525:, sometimes enables it to be a dominant species in certain plant communities. The ptaquiloside content of bracken varies widely across species and changes with the part of the plant, the plant growing site and the collecting season. According to previous studies, the concentrations of ptaquiloside in bracken varied between 0 to 1% of the dry weight of the plant. Generally, ptaquiloside is found to occur in the highest concentrations in the young developing parts of bracken, such as the croziers and unfolding parts during the spring and early summer, while the concentrations of ptaquiloside in the rhizomes are rather low. However, studies on the concentrations of ptaquiloside in Danish bracken by Rasmussen et al. showed that the concentrations of ptaquiloside in the rhizomes were significantly higher than the previously reported values.
643:
768:
834:, to degrade or inactivate ptaquiloside and other toxic agents. Nevertheless, some carcinogenic activity persists even after the treatment. As shown by Kamon and Hirayama, the risk of oesophageal cancer was increased approximately by 2.1 in men and 3.7 in women who regularly consume bracken in Japan. Recent researches have suggested that sulfur-containing amino acids can potentially be used under appropriate conditions as detoxifying agents for ptaquiloside and selenium supplementation can prevent as well as reverse the immunotoxic effects induced by ptaquiloside.
468:
633:
1077:
253:
529:
experiments and the assumption that a person drinks 0.5 litres of milk daily, they estimated that this person might ingest about 10 mg of ptaquiloside per day, although only some of that amount will be absorbed. Ptaquiloside can also leach from the bracken leaves into water and soil. Numerous studies have reported the presence of ptaquiloside in the underground/surface water, and soil near bracken vegetation. The degradation speed of ptaquiloside in the soil is affected by the
24:
879:
374:
1578:
Virgilio, Antonella; Sinisi, Annamaria; Russo, Valeria; Gerardo, Salvatore; Santoro, Adriano; Galeone, Aldo; Taglialatela-Scafati, Orazio; Roperto, Franco (20 May 2015). "Ptaquiloside, the Major
Carcinogen of Bracken Fern, in the Pooled Raw Milk of Healthy Sheep and Goats: An Underestimated, Global
528:
Ptaquiloside can pass into the milk produced by bracken-fed cows and sheep. In 1996, Alonso-Amelot, Smith and co-workers found that ptaquiloside was excreted in milk at a concentration of 8.6 ± 1.2% of the amount ingested by a cow from bracken, and was linearly dose-dependent. On the basis of their
825:
The use of bracken fern as human food is mainly a historical question. The rhizomes of these plants served as human food in
Scotland during the First World War. In America (USA, Canada), Russia, China and Japan, fern is grown commercially for human use. The usual procedure that is performed before
453:
The pure form ptaquiloside is a colorless amorphous compound. It is readily soluble in water and fairly soluble in ethyl acetate. Except in the plants, ptaquiloside has been detected in the milk and meat of affected livestock, as well as in the underground water and dry soil around bracken fern
1397:
Smith, Barry L.; Seawright, Alan A.; Ng, Jack C.; Hertle, Andrew T.; Tomson, John A.; Bostock, Peter D. (1994). "Concentration of ptaquiloside, a major carcinogen in bracken fern (Pteridium spp.), from
Eastern Australia and from a cultivated worldwide collection held in Sydney, Australia".
2027:
Recouso, R. C.; Santos, R. C. Stocco dos; Freitas, R.; Santos, R. C.; Freitas, A. C. de; Brunner, O.; Beçak, W.; Lindsey, C. J. (1 March 2003). "Clastogenic effect of bracken fern (Pteridium aquilinum v. arachnoideum) diet in peripheral lymphocytes of human consumers: preliminary data".
102:
1674:
Ojika, Makoto; Wakamatsu, Kazumasa; Niwa, Haruki; Yamada, Kiyoyuki (January 1987). "Ptaquiloside, a potent carcinogen isolated from bracken fern var.: structure elucidation based on chemical and spectral evidence, and reactions with amino acids, nucleosides, and nucleotides".
723:
Bracken is known to have various biological effects, such as carcinogenicity and its well-defined syndromes in livestock and laboratory animals. Ptaquiloside is proved to be responsible for several of these biological effects, some of which are species specific.
1705:
Shahin, Mahmood; Moore, Michael R.; Worrall, Simon; Smith, Barry L.; Seawright, Alan A.; Prakash, Arungundrum S. (September 1998). "H-rasActivation Is an Early Event in the
Ptaquiloside-Induced Carcinogenesis: Comparison of Acute and Chronic Toxicity in Rats".
2171:
Kigoshi, Hideo; Imamura, Yoshifumi; Mizuta, Kazuhiro; Niwa, Haruki; Yamada, Kiyoyuki (April 1993). "Total synthesis of natural (-)-ptaquilosin, the aglycon of a potent bracken carcinogen ptaquiloside and the (+)-enantiomer, and their DNA cleaving activities".
808:
in many geographical areas of the world. In 1989, Natori and co-workers showed that ptaquiloside had clastogenic effect and caused chromosomal aberration in mammalian cells. In 2003, Santos group reported significantly increased levels of
732:
Cattle that consume bracken ferns develop acute bracken poisoning and chronic bovine enzootic haematuria (BEH). The main feature of acute bracken poisoning in cattle is the depression of bone marrow activity, which gives rise to severe
1275:
Jensen, Pia H.; Jacobsen, Ole S.; Hansen, Hans
Christian B.; Juhler, René K. (12 November 2008). "Quantification of Ptaquiloside and Pterosin B in Soil and Groundwater Using Liquid Chromatography−Tandem Mass Spectrometry (LC−MS/MS)".
1991:
Matsuoka, Atsuko; Hirosawa, Akiko; Natori, Shinasku; Iwasaki, Shigeo; Toshio, Sofuni; Motoi, Ishidate Jr. (December 1989). "Mutagenicity of ptaquiloside, the carcinogen in bracken, and its related illudane-type sesquiterpenes".
1152:
Niwa, Haruki; Ojika, Makoto; Wakamatsu, Kazumasa; Yamada, Kiyoyuki; Ohba, Shigeru; Saito, Yoshihiko; Hirono, Iwao; Matsushita, Kazuhiro (1983). "Stereochemistry of ptaquiloside, a novel norsesquiterpene glucoside from bracken,
699:
breaks to release the adduct. In 1998, Prakash, Smith and co-workers showed that the alkylation of adenine by ptaquiloside in codon 61 followed by depurination and error in the DNA synthesis resulted in the activation of
1534:
Rasmussen, Lars Holm; Bruun Hansen, Hans
Christian; Lauren, Denis (February 2005). "Sorption, degradation and mobility of ptaquiloside, a carcinogenic Bracken (Pteridium sp.) constituent, in the soil environment".
1314:
Rasmussen, Lars H; Kroghsbo, Stine; Frisvad, Jens C; Hansen, Hans
Christian B (April 2003). "Occurrence of the carcinogenic Bracken constituent ptaquiloside in fronds, topsoils and organic soil layers in Denmark".
1184:
Niwa, Haruki; Ojika, Makoto; Wakamatsu, Kazumasa; Yamada, Kiyoyuki; Hirono, Iwao; Matsushita, Kazuhiro (1983). "Ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum".
1088:
have been reported since 1989. In 1994, Padwa and co-workers described the synthesis of the core skeleton of ptaquilosin by a highly convergent approach. In 1995, Cossy and co-workers reported novel routes to the
1490:
Rasmussen, Lars Holm; Jensen, Lasse Sander; Hansen, Hans
Christian Bruun (2003). "Distribution of the Carcinogenic Terpene Ptaquiloside in Bracken Fronds, Rhizomes (Pteridium aquilinum), and Litter in Denmark".
1358:
Kristanc, Luka; Kreft, Samo (June 2016). "European medicinal and edible plants associated with subacute and chronic toxicity part I: Plants with carcinogenic, teratogenic and endocrine-disrupting effects".
2226:
Padwa, Albert; Sandanayaka, Vincent P.; Curtis, Erin A. (March 1994). "Synthetic studies toward
Illudins and Ptaquilosin. A highly convergent approach via the dipolar cycloaddition of carbonyl ylides".
792:
oncogene. Other non-ruminants such as pig, rabbit, and guinea pig, also develop syndromes after ingestion of ptaquiloside, which include haematuria, tumors and organ abnormities (see the diagram).
533:, clay content, carbon content, temperature and presumably microbioactivity. Acidic condition (pH<4) and high temperature (at least 25°C) facilitate ptaquiloside degradation, while the
545:
Main routes that can lead to human exposure to the toxic effects of bracken fern include ingestion of the plant (particularly the croziers and young fronds), inhalation of the airborne
276:
InChI=1S/C20H30O8/c1-9-6-20(28-17-15(25)14(24)13(23)11(8-21)27-17)7-10(2)19(4-5-19)18(3,26)16(20)12(9)22/h7,9,11,13-17,21,23-26H,4-6,8H2,1-3H3/t9-,11-,13-,14+,15-,16-,17+,18+,20-/m1/s1
1956:
Marliére, C. A.; Wathern, P.; Castro, M. C. F. M.; O'Connor, P.; Galvao, M. A. (1 January 2002). "Bracken fern (Pteridium aquilinum) ingestion and oesophageal and stomach cancer".
387:
659:
Under physiological conditions, ptaquiloside readily liberates glucose to produce the ptaquilodienone. The alkylation of amino acids with the dienone mostly takes place at the
1915:
HIRONO, Iwao; ITO, Mitsuya; YAGYU, Shigeru; HAGA, Masanobu; WAKAMATSU, Kazumasa; KISHIKAWA, Teruaki; NISHIKAWA, Osamu; YAMADA, Kiyoyuki; OJIKA, Makoto; KIGOSHI, Hideo (1993).
753:
in cattle after prolonged exposure to bracken. Based on the extensive studies, a positive correlation is shown between the ptquiloside concentration and the incidence of BEH.
2199:
Kigoshi, Hideo; Imamura, Yoshifumi; Niwa, Haruki; Yamada, Kiyoyuki (March 1989). "Total synthesis of ptaquilosin: the aglycon of ptaquiloside, a potent bracken carcinogen".
695:
and cleavage of DNA at adenine base site. In a model reaction with a deoxytetranucleotide (as shown on the right), a covalent adduct is found at a guanine residue and the N-
505:(commonly known as bracken fern) is the most common ptaquiloside-containing fern with a wide geographical and ecological distribution. It is present in all continents from
2254:
Cossy, Janine; Ibhi, Saïd; Kahn, Philippe H.; Tacchini, Laura (October 1995). "A formal synthesis of ptaquilosin the aglycon of a potent bracken carcinogen ptaquiloside".
1117:
Kimiaki Saitoa, T.N.; Nagao, T.; Takatsuki, S.; Koyama, K.; Natori, S. (1990). "The sesquiterpenoid carcinogen of bracken fern, and some analogues, from the pteridaceae".
2074:
Sharma, Rinku; Bhat, Tej K.; Sharma, Om P. (2013). "The
Environmental and Human Effects of Ptaquiloside-Induced Enzootic Bovine Hematuria: A Tumorous Disease of Cattle".
1065:
was obtained. The Yamada's synthesis proceeded in 20 steps with an overall yield of 2.9%. Similarly, the unnatural (+)-enantiomer of ptaquilosin was synthesized from the
2115:
Kamon, S.; Hirayama, T. (1975). "Epidemiology of cancer of the oesophagus in Mye, Nara and Wakayama prefecture with special reference to the role of bracken fern。".
745:
crisis. However, most of the researchers believe ptaquiloside is not the direct causing agent of the acute bracken fern poisoning. The main feature of haematuria is
593:
to afford ptaquilosin, and finally pterosin B. Under weakly alkaline conditions, ptaquiloside and its aglycone ptaquilosin are converted into an unstable conjugated
1744:
Yamada, Kiyoyuki; Ojika, Makoto; Kigoshi, Hideo (2007). "Ptaquiloside, the major toxin of bracken, and related terpene glycosides: chemistry, biology and ecology".
289:
850:
577:
group, but because it also constitutes a cyclopropyl carbinol system, from which the facile formation of the stable non-classical cation is well-known.
454:
vegetation. The prevalence of ptaquiloside in daily sources along with its carcinogenic effects make it an increasing biological hazard in modern days.
846:
800:
Bracken fern increases the oncogenic risk in humans. Epidemiological survey revealed that bracken fern consumption was positively correlated with
513:
areas. Bracken fern is a very adaptable plant and is capable of forming dense, rapidly expanding populations in course of the first phases of the
842:
756:
Sheep fed by a diet containing bracken develop acute haemorrhagic disease and bright blindness. The main features of the blindness include
2091:
1917:"Reproduction of Progressive Retinal Degeneration(Bright Blindness) in Sheep by Administration of Ptaquiloside Contained in Bracken"
1872:
Watson, W.; Barnett, K.; Terlecki, S. (30 December 1972). "Progressive retinal degeneration (Bright Blindness) in sheep: a review".
1779:
Smith, B.L.; Embling, P.P.; Agnew, M.P.; Lauren, D.R.; Holland, P.T. (June 1988). "Carcinogenicity of bracken fern in New Zealand".
267:
642:
936:
was partially hydrolyzed to afford the monomenthyl ester, which was later alkylated with methallyl bromide in the presence of
1829:
Watson, W.; Barlow, R.; Barnett, K. (11 September 1965). "Bright blindness--a condition prevalent in Yorkshire hill sheep".
767:
2296:
1010:
of the cyclopentanone under Noyori's condition using the TASF enolate produced a mixture of isomers. The undesired isomer
788:. Prakash, Smith and co-workers showed that ptaquiloside-induced carcinogenesis was initiated by the activation of the H-
394:
210:
2311:
1097:
ptaquilosin skeleton. Their properly functionalized tricyclic compound would be of great utility for the synthesis of
757:
231:
467:
2306:
858:
857:
detection, immunohistochemical detection of tumor biomarkers, chromosomal aberrations, oxidative stress for EBH,
838:
2326:
2321:
764:
of the blood vessels. In 1993, Yamada group proved ptaquiloside was the compound causing retinal degeneration.
679:, is also observed to a small extent based on the previously reported literature. The dienone reacts with both
632:
826:
eating the plant is to pre-treat the fern with boiling water in the presence of different chemicals, such as
1015:
953:
937:
2301:
2291:
984:
810:
517:
in forest cleanings and other disturbed rural areas. Its aggressive growth, characterized by an extensive
475:
The presence of ptaquiloside has been detected in a variety of ferns, including the species in the genera
450:
under physiological conditions. It was first isolated and characterized by Yamada and co-workers in 1983.
1814:
Pinto, C.; Januário, T.; Geraldes, M.; Machado, J.; Lauren, D. R.; Smith, B. L.; Robinson, R. C. (2004).
597:
intermediate. This ptaquilodienone is the activated form of ptaquiloside and is regarded as the ultimate
2331:
780:
Rats that were given a diet containing ptaquiloside for a prolonged period developed tumors in both the
601:
of bracken ferns. Due to the constitution of a cyclopropyl carbinol system, ptaquilodienone is a strong
514:
36:
1076:
549:, consumption of the milk and meat of affected animals, and drinking ptaquiloside contaminated water.
2286:
1544:
1324:
1228:
1126:
991:
with 81% yield. Desaturation by selenylation/dehydroselenation and basic peroxide oxidation afforded
837:
Ptaquiloside in the aqueous extract of bracken can be detected using different instrumental methods:
248:
2336:
501:
422:
68:
1215:
Alonso-Amelot, Miguel E.; Castillo, Uvidelio; Smith, Barry L.; Lauren, Denis R. (15 August 1996).
1897:
1854:
1516:
1433:
Smith, B. L.; Seawright, A. A.; Ng, J. C.; Hertle, A. T.; Thomson, J. A.; Bostock, P. D. (1994).
1254:
827:
439:
114:
2153:
2097:
2087:
2053:
2045:
2009:
1973:
1965:
1938:
1889:
1846:
1796:
1761:
1723:
1656:
1638:
1596:
1560:
1508:
1472:
1415:
1376:
1340:
1293:
1246:
999:
801:
566:
495:
154:
2316:
2263:
2236:
2208:
2181:
2143:
2079:
2037:
2001:
1928:
1881:
1838:
1788:
1753:
1715:
1684:
1646:
1630:
1588:
1552:
1500:
1464:
1407:
1368:
1332:
1285:
1236:
1194:
1166:
1134:
1094:
949:
914:
738:
410:
312:
219:
78:
785:
696:
252:
565:
is the active form of ptaquiloside and accounts for the observed biological effects. The
1548:
1455:
Vetter, János (March 2009). "A biological hazard of our age: Bracken fern — A Review".
1328:
1232:
1130:
675:. The alkylation at the carboxylate group of each amino acid, forming the corresponding
134:
1651:
1618:
805:
746:
537:
of ptaquiloside in less acidic sandy soil is reported to be between 150 and 180 hours.
443:
365:
23:
1688:
1556:
1336:
1198:
1170:
1050:
was oxidized to the acyl radical for decarbonylation. Stereoselective trapping of the
878:
2280:
2267:
2041:
2005:
1138:
1055:
1039:
980:
854:
586:
353:
199:
1901:
1858:
1520:
1258:
861:, real-time PCR and DNase-SISPA (sequence-independent single primer amplification).
1066:
1027:
972:
692:
625:
under weakly acidic conditions at room temperature (as shown in the scheme below).
602:
570:
2130:
Latorre AO, Caniceiro BD, Wysocki HL, Haraguchi M, Gardner DR, Górniak SL (2011).
2083:
1792:
1007:
668:
610:
2148:
2131:
1504:
1468:
1435:
In Plant-Associated Toxins: Agricultural, Phytochemical and Ecological Aspects
1372:
964:
918:
814:
750:
734:
672:
622:
618:
614:
606:
598:
506:
489:
447:
431:
427:
340:
145:
2049:
1969:
1642:
1592:
971:. On treatment with base and a chloroethyl sulfonium salt, a mixture of spiro
446:
in humans. Ptaquiloside has an unstable chemical structure and acts as a DNA
1619:"Carcinogenic effects of ptaquiloside in bracken fern and related compounds"
1031:
534:
510:
413:
2157:
2101:
2057:
1977:
1800:
1765:
1719:
1660:
1634:
1600:
1564:
1512:
1476:
1380:
1344:
1297:
2013:
1942:
1893:
1850:
1842:
1727:
1419:
1411:
1250:
1885:
1051:
1043:
922:
831:
761:
742:
708:
664:
435:
434:
of the ferns and to be responsible for their biological effects, such as
2240:
2212:
2185:
1933:
1916:
1090:
992:
926:
684:
680:
594:
590:
562:
558:
518:
477:
417:
186:
1289:
1994:
Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis
1757:
1241:
1216:
963:. Hydride reduction, selective oxidation of the allylic alcohol, and
574:
483:
364:
Except where otherwise noted, data are given for materials in their
2132:"Selenium reverses Pteridium aquilinum-induced immunotoxic effects"
853:(LC-MS). The diagnostic tests of ptaquiloside inside cells include
557:
Ptaquiloside has unstable chemical structure and readily undergoes
174:
1075:
1023:
957:
929:
781:
766:
712:
676:
660:
641:
631:
546:
522:
466:
125:
101:
91:
2076:
Reviews of Environmental Contamination and Toxicology Volume 224
701:
165:
1437:. Wallingford: S. M. Colgate and P. R. Dorling. pp. 45–50.
1061:. Under mild reduction, the naturally occurred (-)-ptaquilosin
2078:. Vol. 224. New York: Springer New York. pp. 53–95.
873:
688:
691:
to form the DNA adducts. The alkylation induces spontaneous
236:
913:
In 1989 and 1993, Yamada and co-workers reported the first
530:
948:
was then converted to the acid chloride and treated with
358:
85 to 89 °C (185 to 192 °F; 358 to 362 K)
1084:
Multiple synthetic studies directed towards ptaquilosin
889:
585:
In acidic conditions, ptaquiloside gradually undergoes
382:
646:
Mechanism of ptaquilodienone with deoxytetranucleotide
1210:
1208:
1708:
Biochemical and Biophysical Research Communications
813:, such as chromatid breaks in cultured peripheral
1818:. Wallingford: CABI Publishing. pp. 564–574.
771:Species-specific syndromes caused by ptaquiloside
1739:
1737:
198:
297:C1C2(C=C(C3(CC3)(2C1=O)(C)O)C)O4((((O4)CO)O)O)O
77:
1617:Potter, D. M.; Baird, M. S. (1 October 2000).
1450:
1448:
1446:
1444:
438:disease and bright blindness in livestock and
56:)-7-Hydroxy-2,5,7-trimethyl-3a-oxy-spiro-1-one
2117:Proc. Jpn. Cancer Assoc., 34th Annual Meeting
1309:
1307:
573:, not only because it is conjugated with the
8:
1392:
1390:
1700:
1698:
1581:Journal of Agricultural and Food Chemistry
1278:Journal of Agricultural and Food Chemistry
1270:
1268:
471:Croziers, fronds, rhizomes of bracken fern
251:
153:
15:
2147:
2069:
2067:
1932:
1921:The Journal of Veterinary Medical Science
1650:
1612:
1610:
1240:
218:
2229:Journal of the American Chemical Society
2201:Journal of the American Chemical Society
2174:Journal of the American Chemical Society
967:were then performed to provide compound
925:of ptaquiloside. In the first step, the
569:in the dienone is highly reactive as an
1109:
851:liquid chromatography–mass spectrometry
636:The mechanism of action of ptaquiloside
294:
272:
247:
1816:In Poisonous Plants and Related Toxins
932:of cyclopentane-1,2-dicarboxylic acid
843:high-performance liquid chromatography
1018:in 81% yield to exclusively generate
609:that reacts directly with biological
133:
7:
847:gas chromatography–mass spectrometry
737:(particularly of the granulocytes),
2030:Veterinary and Comparative Oncology
1038:. On treatment with oxygen in warm
189:
173:
1080:Total synthesis of (-)-ptaquilosin
841:–densitometry (TLC-densitometry),
561:liberation. The resulting ptaquilo
430:. It is identified to be the main
14:
1557:10.1016/j.chemosphere.2004.08.088
2042:10.1046/j.1476-5829.2003.00006.x
975:was obtained. The minor product
877:
372:
324:
22:
368:(at 25 °C , 100 kPa).
1781:New Zealand Veterinary Journal
1217:"Bracken ptaquiloside in milk"
1002:, and oxidation gave compound
655:Under physiological conditions
330:
318:
1:
1689:10.1016/S0040-4020(01)87702-4
1337:10.1016/S0045-6535(02)00694-X
1199:10.1016/S0040-4039(00)88276-3
1171:10.1016/S0040-4039(00)87871-5
687:(majorly at N-7) residues of
541:Ways of ptaquiloside exposure
2268:10.1016/0040-4039(95)01552-S
2006:10.1016/0027-5107(89)90182-6
1958:IARC Scientific Publications
1361:Food and Chemical Toxicology
1139:10.1016/0031-9422(90)80104-O
917:total synthesis of both the
2084:10.1007/978-1-4614-5882-1_3
1793:10.1080/00480169.1988.35481
1493:Journal of Chemical Ecology
1054:radical by oxygen gave the
758:progressive retinal atrophy
521:system and rapidly growing
2353:
1457:Acta Veterinaria Hungarica
1014:can be equilibriumed with
2149:10.1016/j.fct.2010.11.026
1623:British Journal of Cancer
1579:Concern of Food Safety".
1469:10.1556/AVet.57.2009.1.18
1373:10.1016/j.fct.2016.04.007
998:. Mild reduction, methyl
839:thin-layer chromatography
811:chromosomal abnormalities
463:In plants and food chains
362:
305:
285:
263:
61:
35:
30:
21:
1593:10.1021/acs.jafc.5b01937
954:Friedel-Crafts acylation
589:with the elimination of
1746:Natural Product Reports
1505:10.1023/A:1022885006742
1016:potassium tert-butoxide
940:to selectively produce
715:of calves fed bracken.
605:and acts as a powerful
1720:10.1006/bbrc.1998.9341
1635:10.1054/bjoc.2000.1368
1081:
985:p-toluenesulfonic acid
886:This section is empty.
772:
747:urinary bladder tumors
647:
637:
472:
1843:10.1136/vr.77.37.1060
1412:10.1002/nt.2620020602
1079:
821:Control and detection
770:
683:(majorly at N-3) and
645:
635:
515:ecological succession
470:
2297:Terpenoid glycosides
1886:10.1136/vr.91.27.665
921:of ptaquilosin, the
2256:Tetrahedron Letters
2241:10.1021/ja00085a076
2213:10.1021/ja00188a054
2186:10.1021/ja00061a003
1934:10.1292/jvms.55.979
1549:2005Chmsp..58..823R
1329:2003Chmsp..51..117R
1233:1996Natur.382..587A
1187:Tetrahedron Letters
1159:Tetrahedron Letters
1157:var. latiusculum".
1155:Pteridium aquilinum
1131:1990PChem..29.1475S
553:Mechanism of action
502:Pteridium aquilinum
423:Pteridium aquilinum
348: g·mol
115:Beilstein Reference
18:
2312:Alkene derivatives
2136:Food Chem. Toxicol
1082:
828:sodium bicarbonate
773:
648:
638:
473:
395:Infobox references
16:
2262:(43): 7877–7880.
1874:Veterinary Record
1837:(37): 1060–1069.
1831:Veterinary Record
1683:(22): 5261–5274.
1587:(19): 4886–4892.
1290:10.1021/jf801986u
1284:(21): 9848–9854.
1193:(38): 4117–4120.
1165:(48): 5371–5372.
1000:Grignard addition
906:
905:
802:esophageal cancer
796:Human populations
652:
651:
581:General mechanism
567:cyclopropyl group
403:Chemical compound
401:
400:
232:CompTox Dashboard
103:Interactive image
2344:
2307:Primary alcohols
2272:
2271:
2251:
2245:
2244:
2235:(6): 2667–2668.
2223:
2217:
2216:
2207:(6): 2302–2303.
2196:
2190:
2189:
2180:(8): 3056–3065.
2168:
2162:
2161:
2151:
2127:
2121:
2120:
2112:
2106:
2105:
2071:
2062:
2061:
2024:
2018:
2017:
1988:
1982:
1981:
1953:
1947:
1946:
1936:
1912:
1906:
1905:
1869:
1863:
1862:
1826:
1820:
1819:
1811:
1805:
1804:
1776:
1770:
1769:
1758:10.1039/B614160A
1741:
1732:
1731:
1702:
1693:
1692:
1671:
1665:
1664:
1654:
1614:
1605:
1604:
1575:
1569:
1568:
1531:
1525:
1524:
1487:
1481:
1480:
1452:
1439:
1438:
1430:
1424:
1423:
1394:
1385:
1384:
1355:
1349:
1348:
1311:
1302:
1301:
1272:
1263:
1262:
1244:
1242:10.1038/382587a0
1212:
1203:
1202:
1181:
1175:
1174:
1149:
1143:
1142:
1125:(5): 1475–1479.
1114:
1095:optically active
950:stannic chloride
915:enantioselective
901:
898:
888:You can help by
881:
874:
739:thrombocytopenia
628:
627:
607:alkylating agent
448:alkylating agent
411:norsesquiterpene
385:
379:
376:
375:
347:
332:
326:
320:
313:Chemical formula
256:
255:
240:
238:
222:
202:
191:
177:
157:
137:
105:
81:
26:
19:
2352:
2351:
2347:
2346:
2345:
2343:
2342:
2341:
2327:Total synthesis
2322:Spiro compounds
2277:
2276:
2275:
2253:
2252:
2248:
2225:
2224:
2220:
2198:
2197:
2193:
2170:
2169:
2165:
2129:
2128:
2124:
2114:
2113:
2109:
2094:
2073:
2072:
2065:
2026:
2025:
2021:
1990:
1989:
1985:
1955:
1954:
1950:
1914:
1913:
1909:
1880:(27): 665–670.
1871:
1870:
1866:
1828:
1827:
1823:
1813:
1812:
1808:
1778:
1777:
1773:
1743:
1742:
1735:
1704:
1703:
1696:
1673:
1672:
1668:
1616:
1615:
1608:
1577:
1576:
1572:
1533:
1532:
1528:
1489:
1488:
1484:
1454:
1453:
1442:
1432:
1431:
1427:
1396:
1395:
1388:
1357:
1356:
1352:
1313:
1312:
1305:
1274:
1273:
1266:
1214:
1213:
1206:
1183:
1182:
1178:
1151:
1150:
1146:
1116:
1115:
1111:
1107:
944:. The product
911:
909:Total synthesis
902:
896:
893:
872:
867:
823:
798:
786:urinary bladder
778:
730:
721:
697:glycosidic bond
657:
583:
555:
543:
465:
460:
420:ferns (majorly
404:
397:
392:
391:
390: ?)
381:
377:
373:
369:
345:
335:
329:
323:
315:
301:
298:
293:
292:
281:
278:
277:
271:
270:
259:
241:
234:
225:
205:
192:
180:
160:
140:
117:
108:
95:
84:
71:
57:
12:
11:
5:
2350:
2348:
2340:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2279:
2278:
2274:
2273:
2246:
2218:
2191:
2163:
2122:
2107:
2092:
2063:
2019:
2000:(2): 179–185.
1983:
1948:
1927:(6): 979–983.
1907:
1864:
1821:
1806:
1771:
1752:(4): 798–813.
1733:
1714:(2): 491–497.
1694:
1666:
1629:(7): 914–920.
1606:
1570:
1543:(6): 823–835.
1526:
1499:(3): 771–778.
1482:
1463:(1): 183–196.
1440:
1425:
1406:(6): 347–353.
1386:
1350:
1323:(2): 117–127.
1303:
1264:
1204:
1176:
1144:
1119:Phytochemistry
1108:
1106:
1103:
910:
907:
904:
903:
884:
882:
871:
868:
866:
863:
822:
819:
806:gastric cancer
797:
794:
777:
774:
729:
726:
720:
717:
656:
653:
650:
649:
639:
582:
579:
554:
551:
542:
539:
464:
461:
459:
456:
444:gastric cancer
402:
399:
398:
393:
371:
370:
366:standard state
363:
360:
359:
356:
350:
349:
343:
337:
336:
333:
327:
321:
316:
311:
308:
307:
303:
302:
300:
299:
296:
288:
287:
286:
283:
282:
280:
279:
275:
274:
266:
265:
264:
261:
260:
258:
257:
249:DTXSID20892005
244:
242:
230:
227:
226:
224:
223:
215:
213:
207:
206:
204:
203:
195:
193:
185:
182:
181:
179:
178:
170:
168:
162:
161:
159:
158:
150:
148:
142:
141:
139:
138:
130:
128:
122:
121:
118:
113:
110:
109:
107:
106:
98:
96:
89:
86:
85:
83:
82:
74:
72:
67:
64:
63:
59:
58:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
2349:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2302:Cyclopentanes
2300:
2298:
2295:
2293:
2292:Cyclopropanes
2290:
2288:
2285:
2284:
2282:
2269:
2265:
2261:
2257:
2250:
2247:
2242:
2238:
2234:
2230:
2222:
2219:
2214:
2210:
2206:
2202:
2195:
2192:
2187:
2183:
2179:
2175:
2167:
2164:
2159:
2155:
2150:
2145:
2142:(2): 464–70.
2141:
2137:
2133:
2126:
2123:
2118:
2111:
2108:
2103:
2099:
2095:
2093:9781461458814
2089:
2085:
2081:
2077:
2070:
2068:
2064:
2059:
2055:
2051:
2047:
2043:
2039:
2035:
2031:
2023:
2020:
2015:
2011:
2007:
2003:
1999:
1995:
1987:
1984:
1979:
1975:
1971:
1967:
1963:
1959:
1952:
1949:
1944:
1940:
1935:
1930:
1926:
1922:
1918:
1911:
1908:
1903:
1899:
1895:
1891:
1887:
1883:
1879:
1875:
1868:
1865:
1860:
1856:
1852:
1848:
1844:
1840:
1836:
1832:
1825:
1822:
1817:
1810:
1807:
1802:
1798:
1794:
1790:
1786:
1782:
1775:
1772:
1767:
1763:
1759:
1755:
1751:
1747:
1740:
1738:
1734:
1729:
1725:
1721:
1717:
1713:
1709:
1701:
1699:
1695:
1690:
1686:
1682:
1678:
1670:
1667:
1662:
1658:
1653:
1648:
1644:
1640:
1636:
1632:
1628:
1624:
1620:
1613:
1611:
1607:
1602:
1598:
1594:
1590:
1586:
1582:
1574:
1571:
1566:
1562:
1558:
1554:
1550:
1546:
1542:
1538:
1530:
1527:
1522:
1518:
1514:
1510:
1506:
1502:
1498:
1494:
1486:
1483:
1478:
1474:
1470:
1466:
1462:
1458:
1451:
1449:
1447:
1445:
1441:
1436:
1429:
1426:
1421:
1417:
1413:
1409:
1405:
1401:
1393:
1391:
1387:
1382:
1378:
1374:
1370:
1366:
1362:
1354:
1351:
1346:
1342:
1338:
1334:
1330:
1326:
1322:
1318:
1310:
1308:
1304:
1299:
1295:
1291:
1287:
1283:
1279:
1271:
1269:
1265:
1260:
1256:
1252:
1248:
1243:
1238:
1234:
1230:
1227:(6592): 587.
1226:
1222:
1218:
1211:
1209:
1205:
1200:
1196:
1192:
1188:
1180:
1177:
1172:
1168:
1164:
1160:
1156:
1148:
1145:
1140:
1136:
1132:
1128:
1124:
1120:
1113:
1110:
1104:
1102:
1100:
1096:
1092:
1087:
1078:
1074:
1072:
1068:
1064:
1060:
1057:
1056:hydroperoxide
1053:
1049:
1045:
1041:
1040:ethyl acetate
1037:
1033:
1029:
1025:
1021:
1017:
1013:
1009:
1005:
1001:
997:
994:
990:
986:
982:
978:
974:
973:cyclopropanes
970:
966:
962:
959:
955:
951:
947:
943:
939:
935:
931:
928:
924:
920:
916:
908:
900:
897:December 2021
891:
887:
883:
880:
876:
875:
869:
864:
862:
860:
856:
855:gene mutation
852:
848:
844:
840:
835:
833:
829:
820:
818:
816:
812:
807:
803:
795:
793:
791:
787:
783:
776:Non-ruminants
775:
769:
765:
763:
759:
754:
752:
748:
744:
740:
736:
727:
725:
718:
716:
714:
710:
706:
705:
698:
694:
690:
686:
682:
678:
674:
670:
666:
662:
654:
644:
640:
634:
630:
629:
626:
624:
620:
616:
612:
608:
604:
600:
596:
592:
588:
587:aromatization
580:
578:
576:
572:
568:
564:
560:
552:
550:
548:
540:
538:
536:
532:
526:
524:
520:
516:
512:
508:
504:
503:
498:
497:
492:
491:
486:
485:
480:
479:
469:
462:
457:
455:
451:
449:
445:
441:
437:
433:
429:
425:
424:
419:
415:
412:
408:
396:
389:
384:
367:
361:
357:
355:
354:Melting point
352:
351:
344:
342:
339:
338:
317:
314:
310:
309:
304:
295:
291:
284:
273:
269:
262:
254:
250:
246:
245:
243:
233:
229:
228:
221:
217:
216:
214:
212:
209:
208:
201:
197:
196:
194:
188:
184:
183:
176:
172:
171:
169:
167:
164:
163:
156:
152:
151:
149:
147:
144:
143:
136:
132:
131:
129:
127:
124:
123:
119:
116:
112:
111:
104:
100:
99:
97:
93:
88:
87:
80:
76:
75:
73:
70:
66:
65:
60:
55:
51:
47:
43:
38:
34:
29:
25:
20:
17:Ptaquiloside
2332:Plant toxins
2259:
2255:
2249:
2232:
2228:
2221:
2204:
2200:
2194:
2177:
2173:
2166:
2139:
2135:
2125:
2116:
2110:
2075:
2036:(1): 22–29.
2033:
2029:
2022:
1997:
1993:
1986:
1961:
1957:
1951:
1924:
1920:
1910:
1877:
1873:
1867:
1834:
1830:
1824:
1815:
1809:
1787:(2): 56–58.
1784:
1780:
1774:
1749:
1745:
1711:
1707:
1680:
1676:
1669:
1626:
1622:
1584:
1580:
1573:
1540:
1536:
1529:
1496:
1492:
1485:
1460:
1456:
1434:
1428:
1403:
1399:
1364:
1360:
1353:
1320:
1316:
1281:
1277:
1224:
1220:
1190:
1186:
1179:
1162:
1158:
1154:
1147:
1122:
1118:
1112:
1098:
1085:
1083:
1070:
1067:diastereomer
1062:
1058:
1047:
1035:
1028:deprotection
1019:
1011:
1003:
995:
988:
976:
968:
960:
945:
941:
933:
912:
894:
890:adding to it
885:
870:Biosynthesis
849:(GCMS), and
836:
824:
799:
789:
779:
755:
743:haemorrhagic
741:, and acute
731:
722:
703:
693:depurination
658:
611:nucleophiles
603:electrophile
584:
571:electrophile
556:
544:
527:
500:
494:
488:
482:
476:
474:
452:
436:haemorrhagic
421:
416:produced by
407:Ptaquiloside
406:
405:
62:Identifiers
53:
49:
45:
41:
2287:Carcinogens
1964:: 379–380.
1677:Tetrahedron
1537:Chemosphere
1400:Nat. Toxins
1367:: 150–164.
1317:Chemosphere
1008:Methylation
919:enantiomers
815:lymphocytes
669:glutathione
623:nucleotides
619:nucleosides
615:amino acids
481:(bracken),
440:oesophageal
306:Properties
135:CHEBI:82527
2337:Glycosides
2281:Categories
1105:References
981:isomerized
965:silylation
952:to effect
751:haematuria
735:leucopenia
673:methionine
613:including
599:carcinogen
490:Microlepia
432:carcinogen
428:metabolism
341:Molar mass
220:F0MN9S5699
146:ChemSpider
90:3D model (
79:87625-62-5
69:CAS Number
37:IUPAC name
2050:1476-5829
1970:0300-5038
1643:0007-0920
1034:afforded
1032:oxidation
1024:Reduction
865:Synthesis
804:and with
728:Ruminants
719:Syndromes
663:group in
591:D-glucose
535:half-life
511:subarctic
507:subtropic
496:Hypolepis
478:Pteridium
426:) during
414:glucoside
2158:21112370
2102:23232919
2058:19379327
1978:12484211
1902:41177293
1859:41320519
1801:16031441
1766:17653360
1661:10970694
1601:25932502
1565:15621196
1521:37286843
1513:12757333
1477:19457786
1381:27090581
1345:12586144
1298:18937485
1259:33439224
1052:tertiary
1044:aldehyde
956:to give
923:aglycone
845:(HPLC),
832:wood ash
762:stenosis
709:oncogene
665:cysteine
200:13962857
155:10312775
120:3632862
2317:Ketones
2014:2601729
1943:8117827
1894:4675711
1851:5890140
1728:9753659
1652:2374682
1545:Bibcode
1420:7704447
1325:Bibcode
1251:8757125
1229:Bibcode
1127:Bibcode
1091:racemic
993:epoxide
979:can be
927:menthyl
711:in the
685:guanine
681:adenine
595:dienone
563:dienone
559:glucose
531:acidity
519:rhizome
458:Sources
418:bracken
388:what is
386: (
346:398.452
187:PubChem
2156:
2119:: 211.
2100:
2090:
2056:
2048:
2012:
1976:
1968:
1941:
1900:
1892:
1857:
1849:
1799:
1764:
1726:
1659:
1649:
1641:
1599:
1563:
1519:
1511:
1475:
1418:
1379:
1343:
1296:
1257:
1249:
1221:Nature
1042:, the
1030:, and
707:proto-
621:, and
547:spores
523:fronds
493:, and
484:Pteris
383:verify
380:
290:SMILES
175:C19515
31:Names
1898:S2CID
1855:S2CID
1517:S2CID
1255:S2CID
983:with
958:enone
930:ester
782:ileum
713:ileum
677:ester
661:thiol
409:is a
268:InChI
126:ChEBI
92:JSmol
2154:PMID
2098:PMID
2088:ISBN
2054:PMID
2046:ISSN
2010:PMID
1974:PMID
1966:ISSN
1939:PMID
1890:PMID
1847:PMID
1797:PMID
1762:PMID
1724:PMID
1657:PMID
1639:ISSN
1597:PMID
1561:PMID
1509:PMID
1473:PMID
1416:PMID
1377:PMID
1341:PMID
1294:PMID
1247:PMID
1093:and
938:HMPA
830:and
784:and
760:and
749:and
671:and
575:keto
211:UNII
166:KEGG
2264:doi
2237:doi
2233:116
2209:doi
2205:111
2182:doi
2178:115
2144:doi
2080:doi
2038:doi
2002:doi
1998:215
1962:156
1929:doi
1882:doi
1839:doi
1789:doi
1754:doi
1716:doi
1712:250
1685:doi
1647:PMC
1631:doi
1589:doi
1553:doi
1501:doi
1465:doi
1408:doi
1369:doi
1333:doi
1286:doi
1237:doi
1225:382
1195:doi
1167:doi
1135:doi
1069:of
1046:on
1022:.
987:to
892:.
859:PCR
790:ras
704:ras
689:DNA
509:to
237:EPA
190:CID
52:,7a
44:,3a
2283::
2260:36
2258:.
2231:.
2203:.
2176:.
2152:.
2140:49
2138:.
2134:.
2096:.
2086:.
2066:^
2052:.
2044:.
2032:.
2008:.
1996:.
1972:.
1960:.
1937:.
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