Dauricine
Names
Preferred IUPAC name
(11 R ,71 R )-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
CAS Number
524-17-4 Y
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.208.622
UNII
8QTO90G5W5 Y
DTXSID90966808
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
Chemical formula
C 38 H 44 N 2 O 6
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).
Infobox references
Chemical compound
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]
^ "CHEBI:4331 - dauricine". ChEBI . Retrieved 30 May 2015 .
^ Kametani, Tetsuji; Fukumoto, Keiichiro (1964). "Total synthesis of (±)-dauricine". Tetrahedron Letters . 5 (38): 2771–2775. doi:10.1016/S0040-4039(00)71728-X.
^ Manske, R.H.F. (1967). The Alkaloids: Chemistry and Physiology V9 . New York: Academic Press. p. 141. ISBN 9780080865331 . Retrieved 30 May 2015 .
^ 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.
^ 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.
^ 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.
^ 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.
^ Qian, JQ (2002). "Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives". Acta Pharmacol Sin . 23 (12): 1086–92. PMID 12466045.
Last Update: 2021-06-30T15:22:08Z
Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid. It has been isolated from the Asian...
Word Count : 376
Last Update: 2023-07-05T23:53:24Z
plants are known to be poisonous. The principal toxin is the alkaloid dauricine . The fruit of Canada Moonseed are poisonous and can be fatal. While foraging...
Word Count : 516
Last Update: 2024-06-25T23:54:44Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 17896
Last Update: 2024-06-15T16:22:11Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 11401
Last Update: 2022-06-09T07:34:11Z
be poisonous, containing dauricine and related isoquinoline alkaloids, and children have died from eating the fruits. Dauricine inhibits cardiac K+ channels...
Word Count : 587
Last Update: 2024-06-13T06:29:33Z
Oxidative addition of phenols (dauricine , tubocurarine) Lactonization (carpaine). Voacamine Villalstonine Toxiferine Dauricine Tubocurarine Carpaine There...
Word Count : 5413
Last Update: 2024-06-17T06:10:20Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 8632
Last Update: 2024-06-18T19:52:16Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 3270
Last Update: 2023-09-19T03:39:21Z
representatives include dauricin, oxyacanthin, tetrandrine, and tiliacorin. dauricine Oxyacanthine Tiliacorine Tubocurarine Bisbenzylisoquinoline alkaloids...
Word Count : 342
Last Update: 2024-06-26T03:45:02Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 5488
Last Update: 2024-04-05T05:21:37Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 1711
Last Update: 2024-06-25T19:57:03Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 7883
Last Update: 2024-05-26T06:54:59Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 8518
Last Update: 2024-06-22T20:56:04Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 4803
Last Update: 2024-06-07T19:24:56Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 2750
Last Update: 2024-05-25T11:10:50Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 2681
Last Update: 2024-06-24T19:07:49Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 1577
Last Update: 2024-05-31T17:06:21Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 7311
Last Update: 2024-06-05T17:17:45Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 4698
Last Update: 2024-06-24T14:30:09Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 8666
Last Update: 2024-06-12T09:23:52Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 6512
Last Update: 2024-04-20T22:39:28Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 4424
Last Update: 2024-06-17T04:06:45Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 3272
Last Update: 2024-06-17T04:58:56Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 4009
Last Update: 2024-05-18T10:53:09Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 3136
Last Update: 2024-05-31T04:01:36Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 7967
Last Update: 2024-06-04T22:00:09Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 3828
Last Update: 2024-06-06T16:01:46Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 8518
Last Update: 2024-04-27T17:50:35Z
Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione...
Word Count : 4530