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 is isolated from the plant Stephania tetrandra,[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
CompTox Dashboard (EPA)
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, Lijin; Geng, Yanling; Duan, Wenjuan; Wang, Daijie; Fu, Maorun; Wang, Xiao (2009). "Ionic liquid-based ultrasound-assisted extraction of fangchinoline and tetrandrine from Stephaniae tetrandrae". Journal of Separation Science. 32 (20): 3550–3554. doi:10.1002/jssc.200900413. PMID 19764054.
  2. Kwan, C. Y.; Achike, F. I. (2002). "Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action". Acta Pharmacologica Sinica. 23 (12): 1057–68. PMID 12466042.
  3. Feng, Dechun; Mei, Yunhua; Wang, Ying; Zhang, Bianhong; Wang, Chen; Xu, Lingyun (2008). "Tetrandrine protects mice from concanavalin A-induced hepatitis through inhibiting NF-κB activation". Immunology Letters. 121 (2): 127–133. doi:10.1016/j.imlet.2008.10.001. PMID 18992279.
  4. Liu, Chaoyang; Gong, Ke; Mao, Xin; Li, Wenhua (2011). "Tetrandrine induces apoptosis by activating reactive oxygen species and repressing Akt activity in human hepatocellular carcinoma". International Journal of Cancer. 129 (6): 1519–1531. doi:10.1002/ijc.25817. PMID 21128229.
  5. Cheng, Zhixiang; Wang, Keming; Wei, Jia; Lu, Xiang; Liu, Baorui (2010). "Proteomic analysis of anti-tumor effects by tetrandrine treatment in HepG2 cells". Phytomedicine. 17 (13): 1000–1005. doi:10.1016/j.phymed.2010.03.018. PMID 20554191.
  6. Deng, W. Y.; Luo, S. X.; Zhou, M. Q.; Li, N.; Chen, X. B.; Han, L. L. (2008). "The study of anti-tumor effect of Tetrandrine combined with Nedaplatin on human liver cancer cell line 7402". Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials. 31 (10): 1522–5. PMID 19230406.
  7. Kitano, Ai; Yamanaka, Osamu; Ikeda, Kazuo; Ishida-Nishikawa, Iku; Okada, Yuka; Shirai, Kumi; Saika, Shizuya (2008). "Tetrandrine Suppresses Activation of Human Subconjunctival Fibroblasts In Vitro". Current Eye Research. 33 (7): 559–565. doi:10.1080/02713680802220817. PMID 18600488.
  8. Kwan, C. Y.; Achike, F. I. (2002). "Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action". Acta Pharmacologica Sinica. 23 (12): 1057–68. PMID 12466042.
  9. Sakurai, Yasuteru; Kolokoltsov, Andrey A.; Chen, Cheng-Chang; Tidwell, Michael W.; Bauta, William E.; Klugbauer, Norbert; Grimm, Christian; Wahl-Schott, Christian; Biel, Martin; Davey, Robert A. (2015). "Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment". Science. 347 (6225): 995–998. Bibcode:2015Sci...347..995S. doi:10.1126/science.1258758. PMC 4550587. PMID 25722412.
  10. Bhakuni, Dewan S.; Jain, Sudha; Singh, Awadhesh N. (1980). "Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine". Phytochemistry. 19 (11): 2347–2350. doi:10.1016/S0031-9422(00)91024-0.
  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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