Morroniside

Names

[ Name ]:
Morroniside

[Synonym ]:
N1489
1H,3H-Pyrano[3,4-c]pyran-5-carboxylic acid, 8-(β-D-glucopyranosyloxy)-4,4a,8,8a-tetrahydro-3-hydroxy-1-methyl-, methyl ester, (1S,4aS,8S,8aS)-
Morroniside
Methyl (1S,3R,4aS,8S,8aS)-8-(β-D-glucopyranosyloxy)-3-hydroxy-1-methyl-4,4a,8,8a-tetrahydro-1H,3H-pyrano[3,4-c]pyran-5-carboxylate
Methyl (1S,4aS,8S,8aS)-8-(β-D-glucopyranosyloxy)-3-hydroxy-1-methyl-4,4a,8,8a-tetrahydro-1H,3H-pyrano[3,4-c]pyran-5-carboxylate
b-Morroniside
1H,3H-Pyrano[3,4-c]pyran-5-carboxylic acid, 8-(β-D-glucopyranosyloxy)-4,4a,8,8a-tetrahydro-3-hydroxy-1-methyl-, methyl ester, (1S,3R,4aS,8S,8aS)-
Morronisid
Morroniside (α+β)

Biological Activity

[Description]:

Morroniside has neuroprotective effect by inhibiting neuron apoptosis and MMP2/9 expression.

[Related Catalog]:

Natural Products >> Terpenoids and Glycosides

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

MMP2

MMP9

[In Vivo]

Morroniside reduces the expression of MMP2 and MMP9 in an I/R injury model. Treatment with Morroniside significantly reduces I/R‑associated neuron apoptosis in a dose dependent manner. The results demonstrate that active caspase‑3 and Bax are significantly upregulated in the model group compared with the control group, while Bcl‑2 is significantly downregulated. The expression of active caspase‑3 and Bax is significantly downregulated by Morroniside treatment in a dose‑dependent manner, while the expression of Bcl‑2 is significantly upregulated[1]. Morroniside has an ameliorative effect on diabetes-induced alterations such as oxidative stress, inflammation, and apoptosis in the liver of type 2 diabetic db/db mice[2].

[Animal admin]

Rats[1] A total of 50 adult male Sprague Dawley rats (age, 7 8 weeks; weight, 260 280 g) are used. Rats are randomly assigned into five groups (n=10 in each). Rats in the control group undergo sham surgery. All other rats undergo suture occluded surgery, with a 0.26 mm nylon monofilament inserted through the right common carotid artery and are divided into groups as follows: The cerebral I/R injury model group (model), no treatment; low dose group, 30 mg/kg/day Morroniside by gavage; moderate dose group, 90 mg/kg/day Morroniside by gavage; high dose group, 270 mg/kg/day Morroniside by gavage. Rats in the control and model groups receive an equal volume of normal saline[1].

[References]

[1]. Zeng G, et al. Morroniside protects against cerebral ischemia/reperfusion injury by inhibiting neuron apoptosis and MMP2/9 expression. Exp Ther Med. 2018 Sep;16(3):2229-2234.

[2]. Park CH, et al. Evaluation of morroniside, iridoid glycoside from Corni Fructus, on diabetes-induced alterations such as oxidative stress, inflammation, and apoptosis in the liver of type 2 diabetic db/db mice. Biol Pharm Bull. 2011;34(10):1559-65.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
635.6±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₂₆O₁₁

[ Molecular Weight ]:
406.382

[ Flash Point ]:
227.0±25.0 °C

[ Exact Mass ]:
406.147522

[ PSA ]:
164.37000

[ LogP ]:
-3.16

[ Vapour Pressure ]:
0.0±4.2 mmHg at 25°C

[ Index of Refraction ]:
1.597

[ Storage condition ]:
2-8C

Morroniside

Names

Biological Activity

Chemical & Physical Properties

Related Compounds