Sennoside A - 81-27-6

Sennoside A

Catalog Number: EVT-338289
CAS Number: 81-27-6
Molecular Formula: C42H38O20
Molecular Weight: 862.7 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description

Sennoside A is a bioactive component found in traditional Chinese medicine, particularly derived from plants such as Rheum palmatum L. and Rheum officinale Baill. It is known for its laxative properties and has been used to treat constipation and obesity. Recent studies have expanded the understanding of Sennoside A, revealing its potential in treating various diseases, including HIV-1 infection, type 2 diabetes, obesity, and different types of cancer1245.

Mechanism of Action

HIV-1 InhibitionSennoside A has been identified as a dual HIV-1 inhibitor, capable of inhibiting both the HIV-1 Reverse Transcriptase (RT)-associated DNA Polymerase (RDDP) and Ribonuclease H (RNase H) activities. It also affects HIV-1 integrase (IN) activity and viral replication. The compound targets the HIV-1 reverse transcription process, which is crucial for viral DNA production1.

Regulation of Microbiota-GLP1 AxisIn the context of obesity and insulin sensitivity, Sennoside A has been shown to improve insulin sensitivity in high-fat diet-induced obese mice. It achieves this by restoring the gut microbiota profile, short-chain fatty acids (SCFAs), and mucosal structure in the colon. Additionally, Sennoside A modulates the levels of glucagon-like peptide 1 (GLP1), which plays a significant role in glucose metabolism2.

Cancer Cell Proliferation and MetastasisSennoside A has demonstrated inhibitory effects on cell proliferation and metastasis in various cancer cell lines, including human osteosarcoma and hepatocellular carcinoma cells. It interferes with signaling pathways such as PDGF, Wnt, TNF, VEGF, and NF-κB, which are involved in cancer cell growth and metastasis35.

Gastroprotective ActivitiesSennoside A and its diastereomer, Sennoside B, have shown gastroprotective activities by increasing prostaglandin E2 (PGE2) levels and inhibiting H+/K+-ATPase, which is responsible for gastric acid secretion. This suggests their potential use in treating gastric diseases6.

Applications in Various Fields

Antiviral ApplicationsSennoside A's ability to inhibit HIV-1 replication positions it as a promising candidate for the development of new antiretroviral drugs with a novel mode of action1.

Metabolic DisordersThe compound's impact on insulin sensitivity and glucose metabolism makes it a potential therapeutic agent for treating metabolic disorders such as type 2 diabetes and obesity24.

Cancer TreatmentThe inhibitory effects of Sennoside A on cancer cell proliferation and metastasis suggest its potential application in developing treatments for various cancers, including osteosarcoma, hepatocellular carcinoma, and chondrosarcoma359.

Gastrointestinal HealthSennoside A's gastroprotective effects and its ability to regulate gut motility indicate its usefulness in treating gastrointestinal disorders68.

Antibacterial and Antifungal ActivitiesSilver nanoparticles capped with Sennoside A have shown antibacterial and antifungal activities, which could be explored for developing new antimicrobial agents10.

Properties

CAS Number

81-27-6

Product Name

Sennoside A

IUPAC Name

(9S)-9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid

Molecular Formula

C42H38O20

Molecular Weight

862.7 g/mol

InChI

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

InChI Key

IPQVTOJGNYVQEO-DBHPJPNJSA-N

SMILES

C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2C5C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)C(=O)O

Synonyms

5,5'-Bis(b-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-,(9R,9'S)-[9,9'-bianthracene]-2,2'-dicarboxylic acid

Canonical SMILES

C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2C5C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)C(=O)O

Isomeric SMILES

C1=CC2=C(C(=C1)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C([C@@H]2[C@H]5C6=C(C(=CC=C6)O[C@@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)C(=O)O

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