Quassinoid

Quassinoids are degraded triterpene lactones (similar to limonoids) of the Simaroubaceae plant family grouped into C-18, C-19, C-20, C-22 and C-25 types.[1] The prototypical member of the group, quassin, was first described in the 19th century from plants of the genus Quassia from which it gets its name.[2] It was isolated in 1937 and its structure elucidated in 1961.

Chemical structure of quassin

They are a biologically potent class of natural products, possessing antimalarial,[3] antifeedant,[4] insecticidal,[5] anti-inflammatory,[6] and anticancer[7] properties. The quassinoid bruceantin reached two separate phase II clinical trials in 1982[8] and 1983.[9]

Other quassinoids include:[10]

References
  1. Vieira, Studies in Natural Products Chemistry 2006 https://www.researchgate.net/profile/Ivo_Vieira/publication/251467805
  2. Winckler, F. L. (1835). Rep. Pharm. 4: 85. {{cite journal}}: Missing or empty |title= (help)
  3. Muhammad, I.; Samoylenko, V. (2007). "Antimalarial quassinoids: Past, present and future". Expert Opin Drug Discov. 2 (8): 1065–84. doi:10.1517/17460441.2.8.1065. PMID 23484873. S2CID 24497786.
  4. Leskinen, V.; Polonsky, J.; Bhatnagar, S. (1984). "Antifeedant activity of quassinoids". J. Chem. Ecol. 10 (10): 1497–507. doi:10.1007/BF00990319. PMID 24318349. S2CID 21117128.
  5. Fang, X.; Di, Y. T.; Xhang, Y.; Xu, Z. P.; Lu, Y.; Chen, Q. Q.; Zheng, Q. T.; Hao, X. J. (2015). "Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata". Angew. Chem. Int. Ed. 54 (19): 5592–5. doi:10.1002/anie.201412126. PMID 25810025.
  6. Hall, I. H.; Lee, K. H.; Imakura, Y.; Okano, M.; Johnson, A. (1983). "Anti-inflammatory Agents III: Structure–Activity Relationships of Brusatol and Related Quassinoids". J. Pharm. Sci. 72 (11): 1282–4. doi:10.1002/jps.2600721111. PMID 6417321.
  7. Fukamiya, N.; Lee, K.H.; Muhammad, I., Murakami, C.; Okano, M.; Harvey, I.; Pelletier, J. (2005). "Structure–activity relationships of quassinoids for eukaryotic protein synthesis". Cancer Letters. 220 (1): 37–48. doi:10.1016/j.canlet.2004.04.023. PMID 15737686.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. Wiseman, C. L.; Yap, H. Y.; Bedikian, A. Y.; Bodey, G. P.; Blumenchein, G. R. (1982). "Phase II trial of bruceantin in metastatic breast carcinoma". Am. J. Clin. Oncol. 5 (4): 389–91. doi:10.1097/00000421-198208000-00007. PMID 7113961. S2CID 27632884.
  9. Arsenau, J. C.; Wolter, J. M.; Kuperminc, M.; Ruckdeschel, J. C. (1983). "Anti–inflammatory agents III: Structure–activity relationships of brusatol and related quassinoids". Invest. New Drugs. 1: 239.
  10. "Quassinoid". Chemical Entities of Biological Interest (ChEBI).
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.