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Dauricine

From Wikipedia, the free encyclopedia

Dauricine
Names
Preferred IUPAC name
(11R,71R)-16,17,76,77-Tetramethoxy-12,72-dimethyl-11,12,13,14,71,72,73,74-octahydro-4-oxa-1,7(1)-diisoquinolina-3(1,3),5(1,4)-dibenzenaheptaphan-34-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.208.622Edit this at Wikidata
UNII
  • InChI=1/C38H44N2O6/c1-39-15-13-26-20-35(42-3)37(44-5)22-29(26)31(39)17-24-7-10-28(11-8-24)46-34-19-25(9-12-33(34)41)18-32-30-23-38(45-6)36(43-4)21-27(30)14-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3/t31-,32-/m1/s1
    Key: AQASRZOCERRGBL-ROJLCIKYBP
  • O(c1cc2c(cc1OC)[C@H](N(C)CC2)Cc6ccc(Oc3c(O)ccc(c3)C[C@@H]5c4c(cc(OC)c(OC)c4)CCN5C)cc6)C
Properties
C38H44N2O6
Molar mass624.778 g·mol−1
Density1.186 g/mL
Melting point115 °C
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Dauricine is a plantmetabolite, chemically classified as aphenol, an aromaticether, and an isoquinolinealkaloid.[1] It has been isolated from the Asian vineMenispermum dauricum, Asian moonseed, and the North American vineMenispermum canadense, Canadian moonseed.[2] Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both theArndt-Eistert reaction andBischler-Napieralski reaction to do so.[3] Dauricine has been studiedin vitro for its potential to inhibit cancer cell growth[4][5][6][7] and to block cardiac transmembrane Na+, K+, and Ca2+ ion currents.[8]

References

[edit]
  1. ^"CHEBI:4331 - dauricine".ChEBI. Retrieved30 May 2015.
  2. ^Kametani, Tetsuji; Fukumoto, Keiichiro (1964). "Total synthesis of (±)-dauricine".Tetrahedron Letters.5 (38):2771–2775.doi:10.1016/S0040-4039(00)71728-X.
  3. ^Manske, R.H.F. (1967).The Alkaloids: Chemistry and Physiology V9. New York: Academic Press. p. 141.ISBN 9780080865331. Retrieved30 May 2015.
  4. ^Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing; Wu, Huihui; Guo, Xizhi; Liu, Mingyao; Li, Dali; Luo, Jian (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells".J. Cell. Physiol.225 (1):266–75.doi:10.1002/jcp.22261.PMID 20509140.S2CID 5501319.
  5. ^Jin, Hua; Dai, Jieyu; Chen, Xiaoyan; Liu, Jia; Zhong, Dafang; Gu, Yansong; Zheng, Jiang (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice".The Journal of Pharmacology and Experimental Therapeutics.332 (3):738–46.doi:10.1124/jpet.109.162297.PMID 20008063.S2CID 21824941.
  6. ^Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009)."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".Acta Pharmacol Sin.30 (5):605–16.doi:10.1038/aps.2009.8.PMC 4002832.PMID 19349962.
  7. ^Wang, Jun; Li, Yuan; Zu, Xiong-Bing; Chen, Min-Feng; Qi, Li (2012)."Dauricine can inhibit the activity of proliferation of urinary tract tumor cells".Asian Pac J Trop Med.5 (12):973–76.doi:10.1016/S1995-7645(12)60185-0.PMID 23199717.
  8. ^Qian, JQ (2002). "Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives".Acta Pharmacol Sin.23 (12):1086–92.PMID 12466045.
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
Retrieved from "https://en.wikipedia.org/w/index.php?title=Dauricine&oldid=1329467077"
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