195:
24:
435:
trees. Once living organism die, the organic molecules they biosynthesized often undergo various chemical transformations in the soil and thus usually retain only basic structures of the molecules that were synthesized. These modified molecules are biomarkers but can often only be used as chemical
436:
tracers for a wide group of organisms. Chamaecydin is rare because it is a polar molecule that is found perfectly preserved millions of years later, and can therefore be used to trace specific species. Despite being a polar compound, chamaecydin is likely preserved because it is found trapped in
960:
Simoneit, Bernd R.T.; Otto, Angelika; Kusumoto, Norihisa; Basinger, James F. (December 2016). "Biomarker compositions of
Glyptostrobus and Metasequoia (Cupressaceae) fossils from the Eocene Buchanan Lake Formation, Axel Heiberg Island, Nunavut, Canada reflect diagenesis from terpenoids of their
593:
island. This is a unique habitat, which required them to be dormant during 3 months of winter darkness. The Arctic Circle at this time was very different from today: it was ice free and warm (12-17 degrees warmer than today) with lots of precipitation. These deposits occur in
1004:
Simoneit, Bernd R.T.; Otto, Angelika; Menor-Sálvan, Cesar; Oros, Daniel R.; Wilde, Volker; Riegel, Walter (February 2021). "Composition of resinites from the Eocene
Geiseltal brown coal basin, Saxony-Anhalt, Germany and comparison to their possible botanical analogues".
116:
858:
Stefanova, Maya; Simoneit, Bernd R.T.; Marinov, Stefan P.; Zdravkov, Alexander; Kortenski, Jordan (June 2016). "Novel polar biomarkers of the
Miocene Maritza-East lignite, Bulgaria".
218:
InChI=1S/C30H40O3/c1-15(2)20-22-21-17(26(33)30(22)12-11-29(16(3)4)14-19(29)30)13-18-27(5,6)9-8-10-28(18,7)23(21)25(32)24(20)31/h15-16,18-19,32H,8-14H2,1-7H3/t18-,19-,28-,29+,30-/m0/s1
547:, deduced by the presence of chamaecydin in the paleorecord, managed to flourish across a wide range of latitudes over Earth's history. Below are some well studied occurrences of
571:
epochs (33.9-2.58 Ma). We can infer that the forested flood plains were dominated by
Taxodioideae because of the presence of chamaecydin. The biomarker is captured in 3 thick
444:. In the paleorecord, it is found in clayey sediments, which prevents further oxidation. Chamaecydin is found in concentrations ranging 3–8.7 mg/g of organic carbon.
234:
692:
Hirose, Yoshiyuki; Hasegawa, Shinichi; Ozaki, Naotake; Iitaka, Yoichi (1983-01-01). "Three new terpenoid quinone methides from the seed of
209:
1071:
1086:
406:
173:
372:
subfamily. The presence and abundance of chamaecydin in the rock record can reveal environmental changes in ancient
333:
1076:
1081:
485:
645:
Su, Wen-Chiung; Fang, Jim-Min; Cheng, Yu-Shia (1993-10-01). "Hexacarbocyclic triterpenes from leaves of
40:
1061:
1014:
970:
867:
805:
658:
479:
454:
190:
364:
functional group. It is well preserved in the rock record and is only found in a specific family of
1066:
590:
497:
82:
563:. The area then experienced alternating dry and wet periods from intense precipitation during the
1038:
837:
775:
491:
1030:
986:
942:
924:
903:"Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS"
883:
829:
821:
767:
713:
674:
595:
560:
510:
415:
402:
394:
314:
1022:
978:
932:
914:
875:
813:
757:
705:
666:
502:
257:
136:
796:
Otto, A. (2002-08-30). "Natural
Product Terpenoids in Eocene and Miocene Conifer Fossils".
194:
92:
556:
360:. It is made up of three six-membered rings and two five-membered rings and has one polar
1018:
974:
871:
809:
662:
937:
902:
327:
709:
161:
1055:
1042:
1026:
879:
670:
398:
361:
298:
841:
779:
536:-cymenylferruginol. The synthesis methods of chamaecydin have not yet been studied.
982:
506:
474:
459:
369:
555:
The paleoflora of the
Maritza-East basin was a marine environment that developed
464:
410:
919:
529:
390:
285:
127:
1034:
990:
928:
887:
825:
771:
717:
678:
575:
beds that formed in the dry periods, with one bed reaching 30 m in thickness.
817:
579:
564:
525:
428:
946:
833:
568:
740:
Fukushima, Jun-ichi; Yatagai, Mitsuyoshi; Ohira, Tatsuro (August 2002).
70:)-1-hydroxy-7,7,10a-trimethyl-1',3-di(propan-2-yl)spirohexane]-2,5-dione
23:
762:
741:
618:
614:
582:
572:
548:
544:
519:
470:
441:
432:
365:
148:
585:
forests were present north of the Arctic Circle (78 N) during the mid
730:
AFI ranges from –1 to +1, with +1 being the most powerful antifeedant
606:
586:
326:
Except where otherwise noted, data are given for materials in their
469:
D. Don. Chamaecydin has since been found to be unique to the swamp
622:
610:
437:
373:
115:
105:
599:
742:"Abietane-type and labdane-type diterpenoids from the cones of
242:
CC(C)C1=C2C3=C(C4(C3=C(C1=O)O)(CCCC4(C)C)C)C(=O)25CC6(5C6)C(C)C
477:), specifically, it has been most studied in these species:
178:
440:
plant material, where it is prevented from bonding to
348:
is a chemical compound with the molecular formula C
303:197–198 °C (387–388 °F; 470–471 K)
160:
91:
901:Simoneit; Otto; Oros; Kusumoto (2019-08-21).
8:
419:and has an antifeedant index (AFI) of +0.44
193:
135:
15:
936:
918:
761:
634:
452:It was first isolated from the seed of
239:
214:
189:
963:Review of Palaeobotany and Palynology
578:Chamaecydin also confirms that large
221:Key: CTGGVCKBMLNHNX-WLHXYQFRSA-N
7:
853:
851:
791:
789:
640:
638:
151:
14:
617:contain chamaecydin and reveal a
613:from brown coal pits in northern
1027:10.1016/j.orggeochem.2020.104138
880:10.1016/j.orggeochem.2016.03.002
409:. Chamaecydin shows significant
389:Chamaecydin is a hexacarboxylic
269:
22:
501:. The molecule is found in the
413:activity against the larvae of
330:(at 25 °C , 100 kPa).
983:10.1016/j.revpalbo.2016.07.012
509:and can be traced back to the
505:, seed cones, and wood of the
462:) and then from the leaves of
275:
263:
1:
710:10.1016/S0040-4039(00)81702-5
514:
671:10.1016/0031-9422(93)85358-X
1103:
961:related extant species".
920:10.3390/molecules24173036
324:
307:
250:
230:
205:
75:
39:
34:
21:
528:for this sub-family are
401:is 197–198 °C. Its
818:10.1126/science.1074225
750:Journal of Wood Science
522: million years ago
431:for certain species of
486:Glyptostrobus pensilis
1072:Tetracyclic compounds
1007:Organic Geochemistry
860:Organic Geochemistry
744:Chamaecyparis obtusa
694:Chamaecyparis obtusa
647:Cryptomeria japonica
559:conditions due to a
480:Cryptomeria japonica
455:Chamaecyparis obtusa
1087:Isopropyl compounds
1019:2021OrGeo.15204138S
975:2016RPaPa.235...81S
872:2016OrGeo..96....1S
810:2002Sci...297.1543O
804:(5586): 1543–1545.
698:Tetrahedron Letters
663:1993PChem..34..779S
498:Taxodium mucronatum
293: g·mol
18:
763:10.1007/bf00831355
492:Taxodium distichum
448:Biological sources
385:Notable properties
334:Infobox references
16:
704:(14): 1535–1538.
561:marine regression
524:). The other key
511:Cretaceous period
427:Chamaecydin is a
416:Spodoptera litura
403:crystal structure
342:Chemical compound
340:
339:
315:Crystal structure
174:CompTox Dashboard
117:Interactive image
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258:Chemical formula
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29:Skeletal diagram
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19:
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1077:Spiro compounds
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191:DTXSID401336838
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27:
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756:(4): 326–330.
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723:
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657:(3): 779–782.
651:Phytochemistry
633:
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628:
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393:with a highly
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328:standard state
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1082:Cyclopropanes
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621:semitropical
620:
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507:cypress trees
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399:melting point
396:
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371:
370:swamp cypress
367:
363:
347:
335:
329:
323:
320:Orthorhombic
319:
316:
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306:
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299:Melting point
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913:(17): 3036.
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749:
743:
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650:
646:
625:environment.
591:Axel Heiberg
543:
533:
496:
490:
484:
478:
475:Taxodioideae
463:
460:Cupressaceae
453:
451:
426:
423:Preservation
414:
407:orthorhombic
388:
345:
344:
76:Identifiers
67:
63:
59:
52:
48:
17:Chamaecydin
1062:Triterpenes
589:(45 Ma) at
473:subfamily (
465:Cryptomeria
411:antifeedant
346:Chamaecydin
251:Properties
1067:Biomarkers
1056:Categories
1013:: 104138.
630:References
600:lacustrine
540:Occurrence
530:ferruginol
526:biomarkers
397:core. Its
395:conjugated
391:triterpene
380:Background
308:Structure
286:Molar mass
128:ChemSpider
104:3D model (
93:86746-82-9
83:CAS Number
41:IUPAC name
1043:228967077
1035:0146-6380
991:0034-6667
969:: 81–93.
929:1420-3049
907:Molecules
888:0146-6380
826:0036-8075
772:1435-0211
718:0040-4039
679:0031-9422
611:resinites
602:settings.
580:deciduous
565:Oligocene
429:biomarker
162:101637219
947:31438610
866:: 1–10.
842:41346998
834:12202827
780:93215171
609:(45 Ma)
605:The mid
569:Pliocene
549:conifers
545:Conifers
503:leaflets
467:japonica
438:resinous
366:conifers
362:hydroxyl
1015:Bibcode
971:Bibcode
938:6751496
868:Bibcode
806:Bibcode
798:Science
659:Bibcode
619:cypress
615:Germany
596:fluvial
583:conifer
573:lignite
532:and 7α-
471:cypress
442:kerogen
433:Conifer
291:448.647
149:PubChem
1041:
1033:
989:
945:
935:
927:
886:
840:
832:
824:
778:
770:
716:
677:
607:Eocene
587:Eocene
557:limnic
517:
495:, and
374:biomes
368:, the
235:SMILES
137:551202
35:Names
1039:S2CID
838:S2CID
776:S2CID
623:swamp
520:145.5
210:InChI
106:JSmol
57:'
46:'
1031:ISSN
987:ISSN
943:PMID
925:ISSN
884:ISSN
830:PMID
822:ISSN
768:ISSN
714:ISSN
675:ISSN
598:and
66:,10a
1023:doi
1011:152
979:doi
967:235
933:PMC
915:doi
876:doi
814:doi
802:297
758:doi
706:doi
696:".
667:doi
649:".
567:to
405:is
179:EPA
152:CID
62:,6a
1058::
1037:.
1029:.
1021:.
1009:.
985:.
977:.
965:.
941:.
931:.
923:.
911:24
909:.
905:.
882:.
874:.
864:96
862:.
850:^
836:.
828:.
820:.
812:.
800:.
788:^
774:.
766:.
754:48
752:.
748:.
712:.
702:24
700:.
673:.
665:.
655:34
653:.
637:^
551:.
515:c.
489:,
483:,
376:.
354:40
350:30
273:40
267:30
55:,5
51:,4
44:(1
1045:.
1025::
1017::
993:.
981::
973::
949:.
917::
890:.
878::
870::
844:.
816::
808::
782:.
760::
746:"
720:.
708::
681:.
669::
661::
534:p
513:(
458:(
358:3
356:O
352:H
279:3
276:O
270:H
264:C
181:)
177:(
108:)
68:S
64:S
60:S
53:S
49:R
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