15662-33-6 Usage
Description
RYANODINE is a potent insecticide alkaloid isolated from the South American plant Ryania speciosa. It is a white to off-white solid and has been identified as a major component of the Ryania insecticide, which is derived from the ground stem wood of the tropical tree Ryania speciosa Vahl. RYANODINE is also a widely used pharmacological tool in the study of calcium release channels in sarcoplasmic reticulum membranes of skeletal and cardiac muscle in both insects and mammals. Additionally, it has potential applications in the treatment of Huntington's disease due to its ability to inhibit Ca2+ release from sarcoplasmic reticulum.
Uses
Used in Insecticide Applications:
RYANODINE is used as an insecticide for controlling and eliminating various insect pests. Its potent action makes it an effective component in the Ryania insecticide, which is derived from the tropical tree Ryania speciosa Vahl.
Used in Pharmaceutical Research:
RYANODINE is used as a pharmacological tool for studying the calcium release channels in sarcoplasmic reticulum membranes of skeletal and cardiac muscle in both insects and mammals. This helps researchers understand the mechanisms of muscle contraction and develop potential treatments for related conditions.
Used in Huntington's Disease Treatment:
RYANODINE is used as a potential therapeutic agent for the treatment of Huntington's disease. It acts as a potent inhibitor of Ca2+ release from sarcoplasmic reticulum, which may help in managing the symptoms and progression of the disease.
Biological Activity
Potent inhibitor of Ca 2+ release from sarcoplasmic reticulum (IC 50 values are 10 and 2.8 nM in skeletal and cardiac muscle respectively).
References
Rogers et ai., J. Amer. Chem. Soc., 70, 3086 (1948)
Kelly, Whittingham, Wusner., Chem. Ind., 857 (1952)
Structure:
Wiesner, Valenta, Findlay., Tetrahedron Lett., 221 (1967)
Hollstein, Rapoport.,J. Amer. Chem. Soc., 90,3864 (1968)
Wong, Hollstein, Rapoport., ibid, 90, 3866 (1968)
Wiesner., Collect. Czech. Chem. Commun., 33, 2656 (1968)
Crystal structure:
Srivastava, Przybylska., Can. J. Chem., 46,795 (1968)
Check Digit Verification of cas no
The CAS Registry Mumber 15662-33-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,6,6 and 2 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 15662-33:
(7*1)+(6*5)+(5*6)+(4*6)+(3*2)+(2*3)+(1*3)=106
106 % 10 = 6
So 15662-33-6 is a valid CAS Registry Number.
15662-33-6Relevant articles and documents
Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine
Masuda, Kengo,Koshimizu, Masaki,Nagatomo, Masanori,Inoue, Masayuki
, p. 230 - 236 (2016/01/25)
(+)-Ryanodine (1) is the ester derivative of 1H-pyrrole-2-carboxylic acid and the complex terpenoid (+)-ryanodol (2), which possesses eleven contiguous stereogenic centers on the ABCDE-ring system. Compound 1 is known to be a potent modulator of intracellular calcium release channels, whereas the activity of 2 is significantly weaker. To chemically construct 1, the multiple oxygen functional groups must be installed on the fused pentacycle in stereoselective fashions and the extremely hindered C3-hydroxy group must be acylated in a site-selective manner. First, the total synthesis of 2 was accomplished by introducing the five stereocenters from the previously prepared enantiopure ABDE-ring 7. Stereoselective construction of the C3-secondary, C2- and C6-tertiary alcohols was achieved by three nucleophilic reactions. The C9- and C10-trisubstituted carbon centers were regio- and stereoselectively introduced by hydroboration/oxidation of the six-membered C-ring, which was formed by the ring-closing metathesis reaction. Direct esterification of the C3-alcohol with pyrrole-2-carboxylic acid proved unsuccessful; therefore, we developed a new, two-step protocol for attachment of the pyrrole moiety. The C3-hydroxy group was first converted into the less sterically cumbersome glycine ester, which was then transformed into the pyrrole ring through condensation with 1,3-bis(dimethylamino)allylium tetrafluoroborate. This procedure resulted in the first total synthesis of 1.
Investigation of the constituents of Ryania Speciosa
Ruest, Luc,Taylor, David R.,Deslongchamps, Pierre
, p. 2840 - 2843 (2007/10/02)
Six new metabolites (2, 5-9) were isolated from the extracts of Ryania Speciosa Vahl.These compounds are closely related to ryanodine, the known insecticidal toxic alkaloid from this plant.
9,21-Didehydroryanodine: a New Principal Toxic Constituent of the Botanical Insecticide Ryania
Waterhouse, Andrew L.,Holden, Ian,Casida, John E.
, p. 1265 - 1266 (2007/10/02)
A major insecticidal constituent of Ryania speciosa is isolated and characterized by n.m.r. and mass spectroscopy as the new alkaloid 9,21-didehydroryanodine (2); reduction of (2) with hydrogen (or tritium) gas yields both ryanodine (1) and 9-epiryanodine (3) (or their 9,21-3H analogues) in a 1 : 9 ratio.
