Dauricin

Structural formula
General
Surname	Dauricin
other names	4 - {[(1 R ) -6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl] methyl} -2- (4 - {[(1 R ) -6, 7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl] methyl} phenoxy) phenol ( IUPAC );
Molecular formula	C 38 H 44 N 2 O 6
External identifiers / databases
EC number	683-103-9
ECHA InfoCard	100.208.622
PubChem	73400
ChemSpider	66117
Wikidata	Q5228100
properties
Molar mass	624.778 g mol −1
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dauricin is a chemical compound from the group of phenolic isoquinoline - alkaloids .

properties

Dauricin is a secondary plant substance in the plants Menispermum dauricum and Menispermum canadense . Dauricin or M. dauricum root preparations are used in China to treat ischemia , angina , arrhythmia and inflammatory diseases . Dauricin modulates Ca ²⁺ - and some Na ⁺ - ion channels . Dauricin has anti- tumor effects in cell cultures by inducing autophagy . The biotransformation of Dauricin leads to a quinone methide, which leads to adducts of proteins and is believed to be toxic. In 1964, Dauricin was first synthesized by Tetsuji Kametani and Keiichiro Fukumoto via the Arndt-Eistert reaction and the Bischler-Napieralski reaction . Dauricin can be detected in the urine by LC-MS .

Individual evidence

↑ ^a ^b data sheet Dauricine, phyproof at Sigma-Aldrich , accessed on November 5, 2019 ( PDF ).
^ RHF Manske: The Alkaloids: Chemistry and Physiology , Volume 9. Academic Press, 1967. ISBN 9780080865331 . P. 141.
↑ JQ Qian: Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives. In: Acta pharmacologica Sinica. Volume 23, Number 12, December 2002, pp. 1086-1092, PMID 12466045 .
↑ KY Feng, CJ Hu, JA Zhou: [Clinical observations on sustained arrhythmias treated with dauricine]. In: Zhonghua xin xue guan bing za zhi. Volume 12, Number 4, December 1984, pp. 265-7, 315, PMID 6544209 .
↑ ^a ^b J. Zhao, Y. Lian, C. Lu, L. Jing, H. Yuan, S. Peng: Inhibitory effects of a bisbenzylisoquinline alkaloid dauricine on HERG potassium channels. In: Journal of ethnopharmacology. Volume 141, Number 2, June 2012, pp. 685-691, doi : 10.1016 / j.jep.2011.08.054 , PMID 21920426 .
↑ Z. Yang, C. Li, X. Wang, C. Zhai, Z. Yi, L. Wang, B. Liu, B. Du, H. Wu, X. Guo, M. Liu, D. Li, J Luo: Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells. In: Journal of cellular physiology. Volume 225, Number 1, October 2010, pp. 266-275, doi : 10.1002 / jcp.22261 , PMID 20509140 .
↑ H. Jin, J. Dai, X. Chen, J. Liu, D. Zhong, Y. Gu, J. Zheng: Pulmonary toxicity and metabolic activation of dauricine in CD-1 mice. In: The Journal of pharmacology and experimental therapeutics. Volume 332, Number 3, March 2010, pp. 738-746, doi : 10.1124 / jpet.109.162297 , PMID 20008063 .
↑ XD Tang, X. Zhou, KY Zhou: Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells. In: Acta pharmacologica Sinica. Volume 30, number 5, May 2009, pp. 605-616, doi : 10.1038 / aps.2009.8 , PMID 19349962 , PMC 4002832 (free full text).
^ S. Byun, E. Lee, KW Lee: Therapeutic Implications of Autophagy Inducers in Immunological Disorders, Infection, and Cancer. In: International Journal of Molecular Sciences . Volume 18, number 9, September 2017, p., Doi : 10.3390 / ijms18091959 , PMID 28895911 , PMC 5618608 (free full text).
↑ H. Xie, Y. Liu, Y. Peng, D. Zhao, J. Zheng: Detection of protein adduction derived from dauricine by alkaline permethylation. In: Analytical and bioanalytical chemistry. Volume 408, Number 15, June 2016, pp. 4111-4119, doi : 10.1007 / s00216-016-9505-0 , PMID 27071763 .
↑ Tetsuji Kametani, Keiichiro Fukumoto: Total synthesis of (±) -dauricine . In: Tetrahedron Letters . 5, No. 38, 1964, pp. 2771-2775. doi : 10.1016 / S0040-4039 (00) 71728-X .
↑ FM Han, ZH Peng, W. Song, HM Zhang, MM Zhu, Y. Chen: Identification of dauricine and its metabolites in rat urine by liquid chromatography-tandem mass spectrometry. In: Journal of Chromatography B . Volume 854, Number 1–2, July 2007, pp. 1–7, doi : 10.1016 / j.jchromb.2007.03.036 , PMID 17448738 .

[Sigma-1] ta sheet Dauricine, phyproof at Sigma-Aldrich , accessed on November 5, 2019 ( PDF ).

[2] RHF Manske: The Alkaloids: Chemistry and Physiology , Volume 9. Academic Press, 1967. ISBN 9780080865331 . P. 141.

[3] JQ Qian: Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives. In: Acta pharmacologica Sinica. Volume 23, Number 12, December 2002, pp. 1086-1092, PMID 12466045 .

[4] KY Feng, CJ Hu, JA Zhou: [Clinical observations on sustained arrhythmias treated with dauricine]. In: Zhonghua xin xue guan bing za zhi. Volume 12, Number 4, December 1984, pp. 265-7, 315, PMID 6544209 .

[Zhao-5] J. Zhao, Y. Lian, C. Lu, L. Jing, H. Yuan, S. Peng: Inhibitory effects of a bisbenzylisoquinline alkaloid dauricine on HERG potassium channels. In: Journal of ethnopharmacology. Volume 141, Number 2, June 2012, pp. 685-691, doi : 10.1016 / j.jep.2011.08.054 , PMID 21920426 .

[6] Z. Yang, C. Li, X. Wang, C. Zhai, Z. Yi, L. Wang, B. Liu, B. Du, H. Wu, X. Guo, M. Liu, D. Li, J Luo: Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells. In: Journal of cellular physiology. Volume 225, Number 1, October 2010, pp. 266-275, doi : 10.1002 / jcp.22261 , PMID 20509140 .

[7] H. Jin, J. Dai, X. Chen, J. Liu, D. Zhong, Y. Gu, J. Zheng: Pulmonary toxicity and metabolic activation of dauricine in CD-1 mice. In: The Journal of pharmacology and experimental therapeutics. Volume 332, Number 3, March 2010, pp. 738-746, doi : 10.1124 / jpet.109.162297 , PMID 20008063 .

[8] XD Tang, X. Zhou, KY Zhou: Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells. In: Acta pharmacologica Sinica. Volume 30, number 5, May 2009, pp. 605-616, doi : 10.1038 / aps.2009.8 , PMID 19349962 , PMC 4002832 (free full text).

[9] S. Byun, E. Lee, KW Lee: Therapeutic Implications of Autophagy Inducers in Immunological Disorders, Infection, and Cancer. In: International Journal of Molecular Sciences . Volume 18, number 9, September 2017, p., Doi : 10.3390 / ijms18091959 , PMID 28895911 , PMC 5618608 (free full text).

[10] H. Xie, Y. Liu, Y. Peng, D. Zhao, J. Zheng: Detection of protein adduction derived from dauricine by alkaline permethylation. In: Analytical and bioanalytical chemistry. Volume 408, Number 15, June 2016, pp. 4111-4119, doi : 10.1007 / s00216-016-9505-0 , PMID 27071763 .

[11] Tetsuji Kametani, Keiichiro Fukumoto: Total synthesis of (±) -dauricine . In: Tetrahedron Letters . 5, No. 38, 1964, pp. 2771-2775. doi : 10.1016 / S0040-4039 (00) 71728-X .

[12] FM Han, ZH Peng, W. Song, HM Zhang, MM Zhu, Y. Chen: Identification of dauricine and its metabolites in rat urine by liquid chromatography-tandem mass spectrometry. In: Journal of Chromatography B . Volume 854, Number 1–2, July 2007, pp. 1–7, doi : 10.1016 / j.jchromb.2007.03.036 , PMID 17448738 .