Dauricine

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title: "Dauricine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["calcium-channel-blockers", "phenols", "norsalsolinol-ethers", "benzylisoquinoline-alkaloids", "tetrahydroisoquinoline-alkaloids"] topic_path: "general/calcium-channel-blockers" source: "https://en.wikipedia.org/wiki/Dauricine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| ImageFile=Dauricine structure.svg | ImageClass = skin-invert-image | ImageSize= 250 | PIN=(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 | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID = 66117 | 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 | InChIKey = AQASRZOCERRGBL-ROJLCIKYBP | CASNo=524-17-4 | CASNo_Ref = | UNII_Ref = | UNII = 8QTO90G5W5 | PubChem= 73400 | ChEBI = 4331 | ChEMBL = 442717 | SMILES = O(c1cc2c(cc1OC)C@HCc6ccc(Oc3c(O)ccc(c3)C[C@@H]5c4c(cc(OC)c(OC)c4)CCN5C)cc6)C |Section2={{Chembox Properties | C=38 | H=44 | N=2 | O=6 | Appearance= | Density=1.186 g/mL | MeltingPt= 115 °C | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid. It has been isolated from the Asian vine Menispermum dauricum, Asian moonseed, and the North American vine Menispermum canadense, Canadian moonseed. Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so. Dauricine has been studied in vitro for its potential to inhibit cancer cell growth and to block cardiac transmembrane Na+, K+, and Ca2+ ion currents.

References

References

  1. "CHEBI:4331 - dauricine".
  2. (1964). "Total synthesis of (±)-dauricine". Tetrahedron Letters.
  3. (1967). "The Alkaloids: Chemistry and Physiology V9". Academic Press.
  4. (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells". J. Cell. Physiol..
  5. (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice". The Journal of Pharmacology and Experimental Therapeutics.
  6. (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.
  7. (2012). "Dauricine can inhibit the activity of proliferation of urinary tract tumor cells". Asian Pac J Trop Med.
  8. (2002). "Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives". Acta Pharmacol Sin.

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calcium-channel-blockersphenolsnorsalsolinol-ethersbenzylisoquinoline-alkaloidstetrahydroisoquinoline-alkaloids