Ryanodine

Ryanodine
Names
Preferred IUPAC name
(1S,2R,2aS,2a1R,3S,3aS,6S,7R,7aR,9S,9aS)-1,2a,2a1,3a,7,9-Hexahydroxy-3,6,9a-trimethyl-1-(propan-2-yl)dodecahydro-3,9-methanobenzo[1,2]pentaleno[1,6-bc]furan-2-yl 1H-pyrrole-2-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH Ryanodine
UNII
  • InChI=1S/C25H35NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12-13,15,17,26-27,29-33H,8-9,11H2,1-5H3/t13-,15+,17+,18-,19+,20-,21-,22+,23+,24+,25+/m0/s1 checkY
    Key: JJSYXNQGLHBRRK-SFEDZAPPSA-N checkY
  • InChI=1/C25H35NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12-13,15,17,26-27,29-33H,8-9,11H2,1-5H3/t13-,15+,17+,18-,19+,20-,21-,22+,23+,24+,25+/m0/s1
    Key: JJSYXNQGLHBRRK-SFEDZAPPBA
  • C[C@H]1CC[C@@]2([C@@]3(C[C@]4([C@@]5([C@]([C@H]([C@@]3([C@]5([C@]2([C@@H]1O)O4)O)O)OC(=O)c6ccc[nH]6)(C(C)C)O)C)O)C)O
Properties
C25H35NO9
Molar mass 493.553 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 checkY☒N ?)

Ryanodine is a poisonous diterpenoid found in the South American plant Ryania speciosa (Salicaceae). It was originally used as an insecticide.

The compound has extremely high affinity to the open-form ryanodine receptor, a group of calcium channels found in skeletal muscle, smooth muscle, and heart muscle cells.[1] It binds with such high affinity to the receptor that it was used as a label for the first purification of that class of ion channels and gave its name to it.

At nanomolar concentrations, ryanodine locks the receptor in a half-open state, whereas it fully closes them at micromolar concentration. The effect of the nanomolar-level binding is that ryanodine causes release of calcium from calcium stores as the sarcoplasmic reticulum in the cytoplasm, leading to massive muscle contractions. The effect of micromolar-level binding is paralysis. This is true for both mammals and insects.[2]

  1. ^ Santulli, Gaetano; Marks, Andrew (2015). "Essential Roles of Intracellular Calcium Release Channels in Muscle, Brain, Metabolism, and Aging". Current Molecular Pharmacology. 8 (2): 206–222. doi:10.2174/1874467208666150507105105. ISSN 1874-4672. PMID 25966694.
  2. ^ Van Petegem, F (2012). "Ryanodine receptors: structure and function". The Journal of Biological Chemistry. 287 (38): 31624–32. doi:10.1074/jbc.r112.349068. PMC 3442496. PMID 22822064.