Catalpol

Names

[ Name ]:
Catalpol

[Synonym ]:
EINECS 219-324-0
catalpinoside
des-p-hydroxybenzoyl-catalposid
CATAPOL
6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2-yl hexopyranoside
Hexopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl
catalposide
methyl iridoid glycoside

Biological Activity

[Description]:

Catalpol, an iridoid glycoside, has neuroprotective, anti-inflammatory, and anti-hepatitis virus effects.IC50 Value:Target: neuroprotective, anti-inflammatory, and anti-hepatitis virus natural product.In vitro: Catalpol could be encapsulated into composite nanofibers and induce differentiation of hASCs into neural-like cells, which might offer new avenues in nerve regeneration [1].In vivo: The pharmacokinetics of catalpol in normal and doxorubicin-induced chronic kidney disease rats after oral administration of Rehmannia glutinosa extract was determined, and the extraction recoverie of catalpol was higher than 68.24% [2]. The protective effect of catalpol on renal IRI mice through suppressing phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt)-endothelial nitric oxide synthase (eNOS) and against inflammation, and the possible underlying mechanism [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Terpenoids and Glycosides

Research Areas >> Others

[References]

[1]. Zhao M, et al.Comparative pharmacokinetics of catalpol and acteoside in normal and chronic kidney disease rats after oral administration of Rehmannia glutinosa extract. Biomed Chromatogr. 2015 May 29.

[2]. Guo JH, et al.Potential Neurogenesis of Human Adipose-Derived Stem Cells on Electrospun Catalpol-Loaded Composite Nanofibrous Scaffolds. Ann Biomed Eng. 2015 Mar 31.

[3]. Zhu J,Catalpol protects mice against renal ischemia/reperfusion injury via suppressing PI3K/Akt-eNOS signaling and inflammation. Int J Clin Exp Med. 2015 Feb 15;8(2):2038-44.

[4]. Xu Z, et al.Mitochondrial fusion/fission process involved in the improvement of catalpol on high glucose-induced hepatic mitochondrial dysfunction. Acta Biochim Biophys Sin (Shanghai). 2015 Jul 2.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
675.6±55.0 °C at 760 mmHg

[ Melting Point ]:
203-205ºC

[ Molecular Formula ]:
C₁₅H₂₂O₁₀

[ Molecular Weight ]:
362.329

[ Flash Point ]:
362.4±31.5 °C

[ Exact Mass ]:
362.121307

[ PSA ]:
161.60000

[ LogP ]:
-4.15

[ Vapour Pressure ]:
0.0±4.7 mmHg at 25°C

[ Index of Refraction ]:
1.679

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ5776816

CHEMICAL NAME :: beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy- 1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran- 2-yl, (1aS-(1a-alpha,1b-beta,2-beta,5a- beta,6-beta,6a-alpha))-

CAS REGISTRY NUMBER :: 2415-24-9

LAST UPDATED :: 199806

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H22-O10

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 64,93,1968

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 64,93,1968

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
LZ5776816

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

HPLC-APCI-MS/MS method for the determination of catalpol in rat plasma and cerebrospinal fluid: application to an in vivo pharmacokinetic study.

J. Pharm. Biomed. Anal. 70 , 337-43, (2012)

Catalpol is a Chinese herb ingredient with potential for the treatment of neurodegenerative disorders. A high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spe...

[Simultaneous determination and optimization of extraction process of catalpol and acteoside from rehmanniae radix].

Zhong Yao Cai 35(8) , 1318-22, (2012)

To establish a method for simultaneously quantification of the Catalpol and Acteoside from Rehmanniae Radix and optimize the extraction process from Rehmanniae Radix by response surface methodology (R...

Synergistic effects of iridoid glycosides on the survival, development and immune response of a specialist caterpillar, Junonia coenia (Nymphalidae).

J. Chem. Ecol. 38(10) , 1276-84, (2012)

Plants use a diverse mix of defenses against herbivores, including multiple secondary metabolites, which may affect herbivores synergistically. Chemical defenses also can affect natural enemies of her...