CATALPOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26O12
Molecular Weight	482.4346
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](OC(=O)C4=CC=C(O)C=C4)[C@@H]5O[C@]5(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=UXSACQOOWZMGSE-RWORTQBESA-N

InChI=1S/C22H26O12/c23-7-12-14(26)15(27)16(28)21(31-12)33-20-13-11(5-6-30-20)17(18-22(13,8-24)34-18)32-19(29)9-1-3-10(25)4-2-9/h1-6,11-18,20-21,23-28H,7-8H2/t11-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12349954
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/12962973

Catalposide is a compound isolated from irinoid-producing plant Catalpa ovata. Catalposide has been shown to possess anti-microbial, anti-tumoral, and anti-inflammatory properties. was found to inhibit the productions of tumor necrosis factor-alpha (TNF- alpha), interleukin-1beta, and interleukin-6 (IL-6), and the activation of nuclear factor kB (NF-kB) in RAW 264.7 macrophages activated with lipopolysaccharide (LPS).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22583896	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
CATALPOL AND METHYLCATALPOL: NATURALLY OCCURRING GLYCOSIDES IN PLANTAGO AND BUDDLEIA SPECIES.	1965-07	14343132

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Catalposide (0.02-0.2 uM) significantly inhibited the production of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages (20h with LPS 1ug/mL) in a dose-dependent manner. RT-PCR and Western blot analyses demonstrated that catalposide (0.02-0.2 uM) suppressed the expression of inducible nitric oxide synthase (iNOS) gene and iNOS protein. Catalposide (0.02-0.2 uM) also inhibited the activation of LPS-induced NF-kappaB as analyzed by electrophoretic mobility shift assay (EMSA). In addition to the inhibitory effect on NO production in LPS-stimulated RAW 264.7 cells, catalposide (0.02-0.4 uM) significantly inhibited the NO production in cytokine-stimulated human DLD-1 and rat vascular smooth muscle (VSM) cells in a dose-dependent manner.

Name

Type

Language

(HYDROXYBENZOYL)CATALPOL

Preferred Name

English

CATALPOSIDE

Common Name

English

CATALPOSIDE [MI]

Common Name

English

CATALPIN

Common Name

English

.BETA.-D-GLUCOPYRANOSIDE, (1AS,1BS,2S,5AR,6S,6AS)-1A,1B,2,5A,6,6A-HEXAHYDRO-6-((4-HYDROXYBENZOYL)OXY)-1A-(HYDROXYMETHYL)OXIRENO(4,5)CYCLOPENTA(1,2-C)PYRAN-2-YL

Common Name

English

CATALPOL 6-P-HYDROXYBENZOATE

Common Name

English

Code System Code Type Description

CAS

6736-85-2