Canadin

Structural formula
General
Surname	Canadin
other names	Xanthopuccin; ( S ) -tetrahydroberine; ( S ) -Canadine; (-) - Canadin;
Molecular formula	C 20 H 21 NO 4
External identifiers / databases
EC number	208-338-2
ECHA InfoCard	100.007.582
PubChem	21171
ChemSpider	19910
Wikidata	Q4382087
properties
Molar mass	339.4 g mol −1
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 264-270-301 + 312 + 330
Toxicological data	940 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Canadine is a benzylisoquinoline alkaloid (BIA) from the structural subgroup of protoberberine alkaloids .

Occurrence

Canadian orange root

Canadin is found primarily in the Canadian orange root . But it is also present in many plants of the Papaveraceae family , such as B. Corydalis yanhusuo and Corydalis turchaninovii .

Extraction and presentation

Canadin contains - like the other protoberberine alkaloids - a benzylisoquinoline structural unit. The so-called berberine bridge is thereby formed. This is done by oxidative cyclization involving the nitrogen - methyl group . The full synthesis usually begins with a phenylethylamine . There the isoquinoline ring is closed by a Bischler-Napieralski reaction .

properties

Canadin has various effects in vitro : It stimulates myogenesis and inhibits the breakdown of muscle proteins. It also blocks K (ATP) channels in dopamine . It can also block voltage-dependent calcium channels , but the effect is significantly lower than that of verapamil .

Individual evidence

↑ ^a ^b ^c Canadine data sheet at Sigma-Aldrich , accessed on May 29, 2020 ( PDF ).

↑ Entry on Protoberberine Alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on July 5, 2020.

↑ Hyejin Lee, Sang-Jin Lee, Gyu-Un Bae, Nam-In Baek, Jae-Ha Ryu: Canadine from Corydalis turtschaninovii Stimulates Myoblast Differentiation and Protects against Myotube Atrophy . In: International Journal of Molecular Sciences . 18, No. 12, 2017, p. 2748. doi : 10.3390 / ijms18122748 . PMID 29258243 . PMC 5751347 (free full text).

↑ Chen Wu, Kechun Yang, Qiang Liu, Matoko Wakui, Guo-zhang Jin, Xuechu Zhen, Jie Wu: Tetrahydroberberine blocks ATP-sensitive potassium channels in dopamine neurons acutely-dissociated from rat substantia nigra pars compacta . In: Neuropharmacology . 59, No. 7-8, 2010, pp. 567-72. doi : 10.1016 / j.neuropharm.2010.08.018 . PMID 20804776 .

↑ Jie Wu, Guo Zhang Jin: Tetrahydroberberine blocks membrane K + channels underlying its inhibition of intracellular message-mediated outward currents in acutely dissociated CA1 neurons from rat hippocampus . In: Brain Research . 775, No. 1-2, 1997, pp. 214-8. doi : 10.1016 / s0006-8993 (97) 00960-8 . PMID 9439847 .

↑ S Yang, YS Miao, Q Han, MH Jiang, GZ Jin: Effects of (-) - stepholidine and tetrahydroberberine on high potassium-evoked contraction and calcium influx in rat artery . In: Zhongguo Yao Li Xue Bao . 14, No. 3, 1993, pp. 235-237. PMID 8237399 .

[Sigma-1] Canadine data sheet at Sigma-Aldrich , accessed on May 29, 2020 ( PDF ).

[Römpp-2] Entry on Protoberberine Alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on July 5, 2020.

[3] Hyejin Lee, Sang-Jin Lee, Gyu-Un Bae, Nam-In Baek, Jae-Ha Ryu: Canadine from Corydalis turtschaninovii Stimulates Myoblast Differentiation and Protects against Myotube Atrophy . In: International Journal of Molecular Sciences . 18, No. 12, 2017, p. 2748. doi : 10.3390 / ijms18122748 . PMID 29258243 . PMC 5751347 (free full text).

[4] Chen Wu, Kechun Yang, Qiang Liu, Matoko Wakui, Guo-zhang Jin, Xuechu Zhen, Jie Wu: Tetrahydroberberine blocks ATP-sensitive potassium channels in dopamine neurons acutely-dissociated from rat substantia nigra pars compacta . In: Neuropharmacology . 59, No. 7-8, 2010, pp. 567-72. doi : 10.1016 / j.neuropharm.2010.08.018 . PMID 20804776 .

[5] Jie Wu, Guo Zhang Jin: Tetrahydroberberine blocks membrane K + channels underlying its inhibition of intracellular message-mediated outward currents in acutely dissociated CA1 neurons from rat hippocampus . In: Brain Research . 775, No. 1-2, 1997, pp. 214-8. doi : 10.1016 / s0006-8993 (97) 00960-8 . PMID 9439847 .

[6] S Yang, YS Miao, Q Han, MH Jiang, GZ Jin: Effects of (-) - stepholidine and tetrahydroberberine on high potassium-evoked contraction and calcium influx in rat artery . In: Zhongguo Yao Li Xue Bao . 14, No. 3, 1993, pp. 235-237. PMID 8237399 .