• Title/Summary/Keyword: (-)-Catechin

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Tyrosinase Inhibition-mediated Anti-melanogenic Effects by Catechin Derivatives Extracted from Ulmus parvifolia (참느릅나무에서 추출된 catechin 유도체 화합물의 멜라닌 생성 억제 효과)

  • Taehyeok Hwang;Hyo Jung Lee;Dong-Min Kang;Kyoung Mi Moon;Jae Cheal Yoo;Mi-Jeong Ahn;Dong Kyu Moon;Dong Kyun Woo
    • Journal of Life Science
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    • v.33 no.2
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    • pp.169-175
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    • 2023
  • As a protective defensive mechanism against ultraviolet (UV) light exposure in skin tissue, melanocytes produce the pigment melanin. Tyrosinase plays a key role in melanin production in melanocytes. However, the overproduction of melanin can lead to lesions, such as freckles and dark spots. Thus, it is clinically important to find a modulating molecule to control melanogenesis by regulating tyrosinase expression and/or activity. It is known that catechin, a plant flavonoid, can reduce melano- genesis through the downregulation of tyrosinase expression. Here, we tested whether catechin derivatives isolated from the stem bark of Ulmus parvifolia have an effect on melanin production by regulating tyrosinase in mouse melanoma cells and in vitro mushroom tyrosinase. The catechin derivatives used in this study included C5A, C7A, C7G, and C7X. Treatments using these catechin derivatives reduced melanin production in mouse melanoma B16F10 cells in which melanogenesis was stimulated by α-MSH. Notably, the anti-melanogenic effects of catechin derivatives were similar to those of kojic acid, a well-known anti-melanogenic molecule. Both C5A and C7A directly inhibited the activity of tyrosinase isolated from mushrooms in vitro. Furthermore, our in silico computational simulation showed that these two compounds were expected to bind to the active site of tyrosinase, which is similar to kojic acid. In addition, all four catechin derivatives reduced tyrosinase protein expression. In summary, our results showed that catechin derivatives can reduce melanogenesis by regulating tyrosinase activity or expression. Thus, this study suggests that catechin derivatives isolated from U. parvifolia can be novel modulators of melanin production.

Preventive Effects of Vitamin E and Catechin on Spermatogenic Disturbance Induced by Di-(2-Ethylhexyl) Phthalate in Rat (쥐에서 Di-(2-Ethylhexyl) Phthalate로 유발된 정자 형성 장애에 대한 Vitamin E와 Catechin의 예방 효과)

  • Lee, J.W.;Lee, K.K.;Cheong, J.T.;Yun, Y.M.;Lee, J.M.;Park, H.J.;Woo, H.C.;Yoo, J.G.;Son, W.J.;Kang, M.S.;Kang, T.Y.
    • Journal of Embryo Transfer
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    • v.22 no.2
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    • pp.81-87
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    • 2007
  • The purpose of the present study was to determine the preventive effects of the two antioxidant vitamin E and catechin on DEHP-induced disturbance of spermatogenesis in male rats. Rats at 4 weeks of age were randomly allocated into five groups with 20 animals per group. The first group was not any administrated as control. The second group was administrated DEHP (2 g/kg) daily for 14 days. The third group was administrated vitamin E (500 IU/kg) following DEHP treatment by the same method (daily for 14 days). The fourth group was administrated catechin (200 mg/kg) following DEHP treatment by the same method. The fifth group was co-administrated vitamin E (500 IU/kg) and catechin (200 mg/kg) following DEHP treatment by the same method. In order to determine the preventive effects, we examined pathological changes of testis with apoptotic index, and characteristics of sperm with computer assisted sperm analysis (CASA). Vitamin E and catechin supplementation were significantly prevented the testicular atrophy, apoptosis of germ cells in the seminiferous tubules and abnormal rate of sperm. Moreover, sperm concentration, viability and motility was significantly recovered in groups of alone and along with vitamin E and catechin. The results suggest that preventive effects of alone and along administration of vitamin E and catechin on DEHP-induced testicular atrophy damages have been demonstrated.

Effects of Green Tea Catechin on Platelet Phospholipase $A_{2}$ Activity and the Liver Antioxidative Defense System in Streptozotocin-induced Diabetic Rats

  • Yang, Jeong-Ah;Rhee, Soon-Jae
    • Preventive Nutrition and Food Science
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    • v.5 no.4
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    • pp.213-218
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    • 2000
  • The purpose of the study was to investigate the effects of dietary green tea catechin and vitamin E on the phospholipse {TEX}$A_{2}${/TEX} activity and th antioxidative defense system in streptozotocin (STZ)-induced diabetic rats. Sprague-Dawley male rats weighing 100$\pm$10 gm were randomly assigned to one normal and five STZ-induced diabetic groups. The diabetic groups were assigned either a catechin-free diet (DM group), 0.5% catechin diet (DM-0.5C group), 1% catechin diet (DM-1C group), vitamin E-free diet (DM-0E group), and 400 mg vitamin E per kg diet (DM-400E group) according to the levels of dietary catechin or vitamin E supplementation. The vitamin E levels of the normal, DM, DM-0.5C, and DM-1C groups were 40 mg per kg diet. Diabetes was experimentally induced by an intravenous injection of streptozotocin after 4 weeks of feeding the five experimental diets. The animals were sacrificed on the 6th day of he diabetic state. The body weight gains were lower in all five diabetic groups after the STZ injection. The platelet phospholipase {TEX}$A_{2}${/TEX}({TEX}$PLA_{2}${/TEX}) activity in the diabetic groups was higher than that in the normal group. However, the enzyme activity in the DM-0.5C, DM-1C, and DM-400E groups was lower than that in the DM and DM-0E groups. The cytochrome {TEX}$P_{450}${/TEX} and cytochrome {TEX}$b_{5}${/TEX} content and NADPH-cytochrome {TEX}$P_{450}${/TEX} reductase activity were about 50~110% higher in the DM and DM-0E groups than in the normal group, yet significantly reduced by either catechin or vitamin E supplementation. The superoxide dismutase (SOD) content in the liver did not differ significantly in any of the groups. However, the glutathione peroxidase (GSHpx) activity was generally lower in the diabetic groups, compared with the normal group, whereas that of the DM-0.5C, DM-1C, and DM-400E groups was significantly higher compared with that of the DM and DM-0E groups. The levels of thiobarbituric acid reactive substances (TBARS) in the liver tissue were 148% and 201% higher in the DM and DM-0E groups, respectively, compared with the normal group, however, these levels were reduced by either catechin or vitamin E supplementation (DM-0.5, DM-1C and DM-400E). Accordingly, the present results indicate that STZ-induced diabetic rats exhibited an imbalance between free radical generation and scavenger systems in the liver which led to the acceleration of lipid peroxidation. However, these abnormalities were reduced and the antioxidative defense system was restored by either dietary catechin or vitamin E supplementation. In conclusion, the effects of dietary catechin or vitamin E in streptozotocin-induced diabetic rats would appear to inhibit lipid peroxidation as an anti-oxidant by regulating the activity of {TEX}$PLA_{2}${/TEX}.

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Development of Simultaneous Analysis of Ferulic Acid, Caffeic Acid, Catechin and Taxifolin from Health Functional Food Pinus Pinaster Bark Extract by UPLC-MS/MS (건강기능식품 프랑스해안송껍질추출물 중 UPLC-MS/MS를 이용한 Ferulic acid, Caffeic acid, Catechin, Taxifolin 동시분석법 개발 연구)

  • Oh, Jae-Myoung;Kim, Ji An;Hu, Soo Jung;Choi, Yoon Hee;Oh, Keum Soon
    • Journal of Food Hygiene and Safety
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    • v.34 no.5
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    • pp.431-437
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    • 2019
  • This study was conducted to develop a simultaneous analysis method for ferulic acid, caffeic acid, catechin and taxifolin from Health Functional Food (HFF) Pinus Pinaster bark extract. The simultaneous analytical method for ferulic acid, caffeic acid, catechin and taxifolin is carried out using UPLC-MS/MS. The method validation was performed to determine selectivity, linearity, accuracy, limit of detection (LOD), limit of quantification (LOQ) and precision for ferulic acid, caffeic acid, catechin and taxifolin. LC-MS/MS method was established using an Acquity UPLC BEH $C_{18}$ Column and was applied for these 4 compounds. Product-ion traces, at m/z $194.2{\rightarrow}133$, $180.2{\rightarrow}135$, $290.3{\rightarrow}245$, $304.3{\rightarrow}248$, were used for quantitative analysis of ferulic acid, caffeic acid, catechin and taxifolin, respectively. Excellent linearity ($r^2=0.999$) was observed for ferulic acid, caffeic acid, catechin and taxifolin in the concentration range (50-2500 mg/L). The observed recoveries of these 4 compounds were found to be between 84.9 and 104.9%, while precision was between 1.20 and 4.43% relative standard deviation (% RSD).

Studies on the Comparison of Antibacterial Activity by Catechin Concentration in Green Tea Extract (녹차 추출물 중 카테킨 성분 농도에 따른 항균활성 비교 연구)

  • Choi Kyung-Min;Yun Young-Gab;Jiang Jing-Hua;Oh Sung-Su;Yang Hwan-Deok;Kim Hyoung-Jun;Jeon Byung-Hun;Park Hyun
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.19 no.5
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    • pp.1233-1237
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    • 2005
  • Catechin products in green tea extract was prepared to investigate antibacterial activity on the pathogenic bacteria. Survival of pathogenic bacteria (MASA - methicillin resistant Staphylocouus aureus, E.coli O157 and S. typhimurium Sal-13) in tryptic soy agar(TSA) containing Catechin products powder incubated at various concentration was evaluated. TSA containing $0{\sim}2%(w/v)$ of Catechin products was inoculated approximately $10^4\;CFU/ml$ of pathogenic bacteria and incubated at $37^{\circ}C$ for 24 hours. The plate counting technique and clear zoon test were used to test survival effect of the Catechin products. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was derived from the survival curves of pathogenic bacteria. S. typhimurium Sal-13 was the most sensitive strain to Catechin products. This result suggested that Catechin products can be used as an effective natural antibacterial agent.

Synergistic Effects of Catechin or Ascorbic Acid on Antioxidative Activities of Hexane and Methanol Extracts from Rosemary, Sage, Oregano, and Ginger (Rosemary, Sage, Oregano와 Ginger의 메탄올과 헥산 추출물의 항산화 작용에 대한 카테킨과 아스코르브산의 상승 효과)

  • Ahn, Chae-Kyung;Han, Daeseok;Rhee, Young-Kyung;Lee, Young-Chul
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.34 no.5
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    • pp.586-592
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    • 2005
  • This study was peformed to investigate the synergistic effects of catechin and ascorbic acid on antioxidative activities of methanol and hexane extracts (500 ppm) from rosemary, sage, oregano, and ginger. Ascorbic acid (200 ppm) and (-)-catechin (200 ppm) could be solubilized in a rice bran oil via a reverse micelles using small amount of water and dioctyl sulfosuccinate as the sufactant. Methanol extracts from rosemary, sage, oregano, and ginger showed the synergistic effects by (-)-catechin. However, methanol extracts showed the synergistic effect by ascorbic acid except that of ginger. The synergistic effects of (-)-catechin on methanol extracts were higher than those of ascorbic acid. Hexane extracts of oregano and ginger showed the synergistic effects by (-)-catechin, and no synergistic effects by ascorbic acid. On the other hand, rosemary and sage showed the synergistic effects by ascorbic acid and no synergistic effects by (-)-catechin.

Isolation of main component and antioxidant activities on the stem and root of Rosa rugosa (해당화 줄기 및 뿌리의 주성분 분리 및 항산화활성)

  • Park, byoung-Jae
    • Korean Journal of Plant Resources
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    • v.21 no.5
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    • pp.402-407
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    • 2008
  • Total phenol content was obtained from the stem extract of 7.8 (g/100g, D.W.) and root extract of 10.5 (g/100g, D.W.) on Rosa rugosa. S-4 and R-2 compounds were isolated from the stem and root of R. rugosa. The structure of S-4 and R-2 compounds was assigned as catechin by $^{1}H,\;^{13}C$ CNMR signal and TOF-MS. The tannin content of stem extract was 752.5 (mg/100g, D.W.) as 6.3 of gallic acid, 61.5 of epicatechin and 684.8 of catechin. The tannin content of root extract was higher about 2 times (1676.0) as 6.8 of gallic acid, 160.3 of epicatechin and 1508.5 of catechin than that of stem. It was shown that catechin was main compound in the stem and root extracts of R. rugosa. Antioxidant activities were stronger low concentration, and were not different of stem and root extracts. As the results, stem and root of R. rugosa were evaluated, as natural antioxidant resource.

Catechin hydrate prevents cisplatin-induced spermatogonia GC-1 spg cellular damage

  • Hyeon Woo Shim;Won-Yong Lee;Youn-Kyung Ham;Sung Don Lim;Sun-Goo Hwang;Hyun-Jung Park
    • Journal of Animal Reproduction and Biotechnology
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    • v.39 no.2
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    • pp.145-152
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    • 2024
  • Background: Despite its anticancer activity, cisplatin exhibits severe testicular toxicity when used in chemotherapy. Owing to its wide application in cancer therapy, the reduction of damage to normal tissue is of imminent clinical need. In this study, we evaluated the effects of catechin hydrate, a natural flavon-3-ol phytochemical, on cisplatin-induced testicular injury. Methods: Type 2 mouse spermatogonia (GC-1 spg cells) were treated with 0-100 μM catechin and cisplatin. Cell survival was estimated using a cell proliferation assay and Ki-67 immunostaining. Apoptosis was assessed via flow cytometry with the Dead Cell Apoptosis assay. To determine the antioxidant effects of catechin hydrate, Nrf2 expression was measured using qPCR and CellROX staining. The anti-inflammatory effects were evaluated by analyzing the gene and protein expression levels of iNOS and COX2 using qPCR and immunoblotting. Results: The 100 μM catechin hydrate treatment did not affect healthy GC-1 spg cells but, prevented cisplatin-induced GC-1 spg cell death via the regulation of anti-oxidants and inflammation-related molecules. In addition, the number of apoptotic cells, cleaved-caspase 3 level, and BAX gene expression levels were significantly reduced by catechin hydrate treatment in a cisplatin-induced GC-1 spg cell death model. In addition, antioxidant and anti-inflammatory marker genes, including Nrf2, iNOS, and COX2 were significantly downregulated by catechin hydrate treatment in cisplatintreated GC-1 cells. Conclusions: Our study contributes to the opportunity to reintroduce cisplatin into systemic anticancer treatment, with reduced testicular toxicity and restored fertility.

Catechin Degradation by Several Fungal Strains Isolated from Mexican Desert

  • Aguilar Cristobal Noe;Mario Cruz;Raul Rodriguez;Gerardo Gutierrez-Sanchez;Ascencion Ramirez-Coronel;Christopher Augur
    • Journal of Microbiology and Biotechnology
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    • v.14 no.2
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    • pp.426-429
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    • 2004
  • Eleven fungal strains previously isolated from the Mexican desert were evaluated for their capacity to use catechin as carbon source in submerged cultures. At 2 g/l of catechin, all strains grew better than the control strains, Aspergillus niger Aa-20. Aspergillus niger PSH and Penicillium commune EH2 degraded 79.33% and 76.35% with degradation rates of 0.0065 and 0.0074 g/l/h, respectively, when an initial catechin concentration of 3 g/l was used. Obtained results demonstrated the potential biotechnological capacity of these fungal strains to use condensed tannins as carbon source.

[$^{13}C-NMR$ of the Phenolic Compounds

  • Ahn, Byung-Zun
    • Korean Journal of Pharmacognosy
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    • v.11 no.3_4 s.43
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    • pp.153-162
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    • 1980
  • 1) The hydroxy-substitution in the simple phenolic compounds follows an additivity rule in the chemical shifts of their aromatic carbon atoms. In para-and ortho-effects is a good agreement between calculated and measured values, but the meta-effect is not certain. 2) The additivity rule was applied to assign the chemical shifts of catechins. 3) The nuclear overhauser effect was applied to assign the chemical shifts of C-8 and C-6 atoms of catechins and their polymer. The signal of C-8 is lower in intensity and appear in lower field than C-6. 4) The results of the NOE were applied to determine the bonding positions of catechin units in the catechin dimer and trimer. The bonding positions are C-8a and C-8b atoms of the second and third catechin units. 5) It was tried to determine the conformation of the catechin dimer and trimer by analysing the signal shapes of C-3' and C-4' atoms in the catechol moieties. The catechol moieties lie in opposite side in the dimer and trimer structure. A combined analysis of $^{13}C-and\;^1H-NMR$ results lead to the suggestion that such a catechin polymer is a zigzag planar form.

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