Chemistry:Quassinoid

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Chemical structure of quassin

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,[3] and its structure elucidated in 1961. XIX (R1 = H; R2 = CH3) [4]

Sources

More than 200 currently-known quassinoids have been isolated and identified from various species of simaroubaceae family.[5]

Quassinoids can also be extracted from various Simaroubaceae family species such as; Ailanthus excelsa,[6] Ailanthus vilmoriniana,[7] (the fruits of) Brucea javanica,[8] Hannoa klaineana,[9][10] Pierreodendron kerstingii,[11] Quassia africana,[12][13] Quassia amara,[14][15] (the wood of ) Picrasma ailanthoides,[16] Picrasma javanica,[17] Picrolemma pseudocoffea,[18] Simaba guianensis,[19] and Simaruba glauca.[20]

They are found in species from American and West African genera (belonging mainly to the tribe Simaroubeae) and from the East African and Asian genera (belonging mainly to Picrasmeae and Soulameae tribes).[21]

Uses

They are a biologically potent class of natural products, possessing antimalarial,[15][22] antifeedant,[23] insecticidal,[24] anti-inflammatory,[25] and anticancer (or anti-leukemic),[11][26][27] properties. The quassinoid bruceantin reached two separate phase II clinical trials in 1982[28] and 1983.[29]

Other quassinoids include:[30]

  • Bruceanols
  • Bruceolide
  • Eurycomanone
  • Gutolactone
  • Isobrucein A
  • Neoquassin
  • Nigakihemiacetal A
  • Odyendanol[10]
  • Picrasinol D[16]
  • Quassimarin
  • Samaderines
  • Simalikalactones (including Simalikalactones A, B, C,[13] Simalikalactone D [12][14] Simalikalactone E,[31])

References

  1. ↑ Vieira, Studies in Natural Products Chemistry 2006 https://www.researchgate.net/profile/Ivo_Vieira/publication/251467805
  2. ↑ Winckler, F. L. (1835). "Quassin I. The preparation and purification of quassin and neoquassin, with information concerning their molecular formulas". Rep. Pharm. 4: 85. 
  3. ↑ E.P. Clark, J. Amer. Chem. Soc. (1937)
  4. ↑ Valenta, Z.; Papadopoulos, S.; Podešva, C. (1961). "Quassin and Neoquassin". Tetrahedron 15 (1–4): 100–110. doi:10.1016/0040-4020(61)80013-6. 
  5. ↑ Curcino Vieira, I.J.; Braz-Filho, R. (2006). "_structural diversity, biological activity and synthetic studies_". Stud. Nat. Prod. Chem. 33: 433-492.. 
  6. ↑ Joshi, B.C.; Pandei, A.; Sharma, R.P.; Khare, A. (2003). "Quassinoids from Ailanthus excelsa". Phytochemistry 62 (4): 579–584. doi:10.1016/S0031-9422(02)00493-4. PMID 12560029. Bibcode: 2003PChem..62..579J. 
  7. ↑ Takeya, K.; Kobata, H.; Ozeki, A.; Morita, H.; Itokawa, H. (1998). "Quassinoids from Ailanthus vilmoriniana". Phytochemistry 48: 565. 
  8. ↑ Anderson, M.M.; O’Neill, M.J.; Phillipson, J.D.; Warhurst, D.C. (1991). "In vitro cytotoxicity of a series of quassinoids from Brucea javanica fruits against KB cells". Planta Med. 57 (1): 62–64. doi:10.1055/s-2006-960020. PMID 2062960. 
  9. ↑ Lumonadio, L.; Atassi, G.; Vanhaelen, M.; Vanhaelen-Fastre, R. (1991). "Antitumor activity of quassinoids from Hannoa klaineana". J. Ethnopharmacol. 31: 59–65. 
  10. ↑ 10.0 10.1 Donkwe, Suzye Mireille Moladje; Happi, Emmanuel Ngeufa; Wansi, Jean Duplex; Lenta, Bruno Ndjakou; Devkota, Krishna Prasad; Neumann, Beate; Stammler, Hans-Georg; Sewald, Norbert (December 2012). "Oxidative burst inhibitory and cytotoxic activity of constituents of the fruits of Odyendyea gabonensis". Planta Med. 78 (18): 1949-56.. doi:10.1055/s-0032-1327878. PMID 23136063. 
  11. ↑ 11.0 11.1 Kupchan, S.M.; Lacadie, J.A. (1975). "Dehydroailanthinone, a new antileukemic quassinoid from Pierreodendron kerstingii". J. Org. Chem. 40: 654.. 
  12. ↑ 12.0 12.1 Apers, S.; Cimanga, K.; Vanden Berghe, D.; Van Meenen, E.; Longanga, A.O.; Foriers, A.; Vlietinck, A.; Pieters, L. (2002). "Antiviral activity of Simalikalactone D, a quassinoid from Quassia africana". Planta Med. 68 (1): 20–24. doi:10.1055/s-2002-19870. PMID 11842321. 
  13. ↑ 13.0 13.1 Tresca, J.P.; Alais, L.; Polonsky, J. (1971). "Bitter constituents of Quassia africana Baill. (Simarubaceae). Simalikalactones A, B, C and D and simalikaliacetal A.". C. R. Acad.Sci. Paris 273: 601. 
  14. ↑ 14.0 14.1 Bertani, S.; Houël, E.; Stien, D.; Chevolot, L.; Jullian, V.; Garavito, G.; Bourdy, G.; Deharo, E. (2006). "Simalikalactone D is responsible for the antimalarial properties of an amazonian traditional remedy made with Quassia amara L. (Simaroubaceae)". J. Ethnopharmacol. 108 (1): 155–157. doi:10.1016/j.jep.2006.04.017. PMID 16730421. 
  15. ↑ 15.0 15.1 Bertani, S.; Houël, E.; Stien, D.; Chevolot, L.; Jullian, V.; Garavito, G.; Bourdy, G.; Deharo, E. (2012). "New findings on simalikalactone D, an antimalarial compound from Quassia amara L. (Simaroubaceae)". Exp. Parasitol. 130 (4): 341–347. doi:10.1016/j.exppara.2012.02.013. PMID 22374406. 
  16. ↑ 16.0 16.1 Daido, M.; Fukamiya, N.; Okano, M. (1995). "Picrasinol D, a new quassinoid from the stem wood of Picrasma ailanthoides". J. Nat. Prod. 58 (4): 605–608. doi:10.1021/np50118a022. 
  17. ↑ Koike, K.; Ishi, K.; Mitsunaga, K.; Ohmoto, T. (1991). "Quassinoids from Picrasma javanica". Phytochemistry 30 (3): 933–936. doi:10.1016/0031-9422(91)85282-5. Bibcode: 1991PChem..30..933K. 
  18. ↑ Moretti, C.; Polonsky, J.; Vuilhorgne, M.; Prange, T. (1982). "Isolation and structure of sergeolide, a potent cytotoxic quassinoid from Picrolemma pseudocoffea". Tetrahedron Lett 23: 647. 
  19. ↑ Cabral, J.A.; McChesney, J.D.; Milhous, W.K. (1993). "A new anti-malarial quassinoid from Simaba guianensis". J. Nat. Prod. 56: 1954. 
  20. ↑ Moron, J.; Merrien, M.A.; Polonsky, J. (1971). "On the biosynthesis of quassinoids Simaruba glauca (Simarubaceae).". Phytochemistry 10: 585. 
  21. ↑ Simão, Sheila M.; Barreiros, Euclides L.; das G.F. Da Silva, M.Fátima; Gottlieb, Otto R. (1991). "Chemogeographical evolution of quassinoids in simaroubaceae". Phytochemistry 30 (3): 853-865. doi:10.1016/0031-9422(91)85267-4. 
  22. ↑ 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. 
  23. ↑ Leskinen, V.; Polonsky, J.; Bhatnagar, S. (1984). "Antifeedant activity of quassinoids". J. Chem. Ecol. 10 (10): 1497–507. doi:10.1007/BF00990319. PMID 24318349. 
  24. ↑ 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. 
  25. ↑ 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. 
  26. ↑ 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. 
  27. ↑ Fiaschetti, G.; Grotzer, M.A.; Shalaby, T.; Castelletti, D.; Arcaro, A. (2011). "_from traditional drugs to new cancer therapists_". Curr. Med. Chem. 18: 316. 
  28. ↑ 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. 
  29. ↑ 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. 
  30. ↑ "Quassinoid". Chemical Entities of Biological Interest (ChEBI). http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72485. 
  31. ↑ Cachet, N.; Valentin, A.; Jullian, V.; Stien, D.; Houël, E.; Gornitzka, H.; Fillaux, J.; Chevalley, S. et al. (2009). "Antimalarial activity of simalikalactone E, a new quassinoid of Quassia amara L. (Simaroubaceae)". Antimicrob. Agents Ch. 53 (10): 4393–4398. doi:10.1128/AAC.00951-09. PMID 19667291. 

Other sources

  • Z. Guo, S. Vangapandu, R.W. Sindelar, L.A. Walker, R.D. Sindelar., Biologically active quassinoids and their chemistry: potential leads for drug design, Frontier. Med. Chem., 4 (2009), pp. 285-308

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