Forskolin

Structural formula
General
Surname	Forskolin
other names	Colforsin ( INN ); Coleonol; (3 R , 4a R , 5 S , 6 S , 6a S , 10 S , 10a R , 10b S ) -dodecahydro-5,6,10,10b-tetrahydroxy-3,4a, 7,7,10a-pentamethyl- 1-oxo-3-vinyl-1 H -naphtho [2,1- b ] pyran-5-yl acetate ( IUPAC );
Molecular formula	C 22 H 34 O 7
Brief description	colorless to yellow solid
External identifiers / databases
EC number	266-410-9
ECHA InfoCard	100.060.354
PubChem	47936
ChemSpider	43607
DrugBank	DB02587
Wikidata	Q412747
properties
Molar mass	410.50 g mol −1
Physical state	firmly
Melting point	230-232 ° C
solubility	soluble in ethanol, chloroform and DMSO
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 312
	P: 280
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Forskolin (also Colforsin ( INN ), Coleonol ) is in the harp shrub Plectranthus barbatus occurring chemical compound belonging to the group of the diterpene belongs. As a direct stimulator of the enzyme adenylyl cyclase , forskolin has a wide range of effects on the human and animal organism . Therefore it is used experimentally in biochemistry and pharmacology .

Occurrence

Diterpenes are widespread in the genus of the harp shrubs. Forskolin, on the other hand, has so far only been isolated in significant quantities from Plectranthus barbatus ( Coleus forskolii ).

pharmacology

Forskolin (stick model) bound to an adenylyl cyclase (surface model, gray) based on X-ray crystal structure data

Forskolin is a non-selective stimulator of the isoenzymes of the adenylyl cyclase group. With the exception of adenylyl cyclase IX, it activates all isoenzymes in low micromolar concentrations. Forskolin uses hydrophobic interactions to bind within a binding pocket between the C ₁ and C ₂ domains of adenylyl cyclase.

As a result of the enzyme activation, the conversion of adenosine triphosphate (ATP) to the signal substance cyclic adenosine monophosphate (cAMP) is catalyzed in the cell . In this way, forskolin intervenes centrally in the signal transduction pathways of many G-protein-coupled receptors . Therefore, an increase in the cAMP level in the cell caused by forskolin results in numerous biological reactions. It has a positive inotropic effect on the heart . Forskolin has a vasodilator effect in the blood vessels . In addition, it has anti-coagulant , lipolytic and spasmolytic effects under experimental conditions .

use

The forskolin-containing plant Plectranthus barbatus has an ethnopharmacological importance in Ayurvedic medicine as well as in the folk medicines of Brazil , Africa and China . It is used, among other things, for the treatment of gastrointestinal disorders, disorders of the respiratory tract as well as heart and nervous diseases. At least part of its effects are attributed to the ingredient forskolin.

Forskolin is mainly used experimentally as a model substance to increase cellular cAMP levels in basic biochemical and medical research. Due to its diverse effects, a possible use in the therapy of heart disease, asthma , thrombosis and obesity was discussed. Forskolin-containing plant extracts are marketed among bodybuilders as alleged "fat burners", although their effectiveness has not been adequately proven.

Colforsin daropathydrochlorid is a highly water-soluble derivative of colforsin .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Forskolin from Coleus forskohlii, ≥ 98% (HPLC) from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).
↑ ^a ^b Kavitha C, Rajamani K, Vadivel E: Coleus forskohlii: A comprehensive review on morphology, phytochemistry and pharmacological aspects . In: J. Med. Plants Res . 4, No. 4, 2010, pp. 278-285.
↑ Hanoune J, Defer N: Regulation and role of adenylyl cyclase isoforms . In: Annu. Rev. Pharmacol. Toxicol. . 41, 2001, pp. 145-174. doi : 10.1146 / annurev.pharmtox.41.1.145 . PMID 11264454 .
↑ Tang WJ, Hurley JH: Catalytic mechanism and regulation of mammalian adenylyl cyclases . In: Mol Pharmacol . 54, No. 2, August 1998, pp. 231-40. PMID 9687563 .
↑ Daly JW: Forskolin, adenylate cyclase, and cell physiology: an overview . In: Adv Cyclic Nucleotide Protein Phosphorylation Res . 17, 1984, pp. 81-89. PMID 6328947 .
↑ Alasbahi RH, Melzig MF: Plectranthus barbatus: a review of phytochemistry, ethnobotanical uses and pharmacology - Part 1 . In: Planta Med . 76, No. 7, May 2010, pp. 653-61. doi : 10.1055 / s-0029-1240898 . PMID 20178070 .
↑ Shonteh Henderson, Bahrat Magu, Chris Rasmussen, Stacey Lancaster, Chad Kerksick: Effects of Coleus Forskohlii Supplementation on Body Composition and Hematological Profiles in Mildly Overweight Women . In: Journal of the International Society of Sports Nutrition . tape 2 , no. 2 , December 9, 2005, p. 54-62 , PMID 18500958 , PMC 2129145 (free full text).
↑ Kreider RB, Wilborn CD, Taylor L, et al. : ISSN exercise & sport nutrition review: research & recommendations . In: J Int Soc Sports Nutr . 7, 2010, p. 7. doi : 10.1186 / 1550-2783-7-7 . PMID 20181066 . PMC 2853497 (free full text).

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet Forskolin from Coleus forskohlii, ≥ 98% (HPLC) from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

[Kavitha_C_et_al._(2010)-2] Kavitha C, Rajamani K, Vadivel E: Coleus forskohlii: A comprehensive review on morphology, phytochemistry and pharmacological aspects . In: J. Med. Plants Res . 4, No. 4, 2010, pp. 278-285.

[Hanoune_J_and_Defer_N_(2001)-3] Hanoune J, Defer N: Regulation and role of adenylyl cyclase isoforms . In: Annu. Rev. Pharmacol. Toxicol. . 41, 2001, pp. 145-174. doi : 10.1146 / annurev.pharmtox.41.1.145 . PMID 11264454 .

[Tang_WJ_&_Hurley_JH_(1998)-4] Tang WJ, Hurley JH: Catalytic mechanism and regulation of mammalian adenylyl cyclases . In: Mol Pharmacol . 54, No. 2, August 1998, pp. 231-40. PMID 9687563 .

[Daly_JW_(1984)-5] Daly JW: Forskolin, adenylate cyclase, and cell physiology: an overview . In: Adv Cyclic Nucleotide Protein Phosphorylation Res . 17, 1984, pp. 81-89. PMID 6328947 .

[Alasbahi_RH_&_Melzig_MF_(2010)-6] Alasbahi RH, Melzig MF: Plectranthus barbatus: a review of phytochemistry, ethnobotanical uses and pharmacology - Part 1 . In: Planta Med . 76, No. 7, May 2010, pp. 653-61. doi : 10.1055 / s-0029-1240898 . PMID 20178070 .

[7] Shonteh Henderson, Bahrat Magu, Chris Rasmussen, Stacey Lancaster, Chad Kerksick: Effects of Coleus Forskohlii Supplementation on Body Composition and Hematological Profiles in Mildly Overweight Women . In: Journal of the International Society of Sports Nutrition . tape 2 , no. 2 , December 9, 2005, p. 54-62 , PMID 18500958 , PMC 2129145 (free full text).

[Kreider_RB_et_al._(2010)-8] Kreider RB, Wilborn CD, Taylor L, et al. : ISSN exercise & sport nutrition review: research & recommendations . In: J Int Soc Sports Nutr . 7, 2010, p. 7. doi : 10.1186 / 1550-2783-7-7 . PMID 20181066 . PMC 2853497 (free full text).