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Malvidin (chloride)

(Synonyms: 氯化锦葵色素,Syringidin) 目录号 : GC44118

A plant pigment with antioxidant properties

Malvidin (chloride) Chemical Structure

Cas No.:643-84-5

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产品描述

Malvidin is an O-methylated anthocyanidin responsible for the pigments in grapes and blueberries. It demonstrates antioxidant capacity with free radical scavenging properties in vitro. [1] [2] It also exhibits antihypertensive activity by inhibiting angiotensin I-converting enzyme, anti-inflammatory effects by blocking the NF-κB pathway, antiproliferative properties by inhibiting various tumor cell lines, and counteracts oxidative stress in neuronal cells.[1] [3] [4]

Reference:
[1]. Huang, W., Zhu, Y., Li, C., et al. Effect of blueberry anthocyanins malvidin and glycosides on the antioxidant properties in endothelial cells. Oxid.Med.Cell Longev. 2016:1591803, (2016).
[2]. Cui, C., Zhang, S., You, L., et al. Antioxidant capacity of anthocyanins from Rhodomyrtus tomentosa (Ait.) and identification of the major anthocyanins. Food Chemistry 139(1-4), 1-8 (2013).
[3]. Andriambeloson, E., Magnier, C., Haan-Archipoff, G., et al. Natural dietary polyphenolic compounds cause endothelium-dependent vasorelaxation in rat thoracic aorta. Journal of Nutrition 128, 2324-2333 (1998).
[4]. Shih, P.H., Wu, C.H., Yeh, C.T., et al. Protective effects of anthocyanins against amyloid β-peptide-induced damage in neuro-2A cells. Journal of Agricultural and Food Chemistry 59(5), 1683-1689 (2011).

Chemical Properties

Cas No. 643-84-5 SDF
别名 氯化锦葵色素,Syringidin
化学名 3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium, monochloride
Canonical SMILES OC1=CC(O)=C(C=C(O)C(C2=CC(OC)=C(O)C(OC)=C2)=[O+]3)C3=C1.[Cl-]
分子式 C17H15O7•Cl 分子量 366.8
溶解度 16mg/mL in ethanol, 25mg/mL in DMSO 储存条件 Store at -20°C
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1 mM 2.7263 mL 13.6314 mL 27.2628 mL
5 mM 0.5453 mL 2.7263 mL 5.4526 mL
10 mM 0.2726 mL 1.3631 mL 2.7263 mL
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Research Update

Antiamnesic Potential of Malvidin on Aluminum chloride Activated by the Free Radical Scavenging Property

ACS Omega 2022 Jul 1;7(28):24231-24240.PMID:35874261DOI:10.1021/acsomega.2c01406.

Objectives: Malvidin, a dietary anthocyanin can be a potent drug for the treatment of neuronal toxicity. The investigation was aimed to study the antioxidant role of Malvidin against aluminum chloride (AlCl3)-induced neurotoxicity in rats. Methods: To evaluate the neuroprotective role of Malvidin, the rats were divided into four different groups: group I received saline, group II received AlCl3, and groups III and IV were administered with 100 and 200 mg/kg Malvidin after AlCl3 for 60 days. During the evaluation period, all the groups were subjected to a behavioral test. On the 61st day of the study, rat brains were removed and used for a neurochemical assay. Results: From the present study, Malvidin ameliorated the effects of AlCl3 on behavioral parameters. Biochemical investigation revealed that oral treatment of Malvidin shows neuroprotective effects through regulation of antioxidant levels and neuroinflammation in the AlCl3-exposed rats. Conclusion: The results indicate that Malvidin possesses antioxidant activity via acetylcholinesterase inhibition and regulation of oxidative stress in neuronal cells. Hence, Malvidin could be a potential drug in correcting Alzheimer's disease.

Relationship between Hormonal Modulation and Gastroprotective Activity of Malvidin and Cyanidin chloride: In Vivo and In Silico Approach

Pharmaceutics 2022 Mar 4;14(3):565.PMID:35335941DOI:10.3390/pharmaceutics14030565.

Peptic ulcers are lesions that affect the gastrointestinal tract and that can be triggered by external factors such as alcohol use. This study investigated the gastroprotective role of two anthocyanidins, Malvidin and cyanidin chloride, in an ethanol-induced gastric ulcer model in male and female mice (ovariectomized and supplemented with 17β-estradiol or not) and aimed to evaluate the effectiveness of anthocyanidins in preventing the formation of lesions and to identify the underlying mechanisms, while considering hormonal differences. Moreover, in silico comparative analysis was performed to predict the properties and biological behaviors of the molecules. We observed that the hormonal status did not interfere with the gastroprotective action of Malvidin, although antioxidant mechanisms were modulated differently depending on sex. On the other hand, cyanidin showed gastroprotective activity at different doses, demonstrating that, for the same experimental model, there is a need to adjust the effective dose depending on sex. In silico analysis showed that, despite being structurally similar, the interaction with receptors and target proteins in this study (myeloperoxidase, superoxide dismutase, catalase, and reduced glutathione) differed between the two molecules, which explains the difference observed in in vivo treatments.

Hypoglycemic and hypolipidemic effects of blueberry anthocyanins by AMPK activation: In vitro and in vivo studies

Redox Biol 2021 Oct;46:102100.PMID:34416477DOI:10.1016/j.redox.2021.102100.

Blueberries are rich in bioactive anthocyanins, with a high level of Malvidin, which is associated with antioxidant benefits that contribute to reducing the risk of diabetes. The objective of this study was to investigate the hypoglycemic and hypolipidemic effects of blueberry anthocyanin extract (BAE), Malvidin (Mv), malvidin-3-glucoside (Mv-3-glc), and malvidin-3-galactoside (Mv-3-gal) in both human hepatocarcinoma cell line HepG2 and in a high-fat diet combining streptozotocin-induced diabetic mice. High glucose treatment significantly increased hepatic oxidative stress up to 6-fold and decreased HepG2 cell viability. Pretreatment with BAE, Mv, Mv-3-glc and Mlv-3-gal significantly mitigated these damages by lowering the reactive oxygen species (ROS) by 87, 80, 76, and 91%, and increasing cell viability by 88, 79, 73, and 98%, respectively. These pretreatments also effectively inhibited hyperglycemia and hyperlipidemia, respectively by reducing the expression levels of enzymes participating in gluconeogenesis and lipogenesis and enhancing those involved in glycogenolysis and lipolysis, via adenosine monophosphate-activated protein kinase (AMPK) signaling pathway in HepG2 cells. To determinate the role of AMPK in BAE-induced reaction of glucose and lipid metabolism in vivo, doses of 100 mg/kg (blueberry anthocyanin extracts - low concentration, BAE-L) and 400 mg/kg (blueberry anthocyanin extracts - high concentration, BAE-H) were administrated per day to diabetic mice for 5 weeks. BAE treatments had a significant (P < 0.05) effect on body weight and increased the AMPK activity, achieving the decrease of blood- and urine-glucose, as well as triglyceride and total cholesterol. This research suggested that anthocyanins contributed to the blueberry extract-induced hypoglycemia and hypolipidemia effects in diabetes and BAE could be a promising functional food or medicine for diabetes treatment.

Malvidin Protects WI-38 Human Fibroblast Cells Against Stress-induced Premature Senescence

J Cancer Prev 2016 Mar;21(1):32-40.PMID:27051647DOI:10.15430/JCP.2016.21.1.32.

Background: Malvidin is one of the most abundant components in red wines and black rice. The effects of Malvidin on aging and lifespan under oxidative stress have not been fully understood. This study focused on the anti-aging effect of Malvidin on stress-induced premature senescence (SIPS) in WI-38 human lung-derived diploid fibroblasts. Methods: In order to determine the viability of WI-38 cells, MTT assay was conducted, and malondialdehyde level was determined using thiobarbituric acid-reactive substance assay. Protein expression of inflammation-related factors was also evaluated by Western blot analysis. Results: Acute and chronic oxidative stress via hydrogen peroxide (H2O2) treatment led to SIPS in WI-38 cells, which showed decreased cell viability, increased lipid peroxidation, and a shortened lifespan in comparison with non-H2O2-treated WI-38 cells. However, Malvidin treatment significantly attenuated H2O2-induced oxidative stress by inhibiting lipid peroxidation and increasing cell viability. Furthermore, the lifespan of WI-38 cells was prolonged by Malvidin treatment. In addition, Malvidin downregulated the expression of oxidative stress-related proteins, including NF-κB, COX-2, and inducible nitric oxide synthase. Furthermore, protein expression levels of p53, p21, and Bax were also regulated by Malvidin treatment in WI-38 cells undergoing SIPS. Conclusions: Malvidin may potentially inhibit the aging process by controlling oxidative stress.

Malvidin protects against lipopolysaccharide-induced acute liver injury in mice via regulating Nrf2 and NLRP3 pathways and suppressing apoptosis and autophagy

Eur J Pharmacol 2022 Oct 15;933:175252.PMID:36063870DOI:10.1016/j.ejphar.2022.175252.

Sepsis-related acute liver injury (ALI) is a fatal disease associated with many complications. Recent studies indicate that Malvidin, an active flavonoid, has multiple bioactivities including anti-oxidant and anti-inflammation. However, the protective roles of Malvidin against LPS-induced ALI are unknown. The purpose of this research is to explore whether Malvidin has biological activities on LPS-induced ALI in mice and the underlying mechanisms. Male C57 mice were injected intraperitoneally with Malvidin for five days and the mice were euthanized 6 h after LPS (10 mg/kg body weight) intraperitoneal injection. Multiple methods of H&E staining, biochemical kits, qRT-PCR assay, western blotting analysis, TUNEL and transmission electron microscope (TEM) were used. Results showed that decreased ALT, AST levels and alleviated histopathological damage of liver tissue were observed in Malvidin pretreatment group in mice. Then, Malvidin prevented LPS-induced reduction of antioxidant enzyme activities such as superoxide dismutase (SOD), glutathione peroxidase (GSH-PX) and catalase (CAT) via up-regulating nuclear factor E2-related factor2 (Nrf2) pathway. In addition, in Malvidin pretreatment groups, mRNA levels of pro-inflammatory cytokines (TNF-α,IL-1β, IL-6) and protein levels of NOD-like receptor protein 3 (NLRP3) inflammasome in the liver were significantly down-regulated. We also found that the Malvidin could reduce the expression of apoptosis key protein and TUNEL-labeled apoptotic hepatocytes. Furthermore, Malvidin inhibited the protein expression of ATG5, p62 and the ratio of LC3-II/LC3-I. In conclusion, our study firstly suggests that Malvidin is a potentially protective agent against LPS-induced ALI through up-regulating Nrf2 signaling pathway, suppressing NLRP3 inflammasome and inhibiting apoptosis and autophagy.