66575-29-9 Usage
Description
Forskolin (66575-29-9) is a widely used adenylate cyclase activator.1 Forskolin also is a positive inotropic agent, vasodilator and induces platelet activation among other activities.2-5
Uses
Different sources of media describe the Uses of 66575-29-9 differently. You can refer to the following data:
1. Forskolin is a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.
2. adenylate cyclase activator, antiglaucoma, hypotensive, vasodilator
3. Cyclic AMP (cAMP) is an important signal carrier necessary for the proper biological response of cells to hormones, neurotransmitters, and other extracellular signals Forskolin is a naturally occurring diterpene that is produced by the Indian Coleus plant (C. forskohlii). It directly activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations. Forskolin binds to adenylyl cyclase in membranes from stably transfected Sf9 cells expressing type 1 adenylyl cyclase with an IC50 value of 41 nM and demonstrates an EC50 value of 0.5 μM in an activation assay assessing formation of cAMP from ATP. Forskolin also interacts with glucose transporters and certain ion channels and has been used for examining adenylyl cyclase expression, regulation, and G protein signaling.[Cayman Chemical]
4. An adenylate cyclase activator and MAP kinase inhibitor
5. In purification of adenylate cyclase.
General Description
Forskolin, present predominantly in the root of Coleus forskohlii plant, is a potential pharmacological compound. It is used for treating hypertension, respiratory disorders and obesity. Forskolin is a diterpenoid capable of modulating adenylate cyclase enzyme and cyclic adenosine monophosphate (cAMP) levels. Engineering forskolin biosynthetic pathway caters its commercial production for pharmacological use. Forskolin has antioxidant and anti-inflammatory property and reduces hyperglycemia by stimulating insulin release. Forskolin promotes differentiation of hepatoma HepaRG cells and activates farnesoid X receptor (FXR) and pregnane X receptor(PXR).
Biological Activity
Cell-permeable activator of adenylyl cyclase. Hypotensive and vasodilatory agent. Induces neuronal differentiation in stem cells and in several neuroblastoma. Also available as part of the PKA Tocriset? .
Biochem/physiol Actions
Cell permeable: yes
Purification Methods
It is an antihypertensive, a positive ionotropic, a platelet aggregation inhibitor, and it has adenylate cyclase activating properties [Chem Abstr 89 244150 1978, de Souza et al. Med Res Rev 3 201 1983, X-ray: Tandon et al. Indian J Chem 15B 880 1977]. [Beilstein 18/5 V 55.]
References
1) Awad et al (1983) Interactions of forskolin and adenylate cyclase; J. Biol. Chem., 258 2960
2) Bhat et al (1983) The antihypertensive and positive inotropic diterpene forskolin: effects of structural modifications on its activity; J. Med. Chem., 26 486
3) de Souza et al. (1983) Forskolin: a labdane diterpenoid with antihypertensive, positive inotropic, platelet aggregation inhibitory, and adenylate cyclase activating properties; Med. Res. Rev. 3 201
4) Aylwin & White (1992) Forskolin acts as a noncompetitive inhibitor of nicotinic acetylcholine receptors; Mol. Pharmacol. 41 908
5) Insel & Ostrom (2003) Forskolin as a tool for examining adenylyl cyclase expression, regulation, and G protein signaling; Cell Mol. Neurobiol., 23 305
Check Digit Verification of cas no
The CAS Registry Mumber 66575-29-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,5,7 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 66575-29:
(7*6)+(6*6)+(5*5)+(4*7)+(3*5)+(2*2)+(1*9)=159
159 % 10 = 9
So 66575-29-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16?,17-,19-,20-,21+,22-/m0/s1
66575-29-9Relevant articles and documents
A Radical-Polar Crossover Annulation to Access Terpenoid Motifs
Thomas, William P.,Schatz, Devon J.,George, David T.,Pronin, Sergey V.
supporting information, p. 12246 - 12250 (2019/08/27)
A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.
Expedient synthetic transformation of ptychantins into Forskolin
Hagiwara, Hisahiro,Tsukagoshi, Masashi,Hoshi, Takashi,Suzuki, Toshio,Hashimoto, Toshihiro,Asakawa, Yoshinori
, p. 929 - 931 (2008/12/22)
Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort Ptychanthus striatus in good yield. The 1α-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9α-hydroxy group was introduced stereoselectively by epoxidation of Δ9,11-enol ether. Georg Thieme Verlag Stuttgart.
Total synthesis of forskolin - Part II
Delpech, Bernard,Calvo, Daniel,Lett, Robert
, p. 1019 - 1022 (2007/10/03)
The further elaboration of the key-intermediate 5 into forskolin 1 has been achieved via two different routes. Key features of this new total synthesis are: 1) the stereospecific formation of the 6β, 7β, 8α-triol via the BF3-Et2O assisted opening of the epoxy carbamate 8; 2) use of the 8α, 11-di-t-butylsilylene ketal for the specific protection of the 6β, 7β-diol, from the tetrol 10(A); two new sequences for the formation of the dihydro-γ-pyrone ring in high overall yield from 23; 4) the stereoselective divinyl cuprate conjugate α-addition on the dihydro-γ-pyrone 16 or 28, in the presence of BF3-Et2o, with the stereochemistry required for forskolin synthesis.