482-36-0 , 金丝桃苷,
Hyperin,
Quercetin 3-D-galactoside,
CAS:482-36-0
C21H20O12 / 464.38
MFCD00016933
Quercetin 3-b-D-galactoside
Quercetin 3-b-D-galactoside (Q3G) is a natural compound that has been shown to inhibit the apoptosis pathway and postprandial blood glucose levels. It also has an anti-cancer effect, which may be due to its ability to inhibit dinucleotide phosphate. Q3G also inhibits the inflammatory response by inhibiting surfactant sodium dodecyl. Quercetin 3-b-D-galactoside has been shown to have an antiinflammatory property, which may be due to its inhibition of prostaglandin synthesis.
Hyperoside is a flavonoid compound widely found in various plants, such as Hypericum perforatum, Hovenia dulcis, and Camellia sinensis. This compound has attracted great attention from researchers due to its potent biological activities, including its antioxidant, anti-inflammatory, antidiabetic, and anticancer effects. In this paper, we provide a comprehensive review of the definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations and future directions of hyperoside.
I. Definition and Background:
Hyperoside (quercetin-3-O-galactoside), also known as isoquercitrin, is a flavonoid glycoside belonging to the flavonol subgroup. This compound is widely found in different plants, including fruits, vegetables, and medicinal herbs. Hyperoside was first identified in the plant Polygonum aviculare by French chemist Philippe-Marie-Francois Pascal, in 1817.
II. Physical and Chemical Properties:
Hyperoside is a yellow crystalline solid with a molecular weight of 464.38 g/mol. Its chemical structure consists of a quercetin aglycone moiety, linked to a galactose sugar unit via a β-glycosidic bond. Hyperoside is sparingly soluble in water and ethanol, but soluble in hot water and methanol. It exhibits a broad absorption band in the UV region, with a maximum absorption wavelength of 354 nm.
III. Synthesis and Characterization:
Hyperoside can be synthesized via various methods, including enzymatic glycosylation, chemical glycosylation, and biotransformation. Enzymatic glycosylation involves the use of plant-derived or microbial-derived glycosyltransferases to transfer the sugar moiety onto the aglycone structure of quercetin. Chemical glycosylation, on the other hand, employs chemical methods to introduce the sugar unit onto quercetin. Biotransformation involves the use of microbial cultures to convert quercetin to hyperoside. The synthesized hyperoside can be characterized using various spectroscopic techniques, including UV-Visible, IR, NMR, and MS.
IV. Analytical Methods:
Various analytical methods have been developed to detect and quantify hyperoside, including HPLC, LC-MS/MS, and capillary electrophoresis. These methods are highly sensitive and selective, enabling the determination of hyperoside in complex plant matrices.
V. Biological Properties:
Hyperoside exhibits potent biological activities, which have been extensively studied in vitro and in vivo. Its notable biological properties include its antioxidant, anti-inflammatory, antidiabetic, and anticancer effects. Hyperoside has been shown to scavenge free radicals and inhibit lipid peroxidation. It also suppresses the expression of pro-inflammatory cytokines and enzymes, such as TNF-α, IL-1β, and COX-2. In addition, hyperoside improves glucose homeostasis and insulin resistance, making it a promising natural agent to manage diabetes. Lastly, hyperoside inhibits the proliferation, migration, and invasion of cancer cells, making it a potential therapeutic agent for cancer treatment.
VI. Toxicity and Safety in Scientific Experiments:
Hyperoside has been found to be generally safe with low toxicity in scientific experiments. Acute toxicity studies in animals showed no lethal effects or significant changes in behavior, clinical signs, or serum biochemistry. Subchronic and chronic toxicity studies also demonstrated no remarkable toxicity or adverse effects of hyperoside.
VII. Applications in Scientific Experiments:
Hyperoside has various applications in scientific experiments, including its use as an antioxidant, anti-inflammatory, antidiabetic, anticancer, and neuroprotective agent. It has also been used as a natural colorant and flavor enhancer in food products.
VIII. Current State of Research:
Hyperoside has been extensively studied for its biological activities and potential therapeutic applications. However, more studies are needed to fully understand its mechanism of action, pharmacokinetics, and safety profiles. Moreover, further research is needed to explore its potential applications in cosmetic and nutraceutical industries.
IX. Potential Implications in Various Fields of Research and Industry:
Hyperoside has the potential to be used in various fields of research and industry, including medicinal chemistry, drug discovery, food chemistry, cosmetic chemistry, and nutraceuticals. It could be used to develop new drugs for the treatment of oxidative stress-related diseases, such as diabetes, cancer, and neurodegenerative disorders. It could also be used as a natural ingredient in food, cosmetic, and nutraceutical formulations.
X. Limitations and Future Directions:
Despite the promising biological activities and potential applications, there are several limitations of hyperoside that need to be addressed. These include its low solubility and bioavailability, instability, and limited manufacturing sources. Further research is needed to improve its solubility, stability, and bioavailability. In addition, more large-scale manufacturing methods are needed to make hyperoside accessible for biomedical and industrial applications. Future research directions for hyperoside include exploring its potential as a natural preservative, developing novel drug delivery systems, and investigating its potential applications in agricultures as a natural pesticide.
Conclusion:
Hyperoside is a promising flavonoid compound with potent biological activities and potential implications in various fields of research and industry. While more research is needed to fully explore its therapeutic potential, it is evident that hyperoside is a valuable natural agent that could be used to manage oxidative stress-related diseases, enhance food and cosmetic products, and develop novel drug delivery systems.
CAS Number | 482-36-0 |
Product Name | Hyperoside |
IUPAC Name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one |
Molecular Formula | C21H20O12 |
Molecular Weight | 464.38 g/mol |
InChI | InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1 |
InChI Key | OVSQVDMCBVZWGM-DTGCRPNFSA-N |
Synonyms | Hyperoside; 2-(3,4-Dihydroxyphenyl)-3-(b-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one; Hyperin |
Canonical SMILES | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O |
Isomeric SMILES | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O |
CAS No: 482-36-0 Synonyms: Hyperoside2-(3,4-Dihydroxyphenyl)-3-(b-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneHyperin MDL No: MFCD00016933 Chemical Formula: C21H20O12 Molecular Weight: 464.38 | |
References: 1. Naturweiss, 1964, 51, p4622. Beilstein Registry Number 5784795 |
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