8-O-Acetylshanzhiside methyl ester

Names

[ Name ]:
8-O-Acetylshanzhiside methyl ester

[Synonym ]:
8-acetylshanzhiside methyl ester
acetylbarlerin
ipolamiidoside
8-O-Acetyl shanzhiside methyl ester
Umbroside
Cyclopenta[c]pyran-4-carboxylic acid, 7-(acetyloxy)-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5-hydroxy-7-methyl-, methyl ester, (1S,4aS,5R,7S,7aS)-
8-O-acetylshanziside
Methyl (1S,4aS,5R,7S,7aS)-7-acetoxy-1-(β-D-glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Ac-Shanz-ME
Barlerin
O-Acetyl Shanzhiside Methyl Ester, 8-

Biological Activity

[Description]:

8-O-Acetyl shanzhiside methyl ester (ND01) is an iridoid glucoside isolated from the leaves of Lamiophlomis rotata Kudo, a Chinese folk medicinal plant in Xi-zang. 8-O-Acetyl shanzhiside methyl ester could inhibt NF-κB.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Natural Products >> Terpenoids and Glycosides

[Target]

NF-κB

[In Vitro]

Treatment of SH-SY5Y cells with ND01 blocks TNF-α-induced nuclear transcription factor κB (NF-κB) activation and decreases high-mobility group box-1 (HMGB-1) expression. [1]. Treatment of H9c2 cells with ND01 9 μM blocks TNF-α-induced NF-κB phosphorylation by blocking High-mobility group box1 (HMGB1) expression[2].

[In Vivo]

8-O-Acetyl shanzhiside methyl ester 40 mg/kg demonstrates significant neuroprotective effect even after delayed administration at 4 hr after I/R. 8-O-Acetyl shanzhiside methyl ester 40 mg/kg attenuates the histopathological damage, decreases brain swelling, inhibits NF-κB activation and reduces HMGB-1 expression in ischaemic brain tissue[1]. 8-O-Acetyl shanzhiside methyl ester significantly promotes angiogenesis in the ischaemic brain and improves functional outcome after stroke. 8-O-Acetyl shanzhiside methyl ester also significantly increases vascularization compared with vehicle treatment. It increases the expression of VEGF, Ang1, phosphorylation of Tie2 and Akt VEGF[3]. 8-O-Acetyl shanzhiside methyl ester significantly shortens capillary blood clotting time and reduces blood loss volume, but does not influence mice activated partial thromboplastin time, prothrombin time or thrombin time. It significantly prolongs euglobulin clot lysis time in hyperfibrinolysis mice[4].

[Cell Assay]

Prior to hypoxia, cells are pretreated with various concentrations (1, 3, 9 and 27μM) of ND01 for 24 h. Cell viability are determined by MTT assay[2].

[Animal admin]

Rats: 8-O-Acetyl shanzhiside methyl ester is prepared in saline. Adult male rats are subjected to 1 hr of middle cerebral artery occlusion (MCAO) and reperfusion, and treated with or without different doses (5 and 10 mg/kg) of ND01, starting 24 hr after ischaemia and reperfusion (I/R) and by intravenous injection daily for 14 days. Neurological functional tests are performed and cerebral Evans blue extravasation is measured[3]. Mouse: 8-O-Acetyl shanzhiside methyl ester (ASM) is prepared in saline. Male Balb/C mice (20 to 25g) are randomly divided into five groups (saline group, Hemocoagulase, 0.34 KU/kg, i.v. ASM-L, 100 mg/kg, i.v., ASM-M, 250 mg/kg, i.v., ASM-H, 500 mg/kg, i.v.). The drugs and vehicle are injected through vena caudal is 5 min before anesthetized with sodium pentobarbital (200 mg/kg, i.p.). Twenty minutes after injection, blood are drawn from heart. Activated partial thromboplastin time, prothrombin time, thrombin time and fibrinogen are assayed[4].

[References]

[1]. Zhang L, et al. 8-O-acetyl shanzhiside methylester attenuates cerebral ischaemia/reperfusion injury through an anti-inflammatory mechanism in diabetic rats. Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):481-7.

[2]. Kang ZC, et al. Cardioprotection with 8-O-acetyl shanzhiside methylester on experimental myocardial ischemia injury. Eur J Pharm Sci. 2012 Aug 30;47(1):124-30.

[3]. Jiang WL, et al. Effect of 8-O-acetyl shanzhiside methylester increases angiogenesis and improves functional recovery after stroke. Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):21-7.

[4]. Fan PC, et al. A new anti-fibrinolytic hemostatic compound 8-O-acetyl shanzhiside methylester extracted from Lamiophlomis rotata. J Ethnopharmacol. 2016 Jul 1;187:232-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.52 g/cm3

[ Boiling Point ]:
634.2±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₉H₂₈O₁₂

[ Molecular Weight ]:
448.418

[ Flash Point ]:
220.0±25.0 °C

[ Exact Mass ]:
448.158081

[ PSA ]:
181.44000

[ LogP ]:
-2.76

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

[ Index of Refraction ]:
1.594

[ Storage condition ]:
-20°C

Safety Information

[ Safety Phrases ]:
24/25

Precursor & DownStream

Precursor

DownStream

Related Compounds

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