Cannabaceae

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 InfoCard 100.208.612 Edit 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 mass 384.476 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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) and Mitragyna tubulosa,[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[edit]

References[edit]

  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. S2CID 40280160.
  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.

One thought on “Cannabaceae

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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