ダウリシン

ダウリシン
	IUPAC名 4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-(4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)phenol
識別情報
CAS登録番号	524-17-4
PubChem	73400
ChemSpider	66117
ChEBI	CHEBI:4331;
ChEMBL	CHEMBL442717
	SMILES 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;
	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;
特性
化学式	C38H44N2O6
モル質量	624.77 g mol−1
密度	1.186 g/mL
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

ダウリシン(Dauricine)は、フェノール、芳香族エーテル、イソキノリンアルカロイドに分類される植物代謝物である^[1]。どちらもコウモリカズラ属のつる植物であるアジアのMenispermum dauricumと北米のMenispermum canadenseから単離された^[2]。日本の亀谷哲治と福本圭一郎により、アーント・アイシュタート合成とビシュラー・ナピエラルスキー反応を用いて、1964年に初めて合成された^[3]。がん細胞の成長阻害^[4]^[5]^[6]^[7] や心臓の膜貫通Na⁺、K⁺、Ca²⁺イオン電流の遮断作用^[8] についての研究がin vitroで行われている。

出典

^ “CHEBI:4331 - dauricine”. ChEBI. 30 May 2015閲覧。
^ 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 30 May 2015閲覧。
^ Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing et al. (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.
^ 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 30 May 2015閲覧。.
^ 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.

[1] “CHEBI:4331 - dauricine”. ChEBI. 30 May 2015閲覧。

[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 30 May 2015閲覧。

[4] Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing et al. (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.

[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 30 May 2015閲覧。.

[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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