Cyanidin-3-O-(2"-xylosyl)-glucoside, an Anthocyanin from Siberian ginseng (Acanthopanax senticosus) Fruits, Inhibits UVB-induced COX-2 Expression and AP-1 Transactivation

정성근,임태규,서상권,이형주,황영선,정명근,이기원 한국식품과학회 2013 Food Science and Biotechnology Vol.22 No.2

Cyanidin-3-O-(2"-xylosyl)-glucoside (C-3-O-(2"-xylosyl)-G) was analyzed as an active constituent from the fruit of Siberian ginseng (Acanthopanax senticosus)using a HPLC diode array detection-electrospray ionization/mass spectrometry analysis system and the effect of C-3-O-(2''-xylosyl)-G on UVB-induced inflammatory signaling in JB6 P+ cells was investigated. C-3-O-(2"-xylosyl)-G inhibited UVB-induced cyclooxygenase (COX)-2 expression and promoter binding activity in JB6 P+ cells and JB6 P+cells stably transfected with the COX-2 luciferase reporter plasmid. It inhibited both the UVB-induced activator protein-1 (AP-1) and nuclear factor (NF)-κB transactivation in JB6 P+ cells stably transfected with the AP-1 and NF-κB luciferase reporter plasmids. Additionally, C-3-O-(2"-xylosyl)-G significantly suppressed UVB-induced upregulated phosphorylation of c-Jun N terminal kinase,MEK/extracellular signaling kinase, and mitogen activated protein kinase kinase (MAPKK) 3/6 in JB6 P+ cells. These results indicate that C-3-O-(2"-xylosyl)-G may be a promising chemopreventive material that acts by suppressing COX-2expression and AP-1 and NF-κB transactivation and JNK,MAPKK3/6, and MEK/ERK1/2 phosphorylation.

Protection Effect of Cyanidin 3-O-Glucoside Against Oxidative Stress-induced HepG2 Cell Death Through Activation of Akt and Extracellular Signal-regulated Kinase Pathways

박준언,강기성,이해정 대한화학회 2017 Bulletin of the Korean Chemical Society Vol.38 No.11

The attack of reactive oxygen species (ROS) on unsaturated fatty acids causes peroxidation. The membranes of liver cells are rich in unsaturated fatty acids, which are a target of lipid peroxidation by free radicals. The purpose of the present study was to identify the hepatoprotective potential of Lonicera caerulea and its active compound, cyanidin 3-O-glucoside, on tertiary butyl hydroperoxide (tBHP)-induced oxidative damage in HepG2 cells. L. caerulea extract and its active compound, cyanidin 3-O-glucoside, showed a dose-dependent hepatoprotective effect on tBHP-induced HepG2 cell damage. In addition, L. caerulea and cyanidin 3-O-glucoside inhibited the production of intracellular ROS in tBHP-treated HepG2 cells. The protein expression of phosphorylated-extracellular signal-regulated kinases and Akt, which are responsible for cell protection against ROS, were increased after treatment with cyanidin 3-O-glucoside (50 and 100 μM) in a dose-dependent manner. Therefore, cyanidin 3-O-glucoside is the active compound in L. caerulea, which is responsible for the hepatoprotective effects through the inhibition of ROS and the activation of antioxidant mechanisms.

Cyanidin-3-O-glucoside Ameliorates Postprandial Hyperglycemia in Diabetic Mice

Kyungha Choi(최경하),Sung-In Choi(최성인),Mi Hwa Park(박미화),Ji-Sook Han(한지숙) 한국생명과학회 2017 생명과학회지 Vol.27 No.1

Cyanidin-3-O-glucoside (C3G)는 오디와 붉은색의 과일에 풍부하게 함유되어 있으며, 항염증과 항산화 효과와 관련하여 보고되어있다. 그러나, C3G의 식후 혈당에 관한 연구 결과는 보고되지 않았다. α-glucosidase 억제제는 소장에서 탄수화물 소화의 속도를 방해함으로써 식후 고혈당을 조절한다. 본 연구에서는 C3G가 α-글루코시다아제와 α-아밀라아제에 미치는 억제효과 및 스트렙토조토신(STZ)이 유발하는 당뇨병 생쥐의 식후고혈당에 미치는 완화 효과를 조사하였다. ICR 마우스와 streptozothocin (STZ)으로 유도된 당뇨병 마우스에 수용성 전분(2 g/㎏ body weigh)으로 경구부하 후 C3G (10 ㎎/㎏ body weight) 또는 acarbose (10 ㎎/㎏ body weight)를 단독 또는 함께 투여하였다. 혈액 샘플은 꼬리에서 0, 30, 60, 120분 간격으로 채취하였다. α-글루코시다아제와 α-아밀라아제에 대한 C3G의 IC50 값은 각각 13.72와 7.5 μM의 결과값을 나타내어, 양성대조군인 acarbose보다 더 효과적이었다. STZ으로 유발된 당뇨 쥐의 식후 혈당 수치는 대조군에 비해 C3G 투여시 유의적으로 더 낮았다. 게다가, C3G 투여는 당뇨병 흰쥐에서 포도당 반응에 대한 곡선하면적 감소와 관련이 있었다. 그러므로, C3G는 α-글루코시다아제의 강력한 억제제이며 식이 탄수화물의 흡수를 지연시킬 수 있음을 나타낸다. Cyanidin-3-O-glucoside (C3G) shows anti-inflammatory and antioxidant effects; however, its effect on postprandial blood glucose levels remains unknown. Alpha-glucosidase inhibitors regulate postprandial hyperglycemia by impeding carbohydrate digestion in the small intestine. Here, the effect of C3G on α-glucosidase and α-amylase inhibition and its ability to ameliorate postprandial hyperglycemia in streptozotocin (STZ)-induced diabetic mice were evaluated. ICR normal and STZ-induced diabetic mice were orally administered soluble starch alone or with C3G or acarbose. The half-maximal inhibitory concentrations of C3G for α-glucosidase and α-amylase were 13.72 and 7.5 μM, respectively, suggesting that C3G was more effective than acarbose. The increase in postprandial blood glucose levels was more significantly reduced in the C3G groups than in the control group for both diabetic and normal mice. The area under the curve for the diabetic mice was significantly reduced following C3G administration. C3G may be a potent α-glucosidase inhibitor and may delay dietary carbohydrate absorption.

Cyanidin 3-O-glucoside Isolated from Lonicera caerulea Fruit Improves Glucose Response in INS-1 Cells by Improving Insulin Secretion and Signaling

이다혜,함정엽,강기성,이해정 대한화학회 2016 Bulletin of the Korean Chemical Society Vol.37 No.12

Cyaniding 3-O-glucoside is a flavonoid compound isolated from the fruits of the Lonicera caerulea. In the present study, we investigated the effects of L. caerulea extract and its active component cyaniding 3-O-glucoside on insulin release in INS-1 cells. L. caerulea extract and cyanidin 3-O-glucoside activated the secretion of insulin that lead to diminished glucose production in INS-1 cells. Cyanidin 3-O-glucoside also enhanced the phosphorylation of insulin receptor, insulin receptor substrate 1, and phosphoinositide 3-kinase protein expressions in INS-1 cells. These results suggest that cyanidin 3-O-glucoside is an active component of L. caerulea that enhances insulin production and activates insulin signaling.

Cherry fruit anthocyanins cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside protect against blue light-induced cytotoxicity in HaCaT cells

Lee Hyang-Yeol,Kim Jun-Sub 한국응용생명화학회 2023 Applied Biological Chemistry (Appl Biol Chem) Vol.66 No.-

Blue light derived from multiple sources, including sunlight, generates reactive oxygen species (ROS) and negatively affects the skin in a manner similar to that of ultraviolet light. Cyanidin-3-O-glucoside (C3OG) and cyanidin-3-O-rutinoside (C3OR) are anthocyanin antioxidants that have protective effects on various tissues and cell types. However, the effects of anthocyanins on blue light-mediated changes remain unconfirmed. In this study, we determined the protective effects of C3OG and C3OR isolated and purified from waste cherry fruits (Prunus serrulata L. var. tomentella Nakai) against the blue light-induced ROS formation and inflammatory responses in HaCaT cells. It is showed that the treatment of C3OG and C3OR significantly reduced the blue light-induced cytotoxicity and ROS production in a dose dependent manner. Furthermore, we found that focal adhesion kinase (FAK) is a major upstream of blue light-induced expression of inflammatory cytokines (TNF-α, IL-6 and IL-8), and these effects were attenuated by C3OG or C3OR treatment. In the initial reaction, blue lights increased the phosphorylation of inhibitory-κB Kinase α (IKKα), c-jun N-terminal kinase (JNK), and p38. The phosphorylation of these intracellular proteins was reduced via FAK inhibitor, NAC (ROS scavenger), and anthocyanin treatments. After 24 h of blue light irradiation, C3OG or C3OR treatment markedly inhibited caspase-3-mediated apoptosis and cleaved-FAK-mediated anoikis, which is cell detachment-induced apoptosis. Therefore, our results indicate that C3OG and C3OR effectively protected human keratinocytes from harmful blue light-induced cytotoxicity and inflammation.

Cyanidin 3-O-β-D-Glucoside Improves Bone Indices

Lydia Kaume,William Gilbert,Breda J. Smith,Latha Devareddy 한국식품영양과학회 2015 Journal of medicinal food Vol.18 No.6

Oxidative stress (OS) promotes bone loss after menopause, and there is evidence that dietary antioxidants may reduce the level of OS in vivo. This study examined dose-dependent effects of blackberries (BBs) containing mainly cyanidin 3-O-β-D-glucoside (C3G) in preventing bone loss in an ovariectomized (Ovx) rat model. Nine-month-old female (N = 38) Sprague-Dawley rats were scanned using dual-energy X-ray absorptiometry for baseline whole body, bone mineral content (BMC), and bone mineral density (BMD). One group was sham operated (Sham) and three groups were ovariectomized (Ovx). The groups and corresponding diets were Sham + control diet (n = 12), Ovx + control diet (n = 12), Ovx + 5% BB (n = 7), and Ovx + 10% BB (n = 7). Control diet was AIN-93M rodent diet, and the Ovx +5% BB and Ovx + 10% BB were a diet modified to contain powdered, freeze-dried BB at levels of 5% and 10% (w/w). Following 100 days of treatment, whole body BMC and BMD were reassessed and bone specimens, blood, and 24-h urine samples were collected for analyses. Findings indicate that ovariectomy (Ovx) compromised whole body BMC and trabecular microarchitecture of the proximal tibia and fourth lumbar vertebra. C3G-rich BB at the level of 5% modestly protected BMDs, loss of the tibia, lumbar vertebra, and femur by 2.4%, 2.7%, and 4.3% (P < .0013; .0437; .0004), respectively. BB 5% treatment significantly prevented loss of tibial trabecular bone volume and trabecular number by 37% and 21%, respectively (P < .05), and also significantly prevented tibial trabecular separation by 22%. We conclude that C3G-rich BB treatment at the level of 5% (w/w) but not at 10% (w/w) may modestly reduce Ovx-induced bone loss evident by improved tibial, vertebral, and femoral BMD values, and tibial bone microstructural parameters. Bone protective effects may be as a result of the synergistic effects of phenolic compounds; however, further work is required to determine BBs’ specific mechanisms of action.

Cyanidin-3-glucoside Extracted from Mulberry Fruit Can Reduce <i>N</i>-methyl-<i>N</i>-nitrosourea-Induced Retinal Degeneration in Rats

Lee, Seung Hee,Jeong, Eojin,Paik, Sun-Sook,Jeon, Ji Hyun,Jung, Sung Won,Kim, Hyun-Bok,Kim, Muyan,Chun, Myung-Hoon,Kim, In-Beom Informa Healthcare USA, Inc. 2014 Current eye research Vol.39 No.1

<P><I>Purpose</I>: To investigate the effect of cyanidin-3-<I>O</I>-glucoside (C3G) on a rat retinal degeneration (RD) model.</P><P><I>Materials and methods</I>: Experimental RD was induced in rats by the intraperitoneal injection of <I>N</I>-methyl-<I>N</I>-nitrosourea (MNU) at 50 mg/kg. C3G extracted from mulberry (<I>Morus alba </I>L.) fruit (50 mg/kg) was orally administered, daily for 1, 2 and 4 weeks after MNU injection. The effects of C3G administration on MNU-induced RD retinas were histologically and functionally assessed by hematoxylin and eosin staining and electroretinography (ERG), respectively. The degree of retinal injury in C3G-administered RD rats was evaluated by immunohistochemistry with an antibody against glial fibrillary acidic protein (GFAP). The preferential protective effect of C3G on scotopic vision was examined by western blot analysis.</P><P><I>Result</I>s: Marked loss of photoreceptors in the outer nuclear layer (ONL) was observed in RD rats at 2 and 4 weeks after MNU injection, while the ONL in the MNU-induced RD rats given C3G was relatively well preserved. Immunohistochemistry with anti-GFAP showed that retinal injury was also reduced in the retinas of the rats given C3G. Functional assessment by using ERG recordings showed that scotopic ERG responses were significantly increased in RD rats given C3G for 4 weeks (<I>p</I> < 0.01) compared with that of untreated RD rats. In the RD rats given short-term C3G (for 1 and 2 weeks), the increase in ERG responses was not significant. In addition, western blot analysis showed that rhodopsin level in the C3G-administered RD retinas significantly increased compared to that in the non-administered RD retinas (<I>p</I> < 0.05), whereas red/green opsin level did not show any significant difference.</P><P><I>Conclusions</I>: Long-term administration of C3G extracted from mulberry fruit could structurally reduce photoreceptor damage and functionally improve scotopic visual functions in the RD rat model induced by MNU.</P>

Comparative Proteome Analysis of Cyanidin 3-O-glucoside Treated Helicobacter pylori

Sa-Hyun Kim,Jong-Bae Kim 대한의생명과학회 2015 Biomedical Science Letters Vol.21 No.4

Some virulence proteins of Helicobacter pylori, such as vacuolating cytotoxic protein A (VacA) and cytotoxinassociated gene protein A (CagA) have been reported to be causative agents of various gastric diseases including chronic gastritis, gastric ulcer or gastric adenocarcinoma. The expression level of these virulence proteins can be regulated when H. pylori is exposed to the antibacterial agent, cyanidin 3-O-glucoside (C3G) as previously reported. In this study, we analyzed the quantitative change of various virulence proteins including CagA and VacA by C3G treatment. We used 2-dimensional electrophoresis (2-DE) to analyze the quantitative change of representative ten proteome components of H. pylori 60190 (VacA<SUP>+</SUP>/CagA<SUP>+</SUP>; standard strain of Eastern type). After 2-DE analysis, spot intensities were analyzed using ImageMaster<SUP>TM</SUP> 2-DE Platinum software then each spot was identified using matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF-MS) or peptide sequencing using Finnigan LCQ ion trap mass spectrometer (LC-MS/MS). Next, we selected major virulence proteins of H. pylori among quantitatively meaningful ten spots and confirmed the 2-DE results by Western blot analysis. These results suggest that cyanidin 3-O-glucoside can modulate a variety of H. pylori pathogenic determinants.

RP-HPLC method development using analytical QbD approach for estimation of cyanidin-3-O-glucoside in natural biopolymer based microcapsules and tablet dosage form

Deepika Thakur,Ashay Jain,Gargi Ghoshal,U. S. Shivhare,O. P. Katare 한국약제학회 2017 Journal of Pharmaceutical Investigation Vol.47 No.5

Anthocyanin has been proven to impart several health benefits and biological functions. Though, various analytical methods have been reported for single/multicomponent analysis of anthocyanins, found to be tedious, time consuming and difficult to reproduce. Analytical studies on specific anthocyanins for estimation using an approach of Analytical Quality by Design are scarce. USP method is only reliable for cyanidin-3-O-glucoside (CY-3- O-Glu) estimation, but exploring many disadvantage of having high buffer concentration in mobile phase system and gradient elution, hence column blockage. So there is need to develop a novel HPLC method to overcome this problem with the use organic solvents with lesser volume of buffer in isocratic mode of elution. The aim is to develop a robust and precise method for estimation of CY-3-O-Glu in biopolymer based microcapsules and tablets. The optimized method consisted of mobile phase containing solvent A and B, flow rate 0.8 mL/min with 20 min of analysis time. The method was further validated in accordance with current ICH guidelines Q2 (R1) and found to be highly selective for component in the presence of degradation products confirmed by Mass spectra. Therefore, the proposed method was found to be suitable for routine analysis of CY-3-O-Glu in food and pharmaceutical based formulations.

Protective effect of Cyanidin 3-O-glucoside on the acetaminophen-induced hepatotoxicity in rats

Hee Yeon Kim,Ki Yeon Lee,Soo Young Hong,Tae hee Kim,Jai Yun Kim,A-Reum Park,Hee Sun Noh,Si Chang Kim,Mun Seob Ahn,Jong yeol Park,Won Jin Jeong 한국실험동물학회 2018 한국실험동물학회 학술발표대회 논문집 Vol.2018 No.1