quassinoid

More than 200 currently-known quassinoids have been isolated and identified from various species of simaroubaceae family.{{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 }}

Quassinoids can also be extracted from various Simaroubaceae family species such as; Ailanthus excelsa,{{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 }} Ailanthus vilmoriniana,{{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 }} (the fruits of) Brucea javanica,{{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 }} Hannoa klaineana,{{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 }}{{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}} Pierreodendron kerstingii,{{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 }} Quassia africana,{{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 }}{{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}} Quassia amara,{{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 }}{{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 }} (the wood of ) Picrasma ailanthoides,{{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 }} Picrasma javanica,{{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 }} Picrolemma pseudocoffea,{{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 }} Simaba guianensis,{{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 }} and Simaruba glauca.{{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 }}

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).{{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 }}

They are a biologically potent class of natural products, possessing antimalarial,{{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 }} antifeedant,{{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 }} insecticidal,{{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}} anti-inflammatory,{{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 }} and anticancer (or anti-leukemic){{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}}{{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 }} properties. The quassinoid bruceantin reached two separate phase II clinical trials in 1982{{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 }} and 1983.{{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}}

Other quassinoids include:{{cite web | url = http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72485 | title = Quassinoid | publisher = Chemical Entities of Biological Interest (ChEBI)}}

• Bruceanols
• Bruceolide
• Eurycomanone
• Gutolactone
• Isobrucein A
• Neoquassin
• Nigakihemiacetal A
• Odyendanol
• Picrasinol D
• Quassimarin
• Samaderines
• Simalikalactones (including simalikalactones A, B, C, simalikalactone D, and simalikalactone E{{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 }})

{{reflist}}

• 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

• {{commons category-inline|Quassinoids|lcfirst=yes}}
• {{wiktionary inline| quassinoid}}

Category:Heterocyclic compounds with 4 rings

Category:Methoxy compounds