2415-24-9

Basic information

• Product Name: Catalpol
• Synonyms: CATALPOL;CATAPOL;,6-beta,6a-alpha))-;beta-d-glucopyranoside,1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl);catalpinoside;de(p-hydroxybenzoyl)catalposide;des-p-hydroxybenzoyl-catalposid;oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl,(1as-(1a-alpha,1b-beta,2-beta,5a-beta
• CAS NO: 2415-24-9
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.33
• EINECS: 219-324-0
• Product Categories: Iridoids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 2415-24-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 203-205°C
• Boiling Point: 675.6 °C at 760 mmHg
• Flash Point: 362.4 °C
• Appearance: powder
• Density: 1.72 g/cm³
• Vapor Pressure: 3.77E-21mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: ?20°C
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• PKA: 12.79±0.70(Predicted)
• CAS DataBase Reference: Catalpol(CAS DataBase Reference)
• NIST Chemistry Reference: Catalpol(2415-24-9)
• EPA Substance Registry System: Catalpol(2415-24-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: LZ5776816
• Hazardous Substances Data: 2415-24-9(Hazardous Substances Data)

Usage

Description

Catalpol is an iridoid glycoside that has been isolated from R. glutinosa and has diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties. It protects against mitochondrial pathway-dependent apoptosis in PC12 rat adrenal pheochromocytoma cells and H9c2 rat embryonic ventricular myocardial cells when used at a concentration of 10 μM. Catalpol pretreatment reduces apoptosis and improves viability in AHH-1 human lymphocyte cells exposed to ionizing radiation and reduces intestinal damage induced by radiation in mice when used at concentrations and doses ranging from of 25 to 100 μg/ml and 25 to 100 mg/kg, respectively. In a rat model of stroke, catalpol (5 mg/kg, i.p.) increases the expression of erythropoietin and VEGF and improves angiogenesis in the brain.

Chemical Properties

Light brown powder

Uses

Catapol is an iridoid glucoside that has been shown to alleviate neuropathic pain.

InChI:InChI=1/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2

Upstream product

• 81720-06-1 rehmannioside B 
• 1374308-81-2 (1aS,1bS,5aR,6S,6aS)-1a-{[(3,4-dimethoxybenzoyl)oxy]methyl}-1a,1b,2,5a,6,6a-hexahydro-6-methoxyoxireno[4,5]cyclopenta[1,2-c]pyran-2-yl β-D-glucopyranoside 
• 50932-20-2 6-O-(3,4-dihydroxybenzoyl)catalpol 
• 75598-56-0 2',3',4',6',10-Pentaacetyl-6-(4-acetylvanilloyl)catalpol 
• 6910-20-9 2',3',4',6,6',10-Hexaacetylcatalpol 
• 147714-71-4 6-O-[(E)-3,4-dimethoxycinnamoyl]catalpol 

Downstream Products

• 87946-74-5 (-)-specionin 
• 113466-55-0 4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 
• 113466-54-9 (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-ol 
• 103744-70-3 C₂₅H₂₄O₈ 
• 85249-05-4 (1S,2S,6R,7R)-(-)-2-(Benzylthio)-7-hydroxy-3-oxabicyclo<4.3.0>nonan-9-on 
• 97119-20-5 Toluene-4-sulfonic acid (1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester 
• 105562-53-6 2',3',4',6-Tetraacetyl-6',10-bis(triphenylmethyl)catalpol 
• 89255-33-4 (1aS,1bS,2R,5aR,6S,6aS)-1a-Hydroxymethyl-1a,1b,2,5a,6,6a-hexahydro-1,3-dioxa-cyclopropa[a]indene-2,6-diol 

Relevant articles and documents

10-O-acylated iridoid glucosides from leaves of Premna subscandens

From the 1-butanol-soluble fraction of a methanol extract of leaves of Premna subscandens, collected on Ishigaki Island, Okinawa, ten 10-O-acylated derivatives of catalpol and asystasioside E were isolated. The structures of nine new compounds were elucidated by spectroscopic methods and by chemical conversion.

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Isolation, semi-synthesis, docking-based prediction, and bioassay-based activity ofDolichandrone spathaceairidoids: new catalpol derivatives as glucosidase inhibitors

Dolichandrone spathaceairidoids are promising anti-diabetic inhibitors towards α-glucosidase protein (PDB-) and oligo-1,6-glucosidase protein. Five catalpol iridoids(1,2,10,13,14)were isolated from mangrove plantD. spathacea, and their derivatives (3,4,5,6,7,8,9,11,12,15) were obtained from reduction, acetylation,O-alkylation, acetonisation, or hydrolysation starting from naturally isolated compounds. They were identified by spectral methods such as IR, MS, and 1D and 2D NMR. Their glucosidase-related (inhibitability and physiological compatibility were predicted by molecular docking simulation and prescreened based on Lipinski's rule of five. Experimental α-glucosidase inhibition of1-15was evaluated using enzyme assays. Compounds3,4,5,6, and9are new iridoid derivatives, introduced to the literature for the first time, while all fifteen compounds1-15are studied for molecular docking for the first time. Regarding protein, the five strongest predicted inhibitors assemble in the order2>10>1>9>14. In respect to, the corresponding order is14>2>10>5>1=9. Lipinski's criteria suggest10as the candidate with the most potential for oral administration. Thein vitrobioassay revealed that compound10is the most effective inhibitor with a respective IC50value of 0.05 μM, in the order10>2>14>13>1. The computational and experimental results show good consistency. The study opens an alternative approach for diabetes treatment based on inhibitability of natural and semi-synthesised catalpol iridoid derivatives towards carbohydrate-hydrolases.

Eremosides A-C, new iridoid glucosides from Eremostachys loasifolia

Eremosides A-C (1 - 3), three new iridoid glucosides, were isolated from the AcOEt-soluble fraction of the EtOH extract of the whole plant of Eremostachys loasifolia, along with buddlejoside B (4), 10-O-benzoylcatalpol (5), and pakiside A (6) reported for the first time from this species. The structures of these compounds were elucidated by spectroscopic data including 2D-NMR, FAB-MS, ESI-MS, as well as by acid and basic hydrolyses.

PHARMACEUTICAL COMPOSITION COMPRISING AN EXTRACT OF PSEUDOLYSIMACHION LONGIFOLIUM AND THE CATALPOL DERIVATIVES ISOLATED THEREFROM HAVING ANTIINFLAMMATORY, ANTIALLERGIC AND ANTIASTHMATIC ACTIVITY

The present invention relates to a composition comprising an extract of Pseudolysimachion genus plant, and the catalpol derivatives isolated therefrom having anti-inflammatory, antiallergic and anti-asthmatic activity. The extractof Pseudolysimachion genus plantand the catalpol derivatives isolated therefrom shows potent suppressing effect on elevated IgE, IL-4 and IL- 13 levels and eosinophilia in the plasma and BALF, and mucus overproduction in the lung tissues in an OVA-induced asthmatic mouse model. Therefore, it can be used as the therapeutics or functional health food for treating and preventing inflammatory, allergic and asthmatic disease.