Tetrandrine

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Tetrandrine
Tetrandrine.png
Identifiers
CAS number 518-34-3 YesY
PubChem 73078
UNII 29EX23D5AJ N
ChEMBL CHEMBL176045 N
Jmol-3D images Image 1
Properties
Molecular formula C38H42N2O6
Molar mass 622.74988
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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]

Biosynthesis[edit]

Tetrandrine is biosynthesized from a free radical coupled dimerization of S-N-methylcoclaurine:[9]

Tetrandrine proposed biosynthesis.png

Synonyms[edit]

Synonyms include fanchinine, fanchinine, hanfangchin A, NSC 77037, (S,S)-(+)-tetrandrine, sinomenine A, TTD, tetrandrin, and d-tetrandrine.[10]

References[edit]

  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. ^ Dewan S. Bhakuni, Sudha Jain, Awadhesh N. Singh. "Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine" Phytochemistry (1980); 19(11):2347–2350
  10. ^ Tetrandrine(Fanchinine) | CAS 518-34-3 | calcium channel Inhibitor | Fanchinine, Hanfangchin A, NSC 77037, S,S-(+)-Tetrandrine, Sinomenine A, TTD, Tetrandrin, d...