Isorhyncophylline

Modify Date: 2024-01-02 20:17:51

Isorhyncophylline Structure
Isorhyncophylline structure
Common Name Isorhyncophylline
CAS Number 6859-01-4 Molecular Weight 384.47
Density 1.4±0.1 g/cm3 Boiling Point 447.6±25.0 °C at 760 mmHg
Molecular Formula C22H28N2O4 Melting Point 114ºC
MSDS N/A Flash Point 224.5±23.2 °C

 Use of Isorhyncophylline


Isorhynchophylline (IRN), an alkaloid isolated from Uncaria rhynchophylla, possesses the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.IC50 value:Target:In vitro: Isorhynchophylline concentration-dependently inhibited the platelet-derived growth factor (PDGF)-BB-induced proliferation of PASMCs. Fluorescence-activated cell-sorting analysis showed that isorhynchophylline caused G0/G1 phase cell cycle arrest [2]. Isorhynchophylline can significantly attenuate the cardiomyocyte hypertrophy induced by AngⅡ [3].In vivo: Isorhynchophylline significantly improved spatial learning and memory function in the D-gal-treated mice. Isorhynchophylline significantly increased the level of glutathione (GSH) and the activities of superoxide dismutase (SOD) and catalase (CAT), while decreased the level of malondialdehyde (MDA) in the brain tissues of the D-gal-treated mice [1]. Isorhynchophylline prevented monocrotaline induced pulmonary arterial hypertension in rats, as assessed by right ventricular (RV) pressure, the weight ratio of RV to (left ventricular+septum) and RV hypertrophy. Isorhynchophylline significantly attenuated the percentage of fully muscularized small arterioles, the medial wall thickness, and the expression of smooth muscle α-actin (α-SMA) and proliferating cell nuclear antigen (PCNA) [2].

 Names

Name isorhynchophylline
Synonym More Synonyms

 Isorhyncophylline Biological Activity

Description Isorhynchophylline (IRN), an alkaloid isolated from Uncaria rhynchophylla, possesses the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.IC50 value:Target:In vitro: Isorhynchophylline concentration-dependently inhibited the platelet-derived growth factor (PDGF)-BB-induced proliferation of PASMCs. Fluorescence-activated cell-sorting analysis showed that isorhynchophylline caused G0/G1 phase cell cycle arrest [2]. Isorhynchophylline can significantly attenuate the cardiomyocyte hypertrophy induced by AngⅡ [3].In vivo: Isorhynchophylline significantly improved spatial learning and memory function in the D-gal-treated mice. Isorhynchophylline significantly increased the level of glutathione (GSH) and the activities of superoxide dismutase (SOD) and catalase (CAT), while decreased the level of malondialdehyde (MDA) in the brain tissues of the D-gal-treated mice [1]. Isorhynchophylline prevented monocrotaline induced pulmonary arterial hypertension in rats, as assessed by right ventricular (RV) pressure, the weight ratio of RV to (left ventricular+septum) and RV hypertrophy. Isorhynchophylline significantly attenuated the percentage of fully muscularized small arterioles, the medial wall thickness, and the expression of smooth muscle α-actin (α-SMA) and proliferating cell nuclear antigen (PCNA) [2].
Related Catalog
References

[1]. Yan-Fang Xian, et al. Isorhynchophylline improves learning and memory impairments induced by D-galactose in mice. Neurochemistry International Volume 76, October 2014, Pages 42–49

[2]. Guo H, et al. Isorhynchophylline protects against pulmonary arterial hypertension and suppresses PASMCs proliferation. Biochem Biophys Res Commun. 2014 Jul 18;450(1):729-34.

[3]. LI Qiang, et al. Inhibitory effect of isorhynchophylline on cardiomyocyte hypertrophy induced by angiotensinⅡ. West China JOurnal of Pharmaceutical Sciences, 2013-05

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 447.6±25.0 °C at 760 mmHg
Melting Point 114ºC
Molecular Formula C22H28N2O4
Molecular Weight 384.47
Flash Point 224.5±23.2 °C
PSA 78.87000
LogP 1.90
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.677

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GN1605000
CHEMICAL NAME :
Corynoxan-16-carboxylic acid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (16E,20-alpha)-
CAS REGISTRY NUMBER :
6859-01-4
LAST UPDATED :
198909
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C22-H28-N2-O4
MOLECULAR WEIGHT :
384.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
217 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
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: 94,17,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
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: 94,17,1989

 Safety Information

Safety Phrases 24/25

 Synonyms

7-Isorhynchophylline
5-Methoxyindole-3-carboxylic Acid Hydrate
7-Isorhyncophylline
5-Methoxyindole-3-Carboxylic Acid
(16E,20α)-17-Methoxy-2-oxocorynox-16-en-16-carboxylic acid
Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, (αE,3S,6'R,7'S,8'aS)-
Isorhyncophylline
5-methoxyindole-2-carboxylic acid
1H-Indole-3-carboxylic acid, 5-methoxy-
5-Methoxy-1H-indole-3-carboxylic acid
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