Wikipedia

Dauricine

Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid.[1] It has been isolated from the Asian vine Menispermum dauricum, commonly known as Asian moonseed, and the North American vine Menispermum canadense, commonly known as Canadian moonseed.[2] 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.[3] Dauricine has been studied in 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]

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).

References

edit
  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.2771-2775&rft.date=1964&rft_id=info:doi/10.1016/S0040-4039(00)71728-X&rft.aulast=Kametani&rft.aufirst=Tetsuji&rft.au=Fukumoto, Keiichiro&rfr_id=info:sid/en.wikipedia.org:Dauricine" class="Z3988">
  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 5501319.266-75&rft.date=2010&rft_id=https://api.semanticscholar.org/CorpusID:5501319#id-name=S2CID&rft_id=info:pmid/20509140&rft_id=info:doi/10.1002/jcp.22261&rft.aulast=Yang&rft.aufirst=Zhengfeng&rft.au=Li, Chenghai&rft.au=Wang, Xiu&rft.au=Zhai, Chunyan&rft.au=Yi, Zhengfang&rft.au=Wang, Lei&rft.au=Liu, Bisheng&rft.au=Du, Bing&rft.au=Wu, Huihui&rft.au=Guo, Xizhi&rft.au=Liu, Mingyao&rft.au=Li, Dali&rft.au=Luo, Jian&rfr_id=info:sid/en.wikipedia.org:Dauricine" class="Z3988">
  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 21824941.738-46&rft.date=2009&rft_id=https://api.semanticscholar.org/CorpusID:21824941#id-name=S2CID&rft_id=info:pmid/20008063&rft_id=info:doi/10.1124/jpet.109.162297&rft.aulast=Jin&rft.aufirst=Hua&rft.au=Dai, Jieyu&rft.au=Chen, Xiaoyan&rft.au=Liu, Jia&rft.au=Zhong, Dafang&rft.au=Gu, Yansong&rft.au=Zheng, Jiang&rfr_id=info:sid/en.wikipedia.org:Dauricine" class="Z3988">
  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 19349962.605-16&rft.date=2009&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4002832#id-name=PMC&rft_id=info:pmid/19349962&rft_id=info:doi/10.1038/aps.2009.8&rft.aulast=Tang&rft.aufirst=Xu-dong&rft.au=Zhou, Xin&rft.au=Zhou, Ke-yuan&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4002832&rfr_id=info:sid/en.wikipedia.org:Dauricine" class="Z3988">
  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 23199717.973-76&rft.date=2012&rft_id=info:doi/10.1016/S1995-7645(12)60185-0&rft_id=info:pmid/23199717&rft.aulast=Wang&rft.aufirst=Jun&rft.au=Li, Yuan&rft.au=Zu, Xiong-Bing&rft.au=Chen, Min-Feng&rft.au=Qi, Li&rft_id=https://doi.org/10.1016%2FS1995-7645%2812%2960185-0&rfr_id=info:sid/en.wikipedia.org:Dauricine" class="Z3988">
  8. ^ Qian, JQ (2002). "Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives". Acta Pharmacol Sin. 23 (12): 1086–92. PMID 12466045.1086-92&rft.date=2002&rft_id=info:pmid/12466045&rft.aulast=Qian&rft.aufirst=JQ&rfr_id=info:sid/en.wikipedia.org:Dauricine" class="Z3988">
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