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Rhynchophylline

Names

[ CAS No. ]:
76-66-4

[ Name ]:
Rhynchophylline

[Synonym ]:
Methyl-(7β,16E,20α)-16-(methoxymethyliden)-2-oxocorynoxan-17-oat
Methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate
Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate
Mitrinermine
Rhyncophylline
mitrinermin
Methyl (2E)-2-[(3R,6'R,7'S,8a'S)-6'-ethyl-2-oxo-1,2,2',3',6',7',8',8a'-octahydro-5'H-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyacrylate
Methyl (7β,16E,20α)-2-hydroxy-17-methoxy-1,2-didehydrocorynox-16-en-16-carboxylate
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-, methyl ester, (αE,3S,6'S,7'S,8'aS)-
methyl (7β,16E,20α)-16-(methoxymethylidene)-2-oxocorynoxan-17-oate
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-, methyl ester, (αE,3R,6'R,7'S,8'aS)-
Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-2',3',6',7',8',8'a-hexahydro-2-hydroxy-α-(methoxymethylene)-, methyl ester, (αE,3R,6'R,7'S,8'aS)-
rhynchophyllin
RHYNCHOLPHYLLINE

Biological Activity

[Description]:

Rhyncholphylline, an alkaloid isolated from Uncaria, shows potent inhibition of lipopolysaccharide (LPS)-induced NO production in rat primary microglial cells.IC50 value:Target:In vitro: Rhyncholphylline effectively suppresses release of proinflammatory cytokines in LPS-activated microglial cells and the underling molecular mechanism for the inhibition of microglial activation; Attenuated LPS-induced production of proinflammatory cytokines such as TNF-α and IL-1β as well as NO in mouse N9 microglial cells [1]. Rhynchophylline exerts it protective action against ischemia-induced neuronal damage by preventing NMDA, muscarinic M1, and 5-HT2 receptors-mediated neurotoxicity during ischemia [3].In vivo: The neuroprotective effect of rhynchophylline was investigated in a stroke model. Following pMCAO, rhynchophylline treatment not only ameliorated neurological deficits, infarct volume and brain edema, but also increased claudin-5 and BDNF expressions (p < 0.05). Moreover, rhynchophylline could activate PI3K/Akt/mTOR signaling while inhibiting TLRs/NF-κB pathway [2].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Natural Products >> Alkaloid
Research Areas >> Others

[References]

[1]. Dan Yuan, et al. Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism. International Immunopharmacology Volume 9, Issues 13–14, December 2009, Pages 1549–1554

[2]. Houcai Huang, et al. Neuroprotective Effects of Rhynchophylline Against Ischemic Brain Injury via Regulation of the Akt/mTOR and TLRs Signaling Pathways. Molecules 2014, 19 (8): 11196-11210; doi:10.3390/molecules190811196

[3]. Tai-Hyun Kang, et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life Sciences Volume 76, Issue 3, 3 December

[4]. Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of Pharmacology Volume 517, Issue 3, 11 July 2005, Pages 191–199


[Related Small Molecules]

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Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
560.8±50.0 °C at 760 mmHg

[ Melting Point ]:
216°; mp 197-199° (Ban et al., loc. cit.)

[ Molecular Formula ]:
C22H28N2O4

[ Molecular Weight ]:
384.469

[ Flash Point ]:
293.0±30.1 °C

[ Exact Mass ]:
384.204895

[ PSA ]:
67.87000

[ LogP ]:
3.31

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.596

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GN1600000
CHEMICAL NAME :
Corynoxan-16-carboxylic acid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (7- beta,16E,20-alpha)-
CAS REGISTRY NUMBER :
76-66-4
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 :
134 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 :
105 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 ]:
S24/25

[ RTECS ]:
GN1600000

[ HS Code ]:
29399990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds