Chemistry:Tetrandrine

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Tetrandrine
Tetrandrine Structural Formula V4.svg
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
3D model (JSmol)
ChEMBL
KEGG
UNII
Properties
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

Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker.[1] It is isolated from the plant Stephania tetrandra,[2] and other Chinese and Japanese herbs.

Pharmacology

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 vasodilatory properties and can therefore reduce blood pressure.[3] Tetrandrine may have potential use for the treatment of liver disease[4] and liver cancer.[5][6][7] Tetrandrine has potential therapeutic value to prevent excess scarring/fibrosis in conjunctiva following trabeculectomy or in patients with severe conjunctival inflammation.[8] 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.[9] 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.[10][1] Tetrandrine has also been studied and patented as a possible treatment for tinnitus.[11][12][13]

Biosynthesis

Tetrandrine is biosynthesized from a free radical coupled dimerization of S-N-methylcoclaurine:[14]

Tetrandrine proposed biosynthesis.png

Synonyms

Synonyms include fanchinine, hanfangchin A, NSC 77037, (S,S)-(+)-tetrandrine, sinomenine A, TTD, tetrandrin, d-tetrandrine, and GW-201.[15][13]

References

  1. ↑ 1.0 1.1 Bhagya, N; Chandrashekar, KR (1 May 2016). "Tetrandrine – A molecule of wide bioactivity". Phytochemistry 125: 5–13. doi:10.1016/j.phytochem.2016.02.005. ISSN 0031-9422. PMID 26899361. Bibcode: 2016PChem.125....5B. https://www.sciencedirect.com/science/article/abs/pii/S0031942216300218. Retrieved 24 February 2022. 
  2. ↑ 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. 
  3. ↑ 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. 
  4. ↑ 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. 
  5. ↑ 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. 
  6. ↑ 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. 
  7. ↑ 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. 
  8. ↑ 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. 
  9. ↑ 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. 
  10. ↑ Sakurai, Yasuteru; Kolokoltsov, Andrey A.; Chen, Cheng-Chang; Tidwell, Michael W.; Bauta, William E.; Klugbauer, Norbert; Grimm, Christian; Wahl-Schott, Christian et al. (2015). "Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment". Science 347 (6225): 995–998. doi:10.1126/science.1258758. PMID 25722412. Bibcode: 2015Sci...347..995S. 
  11. ↑ & Xiaojie Chen"Methods and compositions for treating hearing disorders" US patent 10434097, published 8 October 2019, assigned to Gateway Biotechnology Inc
  12. ↑ "Targeting multiple signaling pathways for tinnitus prevention and treatment (R44DC018759)". US Department of Health & Human Services. https://taggs.hhs.gov/Detail/AwardDetail?arg_AwardNum=R44DC018759&arg_ProgOfficeCode=45. 
  13. ↑ 13.0 13.1 Dyhrfjeld-Johnsen, Jonas; Cederroth, Christopher R. (1 August 2020). "Current Clinical Trials for Tinnitus". Otolaryngologic Clinics of North America 53 (4): 651–666. doi:10.1016/j.otc.2020.03.012. ISSN 0030-6665. PMID 32334870. https://www.oto.theclinics.com/article/S0030-6665(20)30049-9/abstract. Retrieved 24 February 2022. 
  14. ↑ 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. Bibcode: 1980PChem..19.2347B. 
  15. ↑ 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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