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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28N2O4
Molecular Weight 384.4696
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RHYNCHOPHYLLINE

SMILES

CC[C@@]1([H])CN2CC[C@@]3(c4ccccc4N=C3O)[C@]2([H])C[C@]1([H])/C(=C(/[H])\OC)/C(=O)OC

InChI

InChIKey=DAXYUDFNWXHGBE-KAXDATADSA-N
InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H28N2O4
Molecular Weight 384.4696
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/12433591 | https://www.ncbi.nlm.nih.gov/pubmed/24966905

Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla, Uncaria tomentosa and Gambirplant (Gouteng). The total alkaloid content in Uncaria rhynchophyl-lina is about 0.2 %, in which rhynchophylline (Rhy) is 28 %-50 %, isorhynchophylline is 15 %. The pharmacological effects of Rhynchophylline and Isorhynchophylline were extensively studied, especially in the cardiovascular system. The hypotensive effect of Rhynchophylline was also observed in 1978. The peculiarity of Rhynchophylline was that renal blood flow was not significantly interfered upon lowering of blood pressure. Although the effect of Rhynchophylline on the renin secretion remained unclear, the consequence of Rhynchophylline on the renal blood flow ought to be considered as an advantage. The cardiovascular effects of Rhy were supposed due to calcium channel block. In an experiment with the guinea pig, Rhy inhibited the left atrium post-rest potential enhancement and staircase phenomenon. The post-rest potential enhancement induced by Auxo-frequency stimulation is the characteristic of Ca(‘2+) influx increase, and the calcium antagonists, such as verapamil, can reverse the staircase phenomenon. In isolated strips of rabbit aorta, Rhynchophylline inhibited 45Ca(‘2+) influx induced by K(‘+). Effects of Rhynchophylline on the 45Ca2+ influx and efflux induced by noradrenaline were small. The vasodilative effect of Rhynchophylline was mainly due to the dysfunction of Ca(‘2+) transport, including the influx of extracellular calcium and release of intracellular calcium by blocking the voltage-dependent calcium channel and the receptor-regulation calcium channel. Brachycardia and cardiac contractility repression induced by Rhynchophylline were observed. Rhynchophylline inhibited rabbit platelet aggregation induced by arachidonic acid (AA), collagen, and ADP, and reduced the thromboxane B2 (TXB2) generation in platelet-rich plasma (PRP) induced by collagen but failed to reduce TXB2 generation that induced by AA. Rhynchophylline suppressed malondialdehyde (MDA) formation in platelet suspension stimulated by thrombin, inhibited the platelet factor 4 (PF4) release. It did not alter intraplatelet cAMP concentration. Rhynchophylline 10-20 mg/kg iv showed a significant inhibition of venous thrombosis and cerebral thrombosis in rats. Rhynchophylline can relieve contraction of the respiratory tract smooth muscle and uterus smooth muscle induced by the agonist, in which a mechanism of calcium channel blocking was also proposed. In a cultured brain slice of rats, Rhynchophylline increased the 5-HT content in the hypothalamus and cortex but reduced the dopamine (DA) concentrations in the cortex, amygdala, and spinal cord. Rhynchophylline promoted the release of endogenous DA from hypothalamus, cortex, amygdala, and spinal cord. The release of 5-HT was increased in cortex and amygdala and was decreased in hypothalamus slice. However, Rhynchophylline inhibited the release of both 5-HT and DA evoked by high potassium. Rhynchophylline can protect neurons from damage induced by dopamine, which behaves as a free radical at higher concentration.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline.
2003 Feb
Patents

Patents

Sample Use Guides

Rhynchophylline 10-20 mg/kg iv showed a significant inhibition on venous thrombosis and cerebral thrombosis in rats
Route of Administration: Intravenous
Permeability assay was performed in an air shaking bath (SW 23, Julabo, Seelbach, Germany) at 37°C and 50 rpm to simulate the small intestine motility. The transport experiments were carried out in HBSS with 25 mM HEPES at pH 7.4. All the other drug solutions were adjusted pH 7.4 prior to use. Cell monolayer was washed twice with HBSS, and preincubated in HBSS at 37°C for 20 min in the air shaking bath. After that, TEER crossing the apical (AP) and the basolateral (BL) sides was monitored before transport studies. Those monolayer with TEER more than 800 Ω•cm2 was used in the transport studies. In the permeability assay of Rhy (Rhynchophylline) (add little hydrochloric acid solution for better dissolution), HBSS solution on both sides of the cell monolayer was removed by aspiration. For the transport from AP to BL side, 500 µL of HBSS containing Rhy was added to the AP side and 1500 µL HBSS was added to the BL side. For the transport from BL to AP, 1500 µL of HBSS containing Rhy was added to the BL side and 500 µL of HBSS was added to the AP side. To test the effect of a chemical inhibitor on the bidirectional transport of Rhy, HBSS containing Rhy and inhibitor was loaded onto the donor side. The quantity of Rhy in the samples from the receiver compartment was analyzed using HPLC
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:29:25 UTC 2021
Edited
by admin
on Sat Jun 26 14:29:25 UTC 2021
Record UNII
46BQ79VJ8D
Record Status Validated (UNII)
Record Version
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Name Type Language
RHYNCHOPHYLLINE
MI  
Common Name English
MITRINERMINE
Common Name English
RHYNCHOPHYLLINE [MI]
Common Name English
MITRINERMIN
Common Name English
RHYNCHOPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC]
Common Name English
RHYNCHOPHYLLIN
Common Name English
CORYNOXAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-17-METHOXY-2-OXO-, METHYL ESTER, (7.BETA.,16E,20.ALPHA.)
Systematic Name English
RHYNCOPHYLLINE
Common Name English
NSC-21731
Code English
Code System Code Type Description
MERCK INDEX
M9592
Created by admin on Sat Jun 26 14:29:25 UTC 2021 , Edited by admin on Sat Jun 26 14:29:25 UTC 2021
PRIMARY Merck Index
FDA UNII
46BQ79VJ8D
Created by admin on Sat Jun 26 14:29:25 UTC 2021 , Edited by admin on Sat Jun 26 14:29:25 UTC 2021
PRIMARY
PUBCHEM
5281408
Created by admin on Sat Jun 26 14:29:25 UTC 2021 , Edited by admin on Sat Jun 26 14:29:25 UTC 2021
PRIMARY
CAS
76-66-4
Created by admin on Sat Jun 26 14:29:25 UTC 2021 , Edited by admin on Sat Jun 26 14:29:25 UTC 2021
PRIMARY
WIKIPEDIA
Rhynchophylline
Created by admin on Sat Jun 26 14:29:25 UTC 2021 , Edited by admin on Sat Jun 26 14:29:25 UTC 2021
PRIMARY
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PARENT -> CONSTITUENT ALWAYS PRESENT
Constituent of Uncaria tomentosa stem?s inner bark of Uncaria tomentosa stem.
PARENT -> CONSTITUENT ALWAYS PRESENT