourette syndrome than cognitive processes engaged in linking and restructuring of perception-action association. A broader cognitive framework encompassing perception and action appears well suited to opening new routes for the understanding of Tourette syndrome.
2. Identification and characterization of the cuevaene A biosynthetic gene cluster in streptomyces sp. LZ35
Yuhai Jiang, Haoxin Wang, Chunhua Lu, Yanjiao Ding, Yaoyao Li, Yuemao Shen Chembiochem. 2013 Aug 19;14(12):1468-75. doi: 10.1002/cbic.201300316. Epub 2013 Jul 3.
Genome sequence analysis of Streptomyces sp. LZ35 has revealed a large number of secondary metabolite pathways, including one encoded in an orphan type I polyketide synthase gene cluster that contains a putative chorismatase/3-hydroxybenzoate synthase gene. Mutagenesis and comparative metabolic profiling led to the identification of cuevaene A as the metabolic product of the gene cluster, thus making it the first 3-HBA containing polyketide biosynthetic gene cluster described to date. Cuv10 was proven to be responsible for the conversion of chorismate into 3-HBA; Cuv18 is speculated to be responsible for the 6-hydroxylation of 3-HBA during polyketide chain elongation. Additionally, several pathway-specific regulatory factors that affect the production of cuevaene A were identified. Our results indicate that targeted inactivation of a gene followed by comparative metabolic profiling is a useful approach to identify and characterize cryptic biosynthetic gene clusters.
3. Cuevaenes C-E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI
Jing-Jing Deng, Chun-Hua Lu, Yao-Yao Li, Shan-Ren Li, Yue-Mao Shen Beilstein J Org Chem. 2014 Apr 15;10:858-862. doi: 10.3762/bjoc.10.82. eCollection 2014.
Two pairs of geometrical isomers - cuevaenes A (1) and C (3) as well as cuevaenes D (4) and E (5) - and cuevaene B (2) were isolated from gdmAI-disrupted Streptomyces sp. LZ35. The constitution of cuevaene C (3) was found to be identical to cuevaene A (1) by means of NMR spectroscopy and high resolution mass spectrometry. However, the relative configurations of the triene side chain moieties were determined to be different. It was established on the basis of spectroscopic data that cuevaenes D (4) and E (5) are amides and geometrical isomers. Cuevaenes A-C (1-3) displayed moderate activity against Gram-positive bacteria (e.g., Bacillus subtilis strain ATCC 11060) and modest activity against fungi (e.g., Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4). However, cuevaenes D (4) and E (5) showed no inhibitory activity against any of the tested microbes.
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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 ╳
