{{Short description|Class of chemical compounds}} [[File:Quassin test ACS.png|thumb|right|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.<ref>{{cite book | doi = 10.1016/S1572-5995(06)80032-3 | title = Quassinoids: Structural Diversity, Biological Activity and Synthetic Studies | series = Studies in Natural Products Chemistry | date = 2006 | last1 = Curcino Vieira | first1 = Ivo J. | last2 = Braz-Filho | first2 = Raimundo | volume = 33 | pages = 433–492 | isbn = 978-0-444-52717-2 }}</ref> 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.<ref>{{cite journal |title=Quassin I. The preparation and purification of quassin and neoquassin, with information concerning their molecular formulas | author = Winckler, F. L. | journal = Rep. Pharm. | year = 1835 | volume = 4 | page = 85}}</ref> It was isolated in 1937,<ref>E.P. Clark, J. Amer. Chem. Soc. (1937)</ref> and its structure elucidated in 1961.<ref>{{cite journal |last1=Valenta |first1=Z. |last2=Papadopoulos |first2=S. |last3=Podešva |first3=C. |title=Quassin and Neoquassin |journal=Tetrahedron |date=1961 |volume=15 |issue=1–4 |pages=100–110 |doi=10.1016/0040-4020(61)80013-6}}</ref>
==Sources== More than 200 currently-known quassinoids have been isolated and identified from various species of simaroubaceae family.<ref>{{cite journal |last1=Curcino Vieira |first1=I.J. |last2=Braz-Filho |first2=R. |title=_structural diversity, biological activity and synthetic studies_ |journal=Stud. Nat. Prod. Chem. |date=2006 |volume=33 |pages=433–492|doi=10.1016/S1572-5995(06)80032-3 }}</ref>
Quassinoids can also be extracted from various Simaroubaceae family species such as; ''Ailanthus excelsa'',<ref>{{cite journal |last1=Joshi |first1=B.C. |last2=Pandei |first2=A. |last3=Sharma |first3=R.P. |last4=Khare |first4=A. |title=Quassinoids from ''Ailanthus excelsa'' |journal=Phytochemistry |date=2003 |volume=62 |issue=4 |pages=579–584|doi=10.1016/S0031-9422(02)00493-4 |pmid=12560029 |bibcode=2003PChem..62..579J |doi-access=free }}</ref> ''Ailanthus vilmoriniana'',<ref>{{cite journal |last1=Takeya |first1=K. |last2=Kobata |first2=H. |last3=Ozeki |first3=A. |last4=Morita |first4=H. |last5=Itokawa |first5=H. |title=Quassinoids from ''Ailanthus vilmoriniana'' |journal=Phytochemistry |date=1998 |volume=48 |issue=3 |page=565|doi=10.1016/S0031-9422(97)00893-5 |bibcode=1998PChem..48..565T }}</ref> (the fruits of) ''Brucea javanica'',<ref>{{cite journal |last1=Anderson |first1=M.M. |last2=O’Neill |first2=M.J. |last3=Phillipson |first3=J.D. |last4=Warhurst |first4=D.C. |title=In vitro cytotoxicity of a series of quassinoids from ''Brucea javanica'' fruits against KB cells |journal=Planta Med. |date=1991 |volume=57 |issue=1 |pages=62–64|doi=10.1055/s-2006-960020 |pmid=2062960 |s2cid=21082303 }}</ref> ''Hannoa klaineana'',<ref name="Lumonadio1991">{{cite journal |last1=Lumonadio |first1=L. |last2=Atassi |first2=G. |last3=Vanhaelen |first3=M. |last4=Vanhaelen-Fastre |first4=R. |date=1991 |journal=J. Ethnopharmacol. |title=Antitumor activity of quassinoids from ''Hannoa klaineana'' |volume=31 |issue=1 |pages=59–65|doi=10.1016/0378-8741(91)90144-3 |pmid=2030594 }}</ref><ref name="Donkwe2012">{{cite journal |last1=Donkwe |first1=Suzye Mireille Moladje |last2=Happi |first2=Emmanuel Ngeufa |last3=Wansi |first3=Jean Duplex |last4=Lenta |first4=Bruno Ndjakou |last5=Devkota |first5=Krishna Prasad |last6=Neumann |first6=Beate |last7=Stammler |first7=Hans-Georg |last8=Sewald |first8=Norbert |title=Oxidative burst inhibitory and cytotoxic activity of constituents of the fruits of ''Odyendyea gabonensis'' |journal=Planta Med. |date=December 2012 |volume=78 |issue=18 |pages=1949–56 |doi=10.1055/s-0032-1327878 |pmid=23136063}}</ref> ''Pierreodendron kerstingii'',<ref name="Kupchan1975">{{cite journal |last1=Kupchan |first1=S.M. |last2=Lacadie |first2=J.A. |title=Dehydroailanthinone, a new antileukemic quassinoid from Pierreodendron kerstingii |journal=J. Org. Chem. |date=1975 |volume=40 |issue=5 |pages=654–656 |doi=10.1021/jo00893a024 |pmid=1133628 }}</ref> ''Quassia africana'',<ref name=Apers>{{cite journal |last1=Apers |first1=S. |last2=Cimanga |first2=K. |last3=Vanden Berghe |first3=D. |last4=Van Meenen |first4=E. |last5=Longanga |first5=A.O. |last6=Foriers |first6=A. |last7=Vlietinck |first7=A. |last8=Pieters |first8=L. |title=Antiviral activity of Simalikalactone D, a quassinoid from ''Quassia africana'' |journal=Planta Med. |date=2002 |volume=68 |issue=1 |pages=20–24|doi=10.1055/s-2002-19870 |pmid=11842321 |s2cid=260284246 }}</ref><ref name="Tresca1971">{{cite journal |last1=Tresca |first1=J.P. |last2=Alais |first2=L. |last3=Polonsky |first3=J. |title=Bitter constituents of ''Quassia africana'' Baill. (Simarubaceae). Simalikalactones A, B, C and D and simalikaliacetal A. |journal=C. R. Acad. Sci. Paris |date=1971 |volume=273 |page=601}}</ref> ''Quassia amara'',<ref name="Bertani2006">{{cite journal |last1=Bertani |first1=S. |last2=Houël |first2=E. |last3=Stien |first3=D. |last4=Chevolot |first4=L. |last5=Jullian |first5=V. |last6=Garavito |first6=G. |last7=Bourdy |first7=G. |last8=Deharo |first8=E. |title=Simalikalactone D is responsible for the antimalarial properties of an amazonian traditional remedy made with ''Quassia amara'' L. (Simaroubaceae) |journal=J. Ethnopharmacol. |date=2006 |volume=108 |issue=1 |pages=155–157|doi=10.1016/j.jep.2006.04.017 |pmid=16730421 }}</ref><ref name="Bertani2012">{{cite journal |last1=Bertani |first1=S. |last2=Houël |first2=E. |last3=Stien |first3=D. |last4=Chevolot |first4=L. |last5=Jullian |first5=V. |last6=Garavito |first6=G. |last7=Bourdy |first7=G. |last8=Deharo |first8=E. |title=New findings on simalikalactone D, an antimalarial compound from ''Quassia amara'' L. (Simaroubaceae) |journal=Exp. Parasitol. |date=2012 |volume=130 |issue=4 |pages=341–347|doi=10.1016/j.exppara.2012.02.013 |pmid=22374406 }}</ref> (the wood of ) ''Picrasma ailanthoides'',<ref name=Daido1995>{{cite journal |last1=Daido |first1=M. |last2=Fukamiya |first2=N. |last3=Okano |first3=M. |title=Picrasinol D, a new quassinoid from the stem wood of ''Picrasma ailanthoides'' |journal=J. Nat. Prod. |date=1995 |volume=58 |issue=4 |pages=605–608|doi=10.1021/np50118a022 }}</ref> ''Picrasma javanica'',<ref>{{cite journal |last1=Koike |first1=K. |last2=Ishi |first2=K. |last3=Mitsunaga |first3=K. |last4=Ohmoto |first4=T. |title=Quassinoids from ''Picrasma javanica'' |journal=Phytochemistry |date=1991 |volume=30 |issue=3 |pages=933–936|doi=10.1016/0031-9422(91)85282-5 |bibcode=1991PChem..30..933K }}</ref> ''Picrolemma pseudocoffea'',<ref>{{cite journal |last1=Moretti |first1=C. |last2=Polonsky |first2=J. |last3=Vuilhorgne |first3=M. |last4=Prange |first4=T. |title=Isolation and structure of sergeolide, a potent cytotoxic quassinoid from ''Picrolemma pseudocoffea'' |journal=Tetrahedron Lett |date=1982 |volume=23 |issue=6 |page=647|doi=10.1016/S0040-4039(00)86912-9 }}</ref> ''Simaba guianensis'',<ref>{{cite journal |last1=Cabral |first1=J.A. |last2=McChesney |first2=J.D. |last3=Milhous |first3=W.K. |title=A new anti-malarial quassinoid from ''Simaba guianensis'' |journal=J. Nat. Prod. |date=1993 |volume=56 |issue=11 |pages=1954–1961 |doi=10.1021/np50101a014 |pmid=8289064 }}</ref> and ''Simaruba glauca''.<ref>{{cite journal |last1=Moron |first1=J. |last2=Merrien |first2=M.A. |last3=Polonsky |first3=J. |title=On the biosynthesis of quassinoids ''Simaruba glauca'' (Simarubaceae). |journal=Phytochemistry |date=1971 |volume=10 |page=585|doi=10.1016/S0031-9422(00)94702-2 }}</ref>
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).<ref>{{cite journal |last1=Simão |first1=Sheila M. |last2=Barreiros |first2=Euclides L. |last3=das G.F. Da Silva |first3=M.Fátima |last4=Gottlieb |first4=Otto R. |title=Chemogeographical evolution of quassinoids in simaroubaceae |journal=Phytochemistry |date=1991 |volume=30 |issue=3 |pages=853–865 |doi=10.1016/0031-9422(91)85267-4|bibcode=1991PChem..30..853S }}</ref>
==Uses== They are a biologically potent class of natural products, possessing antimalarial,<ref name="Bertani2012"/><ref>{{cite journal |author1=Muhammad, I. |title=Antimalarial quassinoids: Past, present and future |author2=Samoylenko, V. | journal = Expert Opin Drug Discov | year = 2007 | volume = 2 |issue=8 |pages=1065–84 |doi=10.1517/17460441.2.8.1065 |pmid=23484873 |s2cid=24497786 }}</ref> antifeedant,<ref>{{cite journal |author1=Leskinen, V. |title=Antifeedant activity of quassinoids |author2=Polonsky, J. |author3=Bhatnagar, S. | journal = J. Chem. Ecol. | year = 1984 | volume = 10 |issue=10 |pages=1497–507 |doi=10.1007/BF00990319 |pmid=24318349 |bibcode=1984JCEco..10.1497L |s2cid=21117128 }}</ref> insecticidal,<ref>{{cite journal |author1=Fang, X. |author2=Di, Y. T. |author3=Xhang, Y. |author4=Xu, Z. P. |author5=Lu, Y. |author6=Chen, Q. Q. |author7=Zheng, Q. T. |author8=Hao, X. J. | journal = Angew. Chem. Int. Ed. | year = 2015 | volume = 54 |issue=19 |pages=5592–5 | doi = 10.1002/anie.201412126 |pmid=25810025 | title=Unprecedented Quassinoids with Promising Biological Activity from ''Harrisonia perforata''}}</ref> anti-inflammatory,<ref>{{cite journal |author1=Hall, I. H. |title=Anti-inflammatory Agents III: Structure–Activity Relationships of Brusatol and Related Quassinoids |author2=Lee, K. H. |author3=Imakura, Y. |author4=Okano, M. |author5=Johnson, A. | journal = J. Pharm. Sci. | year = 1983 | volume = 72 |issue=11 |pages=1282–4 |doi=10.1002/jps.2600721111 |pmid=6417321 }}</ref> and anticancer (or anti-leukemic)<ref name="Kupchan1975"/><ref>{{cite journal |author1=Fukamiya, N. |author2=Lee, K.H. |author3=Muhammad, I. |author4=Murakami, C. |author5=Okano, M. |author6=Harvey, I. |author7=Pelletier, J. | journal = Cancer Letters | year = 2005 | volume = 220 |issue=1 |pages=37–48 | doi = 10.1016/j.canlet.2004.04.023 |pmid=15737686 | title=Structure–activity relationships of quassinoids for eukaryotic protein synthesis}}</ref><ref>{{cite journal |last1=Fiaschetti |first1=G. |last2=Grotzer |first2=M.A. |last3=Shalaby |first3=T. |last4=Castelletti |first4=D. |last5=Arcaro |first5=A. |title=_from traditional drugs to new cancer therapists_ |journal=Curr. Med. Chem. |date=2011 |volume=18 |issue=3 |pages=316–328 |doi=10.2174/092986711794839205 |pmid=21143123 }}</ref> properties. The quassinoid bruceantin reached two separate phase II clinical trials in 1982<ref>{{cite journal |author1=Wiseman, C. L. |title=Phase II trial of bruceantin in metastatic breast carcinoma |author2=Yap, H. Y. |author3=Bedikian, A. Y. |author4=Bodey, G. P. |author5=Blumenchein, G. R. | journal = Am. J. Clin. Oncol. | year = 1982 | volume = 5 |issue=4 |pages=389–91 |doi=10.1097/00000421-198208000-00007 |pmid=7113961 |s2cid=27632884 }}</ref> and 1983.<ref>{{cite journal |author1=Arsenau, J. C. |author2=Wolter, J. M. |author3=Kuperminc, M. |author4=Ruckdeschel, J. C. | journal = Invest. New Drugs | year = 1983 | volume = 1 | page = 239 |title=Anti–inflammatory agents III: Structure–activity relationships of brusatol and related quassinoids}}</ref>
Other quassinoids include:<ref>{{cite web | url = http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72485 | title = Quassinoid | publisher = Chemical Entities of Biological Interest (ChEBI)}}</ref> * Ailanthone * Bruceanols * Bruceolide * Eurycomanone * Gutolactone * Isobrucein A * Neoquassin * Nigakihemiacetal A * Odyendanol<ref name="Donkwe2012"/> * Picrasinol D<ref name=Daido1995/> * Quassimarin * Samaderines * Simalikalactones (including simalikalactones A, B, C,<ref name="Tresca1971"/> simalikalactone D,<ref name=Apers/><ref name="Bertani2006"/> and simalikalactone E<ref>{{cite journal |last1=Cachet |first1=N. |last2=Valentin |first2=A. |last3=Jullian |first3=V. |last4=Stien |first4=D. |last5=Houël |first5=E. |last6=Gornitzka |first6=H. |last7=Fillaux |first7=J. |last8=Chevalley |first8=S. |last9=Hoakwe |first9=F. |last10=Bertani |first10=S. |last11=Bourdy |first11=G. |last12=Deharo |first12=E. |title=Antimalarial activity of simalikalactone E, a new quassinoid of ''Quassia amara'' L. (Simaroubaceae) |journal= Antimicrobial Agents and Chemotherapy|date=2009 |volume=53 |issue=10 |pages=4393–4398|doi=10.1128/AAC.00951-09 |pmid=19667291 |pmc=2764154 }}</ref>)
== Properties and effects == In addition to their intensely bitter taste, they exhibit antifeedant activity against insects.<ref name="Römpp">Jürgen Falbe, Manfred Regitz (Hrsg.): ''Römpp Chemie Lexikon,'' 9. Auflage, Georg Thieme Verlag, Stuttgart 1990, ISBN 3-13-735009-3, S. 3735–3736.</ref> An antileukemic effect has also been reported.<ref name="Polonsky2">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.</ref><ref>{{citation|author=G. Fiaschetti, M. A. Grotzer, T. Shalaby, D. Castelletti, A. Arcaro |date=2011 |issue=3 |pages=316–328 |periodical=Current Medicinal Chemistry |pmid=21143123 |title=Quassinoids: From traditional drugs to new cancer therapeutics |volume=18}}<!-- auto-translated from German by Module:CS1 translator --></ref> Furthermore, numerous studies have attributed antiviral, antiparasitic (particularly antimalarial<ref>{{citation|author=Ilias Muhammad, Volodymyr Samoylenko |date=2007-08-01 |doi=10.1517/17460441.2.8.1065 |issue=8 |pages=1065–1084 |periodical=Expert Opinion on Drug Discovery |pmid=23484873 |title=Antimalarial quassinoids: past, present and future |volume=2}}<!-- auto-translated from German by Module:CS1 translator --></ref>), insecticidal, amoebicidal, and anti-inflammatory properties to many quassinoids.<ref name="Römpp" />
==References== {{reflist}}
==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
==External links== * {{commons category-inline|Quassinoids|lcfirst=yes}} * {{wiktionary inline| quassinoid}}
Category:Quassinoids Category:Heterocyclic compounds with 4 rings Category:Methoxy compounds