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Rhynchophylline

From Wikipedia, the free encyclopedia
Rhynchophylline
Chemical structure of rhynchophylline
Names
IUPAC name
Methyl (7R,16E)-17-methoxy-2-oxo-16,17-didehydro-20α-corynoxan-16-carboxylate
Systematic IUPAC name
Methyl (2E)-2-[(1′R,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-methoxyprop-2-enoate
Other names
  • Rhyncophylline
  • Mitrinermin
  • Mitrinermine
  • Rhynchophyllin
  • Rhynocophylline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.208.612Edit this at Wikidata
KEGG
UNII
  • 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
    Key: DAXYUDFNWXHGBE-KAXDATADSA-N
  • InChI=1/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
    Key: DAXYUDFNWXHGBE-KAXDATADBC
  • CC[C@H]1CN2CC[C@]3([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O
Properties
C22H28N2O4
Molar mass384.476 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Rhynchophylline is analkaloid found in certainUncaria species (Rubiaceae), notablyUncaria rhynchophylla[1] andUncaria tomentosa.[2] It also occurs in the leaves ofMitragyna speciosa (kratom) and Mitragyna tubulosa,[3] a tree native to Thailand. Chemically, it is related to the alkaloidmitragynine.

Rhynchophylline is a non-competitiveNMDA antagonist (IC50 = 43.2 μM) and acalcium channel blocker.[4][5]

Uncaria species have had a variety of uses intraditional herbal medicine, such as for lightheadedness, convulsions, numbness, and hypertension.[6] These uses have been associated with the presence of rhynchophylline and have encouraged its investigation as a drug candidate for several cardiovascular and central nervous system diseases; however, few clinically relevant studies have been conducted.[6]

See also

[edit]

References

[edit]
  1. ^Shi JS, Yu JX, Chen XP, Xu RX (2003)."Pharmacological Actions ofUncaria Alkaloids, Rhynchophylline and Isorhynchophylline"(PDF).Acta Pharmacologica Sinica.24 (2):97–101.PMID 12546715.
  2. ^Mohamed AF, Matsumoto K, Tabata K, Takayama H, Kitajima M, Watanabe H (2000)."Effects ofUncaria tomentosa Total Alkaloid and its Components on Experimental Amnesia in Mice: Elucidation Using the Passive Avoidance Test".Journal of Pharmacy and Pharmacology.52 (12):1553–1561.doi:10.1211/0022357001777612.PMID 11197086.S2CID 40280160.
  3. ^"Mitragyna Speciosa (Kratom) - World Roots". Archived fromthe original on 2024-12-08. Retrieved2017-05-02.
  4. ^Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H (2002). "Rhynchophylline and Isorhynchophylline Inhibit NMDA Receptors Expressed inXenopus Oocytes".European Journal of Pharmacology.455 (1):27–34.doi:10.1016/S0014-2999(02)02581-5.PMID 12433591.
  5. ^Kang TH, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H, Matsumoto K (2004). "Protective Effect of Rhynchophylline and Isorhynchophylline onin vitro Ischemia-Induced Neuronal Damage in the Hippocampus: Putative Neurotransmitter Receptors Involved in their Action".Life Sciences.76 (3):331–343.doi:10.1016/j.lfs.2004.08.012.PMID 15531384.
  6. ^abZhou J, Zhou S (2010). "Antihypertensive and neuroprotective activities of rhynchophylline: the role of rhynchophylline in neurotransmission and ion channel activity".Journal of Ethnopharmacology.132 (1):15–27.doi:10.1016/j.jep.2010.08.041.PMID 20736055.
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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