511:
574:
583:
24:
501:
653:
492:
1927:
Setzer WN, Holland MT, Bozeman CA, Rozmus GF, Setzer MC, Moriarity DM, Reeb S, Vogler B, Bates RB, Haber WA (2001). "Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of
Salacia petenensis".
1083:
Zhu H, Liu XW, Cai TY, Cao J, Tu CX, Lu W, He QJ, Yang B (2010). "Celastrol acts as a potent antimetastatic agent targeting beta1 integrin and inhibiting cell-extracellular matrix adhesion, in part via the p38 mitogen-activated protein kinase pathway".
1212:
Murayama T, Eizuru Y, Yamada R, Sadanari H, Matsubara K, Rukung G, Tolo FM, Mungai GM, Kofi-Tsekpo M (2007). "Anticytomegalovirus activity of pristimerin, a triterpenoid quinone methide isolated from
Maytenus heterophylla (Eckl. & Zeyh.)".
1264:
1174:
Avilla J, Teixidò A, Velázquez C, Alvarenga N, Ferro E, Canela R (2000). "Insecticidal activity of
Maytenus species (Celastraceae) nortriterpene quinone methides against codling moth, Cydia pomonella (L.) (Lepidoptera: tortricidae)".
1129:
Byun; et al. (2009). "Reactive oxygen species-dependent activation of Bax and Poly(ADP)-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid
Pristimerin in human cervical cancer cells".
1545:"Syntheses and antibacterial activities of diterpene catechol derivatives with abietane, totarane and podocarpane skeletons against methicillin-resistant Staphylococcus aureus and Propionibacterium acnes"
565:
that displays antitumor and antiviral activities. Pristimerin has also been found to have a contraceptive effect due to its inhibiting effect on the calcium channel of sperm (CatSper).
370:. Nucleophilic addition at the exo-cyclic double bond will result in rearomatisation, making such reactions highly favourable. As a result, quinone methides are excellent, electrophilic
944:
Kim DH, Shin EK, Kim YH, Lee BW, Jun JG, Park JH, Kim JK (2009). "Suppression of inflammatory responses by celastrol, a quinone methide triterpenoid isolated from
Celastrus regelii".
1319:
Kupchan, S. M.; Karim, A; Marcks, C. (1968). "Tumor inhibitors. XXXIV. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from
Taxodium distichum".
899:
Allison AC, Cacabelos R, Lombardi VR, Alvarez XA, Vigo C (2001). "Celastrol, a potent antioxidant and anti-inflammatory drug, as a possible treatment for
Alzheimer's disease".
1688:
Norihisa
Kusumoto; Tatsuya Ashitani; Yuichi Hayasaka; Tetsuya Murayama; Koichi Ogiyama; Koetsu Takahashi (2009). "Antitermitic Activities of Abietane-type Diterpenes from
525:(formation of exoskeletons of arthropods. The middle step involving conversion of the ortho quinone to quinone methide, is catalyzed by the enzyme quinone isomerase.<
1439:
1854:
Jansen R, Gerth K, Steinmetz H, Reinecke S, Kessler W, Kirschning A, Müller R (2011). "Elansolid A3, a Unique p-Quinone
Methide Antibiotic from Chitinophaga sancti".
1772:
806:
Stich, T. A.; Myers, W. K.; Britt, R. D., "Paramagnetic intermediates generated by radical S-adenosylmethionine (SAM) enzymes", Acc. Chem. Res. 2014, 47, 2235-2243.
1034:"Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo"
402:
in the absence of nucleophiles. Sterically hindered quinone methides can be sufficiently stable to be isolated, with some examples being commercially available.
699:
that displays antibiotic activity. Antibacterial quinone methides, 20-epi-isoiguesterinol, 6-oxoisoiguesterin, isoiguesterin and isoiguesterinol were found in
225:
1177:
1639:
Norihisa
Kusumoto; Tatsuya Ashitani; Tetsuya Murayama; Koichi Ogiyama; Koetsu Takahashi (2010). "Antifungal Abietane-Type Diterpenes from the Cones of
901:
827:
Wang P, Song Y, Zhang L, He H, Zhou X (2005). "Quinone methide derivatives: important intermediates to DNA alkylating and DNA cross-linking actions".
2002:
González AG, Alvarenga NL, Bazzocchi IL, Ravelo AG, Moujir L (1998). "A new bioactive norquinone-methide triterpene from Maytenus scutioides".
1502:
Vivek K. Bajpai; Minkyun Na; Sun Chul Kang (2010). "The role of bioactive substances in controlling foodborne pathogens derived from
190:
1965:
Chávez H, Estévez-Braun A, Ravelo AG, González AG (1999). "New phenolic and quinone-methide triterpenes from Maytenus amazonica".
1410:, Gülaçti Topçu, Hee-Byung Chai and John M. Pezzuto (1999). "Cytotoxic Activity of Diterpenoids Isolated from Salvia hypargeia".
2066:
Van De Water RW, Pettus TR (2002). "o-Quinone methides: intermediates underdeveloped and underutilized in organic synthesis".
1743:
1815:
H B Bode & A Zeeck (2000). "Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces".
299:
1508:
167:
1841:
1694:
1645:
347:
343:
1739:"Short communication. The antifeedant activity of natural plant products towards the larvae of Spodoptera littoralis"
717:. An antimicrobial quinone methide, 15 alpha-hydroxypristimerin, was isolated from a South American medicinal plant,
815:
417:
Quinone methides can be produced in aqueous solution by photochemical dehydration of o-hydroxybenzyl alcohols (i.e.
2101:
675:
2096:
2060:
760:
711:. Nortriterpenoid quinone methide amazoquinone and (7S, 8S)-7-hydroxy-7,8-dihydro-tingenone were isolated from
383:
81:
780:
Cavitt, S. B.; R., H. Sarrafizadeh; Gardner, P. D. (April 1962). "The Structure of o-Quinone Methide Trimer".
701:
991:"Enhancement of radiation sensitivity in lung cancer cells by celastrol is mediated by inhibition of Hsp90"
1596:
1459:
1412:
1215:
610:
538:
719:
695:
73:
1788:
1766:
1433:
713:
645:
561:
395:
544:
483:. Oxidation to a reactive quinone methide is the mechanistic basis of many phenolic anti-cancer drugs.
1605:
1273:
1086:
552:(15 times the potency of α-tocopherol), anti-inflammatory, anticancer, and insecticidal activities.
331:
1890:
Thiem DA, Sneden AT, Khan SI, Tekwani BL (2005). "Bisnortriterpenes from Salacia madagascariensis".
1453:
Vivek K. Bajpai & Sun Chul Kan (2010). "Antibacterial abietane-type diterpenoid, taxodone from
683:
680:
391:
37:
2050:
2029:
1719:
1670:
1484:
1389:
1240:
1156:
1111:
971:
926:
707:
604:
399:
93:
1260:"Regulation of the sperm calcium channel CatSper by endogenous steroids and plant triterpenoids"
989:
Lee JH, Choi KJ, Seo WD, Jang SY, Kim M, Lee BW, Kim JY, Kang S, Park KH, Lee YS, Bae S (2011).
2055:
2021:
1984:
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2013:
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873:
838:
789:
515:
371:
319:
253:
176:
1549:
1362:
1132:
1038:
643:
Maytenoquinone, an isomer of taxodione, is a biologically active quinone methide found in
418:
342:
oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either
48:
1609:
1277:
122:
114:
1587:
1407:
1296:
1259:
1060:
1033:
522:
510:
323:
293:
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914:
573:
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1801:
1321:
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666:
625:
454:
351:
148:
2033:
1723:
1674:
1488:
1393:
1244:
1115:
930:
410:
Quinone methides are often prepared by oxidation of the corresponding ortho or para
1160:
687:
533:
430:
375:
156:
1051:
756:
637:
629:
599:
549:
476:
398:
that are not stable enough to be isolated under normal circumstances, they will
339:
1757:
1738:
1425:
1265:
Proceedings of the National Academy of Sciences of the United States of America
1228:
877:
842:
2004:
1967:
1930:
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659:
621:
480:
278:
23:
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1099:
670:
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633:
582:
529:
472:
468:
2025:
1988:
1951:
1913:
1876:
1868:
1786:
J. D. Martín (1973). "New diterpenoids extractives of Maytenus dispermus".
1715:
1666:
1625:
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1529:
1480:
1385:
1376:
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1305:
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967:
922:
885:
850:
2017:
1737:
M. C. Ballesta-Acosta1, M. J. Pascual-Villalobos and B. Rodríguez (2008).
1586:
Ufuk Kolak; Ahmed Kabouche; Mehmet Öztürk; Zahia Kabouche; Gülaçtl Topçu;
1342:
1009:
990:
864:
Andersen, Svend Olav (2010). "Insect Cuticular Sclerotization: A Review".
652:
1943:
732:
595:
461:
442:
367:
327:
1980:
1334:
793:
500:
1563:
1544:
335:
134:
1905:
1358:"Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.)"
1190:
755:
methides (the topic of this article) by replacing the keto group with
491:
1828:
1617:
705:. Quinone methides tingenone and netzahualcoyonol were isolated from
616:
458:
450:
411:
292:
Except where otherwise noted, data are given for materials in their
453:. Various quinone methides are directly involved in the process of
651:
556:
509:
104:
80:
72:
61:
1258:
Nadja Mannowetza; Melissa R. Millera; Polina V. Lishko (2017).
559:
of celasterol, is a triterpenoid quinone methide isolated from
350:
to each other. There are some examples of transient synthetic
1543:
Tada M, Kurabe J, Yoshida T, Ohkanda T, Matsumoto Y (2010).
2061:
Reactive intermediates. Some chemistry of quinone methides
433:, but are rarely observed as long-lived intermediates.
382:
via a similar process, a behaviour exploited by certain
2056:
Quinone methide intermediates in organic Photochemistry
598:
and its oxidized rearrangement product, taxodione, are
1356:
Zaghloul AM, Gohar AA, Naiem ZA, Abdel Bar FM (2008).
467:
Quinone methides have been implicated as the ultimate
693:
Elansolid A3 is a quinone methide from the bacterium
394:. Simple unhindered quinone methides are short lived
1590:(2009). "Antioxidant diterpenoids from the roots of
441:
Quinone methide itself arises by the degradation of
209:
p-: InChI=1S/C7H6O/c1-6-2-4-7(8)5-3-6/h2-5H,1H2
199:
o-: InChI=1S/C7H6O/c1-6-4-2-3-5-7(6)8/h2-5H,1H2
378:and can be easily reduced. They are able to act as
2051:Formation and Stability of Simple Quinone Methides
735:(or "xylylene") is a compound with the formula C
155:
147:
47:
471:responsible for the effects of such agents as
334:or extended alkene unit. It is analogous to a
8:
1438:: CS1 maint: multiple names: authors list (
1771:: CS1 maint: numeric names: authors list (
1178:Journal of Agricultural and Food Chemistry
429:Quinones methides are commonly invoked in
15:
1756:
1562:
1375:
1295:
1285:
1059:
1008:
902:Prog Neuropsychopharmacol Biol Psychiatry
866:Insect Biochemistry and Molecular Biology
175:
1744:Spanish Journal of Agricultural Research
772:
620:species and other plants, that display
230:
195:
1764:
1431:
212:Key: OJPNKYLDSDFUPG-UHFFFAOYSA-N
202:Key: NSDWWGAIPUNJAX-UHFFFAOYSA-N
121:
113:
7:
514:Proposed sequence of reactions with
751:. Thus they are related to quinone
137:
673:first isolated from the bacterium
390:than quinones, and therefore more
14:
816:Quinone Methides in Lignification
960:10.1111/j.1365-2362.2009.02186.x
782:The Journal of Organic Chemistry
581:
572:
499:
490:
265:
22:
1032:Tiedemann; et al. (2009).
679:. It has potent activity as an
640:, and antifeedant activities.
296:(at 25 °C , 100 kPa).
536:quinone methide isolated from
437:Biosynthesis of dehydroglycine
271:
259:
1:
2080:10.1016/S0040-4020(02)00496-9
915:10.1016/S0278-5846(01)00192-0
1802:10.1016/0040-4020(73)80172-3
1509:Food and Chemical Toxicology
1504:Metasequoia glyptostroboides
1455:Metasequoia glyptostroboides
1052:10.1182/blood-2008-09-179796
759:. A well studied example is
386:. Quinone methides are more
1695:Journal of Chemical Ecology
1646:Journal of Chemical Ecology
425:Occurrence and applications
2118:
1426:10.1076/phbi.37.2.148.6082
1229:10.1177/095632020701800303
878:10.1016/j.ibmb.2009.10.007
843:10.2174/092986705774454724
676:Streptomyces violaceoruber
602:quinone methides found in
542:(Thunder of God vine) and
521:as substrate resulting in
1817:J Chem Soc Perkin Trans 1
1708:10.1007/s10886-009-9646-0
1659:10.1007/s10886-010-9875-2
1522:10.1016/j.fct.2010.04.041
1473:10.1007/s12038-010-0061-z
384:polymerisation inhibitors
290:
246:
238:p-: C=C1C=CC(=O)C=C1
221:
186:
30:
21:
1758:10.5424/sjar/2008061-304
761:tetracyanoquinodimethane
702:Salacia madagascariensis
555:Pristimerin, the methyl
445:, leading ultimately to
338:, but having one of the
1844:University of Wisconsin
1287:10.1073/pnas.1700367114
1100:10.1124/jpet.110.165654
233:o-: C=C1C=CC=CC1=O
1869:10.1002/chem.201100457
1597:Phytochemical Analysis
1460:Journal of Biosciences
1413:Pharmaceutical Biology
1377:10.1515/znc-2008-5-608
1216:Antivir Chem Chemother
1145:10.1124/mol.109.056259
656:
611:Rosmarinus officinalis
539:Tripterygium wilfordii
526:
396:reactive intermediates
2018:10.1055/s-2006-957581
1010:10.3892/ijmm.2011.601
655:
562:Maytenus heterophylla
513:
457:(creation of complex
374:, react quickly with
362:Quinone methides are
1944:10.1055/s-2001-10879
1842:Burke Research Group
1087:J Pharmacol Exp Ther
614:(rosemary), several
1610:2009PChAn..20..320K
1335:10.1021/ja01023a061
1278:2017PNAS..114.5743M
794:10.1021/jo01051a021
720:Maytenus scutioides
696:Chitinophaga sancti
681:endothelin receptor
392:chemically reactive
286: g·mol
94:Beilstein Reference
18:
1690:Taxodium distichum
1641:Taxodium distichum
1564:10.1248/cpb.58.818
727:Quinone dimethides
714:Maytenus amazonica
708:Salacia petenensis
657:
646:Maytenus dispermus
605:Taxodium distichum
527:
380:radical scavengers
354:quinone methides.
300:Infobox references
16:
2102:Functional groups
2074:(27): 5367–5405.
1981:10.1021/np980412+
1906:10.1021/np0497088
1796:(17): 2553–2559.
1653:(12): 1381–1386.
1592:Salvia barrelieri
1272:(22): 5743–5748.
1191:10.1021/jf990008w
947:Eur J Clin Invest
837:(24): 2893–2913.
733:quinone dimethide
545:Celastrus regelii
372:Michael acceptors
330:and an exocyclic
308:Chemical compound
306:
305:
82:Interactive image
74:Interactive image
2109:
2097:Quinone methides
2083:
2038:
2037:
1999:
1993:
1992:
1962:
1956:
1955:
1924:
1918:
1917:
1887:
1881:
1880:
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1839:
1833:
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1829:10.1039/a908387a
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1618:10.1002/pca.1130
1583:
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1534:
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1516:(7): 1945–1949.
1499:
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1492:
1450:
1444:
1443:
1437:
1429:
1404:
1398:
1397:
1379:
1370:(5–6): 355–360.
1353:
1347:
1346:
1316:
1310:
1309:
1299:
1289:
1255:
1249:
1248:
1209:
1203:
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1063:
1029:
1023:
1022:
1012:
986:
980:
979:
941:
935:
934:
909:(7): 1341–1357.
896:
890:
889:
861:
855:
854:
824:
818:
813:
807:
804:
798:
797:
788:(4): 1211–1216.
777:
669:quinone methide
608:(bald cypress),
585:
576:
503:
494:
364:cross-conjugated
320:organic compound
285:
273:
267:
261:
254:Chemical formula
179:
159:
151:
139:
125:
117:
84:
76:
51:
26:
19:
17:Quinone methide
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2110:
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2001:
2000:
1996:
1964:
1963:
1959:
1926:
1925:
1921:
1889:
1888:
1884:
1863:(28): 7739–44.
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1836:
1814:
1813:
1809:
1785:
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1550:Chem Pharm Bull
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1363:Z Naturforsch C
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1133:Mol. Pharmacol.
1128:
1127:
1123:
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1081:
1077:
1046:(17): 4027–37.
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1026:
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987:
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750:
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729:
593:
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586:
578:
577:
519:-acetyldopamine
508:
507:
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505:
504:
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495:
439:
427:
419:salicyl alcohol
408:
360:
322:that contain a
313:quinone methide
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2045:External links
2043:
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2012:(8): 767–771.
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1975:(3): 434–436.
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1823:(3): 323–328.
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1604:(4): 320–327.
1588:Ayhan Ulubelen
1578:
1557:(6): 818–824.
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1494:
1467:(4): 533–538.
1445:
1420:(2): 148–151.
1408:Ayhan Ulubelen
1399:
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1223:(3): 133–139.
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1094:(2): 489–499.
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819:
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588:Maytenoquinone
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548:that exhibits
523:sclerotization
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638:insecticide
630:antioxidant
600:diterpenoid
550:antioxidant
477:antibiotics
406:Preparation
332:methylidene
247:Properties
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317:conjugated
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