ABSTRACT
Properties of Lactobacillus plantarum group strains isolated from two kinds of Japanese post-fermented teas, Ishizuchi-kurocha and Awa-bancha, were compared. Although lactic acid bacteria isolated from the fermented teas were identified as L. plantarum via homology comparison of 16S ribosomal RNA gene sequences, classification of L. plantarum based on ribosomal proteins showed that the strains isolated from Ishizuchi-kurocha and Awa-bancha were different. According to classification by the ribosomal protein typing, Ishizuchi-kurocha-derived strains belong to the same group as L. plantarum subsp. plantarum JCM 1149T. Awa-bancha-derived strains were assigned to a different group. This pattern was also applicable to strains isolated more than 10 years ago. A further analysis based on recA and a dnaK gene showed that Awa-bancha-derived strains were closely related to L. pentosus. The interactions with cultured cells were different between strain JCM 1149T and the Ishizuchi-kurocha-derived strains. The Ishizuchi-kurocha-derived strains showed strong adhesion to Caco-2 cells. In contrast, strain JCM 1149T and the Awa-bancha-derived strains hardly adhered to Caco-2 cells. According to the ribosomal protein typing, sugar utilization, and interaction with Caco-2 cells, although these properties were dependent on the strain strictly speaking, the L. plantarum group strains in this study can be subdivided into two groups: (1) type strain JCM 1149T and Ishizuchi-kurocha-derived strains and (2) Awa-bancha-derived strains. A regionally unique microorganism may persist in each traditional fermented drink.
ABSTRACT
Since procyanidins (oligomeric catechin or epicatechin) were reported to exhibit health benefits, much attention has been paid to the synthesis of these compounds, especially those that are longer than trimers. In the present study, syntheses of cinnamtannin A3 (epicatechin pentamer), A4 (epicatechin hexamer), catechin tetramer, pentamer, arecatannin A2 (epicatechin-epicatechin-epicatechin-catechin) and A3 (epicatechin-epicatechin-epicatechin-epicatechin-catechin) were achieved. The key reaction was a Lewis acid mediated equimolar condensation. The antitumor effects of these synthesized compounds against a human prostate cancer cell line (PC-3) were investigated. Among the tested compounds, cinnamtannin A3, A4 and arecatannin A3, which possess epicatechin oligomers longer than tetramers as the basic scaffold, showed significant activities for suppression of cell growth, invasion and FABP5 (fatty acid-binding protein 5) gene expression. Effects on cell cycle distribution showed that cell cycle arrest in the G2 phase was induced. Furthermore, these epicatechin oligomers suppressed significantly the expression of the cancer-promoting gene, FABP5, which is related to cell proliferation and metastasis in various cancer cells. Interestingly, the suppressive activities were associated with the degree of oligomerization of epicatechin. Thus, synthetic studies clearly demonstrate that epicatechin oligomers longer than trimers have significant anti-tumorigenic activities, but not the catechin counterparts.
Subject(s)
Antineoplastic Agents/chemical synthesis , Catechin/analogs & derivatives , Antineoplastic Agents/pharmacology , Cell Cycle/drug effects , Cell Line, Tumor , Cell Proliferation/drug effects , Fatty Acid-Binding Proteins/genetics , Fatty Acid-Binding Proteins/metabolism , Humans , PolymerizationABSTRACT
Synthesis of arrecatannin A1 (1) was accomplished from dimeric epicatechin electrophile, which was prepared by Zn(OTf)2 mediated self-condensation, and monomeric catechin nucleophile. The condensation was successfully worked using Yb(OTf)3 as a Lewis acid in good yield.
Subject(s)
Catechin/chemical synthesis , Catechin/chemistry , Dimerization , Molecular StructureABSTRACT
Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)3. Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3.
