テトランドリン

テトランドリン
	IUPAC名 6,6',7,12-tetramethoxy-2,2'-dimethyl-1 beta-berbaman
識別情報
CAS登録番号	518-34-3
PubChem	73078
UNII	29EX23D5AJ
KEGG	C09654
ChEMBL	CHEMBL176045
	SMILES CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)OC)OC;
特性
化学式	C38H42N2O6
モル質量	622.74988
	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。

テトランドリン（Tetrandrine）はビス-イソキノリン系のアルカロイドであり、カルシウムチャネル阻害作用を持つ。また肥満細胞の脱顆粒を抑制するので抗炎症作用、抗アレルギー作用を持つ。そのほか、「キニジン様」の抗不整脈作用を持つ。シマハスノハカズラ（学名：Stephania tetrandra S Moore）から単離^[1]された他、中国や日本の草木に含まれている。血管拡張作用を持ち、血圧を低下させる^[2]。

テトランドリンは肝障害の治療^[3]や肝癌の治療^[4]^[5]^[6]に有用である可能性がある。線維柱帯切除術施行後患者または重度の結膜炎患者に対する結膜の過剰な瘢痕化・線維化を予防できると期待される^[7]。テトランドリンならびにその誘導体の抗炎症・抗線維化効果は、珪肺、肝硬変、関節リウマチの治療に応用できる可能性がある^[8]。テトランドリンはin vitro でエボラウイルスの宿主細胞への侵入を阻止し、マウスを用いた初期研究でエボラ出血熱の治療効果を示した^[9]。

生合成

テトランドリンはS-N-メチルコクラウリンのラジカル二量化により合成される^[10]。

別名

ファンチニン（Fanchinine）、ハンファンチンA（hanfangchin A）、NSC-77037、(S,S)-(+)-テトランドリン、シノメニンA（sinomenine A）、d-テトランドリン^[11]

出典

^ Zhang L, Geng Y, Duan W, Wang D, Fu M, Wang X.,"Ionic liquid-based ultrasound-assisted extraction of fangchinoline and tetrandrine from Stephaniae tetrandrae. J Sep Sci. 2009 Oct;32(20):3550-4
^ Kwan CY, Achike FI.,"Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: cardiovascular effects and mechanisms of action." Acta Pharmacol Sin. 2002 Dec;23(12):1057-68.
^ Feng D, Mei Y, Wang Y, Zhang B, Wang C, Xu L.,"Tetrandrine protects mice from concanavalin A-induced hepatitis through inhibiting NF-kappaB activation." Immunol Lett. 2008 Dec 22;121(2):127-33
^ Liu C, Gong K, Mao X, Li W.,"Tetrandrine induces apoptosis by activating reactive oxygen species and repressing Akt activity in human hepatocellular carcinoma." Int J Cancer. 2011 Sep 15;129(6):1519-31
^ Cheng Z, Wang K, Wei J, Lu X, Liu B"Proteomic analysis of anti-tumor effects by tetrandrine treatment in HepG2 cells." Phytomedicine. 2010 Nov;17(13):1000-5
^ Zhong Yao Cai. .,"[The study of anti-tumor effect of Tetrandrine combined with Nedaplatin on human liver cancer cell line 7402]" 2008 Oct;31(10):1522-5 Authors: Deng WY, Luo SX, Zhou MQ, Li N, Chen XB, Han LL
^ Kitano A, Yamanaka O, Ikeda K, Ishida-Nishikawa I, Okada Y, Shirai K, Saika S"Tetrandrine suppresses activation of human subconjunctival fibroblasts in vitro." Curr Eye Res. 2008 Jul;33(7):559-65
^ Kwan CY, Achike FI.,"Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: cardiovascular effects and mechanisms of action." Acta Pharmacol Sin. 2002 Dec;23(12):1057-68.
^ Sakurai Y, et al. Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment. Science 2015;347(6225):995-998. DOI 10.1126/science.1258758
^ Dewan S. Bhakuni, Sudha Jain, Awadhesh N. Singh. "Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine" Phytochemistry (1980); 19(11):2347–2350
^ Tetrandrine(Fanchinine) | CAS 518-34-3 | calcium channel Inhibitor | Fanchinine, Hanfangchin A, NSC 77037, S,S-(+)-Tetrandrine, Sinomenine A, TTD, Tetrandrin, d...

[1] Zhang L, Geng Y, Duan W, Wang D, Fu M, Wang X.,"Ionic liquid-based ultrasound-assisted extraction of fangchinoline and tetrandrine from Stephaniae tetrandrae. J Sep Sci. 2009 Oct;32(20):3550-4

[2] Kwan CY, Achike FI.,"Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: cardiovascular effects and mechanisms of action." Acta Pharmacol Sin. 2002 Dec;23(12):1057-68.

[3] Feng D, Mei Y, Wang Y, Zhang B, Wang C, Xu L.,"Tetrandrine protects mice from concanavalin A-induced hepatitis through inhibiting NF-kappaB activation." Immunol Lett. 2008 Dec 22;121(2):127-33

[4] Liu C, Gong K, Mao X, Li W.,"Tetrandrine induces apoptosis by activating reactive oxygen species and repressing Akt activity in human hepatocellular carcinoma." Int J Cancer. 2011 Sep 15;129(6):1519-31

[5] Cheng Z, Wang K, Wei J, Lu X, Liu B"Proteomic analysis of anti-tumor effects by tetrandrine treatment in HepG2 cells." Phytomedicine. 2010 Nov;17(13):1000-5

[6] Zhong Yao Cai. .,"[The study of anti-tumor effect of Tetrandrine combined with Nedaplatin on human liver cancer cell line 7402]" 2008 Oct;31(10):1522-5 Authors: Deng WY, Luo SX, Zhou MQ, Li N, Chen XB, Han LL

[7] Kitano A, Yamanaka O, Ikeda K, Ishida-Nishikawa I, Okada Y, Shirai K, Saika S"Tetrandrine suppresses activation of human subconjunctival fibroblasts in vitro." Curr Eye Res. 2008 Jul;33(7):559-65

[8] Kwan CY, Achike FI.,"Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: cardiovascular effects and mechanisms of action." Acta Pharmacol Sin. 2002 Dec;23(12):1057-68.

[9] Sakurai Y, et al. Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment. Science 2015;347(6225):995-998. DOI 10.1126/science.1258758

[10] Dewan S. Bhakuni, Sudha Jain, Awadhesh N. Singh. "Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine" Phytochemistry (1980); 19(11):2347–2350

[11] Tetrandrine(Fanchinine) | CAS 518-34-3 | calcium channel Inhibitor | Fanchinine, Hanfangchin A, NSC 77037, S,S-(+)-Tetrandrine, Sinomenine A, TTD, Tetrandrin, d...

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