CAS 82854-37-3|Echinacoside

Introduction：Basic information about CAS 82854-37-3|Echinacoside, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Echinacoside BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles31
7. Synonyms

Common Name	Echinacoside
CAS Number	82854-37-3	Molecular Weight	786.728
Density	1.7±0.1 g/cm3	Boiling Point	1062.7±65.0 °C at 760 mmHg
Molecular Formula	C₃₅H₄₆O₂₀	Melting Point	/
MSDS	USA	Flash Point	327.9±27.8 °C

Names

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
Synonym	More Synonyms

Echinacoside BiologicalActivity

Description	Echinacoside is a natural polyphenolic compound, has various kinds of pharmacological activities, such as antioxidative, anti-inflammatory, neuroprotective, hepatoprotective, nitric oxide radical-scavenging and vasodilative ones.IC50 value:Target:in vitro: Echinacoside(ECH) dose dependently inhibited HEWL aggregation, and this inhibition occurred in different fiber-forming stages. ECH could also scavenge the DPPH and OH free radicals in a concentration-dependent manner. ECH could increase viability of rat pheochromocytoma PC12 cells injured by Aβ and suppress the increase in intracellular reactive oxygen species (ROS) triggered by Aβ [1]. Transient treatment with echinacoside inhibits cytochrome c release and caspase-3 activation caused by ensuing rotenone exposure via activating Trk-extracellular signal-regulated kinase (ERK) pathway in neuronal cells [2]. ECH caused a significant increase in cell proliferation, ALP activity, COL I contents, OCN levels and an enhancement of mineralization in osteoblasts at the concentration range from 0.01 to 10nmol·L(-1) (p<0.05), suggesting that ECH has a stimulatory effect on osteoblastic bone formation or has potential activity against osteoporosis [4]. in vivo: In OVX rats, the increases of body weight, serum hydroxyproline (HOP) levels, and the decreases of uterus wet weight and BMD were significantly reversed by ECH treatment [3]. Echinacoside (60 mg/kg) was given intraperitoneally to mice at 1 h prior to GalN/LPS exposure. Pretreatment with echinacoside remarkably improved the survival rate of GalN/LPS-treated mice and attenuated acute hepatotoxicity, as demonstrated by decreased ALT levels and improved histological signs. Echinacoside shows both anti-apoptotic and anti-inflammatory properties, characterized by a substantial inhibition of hepatocyte apoptosis and a significant reduction in the inflammatory markers, including myeloperoxidase, extracellular nucleosomes, high-mobility group box 1, and inflammatory cytokines in the plasma of mice, which may be important mechanisms related to its protective effect [5].
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Neurological DiseaseNatural Products >>Phenols
References	[1]. Zhang D, et al. Echinacoside inhibits amyloid fibrillization of HEWL and protects against Aβ-induced neurotoxicity. Int J Biol Macromol. 2014 Sep 2;72C:243-253. [2]. Zhu M, et al. Transient exposure to echinacoside is sufficient to activate Trk signaling and protect neuronal cells from rotenone. J Neurochem. 2013 Feb;124(4):571-80. [3]. Li F, et al. Antiosteoporotic activity of echinacoside in ovariectomized rats. Phytomedicine. 2013 Apr 15;20(6):549-57. [4]. Li F, et al. Echinacoside promotes bone regeneration by increasing OPG/RANKL ratio in MC3T3-E1 cells. Fitoterapia. 2012 Dec;83(8):1443-50. [5]. Li X, et al. Echinacoside ameliorates D-galactosamine plus lipopolysaccharide-induced acute liver injury in mice via inhibition of apoptosis and inflammation. Scand J Gastroenterol. 2014 Aug;49(8):993-1000.

Description

Echinacoside is a natural polyphenolic compound, has various kinds of pharmacological activities, such as antioxidative, anti-inflammatory, neuroprotective, hepatoprotective, nitric oxide radical-scavenging and vasodilative ones.IC50 value:Target:in vitro: Echinacoside(ECH) dose dependently inhibited HEWL aggregation, and this inhibition occurred in different fiber-forming stages. ECH could also scavenge the DPPH and OH free radicals in a concentration-dependent manner. ECH could increase viability of rat pheochromocytoma PC12 cells injured by Aβ and suppress the increase in intracellular reactive oxygen species (ROS) triggered by Aβ [1]. Transient treatment with echinacoside inhibits cytochrome c release and caspase-3 activation caused by ensuing rotenone exposure via activating Trk-extracellular signal-regulated kinase (ERK) pathway in neuronal cells [2]. ECH caused a significant increase in cell proliferation, ALP activity, COL I contents, OCN levels and an enhancement of mineralization in osteoblasts at the concentration range from 0.01 to 10nmol·L(-1) (p<0.05), suggesting that ECH has a stimulatory effect on osteoblastic bone formation or has potential activity against osteoporosis [4]. in vivo: In OVX rats, the increases of body weight, serum hydroxyproline (HOP) levels, and the decreases of uterus wet weight and BMD were significantly reversed by ECH treatment [3]. Echinacoside (60 mg/kg) was given intraperitoneally to mice at 1 h prior to GalN/LPS exposure. Pretreatment with echinacoside remarkably improved the survival rate of GalN/LPS-treated mice and attenuated acute hepatotoxicity, as demonstrated by decreased ALT levels and improved histological signs. Echinacoside shows both anti-apoptotic and anti-inflammatory properties, characterized by a substantial inhibition of hepatocyte apoptosis and a significant reduction in the inflammatory markers, including myeloperoxidase, extracellular nucleosomes, high-mobility group box 1, and inflammatory cytokines in the plasma of mice, which may be important mechanisms related to its protective effect [5].

Related Catalog

Signaling Pathways >>Others >>OthersResearch Areas >>Neurological DiseaseNatural Products >>Phenols

References

[1]. Zhang D, et al. Echinacoside inhibits amyloid fibrillization of HEWL and protects against Aβ-induced neurotoxicity. Int J Biol Macromol. 2014 Sep 2;72C:243-253.

[2]. Zhu M, et al. Transient exposure to echinacoside is sufficient to activate Trk signaling and protect neuronal cells from rotenone. J Neurochem. 2013 Feb;124(4):571-80.

[3]. Li F, et al. Antiosteoporotic activity of echinacoside in ovariectomized rats. Phytomedicine. 2013 Apr 15;20(6):549-57.

[4]. Li F, et al. Echinacoside promotes bone regeneration by increasing OPG/RANKL ratio in MC3T3-E1 cells. Fitoterapia. 2012 Dec;83(8):1443-50.

[5]. Li X, et al. Echinacoside ameliorates D-galactosamine plus lipopolysaccharide-induced acute liver injury in mice via inhibition of apoptosis and inflammation. Scand J Gastroenterol. 2014 Aug;49(8):993-1000.

Chemical & Physical Properties

Density	1.7±0.1 g/cm3
Boiling Point	1062.7±65.0 °C at 760 mmHg
Molecular Formula	C₃₅H₄₆O₂₀
Molecular Weight	786.728
Flash Point	327.9±27.8 °C
Exact Mass	786.258240
PSA	324.44000
LogP	0.14
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.698
InChIKey	FSBUXLDOLNLABB-ISAKITKMSA-N
SMILES	CC1OC(OC2C(O)C(OCCc3ccc(O)c(O)c3)OC(COC3OC(CO)C(O)C(O)C3O)C2OC(=O)C=Cc2ccc(O)c(O)c2)C(O)C(O)C1O
Storage condition	2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ5786500

CHEMICAL NAME :: Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-alpha-L-mannopyranosyl-(1-3)- O-(beta-D-glucopyranosyl-(1-6))-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), beta-D-

CAS REGISTRY NUMBER :: 82854-37-3

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C35-H40-O20

MOLECULAR WEIGHT :: 780.75

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 140 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 105,1131,1985

Safety Information

Hazard Codes	T+
Safety Phrases	24/25
RIDADR	NONH for all modes of transport
RTECS	LZ5786500

Articles31

Plantago lanceolata L. water extract induces transition of fibroblasts into myofibroblasts and increases tensile strength of healing skin wounds.

J. Pharm. Pharmacol. 67(1) , 117-25, (2014)

Although the exact underlying mechanisms are still unknown, Plantago lanceolata L. (PL) water extracts are frequently used to stimulate wound healing and to drain abscesses. Therefore, in this experim...

Echinacoside Induces Apoptosis in Human SW480 Colorectal Cancer Cells by Induction of Oxidative DNA Damages.

Int. J. Mol. Sci. 16 , 14655-68, (2015)

Echinacoside is a natural compound with potent reactive oxygen species (ROS)-scavenging and anti-oxidative bioactivities, which protect cells from oxidative damages. As cancer cells are often under in...

Echinacoside induces apoptotic cancer cell death by inhibiting the nucleotide pool sanitizing enzyme MTH1.

Onco. Targets Ther. 8 , 3649-64, (2015)

Inhibition of the nucleotide pool sanitizing enzyme MTH1 causes extensive oxidative DNA damages and apoptosis in cancer cells and hence may be used as an anticancer strategy. As natural products have ...

Synonyms

(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)tetrahydro-2H-pyran-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)acrylate

2-(3,4-Dihydroxyphenyl)ethyl 6-deoxy-α-L-mannopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-β-D-glucopyranoside

2-(3,4-dihydroxyphenyl)ethyl 6-deoxy-α-L-mannopyranosyl-(1-3)-[β-D-glucopyranosyl-(1-6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside

2-(3,4-Dihydroxyphenyl)ethyl-6-deoxy-α-L-mannopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-β-D-glucopyranoside

β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-α-L-mannopyranosyl-(1->3)-O-[β-D-glucopyranosyl-(1->6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-

β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-α-L-mannopyranosyl-(1->3)-O-[β-D-glucopyranosyl-(1->6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-

Echinacoside

2-(3,4-Dihydroxyphenyl)ethyl 6-deoxy-α-L-mannopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside

UNII-I04O1DT48T

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