Ryanodine
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| 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 | |
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3D model (JSmol)
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| ChemSpider | |
| KEGG | |
| MeSH | Ryanodine |
PubChem CID
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CompTox Dashboard (EPA)
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| 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).
Infobox references
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Ryanodine is a poisonous diterpenoid found in the South American plant Ryania speciosa (Salicaceae). It was isolated by Merck chemists in the 1940s from an extract of the plant by following its insecticidal activity.[1] It was sold since the 1940s in a partially purified form as an insecticide,[2][3] and used in organic farming, but was removed from the market in 1997.[4]
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.[5] 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.[6]
See also
- Diamide insecticides, a class of insecticides with the same mechanism of action as ryanodine
- Ryanodine receptor
- Dihydropyridine channel
References
- ^ Rogers, Edward F.; Koniuszy, Frank R.; Shavel, John Jr.; Folkers, Karl (1948). "Plant Insecticides. I. Ryanodine, A New Alkaloid from Ryania Speciosa Vahl". Journal of the American Chemical Society. 70 (9): 3086–3088. Bibcode:1948JAChS..70.3086R. doi:10.1021/ja01189a074. PMID 18882544.
- ^ Metcalf Deceased, Robert L.; Horowitz, Abraham Rami (2014). "Insect Control, 2. Individual Insecticides". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–94. doi:10.1002/14356007.s14_s01. ISBN 978-3-527-30673-2.
- ^ Jacobson, Martin; Crosby, Donald G. (1971). "Chapter 5 II C. Ryania". Naturally Occurring Insecticides. New York: Marcel Dekker. pp. 198–205. ISBN 978-0-8247-1325-6.
- ^ Wilhite, Mark (March 1999). "Reregistration Eligibility Decision (RED) Fact sheet for Ryanodine" (PDF). Office of Pesticide Programs, Environmental Protection Agency. Retrieved 27 April 2026.
- ^ 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.
- ^ 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.
Further reading
- 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. PMID 25966694.
- Bertil Hille, Ionic Channels of Excitable Membranes, 2nd edition, Sinauer Associates, Sunderland, MA, 01375, ISBN 0-87893-323-9