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Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells
- Source :
- Molecules, Vol 25, Iss 2215, p 2215 (2020), Molecules, Volume 25, Issue 9
- Publication Year :
- 2020
- Publisher :
- MDPI AG, 2020.
-
Abstract
- Despite numerous reports on the beneficial effects of catechin or epicatechin contained in tea and cacao extract on human health, a conclusive and precise molecular mechanism has not been elucidated. Metabolism of chemical compounds in gut microbiota recently gained significant attention, and extensive studies have been devoted in this field. In conjunction with these results, our group focused on the anti-inflammatory effects of both enantiomers of DHPV (5-(3&prime<br />4&prime<br />dihydroxyphenyl)-&gamma<br />valerolactone), produced in the intestine by microbiota metabolism, on IEC-6 cells. Divergent and efficient enantioselective synthesis of (S)- and (R)-DHPV was efficiently achieved by cross-metathesis and Sharpless asymmetric dihydroxylation as a key reaction for four steps in 16% and 14% overall yields, respectively. The anti-inflammatory effects of two enantiomers were tested on IEC-6 cells, and we found that (S)-DHPV was more active than (R)-DHPV. This result implicates that the metabolite produced in the gut has beneficial effects on IEC-6 cells of rat intestines, and the chirality of the metabolite is important for its anti-inflammatory activity. This also provided information for the future discovery of novel small molecular therapeutics for the treatment of inflammatory bowel disease.
- Subjects :
- asymmetric dihydroxylation
medicine.drug_class
Metabolite
Anti-Inflammatory Agents
Pharmaceutical Science
IκBα
Gut flora
01 natural sciences
Anti-inflammatory
Article
NF-κB
Analytical Chemistry
Cell Line
lcsh:QD241-441
03 medical and health sciences
chemistry.chemical_compound
Lactones
0302 clinical medicine
lcsh:Organic chemistry
Drug Discovery
medicine
Animals
Physical and Theoretical Chemistry
Intestinal Mucosa
DHPV
biology
010405 organic chemistry
Organic Chemistry
Enantioselective synthesis
Catechin
Metabolism
biology.organism_classification
Inflammatory Bowel Diseases
0104 chemical sciences
Rats
chemistry
Biochemistry
Chemistry (miscellaneous)
anti-inflammatory effect
divergent synthesis
Molecular Medicine
030211 gastroenterology & hepatology
Sharpless asymmetric dihydroxylation
Divergent synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 25
- Issue :
- 2215
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....377e10be1a1858feadf855414a15358f