Quassinoid

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File:Quassin test ACS.png
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.[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]

Properties and effects

In addition to their intensely bitter taste, they exhibit antifeedant activity against insects.[32] An antileukemic effect has also been reported.[33][34] Furthermore, numerous studies have attributed antiviral, antiparasitic (particularly antimalarial[35]), insecticidal, amoebicidal, and anti-inflammatory properties to many quassinoids.[32]

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Curcino Vieira, Ivo J.; Braz-Filho, Raimundo (2006). Quassinoids: Structural Diversity, Biological Activity and Synthetic Studies. Studies in Natural Products Chemistry. Vol. 33. pp. 433–492. doi:10.1016/S1572-5995(06)80032-3. ISBN 978-0-444-52717-2.
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Curcino Vieira, I.J.; Braz-Filho, R. (2006). "_structural diversity, biological activity and synthetic studies_". Stud. Nat. Prod. Chem. 33: 433–492. doi:10.1016/S1572-5995(06)80032-3.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Joshi, B.C.; Pandei, A.; Sharma, R.P.; Khare, A. (2003). "Quassinoids from Ailanthus excelsa". Phytochemistry. 62 (4): 579–584. Bibcode:2003PChem..62..579J. doi:10.1016/S0031-9422(02)00493-4. PMID 12560029.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Takeya, K.; Kobata, H.; Ozeki, A.; Morita, H.; Itokawa, H. (1998). "Quassinoids from Ailanthus vilmoriniana". Phytochemistry. 48 (3): 565. Bibcode:1998PChem..48..565T. doi:10.1016/S0031-9422(97)00893-5.
  8. ^ Page Module:Citation/CS1/styles.css has no content.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. S2CID 21082303.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Lumonadio, L.; Atassi, G.; Vanhaelen, M.; Vanhaelen-Fastre, R. (1991). "Antitumor activity of quassinoids from Hannoa klaineana". J. Ethnopharmacol. 31 (1): 59–65. doi:10.1016/0378-8741(91)90144-3. PMID 2030594.
  10. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ a b Page Module:Citation/CS1/styles.css has no content.Kupchan, S.M.; Lacadie, J.A. (1975). "Dehydroailanthinone, a new antileukemic quassinoid from Pierreodendron kerstingii". J. Org. Chem. 40 (5): 654–656. doi:10.1021/jo00893a024. PMID 1133628.
  12. ^ a b Page Module:Citation/CS1/styles.css has no content.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. S2CID 260284246.
  13. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Koike, K.; Ishi, K.; Mitsunaga, K.; Ohmoto, T. (1991). "Quassinoids from Picrasma javanica". Phytochemistry. 30 (3): 933–936. Bibcode:1991PChem..30..933K. doi:10.1016/0031-9422(91)85282-5.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Moretti, C.; Polonsky, J.; Vuilhorgne, M.; Prange, T. (1982). "Isolation and structure of sergeolide, a potent cytotoxic quassinoid from Picrolemma pseudocoffea". Tetrahedron Lett. 23 (6): 647. doi:10.1016/S0040-4039(00)86912-9.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Cabral, J.A.; McChesney, J.D.; Milhous, W.K. (1993). "A new anti-malarial quassinoid from Simaba guianensis". J. Nat. Prod. 56 (11): 1954–1961. doi:10.1021/np50101a014. PMID 8289064.
  20. ^ Page Module:Citation/CS1/styles.css has no content.Moron, J.; Merrien, M.A.; Polonsky, J. (1971). "On the biosynthesis of quassinoids Simaruba glauca (Simarubaceae)". Phytochemistry. 10: 585. doi:10.1016/S0031-9422(00)94702-2.
  21. ^ Page Module:Citation/CS1/styles.css has no content.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. Bibcode:1991PChem..30..853S. doi:10.1016/0031-9422(91)85267-4.
  22. ^ Page Module:Citation/CS1/styles.css has no content.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.
  23. ^ Page Module:Citation/CS1/styles.css has no content.Leskinen, V.; Polonsky, J.; Bhatnagar, S. (1984). "Antifeedant activity of quassinoids". J. Chem. Ecol. 10 (10): 1497–507. Bibcode:1984JCEco..10.1497L. doi:10.1007/BF00990319. PMID 24318349. S2CID 21117128.
  24. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Fiaschetti, G.; Grotzer, M.A.; Shalaby, T.; Castelletti, D.; Arcaro, A. (2011). "_from traditional drugs to new cancer therapists_". Curr. Med. Chem. 18 (3): 316–328. doi:10.2174/092986711794839205. PMID 21143123.
  28. ^ Page Module:Citation/CS1/styles.css has no content.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.
  29. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Quassinoid". Chemical Entities of Biological Interest (ChEBI).
  31. ^ Page Module:Citation/CS1/styles.css has no content.Cachet, N.; Valentin, A.; Jullian, V.; Stien, D.; Houël, E.; Gornitzka, H.; Fillaux, J.; Chevalley, S.; Hoakwe, F.; Bertani, S.; Bourdy, G.; Deharo, E. (2009). "Antimalarial activity of simalikalactone E, a new quassinoid of Quassia amara L. (Simaroubaceae)". Antimicrobial Agents and Chemotherapy. 53 (10): 4393–4398. doi:10.1128/AAC.00951-09. PMC 2764154. PMID 19667291.
  32. ^ a b Jürgen Falbe, Manfred Regitz (Hrsg.): Römpp Chemie Lexikon, 9. Auflage, Georg Thieme Verlag, Stuttgart 1990, ISBN 3-13-735009-3, S. 3735–3736.
  33. ^ Judith Polonsky: Quassinoid Bitter Principles II, Fortschritte der Chemie organischer Naturstoffe, Nr. 47, 1985, S. 221–264, doi:10.1007/978-3-7091-8790-6_4.
  34. ^ Page Module:Citation/CS1/styles.css has no content.G. Fiaschetti, M. A. Grotzer, T. Shalaby, D. Castelletti, A. Arcaro (2011), "Quassinoids: From traditional drugs to new cancer therapeutics", Current Medicinal Chemistry, vol. 18, no. 3, pp. 316–328, PMID 21143123{{citation}}: CS1 maint: multiple names: authors list (link)
  35. ^ Page Module:Citation/CS1/styles.css has no content.Ilias Muhammad, Volodymyr Samoylenko (2007-08-01), "Antimalarial quassinoids: past, present and future", Expert Opinion on Drug Discovery, vol. 2, no. 8, pp. 1065–1084, doi:10.1517/17460441.2.8.1065, PMID 23484873

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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