RRC ID 38381
著者 Hamada Y, Takano S, Ayano Y, Tokunaga M, Koashi T, Okamoto S, Doi S, Ishida M, Kawasaki T, Hamada M, Nakajima N, Saito A.
タイトル Structure-Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities.
ジャーナル Molecules
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.
巻・号 20(10)
ページ 18870-85
公開日 2015-10-16
DOI 10.3390/molecules201018870
PII molecules201018870
PMID 26501251
PMC PMC6332077
MeSH Antifungal Agents / chemistry Antifungal Agents / pharmacology Antineoplastic Agents / chemistry Antineoplastic Agents / pharmacology Biphenyl Compounds / chemistry Cell Proliferation / drug effects Drug Screening Assays, Antitumor Flavonoids / chemistry* Flavonoids / pharmacology Free Radical Scavengers / chemistry* Free Radical Scavengers / pharmacology Free Radicals / chemistry HeLa Cells Humans Inhibitory Concentration 50 Microbial Sensitivity Tests Picrates / chemistry Saccharomyces cerevisiae / drug effects Structure-Activity Relationship
IF 3.267
引用数 9
WOS 分野 CHEMISTRY, ORGANIC
リソース情報
ヒト・動物細胞 HeLa-S3 WI-38