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
CAS Number	524-17-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4331;
ChEMBL	ChEMBL442717;
ChemSpider	66117;
ECHA InfoCard	100.208.622
PubChem CID	73400;
UNII	8QTO90G5W5 ;
CompTox Dashboard (EPA)	DTXSID90966808 ;
	InChI 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;
	SMILES O(c1cc2c(cc1OC)(N(C)CC2)Cc6ccc(Oc3c(O)ccc(c3)C5c4c(cc(OC)c(OC)c4)CCN5C)cc6)C;
Properties
Chemical formula	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 , 100 kPa). Infobox references

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]

References

^ "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.

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[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.

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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
CAS Number	524-17-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4331
ChEMBL	ChEMBL442717
ChemSpider	66117
ECHA InfoCard	100.208.622
PubChem CID	73400
UNII	8QTO90G5W5^Y
CompTox Dashboard (EPA)	DTXSID90966808
InChI 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
SMILES O(c1cc2c(cc1OC)(N(C)CC2)Cc6ccc(Oc3c(O)ccc(c3)C5c4c(cc(OC)c(OC)c4)CCN5C)cc6)C
Properties
Chemical formula	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 , 100 kPa). Infobox references