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82854-37-3 , Echinacoside, CAS:82854-37-3

82854-37-3, Echinacoside,
CAS:82854-37-3
C35H46O20 / 786.74

Echinacoside, 松果菊苷

Echinacoside is a natural compound found in the roots of several plant species, mainly Echinacea species. The compound has gained a lot of attention in the scientific community due to its potential health benefits and medicinal properties. This paper will discuss the definition and background of Echinacoside, its physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, and safety in scientific experiments. It will also examine the applications of Echinacoside in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and background:

Echinacoside is a natural compound belonging to the flavonoid class of secondary metabolites. It was first isolated from Echinacea angustifolia by Japanese researchers in 1978. The compound has been found in several Echinacea species, including Echinacea purpurea, Echinacea pallida, and Echinacea angustifolia. Echinacoside has received a lot of attention due to its potential health benefits and medicinal properties, including antioxidant, anti-inflammatory, and immunomodulatory activities.

Synthesis and Characterization:

Echinacoside is primarily synthesized from Echinacea species using solvent extraction techniques. The crude extract is purified using various chromatographic techniques such as column chromatography, high-performance liquid chromatography (HPLC), and thin-layer chromatography (TLC).

Analytical Methods:

Several analytical methods have been developed for the determination of Echinacoside in plant extracts and pharmaceutical products. These methods include HPLC, TLC, gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-mass spectrometry (LC-MS). These methods are highly sensitive, precise, and accurate, making them suitable for the analysis of Echinacoside in complex matrices.

Biological Properties:

Echinacoside has been found to possess several biological activities, including antioxidant, anti-inflammatory, and immunomodulatory properties. It has been shown to scavenge free radicals and protect against oxidative stress. Echinacoside also inhibits the production of inflammatory cytokines and mediators, including TNF-α, IL-1β, and COX-2. Moreover, it enhances the production of anti-inflammatory cytokines, such as IL-10 and TGF-β. Echinacoside has also been found to modulate immune cell functions and proliferation, suggesting its potential as an immunomodulatory agent.

Toxicity and Safety in Scientific Experiments:

Several preclinical studies have reported the safety of Echinacoside in animals. Acute toxicity studies have shown that Echinacoside is not toxic at doses up to 2000 mg/kg in rats. Likewise, chronic toxicity studies have shown no significant adverse effects on the liver, kidney, and other major organs. Echinacoside has also been found to be safe in human clinical trials, with no reported adverse effects.

Applications in Scientific Experiments:

Echinacoside has several potential applications in scientific experiments, including:

1. Anti-inflammatory agent: Echinacoside has been found to possess potent anti-inflammatory activities, which makes it a potential candidate for the treatment of inflammatory diseases.

2. Antioxidant: Echinacoside is a potent antioxidant that protects against oxidative stress and damage. It can be used in the development of antioxidant supplements and functional foods.

3. Immunomodulatory agent: Echinacoside has been found to modulate immune cell functions and proliferation, suggesting its potential as an immunomodulatory agent.

Current State of Research:

The research on Echinacoside has gained momentum in recent years, with several preclinical and clinical studies investigating its potential health benefits and medicinal properties. However, more research is needed to fully understand its mechanism of action, safety, and efficacy in different diseases.

Potential Implications in Various Fields of Research and Industry:

Echinacoside has potential implications in various fields of research and industry, including:

1. Pharmaceutical industry: Echinacoside has shown promising results in the treatment of inflammatory diseases, immune disorders, and oxidative stress-related diseases. It can be developed into a new generation of drugs with improved safety and efficacy.

2. Nutraceutical industry: Echinacoside can be used as an antioxidant supplement and functional food ingredient due to its potent antioxidant activities.

3. Cosmeceutical industry: Echinacoside has been found to possess anti-aging properties and can be used in the development of anti-aging creams and other cosmetic products.

Limitations and Future Directions:

Although Echinacoside has shown promising results in several preclinical and clinical studies, more research is needed to fully understand its mechanism of action, safety, and efficacy in different diseases. The following are some potential future directions:

1. Mechanism of action: The mechanism of action of Echinacoside needs to be investigated further to understand how it exerts its biological activities.

2. Clinical trials: More randomized, controlled clinical trials are needed to evaluate the safety and efficacy of Echinacoside in different diseases.

3. Formulation development: The development of new formulations of Echinacoside is needed to improve its bioavailability and therapeutic efficacy.

4. Dose optimization: The optimal dose of Echinacoside needs to be determined for different diseases to maximize its therapeutic benefits.

5. Combination therapy: The potential of Echinacoside in combination therapy with other drugs or natural compounds needs to be investigated further.

6. Toxicity studies: Further toxicity studies are needed to evaluate the safety of Echinacoside in long-term use.

Conclusion:

Echinacoside is a natural compound with potent antioxidant, anti-inflammatory, and immunomodulatory activities. It has potential applications in the pharmaceutical, nutraceutical, and cosmeceutical industries. However, more research is needed to fully understand its mechanism of action, safety, and efficacy in different diseases. The current state of research on Echinacoside shows promising results, and future directions are needed to optimize its therapeutic benefits.

Echinacoside is a caffeic acid derivative naturally found in plants, such as, Echinacea angustifolia DC. Echinacoside belongs to the class of phenylethanoid glycosides. In vitro studies have revealed the mode of action of echinacoside in breast cancer cells; echinacoside suppresses the Wnt/I²-catenin signalling pathway exerting anticancer activity (Tang et al, 2020). Echinacoside has been reported as beneficial for human health in terms of neuroprotection, cardioprotectiony, anti-inflammatory, antioxidant and anti-osteoporotic activity (Liu, 2018).

CAS Number

82854-37-3

Product Name

Echinacoside

IUPAC Name

[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Molecular Formula

C35H46O20

Molecular Weight

786.74 g/mol

InChI

InChI=1S/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1

InChI Key

FSBUXLDOLNLABB-ISAKITKMSA-N

Synonyms

2-(3,4-Dihydroxyphenyl)ethyl 4-(3-(3,4-dihydroxyphenyl)-2-propenoate)-3-O-(b-D-glucopyranose)-6-O-(a-L-rhamnopyranose)-b-D-glucopyranoside

Canonical SMILES

CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O

Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O


CAS No: 82854-37-3 Synonyms: 2-(3,4-Dihydroxyphenyl)ethyl 4-(3-(3,4-dihydroxyphenyl)-2-propenoate)-3-O-(b-D-glucopyranose)-6-O-(a-L-rhamnopyranose)-b-D-glucopyranoside Chemical Formula: C35H46O20 Molecular Weight: 786.74

References: 1. Helvetica Chimica Acta, 1950, 33, p1877


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