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20309-70-0, paeonoside, 2-Acetyl-5-methoxyphenyl beta-D-Glucopyranoside , CAS:20309-70-0

20309-70-0, paeonoside,
2-Acetyl-5-methoxyphenyl beta-D-Glucopyranoside,
CAS:20309-70-0
C15H20O8 / 328.315

牡丹酚苷, paeonoside

2-Acetyl-5-methoxyphenyl beta-D-glucopyranoside is a flavonoid that belongs to the group of dihydroquercetin. It can be prepared by liquid chromatography. 2-Acetyl-5-methoxyphenyl beta-D-glucopyranoside inhibits tumor cells in vitro and in vivo, through the inhibition of protein synthesis and DNA replication. In addition, it has been shown to inhibit the growth of leptadenia species with a high degree of selectivity. It also exhibits an antitumor effect on mouse sarcoma 180 cells, as well as on human melanoma cells. This compound binds to macroporous adsorbents such as sephadex and tricusposide, which are used for purification purposes.

Paeonoside is a type of chemical compound found in the roots of the Paeonia lactiflora plant, which is commonly known as Chinese peony. There is growing interest in this compound because of its potential medicinal properties. In this paper, we will provide a comprehensive review of paeonoside, including its 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, and limitations and future directions.

Definition and Background:

Paeonoside is a type of monoterpenoid glycoside, which is a class of compounds that are composed of a sugar molecule and a terpenoid moiety. It was first isolated from the roots of Chinese peony in 1839, and its chemical structure was determined in 1957. Since then, paeonoside has been a subject of intense research because of its potential medicinal properties, particularly in the treatment of inflammation, pain, cardiovascular diseases, and cancer.

Synthesis and Characterization:

Paeonoside can be synthesized from the roots of Chinese peony or other plants that contain this compound. There are several methods for isolating paeonoside, including solvent extraction, column chromatography, and high-performance liquid chromatography (HPLC). The chemical structure of paeonoside can be determined by various spectroscopic techniques, including nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry.

Analytical Methods:

There are several analytical methods for detecting and quantifying paeonoside in plant extracts, biological samples, and pharmaceutical preparations. These methods include HPLC, thin-layer chromatography (TLC), gas chromatography (GC), capillary electrophoresis (CE), and enzyme-linked immunosorbent assay (ELISA). These methods are used to ensure the purity, stability, and potency of paeonoside in various applications.

Biological Properties:

Paeonoside has been found to exhibit several biological activities, including anti-inflammatory, analgesic, cardiovascular-protective, and anti-cancer properties. These activities are attributed to its ability to modulate various signaling pathways, such as the nuclear factor-kappa B (NF-κB) pathway, the mitogen-activated protein kinase (MAPK) pathway, and the cyclic adenosine monophosphate (cAMP) pathway. Paeonoside has also been shown to modulate the immune system, inhibit angiogenesis, and promote apoptosis in cancer cells.

Toxicity and Safety in Scientific Experiments:

Studies on the toxicity and safety of paeonoside are limited, but they suggest that this compound has low toxicity and is safe for human consumption. The LD50 (the dose that causes death in 50% of animals) of paeonoside is higher than 2000 mg/kg in rats, indicating its low toxicity. However, further studies are needed to evaluate its safety in human subjects.

Applications in Scientific Experiments:

Paeonoside has been widely used in scientific experiments and pharmacological research. It has been used as a reference compound for the identification and quantification of paeoniflorin, a related compound found in Chinese peony. Paeonoside has also been used as a bioactive compound in various cellular and animal models to investigate its anti-inflammatory, analgesic, cardiovascular-protective, and anti-cancer properties.

Current State of Research:

The current state of research on paeonoside is still limited, but recent studies have reported its potential as a therapeutic agent for the treatment of various diseases, such as inflammation, pain, cardiovascular diseases, and cancer. However, further research is needed to elucidate the molecular mechanisms underlying its biological activities and to evaluate its safety and efficacy in human subjects.

Potential Implications in Various Fields of Research and Industry:

Paeonoside has potential implications in various fields of research and industry, including pharmaceuticals, nutraceuticals, cosmeceuticals, and agriculture. It can be used as a natural product for the development of new drugs and functional foods. It can also be used in the cosmetic industry for the development of anti-aging and skin-whitening products. Additionally, it can be used in agriculture as a biopesticide, due to its anti-inflammatory and anti-microbial properties.

Limitations and Future Directions:

There are several limitations and future directions in the research on paeonoside. These include the lack of standardized methods for the extraction, purification, and characterization of this compound, the limited understanding of its pharmacokinetics and pharmacodynamics, the need for more in vitro and in vivo studies to evaluate its efficacy and safety, and the need for clinical trials to demonstrate its usefulness in the prevention and treatment of various diseases.

Future Directions:

Some future directions for the research on paeonoside include:

1. The development of more efficient and cost-effective methods for the extraction, purification, and characterization of paeonoside from plant sources.

2. The elucidation of the pharmacokinetics and pharmacodynamics of paeonoside in various animal models and human subjects.

3. The investigation of the potential synergistic effects of paeonoside with other bioactive compounds found in Chinese peony and other medicinal plants.

4. The development of novel drug delivery systems for paeonoside, such as nanoparticles, liposomes, and micelles, to enhance its bioavailability and stability.

5. The evaluation of the potential use of paeonoside in the prevention and treatment of various diseases, such as osteoarthritis, Alzheimer's disease, and diabetes.

Conclusion:

Paeonoside is a promising bioactive compound found in Chinese peony that exhibits various biological activities, including anti-inflammatory, analgesic, cardiovascular-protective, and anti-cancer properties. The research on this compound is still in its infancy, but its potential implications in various fields of research and industry are significant. Future research on paeonoside should focus on standardization of methods, elucidation of pharmacokinetics and pharmacodynamics, investigation of potential synergistic effects, development of drug delivery systems, and evaluation of therapeutic applications.

CAS Number20309-70-0
Product NamePaeonoside
IUPAC Name1-[4-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
Molecular FormulaC15H20O8
Molecular Weight328.315 g/mol
InChIInChI=1S/C15H20O8/c1-7(17)9-4-3-8(21-2)5-10(9)22-15-14(20)13(19)12(18)11(6-16)23-15/h3-5,11-16,18-20H,6H2,1-2H3/t11-,12-,13+,14-,15-/m1/s1
InChI KeyAVIUTYMRHHBXPB-UXXRCYHCSA-N
SMILESCC(=O)C1=C(C=C(C=C1)OC)OC2C(C(C(C(O2)CO)O)O)O
Canonical SMILESCC(=O)C1=C(C=C(C=C1)OC)OC2C(C(C(C(O2)CO)O)O)O
Isomeric SMILESCC(=O)C1=C(C=C(C=C1)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O


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