Rhynchophylline

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Rhynchophylline
Chemical structure of rhynchophylline
Names
IUPAC name
Methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan- 17-oate
Other names
  • Rhyncophylline
  • Mitrinermin
  • Mitrinermine
  • Rhynchophyllin
  • Rhynocophylline
  • Methyl (E)-2-[(3R,6′R,7′S,8′aS)- 6'-ethyl-2-oxospiro[1H-indole-3,1'- 3,5,6,7,8,8a-hexahydro- 2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
Identifiers
  • 76-66-4 ☑Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:70069
ChEMBL
  • ChEMBL519266
ChemSpider
  • 4444758
ECHA InfoCard 100.208.612
KEGG
  • C09236
PubChem CID
  • 3033948
UNII
  • 46BQ79VJ8D
Properties
C22H28N2O4
Molar mass 384.48 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla[1] and Uncaria tomentosa.[2] It also occurs in the leaves of Mitragyna speciosa (kratom),[3] a tree native to Thailand. Chemically, it is related to the alkaloid mitragynine.

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

Uncaria species have had a variety of uses in traditional 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

References

  1. ^ Shi JS, Yu JX, Chen XP, Xu RX (2003). "Pharmacological Actions of Uncaria 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 of Uncaria 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.
  3. ^ "Mitragyna Speciosa (Kratom) - World Roots".
  4. ^ Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H (2002). "Rhynchophylline and Isorhynchophylline Inhibit NMDA Receptors Expressed in Xenopus 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 on in 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. ^ a b Zhou 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.
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