Dauricine

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 InfoCard 100.208.622 Edit 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 mass 624.778 g·mol−1
Density 1.186 g/mL
Melting point 115 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ↑ "CHEBI:4331 - dauricine". ChEBI. Retrieved 30 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. Retrieved 30 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.