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82854-37-3

82854-37-3 structure
82854-37-3 structure
  • Name: Echinacoside
  • Chemical 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
  • CAS Number: 82854-37-3
  • Molecular Formula: C35H46O20
  • Molecular Weight: 786.728
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-08-22 17:19:17
  • Modify Date: 2025-08-20 23:05:21
  • 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].
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
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
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
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.
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
Storage condition 2-8°C

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