Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)<sub>3</sub>-Catalyzed Condensation with Catechin Nucleophile

Oizumi, Yukiko; Mohri, Yoshihiro; Hirota, Mitsuru; Makabe, Hidefumi

doi:10.1021/jo1009382

Cited by 27 publications

(12 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of procyanidin dimers such as procyanidin B1, B2, B3 and B4 using Yb(OTf) 3 mediated equimolar condensation 14 and their content in apple juice 15 has been reported by us. The anti-inflammatory activity of these compounds has also been reported 16 , 17 . Recently, the synthesis of procyanidin trimers such as procyanidin C1 and C2 using Yb(OTf) 3 or silver Lewis acid mediated equimolar condensation was presented 18 , 19 .…”

Section: Introductionmentioning

confidence: 86%

Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts

Takanashi

Suda

Matsumoto

et al. 2017

Sci Rep

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 86%

Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts

Takanashi

Suda

Matsumoto

et al. 2017

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

“…Procyanidin B3 (B3) is a procyanidin dimer that is widely studied due to its abundance in the human diet [33]–[35]. B3 and other procyanidin dimers can be absorbed by the small intestine [36] and have relevant antioxidant activities [37]. In the present study, we evaluated the role of B3 isolated from grape seed extracts in the differentiation and survival of chondrocytes in vitro .…”

Section: Introductionmentioning

confidence: 99%

Procyanidin B3 Prevents Articular Cartilage Degeneration and Heterotopic Cartilage Formation in a Mouse Surgical Osteoarthritis Model

et al. 2012

View full text Add to dashboard Cite

Osteoarthritis (OA) is a common disease in the elderly due to an imbalance in cartilage degradation and synthesis. Heterotopic ossification (HO) occurs when ectopic masses of endochondral bone form within the soft tissues around the joints and is triggered by inflammation of the soft tissues. Procyanidin B3 (B3) is a procyanidin dimer that is widely studied due to its high abundance in the human diet and antioxidant activity. Here, we evaluated the role of B3 isolated from grape seeds in the maintenance of chondrocytes in vitro and in vivo. We observed that B3 inhibited H2O2-induced apoptosis in primary chondrocytes, suppressed H2O2- or IL-1ß−induced nitric oxide synthase (iNOS) production, and prevented IL-1ß−induced suppression of chondrocyte differentiation marker gene expression in primary chondrocytes. Moreover, B3 treatment enhanced the early differentiation of ATDC5 cells. To examine whether B3 prevents cartilage destruction in vivo, OA was surgically induced in C57BL/6J mice followed by oral administration of B3 or vehicle control. Daily oral B3 administration protected articular cartilage from OA and prevented chondrocyte apoptosis in surgically-induced OA joints. Furthermore, B3 administration prevented heterotopic cartilage formation near the surgical region. iNOS protein expression was enhanced in the synovial tissues and the pseudocapsule around the surgical region in OA mice fed a control diet, but was reduced in mice that received B3. Together, these data indicated that in the OA model, B3 prevented OA progression and heterotopic cartilage formation, at least in a part through the suppression of iNOS. These results support the potential therapeutic benefits of B3 for treatment of human OA and heterotopic ossification.

show abstract

“…This indicates that OPC is liable to absorption in the intestines (20). OPC is widely studied owing to its high content in human diet and its powerful antioxidant properties (21).…”

Section: Introductionmentioning

confidence: 99%

Oligomeric proanthocyanidins inhibit apoptosis of chondrocytes induced by interleukin-1β

Yin

Wang

et al. 2017

Molecular Medicine Reports

View full text Add to dashboard Cite

Oligomeric proanthocyanidin (OPC) is a water-soluble plant polyphenolic compound known for its cytoprotective effects in various tissue types. However, its effect on chondrocytes has not been well characterized. The present study aimed to investigate the effect of OPC on interleukin-1β (IL-1β)-induced apoptosis in chondrocytes, and to determine the mechanisms underlying the protective effects of OPC. Knee articular chondrocytes obtained from 6-week-old SPF Kunming mice were cultured and serially passaged. First-generation chondrocytes were selected for subsequent experiments following toluidine blue staining. Subsequent to IL-1β and OPC administration, an MTT assay was performed to examine the viability rate of chondrocytes, and the optimal drug concentration was determined. The fluorescence dye 2',7'-dichlorofluorescein diacetate was used to determine the intracellular content of reactive oxygen species (ROS). Mitochondrial membrane potential (MMP) was measured using a 5,5',6,6'-tetrachloro-1,1',3,3'-tetraethyl-benzimidazolylcarbocyanine iodide (JC-1) assay. The apoptosis rate of chondrocytes was assessed using an Annexin V-FITC/PI assay and ultrastructural changes were observed under an electron microscope. The results demonstrated that OPC increased the survival rate of chondrocytes against IL-1β-induced apoptosis. The most significant protective effect of OPC was observed at the concentration of 0.050 mg/ml. OPC reversed the increased ROS content and MMP levels, and inhibited IL-1β-induced apoptosis in chondrocytes. In addition, OPC was revealed to protect the ultrastructural integrity of chondrocytes. Taken together, the results of the present study suggest that OPC protects chondrocytes against IL-1β-induced damage by decreasing ROS content and MMP levels.

show abstract

Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)₃-Catalyzed Condensation with Catechin Nucleophile

Cited by 27 publications

References 19 publications

Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts

Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts

Procyanidin B3 Prevents Articular Cartilage Degeneration and Heterotopic Cartilage Formation in a Mouse Surgical Osteoarthritis Model

Oligomeric proanthocyanidins inhibit apoptosis of chondrocytes induced by interleukin-1β

Contact Info

Product

Resources

About

Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)3-Catalyzed Condensation with Catechin Nucleophile

Cited by 27 publications

References 19 publications

Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts

Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts

Procyanidin B3 Prevents Articular Cartilage Degeneration and Heterotopic Cartilage Formation in a Mouse Surgical Osteoarthritis Model

Oligomeric proanthocyanidins inhibit apoptosis of chondrocytes induced by interleukin-1β

Contact Info

Product

Resources

About

Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)₃-Catalyzed Condensation with Catechin Nucleophile