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Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
- Source :
- Molecules, Molecules, Vol 20, Iss 10, Pp 18870-18885 (2015), Volume 20, Issue 10, Pages 18870-18885
- Publication Year :
- 2015
- Publisher :
- MDPI AG, 2015.
-
Abstract
- Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this functionality. In this study, we elucidate the importance of the upper-unit of 4–8 condensed dimeric flavan-3-ols for antimicrobial activity against Saccharomyces cerevisiae (S. cerevisiae) and cervical epithelioid carcinoma cell line HeLa S3 proliferation inhibitory activity. To clarify the important constituent unit of proanthocyanidin, we synthesized four dimeric compounds, (−)-epigallocatechin-[4,8]-(+)-catechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin-3-O-gallate, and (+)-catechin-[4,8]-(−)-epigallocatechin and performed structure–activity relationship (SAR) studies. In addition to antimicrobial activity against S. cerevisiae and proliferation inhibitory activity on HeLa S3 cells, the correlation of 2,2-diphenyl-l-picrylhydrazyl radical scavenging activity with the number of phenolic hydroxyl groups was low. On the basis of the results of our SAR studies, we concluded that B-ring hydroxyl groups of the upper-unit of the dimer are crucially important for strong and effective activity.
- Subjects :
- Antifungal Agents
Free Radicals
synthesis
Stereochemistry
Dimer
Saccharomyces cerevisiae
Pharmaceutical Science
Antineoplastic Agents
Microbial Sensitivity Tests
Article
Analytical Chemistry
lcsh:QD241-441
cancer cell proliferation inhibitory activity
Inhibitory Concentration 50
Structure-Activity Relationship
chemistry.chemical_compound
lcsh:Organic chemistry
Picrates
Flavan
Drug Discovery
Humans
Structure–activity relationship
Physical and Theoretical Chemistry
Cell Proliferation
Flavonoids
antimicrobial activity
biology
Chemistry
Biphenyl Compounds
Organic Chemistry
food and beverages
Biological activity
Free Radical Scavengers
biology.organism_classification
Antimicrobial
Biphenyl compound
Proanthocyanidin
Chemistry (miscellaneous)
Molecular Medicine
DPPH radical scavenging activity
oligomeric flavonoid
Drug Screening Assays, Antitumor
condensed tannins
HeLa Cells
Subjects
Details
- ISSN :
- 14203049
- Volume :
- 20
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....59dccf4b629c1ae29927e133a8cc7763