Structure Database (LMSD)
Common Name
Sennoside A
Systematic Name
Synonyms
3D model of Sennoside A
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Sennoside A is a dianthrone glycoside with laxative and gastroprotective activities.1,2 Ex vivo, sennoside A (30 mg/kg) increases the amplitude of distal colon contractions in circular and longitudinal muscle and decreases the amplitude of proximal colon contractions in circular muscle in mice.1 Sennoside A (100 mg/kg, oral) increases the gastric emptying rate by 71.1% compared to control and increases the intestinal transport rate of a charcoal meal from 61.2 to 81.1% in mice.2 It increases the concentration of prostaglandin E2 (PGE2) in AGS gastric cells in a dose-dependent manner in vitro. Intraduodenal administration of sennoside A (100 mg/kg) increases gastric juice pH and decreases gastric juice secretion volume and total acid output in pylorus-ligated rats. It also reduces lesion indices by 43.1 and 36% in HCl/ethanol-induced gastritis and indomethacin-induced gastric ulcer rat models, respectively, when administered at a dose of 100 mg/kg. Sennoside A is also a non-competitive inhibitor of bovine serum monoamine oxidase in vitro (IC50 = 17 µM).3 Formulations containing sennoside A have been used to treat constipation and to aid in evacuation of the bowel prior to surgery or invasive colonic or rectal examinations.
This information has been provided by Cayman Chemical
References
1. Hiraoka, A., Koike, S., Sakaguchi, S., et al. The sennoside constituents of rhei rhizoma and sennae folium as inhibitors of serum monoamine oxidase. Chem. Pharm. Bull. (Tokyo) 37(10), 2744-2746 (1989).
2. Hwang, I.Y., and Jeong, C.S. Gastroprotective activities of sennoside A and sennoside B via the up-regulation of prostaglandin E2 and the inhibition of H+/K+-ATPase. Biomol. Ther. (Seoul) 23(5), 458-464 (2015).
3. Kobayashi, M., Yamaguchi, T., Odaka, T., et al. Regionally differential effects of sennoside A on spontaneous contractions of colon in mice. Basic Clin. Pharmacol. Toxicol. 101(2), 121-126 (2007).
References
String Representations
InChiKey (Click to copy)
IPQVTOJGNYVQEO-KGFNBKMBSA-N
InChi (Click to copy)
InChI=1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)/t23-,24-,25-,26-,31-,32-,35+,36+,37-,38-,41-,42-/m1/s1
SMILES (Click to copy)
[C@@]1([H])(C2C=CC=C(O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)C=2C(=O)C2C(O)=CC(C(=O)O)=CC1=2)[C@]1([H])C2C=CC=C(O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)C=2C(=O)C2C(O)=CC(C(=O)O)=CC1=2
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
62
Rings
8
Aromatic Rings
4
Rotatable Bonds
9
Van der Waals Molecular Volume
726.24
Topological Polar Surface Area
352.10
Hydrogen Bond Donors
12
Hydrogen Bond Acceptors
20
logP
2.34
Molar Refractivity
208.46
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Created at
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Updated at
20th Feb 2025