Tetrandrine

Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It has anti-inflammatory, immunologic and antiallergenic effects. It inhibits the degranulation of mast cells. It has a "quinidine-like" anti-arrhythmic effect. It has been isolated from Stephania tetrandra S Moore,[1] and other Chinese and Japanese herbs. It has vasodilatory properties and can therefore reduce blood pressure.[2] Tetrandrine may have potential use for the treatment of liver disease[3] and liver cancer.[4][5][6] Tetrandrine has potential therapeutic value to prevent excess scarring/fibrosis in conjunctiva following trabeculectomy or in patients with severe conjunctival inflammation.[7] Tetrandrine has anti-inflammatory and anti-fibrogenic actions, which make tetrandrine and related compounds potentially useful in the treatment of lung silicosis, liver cirrhosis, and rheumatoid arthritis.[8] Tetrandrine has also been shown to inhibit entry of Ebola virus into host cells in vitro and showed therapeutic efficacy against Ebola in preliminary studies on mice.[9]

Tetrandrine
Names
IUPAC name
9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24(32),25,27(31),35-dodecaene
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.208.615
PubChem CID
UNII
Properties
Chemical formula
C38H42N2O6
Molar mass 622.74988
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biosynthesis

Tetrandrine is biosynthesized from a free radical coupled dimerization of S-N-methylcoclaurine:[10]

Synonyms

Synonyms include fanchinine, fanchinine, hanfangchin A, NSC 77037, (S,S)-(+)-tetrandrine, sinomenine A, TTD, tetrandrin, and d-tetrandrine.[11]

References

  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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