530:. However, the discovery of resin fossils provided unaltered natural diterpenoids that can be used to understand botanical diversity during a given geological age. Analysis of macrofossils or clay sediments is also used to identify the presence of ferruginol, though these samples may not be fully preserved. Comparing the composition of fossilized coal or clay from the same region as resin fossils can indicate the original biological precursors of these samples. Additionally, the diagenetic alterations of fossils can be used to understand the environmental changes in the time after they were formed. General abietane diterpenoid abietic acids have been connected to the diagenetic products
652:
245:
555:
24:
386:
635:, limited migration, and caused cell cycle arrest. This impact on cancer cells was dose-dependent, with higher doses of ferruginol more successfully inhibiting migration. When studied against human prostate cancer cells, ferruginol similarly induced cell death by suppressing survival signaling pathways. Specific activity of tumor
1164:
Areche, Carlos; Theoduloz, Cristina; Yåñez, Tania; Souza-Brito, Alba R. M.; Barbastefano, VĂCtor; De Paula, DĂ©Bora; Ferreira, Anderson L.; Schmeda-Hirschmann, Guillermo; RodrĂguez, Jaime A. (2008). "Gastroprotective activity of ferruginol in mice and rats: effects on gastric secretion, endogenous
687:
was used to further understand the sample. The terpenoids analyzed were separated into three groups: monoterpenes, sesquiterpenoids, and diterpenoids. Diterpenoids of the abietanic class were the most abundant in the amber, though they are widely present in all conifer families and therefore less
541:
Due to the improved preservation of ferruginol and other diterpenoids in fossil resin, they have been found to be underrepresented in sediment samples when compared to angiosperms, whose leaf waxes are more free to disperse throughout the sample. Even in regions known to have a high abundance of
1305:
Bispo De Jesus, Marcelo; Zambuzzi, Willian
Fernando; Ruela De Sousa, Roberta Regina; Areche, Carlos; Santos De Souza, Ana Carolina; Aoyama, Hiroshi; Schmeda-Hirschmann, Guillermo; RodrĂguez, Jaime A.; Monteiro De Souza Brito, Alba Regina; Peppelenbosch, Maikel P.; Den Hertog, Jeroen; De Paula,
577:(BSTFA) is used to transform molecules into trimethyl-silyl (TMS) derivatives. It is then chemically extracted into neutral, aromatic, and polar fractions using specified eluents, often hexane, dichloromethane, and methanol, respectively. The aromatic fractions are then analyzed using
542:
conifers, sediment samples have been found to contain little to no unaltered diterpenoids. The relative of abundance of conifers cannot therefore be directly determined from biomarker concentrations in sediment samples, as this will be biased by preservation.
581:(GC-MS), and library data along with fragmentation patterns are used to identify the molecular makeup of each notable peak and their relative concentration in the sample. Ferruginol can be identified with a molecular weight of 286 m/z.
974:
Pereira, Ricardo; Lima, Flaviana Jorge de; Simbras, Felipe M.; Bittar, Sheila Maria Bretas; Kellner, Alexander
Wilhelm Armin; Saraiva, AntĂŽnio Ălamo F.; Bantim, Renan A.M.; SayĂŁo, Juliana M.; Oliveira, Gustavo R. (2020-03-01).
538:. Microbial and abiotic degradation make it so most conifer biomarkers cannot be linked to specific species, so it is especially useful to find resinous samples that are able to provide more detailed identification.
545:
The presence of ferruginol has also been used in more modern samples as biological tracers. For example, analyzing the honeybee product propolis helps establish the main botanical source collected by the bees.
1220:"Ferruginol exhibits anticancer effects in OVCARâ3 human ovary cancer cells by inducing apoptosis, inhibition of cancer cell migration and G2/M phase cell cycle arrest Retraction in /10.3892/mmr.2021.11868"
1429:
Areche, Carlos; Theoduloz, Cristina; Yåñez, Tania; Souza-Brito, Alba R M; Barbastefano, VĂctor; de Paula, DĂ©bora; Ferreira, Anderson L; Schmeda-Hirschmann, Guillermo; RodrĂguez, Jaime A (2008-02-01).
437:
chemical class, meaning it is characterized by three fused six-membered rings and alkyl functional groups. Ferruginol was first identified in 1939 by Brandt and
Neubauer as the main component in the
566:
The sample preparation to measure ferruginol abundance varies depending on form the sample initially takes, though generally follows the same structure. After physically crushing the sample,
399:
106:
683:, having swept in from nearby conifer sources. GC-MS analysis resulted in the chromatogram shown to the right, with the ferruginol peak marked in red. Additionally,
1133:"EXTRACTABLE COMPOUNDS OF NATIVE TREES: CHEMICAL AND BIOLOGICAL STUDY I: Bark of Prumnopytis andina (Podocarpaceae) and Austrocedrus chilensis (Cupressaceae)"
294:
639:(GI) is 2-5 micrograms/milliliter. Beyond anti-cancer activity, studies with mice showed that ferruginol had anti-inflammatory properties against induced
469:, the presence of ferruginol in fossils, mainly resin, is used to describe the density of these conifers in that particular biosphere throughout time.
578:
1431:"Gastroprotective activity of ferruginol in mice and rats: effects on gastric secretion, endogenous prostaglandins and non-protein sulfhydrylsâ "
672:
595:(TOF-SIMS) has been used in combination with GC-MS with samples collected from still living organisms for surface imaging and depth profiling.
716:
The results from the amber samples are consistent with environmental conditions determined from a separate analysis of the bituminous shale.
1390:"Ferruginol alleviates inflammation in dextran sulfate sodium-induced colitis in mice through inhibiting COX-2, MMP-9 and NF-ÎșB signaling"
977:"Biomarker signatures of Cretaceous Gondwana amber from Ipubi Formation (Araripe Basin, Brazil) and their palaeobotanical significance"
477:
Ferruginol is a phenolic abietene, a type of tricyclic diterpenoid derived from terrestrial plants. It has a molecular composition of C
1032:"Localization of ferruginol, a diterpene phenol, in Cryptomeria japonica heartwood by time-of-flight secondary ion mass spectrometry"
918:
Popova, Milena; Trusheva, Boryana; Cutajar, Simone; Antonova, Daniela; Mifsud, David; Farrugia, Claude; Bankova, Vassya (May 2012).
688:
useful in identifying specific contributing species. The detection of ferruginol helped limit the biological origin to the families
259:
1353:
Son, Kh; Oh, Hm; Choi, Sk; Han, Dc; Kwon, Bm (Apr 2005). "Anti-tumor abietane diterpenes from the cones of
Sequoia sempervirens".
1086:
592:
679:
content had been used to date the Ipubi
Formation as Aptian-Albian (125â100.5 mya), and the amber samples were thought to be
708:
as the source. Therefore, the possible botanical sources of the amber collected in the Ipubi
Formation were identified as
268:
InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1
406:
278:
InChI=1/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1
1499:
202:
655:
Total ion chromatogram of amber sample from Ipubi
Formation. The ferruginol peak is marked with a red X. Modified from.
628:
transformed cells as well. Ferruginol has also been found to have antibacterial activity and gastroprotective effects.
873:"Sesqui- and diterpenoid biomarkers preserved in Taxodium-rich Oligocene oxbow lake clays, Weisselster basin, Germany"
776:"Conifer and angiosperm biomarkers in clay sediments and fossil plants from the Miocene Clarkia Formation, Idaho, USA"
223:
1132:
588:
518:
family. In these conifers, it acts as a plant metabolite, along with some protective and antibacterial roles.
826:"Polar aromatic biomarkers of Miocene-aged Chukurovo resinite and correlation with a progenitor macrofossil"
1494:
1307:
976:
872:
825:
775:
527:
442:
146:
1104:
46:
36:
1308:"Ferruginol suppresses survival signaling pathways in androgen-independent human prostate cancer cells"
733:
651:
988:
884:
837:
787:
684:
585:
663:
in Brazil is well known for the diverse and well-preserved collection of fossils. Despite this, the
240:
1489:
72:
1466:
1287:
1279:
1200:
1067:
1012:
640:
920:"Identification of the Plant Origin of the Botanical Biomarkers of Mediterranean type Propolis"
1458:
1450:
1411:
1370:
1335:
1327:
1268:
1249:
1241:
1192:
1059:
1051:
1004:
949:
941:
900:
853:
803:
749:
636:
507:
1442:
1401:
1362:
1319:
1260:
1231:
1182:
1174:
1144:
1043:
996:
931:
892:
845:
795:
741:
317:
166:
211:
1117:
664:
244:
82:
992:
888:
841:
791:
126:
1093:
377:
896:
1483:
1389:
1016:
799:
701:
680:
668:
660:
500:
493:
461:
365:
1149:
1470:
1204:
1071:
1030:
Imai, Takanori; Tanabe, Kinuko; Kato, Toshiyuki; Fukushima, Kazuhiko (2005-06-01).
554:
514:
455:
191:
624:
studies have shown human colon, breast, and lung tumor reduction and reduction in
1323:
1000:
603:
Research published in 2005 found that this and other compounds of the class from
531:
487:
1366:
936:
919:
849:
591:(3C-CPMAS-NMR) to provide more detailed analysis. Additionally, time-of-flight
59:)-4b,8,8-Trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-ol
1131:
C. Flores; J. AlarcĂłn; J. Becerra; M. Bittner; M. Hoeneisen; M. Silva (2001).
1047:
676:
613:
342:
157:
1454:
1415:
1406:
1331:
1245:
1055:
1008:
945:
904:
857:
807:
753:
675:
analyzed amber resin from the black shales that make up the collection site.
671:
is only poorly explored. To better understand the paleoflora, researchers at
584:
Along with GC-MS, ferruginol has also been analyzed using cross polarization/
512:
It is particularly useful as a biomarker because of its concentration in the
1031:
632:
617:
466:
430:
426:
1462:
1374:
1339:
1272:
1264:
1253:
1196:
1063:
953:
1446:
1276:. If this is an intentional citation to a retracted paper, please replace
1236:
1219:
1178:
745:
625:
609:
434:
1430:
1187:
485:
O with a molecular weight of 286 g/mole. Along with its presence in the
774:
Otto, Angelika; Simoneit, Bernd R.T.; Rember, William C. (2005-06-01).
450:
355:
178:
23:
535:
491:
family, it has been found in a variety of conifer families including
422:
137:
1388:
Zhu, Xiao-Yan; Zhang, Chun-Ling; Lin, Yukiat; Dang, Min-Yan (2020).
376:
Except where otherwise noted, data are given for materials in their
567:
438:
117:
105:
95:
643:
and acted as a gastroprotective agent against gastro lesions.
228:
526:
As a polar terpenoid, ferruginol was thought to have poor
1087:"P-168: The Resistance Modifying Activity of Ferruginol"
700:. Further more, the absence callitrisates, kauranes and
1085:
E.C.J. Smith; G.W. Kaatz; E.M. Williamson; S. Gibbons.
394:
1218:
Xiong, Wen-Dong; Gong, Jian; Xing, Chao (2017-11-01).
824:
Stefanova, Maya; Simoneit, Bernd R.T. (2008-08-05).
871:Otto, A.; Walther, H.; PĂŒttmann, W. (1997-01-01).
1306:Eneida; Ferreira, Carmen VerĂssima (2008-06-01).
190:
81:
1394:Asian Pacific Journal of Tropical Biomedicine
1165:prostaglandins and non-protein sulfhydryls".
732:Brandt, C. W.; Neubauer, L. G. (1939-01-01).
8:
1355:Bioorganic & Medicinal Chemistry Letters
558:Mass spectrum of ferruginol, isolated from
1290:|...|intentional=yes}}
243:
165:
15:
1405:
1235:
1186:
1148:
935:
738:Journal of the Chemical Society (Resumed)
631:Against ovarian cancer cells, it induced
210:
981:Journal of South American Earth Sciences
673:Universidade Federal Rural de Pernambuco
650:
553:
724:
449:and has since been isolated from other
299:
264:
239:
1113:
1102:
830:International Journal of Coal Geology
734:"221. Miro resin. Part I. Ferruginol"
302:Oc1c(cc2c(c1)3(CCCC(3CC2)(C)C)C)C(C)C
271:Key: QXNWVJOHUAQHLM-AZUAARDMSA-N
145:
125:
7:
1435:Journal of Pharmacy and Pharmacology
1167:Journal of Pharmacy and Pharmacology
969:
967:
965:
963:
819:
817:
769:
767:
765:
763:
616:and anti-inflammatory properties in
579:gas chromatographyâmass spectrometry
429:substructure. Specifically, it is a
281:Key: QXNWVJOHUAQHLM-AZUAARDMBU
181:
14:
800:10.1016/j.orggeochem.2004.12.004
384:
329:
22:
1150:10.4067/S0366-16442001000100010
593:secondary ion mass spectrometry
380:(at 25 °C , 100 kPa).
924:Natural Product Communications
562:samples. Figure modified from.
335:
323:
1:
897:10.1016/S0146-6380(96)00133-7
1324:10.1016/j.biochi.2008.01.011
1001:10.1016/j.jsames.2019.102413
647:Biomarker case study: Brazil
1516:
1367:10.1016/j.bmcl.2005.02.057
1224:Molecular Medicine Reports
937:10.1177/1934578X1200700505
850:10.1016/j.coal.2008.05.003
589:nuclear magnetic resonance
40:Abieta-8,11,13-trien-12-ol
1048:10.1007/s00425-004-1476-2
374:
310:
290:
255:
65:
45:
35:
30:
21:
1407:10.4103/2221-1691.284945
453:species in the families
1265:10.3892/mmr.2021.11868
1112:Cite journal requires
656:
575:-bistrifluoroacetamide
563:
528:preservation potential
447:Podocarpus ferrugneus)
1447:10.1211/jpp.60.2.0014
1282:|...}}
1259:(Retracted, see
1237:10.3892/mmr.2017.7484
1179:10.1211/jpp.60.2.0014
669:central Santana Group
654:
557:
47:Systematic IUPAC name
1137:Bol. Soc. Chil. QuĂm
877:Organic Geochemistry
780:Organic Geochemistry
746:10.1039/JR9390001031
586:magic angle spinning
1500:Isopropyl compounds
1099:on October 9, 2007.
993:2020JSAES..9802413P
889:1997OrGeo..26..105O
842:2008IJCG...75..166S
792:2005OrGeo..36..907O
350: g·mol
18:
714:Cheirolepidiaceae.
657:
641:ulcerative colitis
564:
407:Infobox references
16:
698:Cheirolepidiaceae
637:growth inhibition
508:Cheirolepidiaceae
415:Chemical compound
413:
412:
224:CompTox Dashboard
107:Interactive image
1507:
1475:
1474:
1426:
1420:
1419:
1409:
1385:
1379:
1378:
1350:
1344:
1343:
1302:
1296:
1295:
1293:
1291:
1283:
1257:
1239:
1230:(5): 7013â7017.
1215:
1209:
1208:
1190:
1161:
1155:
1154:
1152:
1128:
1122:
1121:
1115:
1110:
1108:
1100:
1098:
1092:. Archived from
1091:
1082:
1076:
1075:
1027:
1021:
1020:
971:
958:
957:
939:
915:
909:
908:
883:(1â2): 105â115.
868:
862:
861:
821:
812:
811:
771:
758:
757:
729:
505:and the extinct
397:
391:
388:
387:
349:
337:
331:
325:
318:Chemical formula
248:
247:
232:
230:
214:
194:
183:
169:
149:
129:
109:
85:
26:
19:
1515:
1514:
1510:
1509:
1508:
1506:
1505:
1504:
1480:
1479:
1478:
1428:
1427:
1423:
1387:
1386:
1382:
1352:
1351:
1347:
1304:
1303:
1299:
1285:
1277:
1275:
1258:
1217:
1216:
1212:
1163:
1162:
1158:
1130:
1129:
1125:
1111:
1101:
1096:
1089:
1084:
1083:
1079:
1029:
1028:
1024:
973:
972:
961:
917:
916:
912:
870:
869:
865:
823:
822:
815:
773:
772:
761:
731:
730:
726:
722:
665:Ipubi Formation
649:
601:
552:
524:
484:
480:
475:
416:
409:
404:
403:
402: ?)
393:
389:
385:
381:
347:
334:
328:
320:
306:
303:
298:
297:
286:
283:
282:
279:
273:
272:
269:
263:
262:
251:
233:
226:
217:
197:
184:
172:
152:
132:
112:
99:
88:
75:
61:
60:
41:
12:
11:
5:
1513:
1511:
1503:
1502:
1497:
1492:
1482:
1481:
1477:
1476:
1441:(2): 245â251.
1421:
1380:
1361:(8): 2019â21.
1345:
1318:(6): 843â854.
1297:
1210:
1156:
1123:
1114:|journal=
1077:
1042:(4): 549â556.
1022:
959:
930:(5): 569â570.
910:
863:
836:(3): 166â174.
813:
786:(6): 907â922.
759:
723:
721:
718:
702:phyllocladanes
648:
645:
600:
597:
551:
548:
523:
520:
482:
478:
474:
471:
414:
411:
410:
405:
383:
382:
378:standard state
375:
372:
371:
368:
362:
361:
358:
352:
351:
345:
339:
338:
332:
326:
321:
316:
313:
312:
308:
307:
305:
304:
301:
293:
292:
291:
288:
287:
285:
284:
280:
277:
276:
274:
270:
267:
266:
258:
257:
256:
253:
252:
250:
249:
241:DTXSID20331722
236:
234:
222:
219:
218:
216:
215:
207:
205:
199:
198:
196:
195:
187:
185:
177:
174:
173:
171:
170:
162:
160:
154:
153:
151:
150:
142:
140:
134:
133:
131:
130:
122:
120:
114:
113:
111:
110:
102:
100:
93:
90:
89:
87:
86:
78:
76:
71:
68:
67:
63:
62:
50:
49:
43:
42:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1512:
1501:
1498:
1496:
1495:Phenanthrenes
1493:
1491:
1488:
1487:
1485:
1472:
1468:
1464:
1460:
1456:
1452:
1448:
1444:
1440:
1436:
1432:
1425:
1422:
1417:
1413:
1408:
1403:
1399:
1395:
1391:
1384:
1381:
1376:
1372:
1368:
1364:
1360:
1356:
1349:
1346:
1341:
1337:
1333:
1329:
1325:
1321:
1317:
1313:
1309:
1301:
1298:
1289:
1281:
1274:
1270:
1266:
1262:
1255:
1251:
1247:
1243:
1238:
1233:
1229:
1225:
1221:
1214:
1211:
1206:
1202:
1198:
1194:
1189:
1184:
1180:
1176:
1173:(2): 245â51.
1172:
1168:
1160:
1157:
1151:
1146:
1142:
1138:
1134:
1127:
1124:
1119:
1106:
1095:
1088:
1081:
1078:
1073:
1069:
1065:
1061:
1057:
1053:
1049:
1045:
1041:
1037:
1033:
1026:
1023:
1018:
1014:
1010:
1006:
1002:
998:
994:
990:
986:
982:
978:
970:
968:
966:
964:
960:
955:
951:
947:
943:
938:
933:
929:
925:
921:
914:
911:
906:
902:
898:
894:
890:
886:
882:
878:
874:
867:
864:
859:
855:
851:
847:
843:
839:
835:
831:
827:
820:
818:
814:
809:
805:
801:
797:
793:
789:
785:
781:
777:
770:
768:
766:
764:
760:
755:
751:
747:
743:
740:: 1031â1037.
739:
735:
728:
725:
719:
717:
715:
711:
710:Podocarpaceae
707:
703:
699:
695:
694:Podocarpaceae
691:
686:
682:
681:allochthonous
678:
677:Palynological
674:
670:
666:
662:
661:Araripe Basin
653:
646:
644:
642:
638:
634:
629:
627:
623:
619:
615:
612:
611:
606:
598:
596:
594:
590:
587:
582:
580:
576:
574:
570:
561:
556:
549:
547:
543:
539:
537:
533:
529:
521:
519:
517:
516:
511:
509:
504:
502:
501:Araucariaceae
497:
495:
494:Podocarpaceae
490:
489:
472:
470:
468:
464:
463:
462:Podocarpaceae
458:
457:
452:
448:
444:
440:
436:
432:
428:
424:
421:is a natural
420:
408:
401:
396:
379:
373:
369:
367:
366:Melting point
364:
363:
360:1.0±0.1 g/cm
359:
357:
354:
353:
346:
344:
341:
340:
322:
319:
315:
314:
309:
300:
296:
289:
275:
265:
261:
254:
246:
242:
238:
237:
235:
225:
221:
220:
213:
209:
208:
206:
204:
201:
200:
193:
189:
188:
186:
180:
176:
175:
168:
164:
163:
161:
159:
156:
155:
148:
144:
143:
141:
139:
136:
135:
128:
124:
123:
121:
119:
116:
115:
108:
104:
103:
101:
97:
92:
91:
84:
80:
79:
77:
74:
70:
69:
64:
58:
54:
48:
44:
38:
34:
29:
25:
20:
1438:
1434:
1424:
1397:
1393:
1383:
1358:
1354:
1348:
1315:
1311:
1300:
1286:{{
1278:{{
1227:
1223:
1213:
1188:10533/139107
1170:
1166:
1159:
1140:
1136:
1126:
1105:cite journal
1094:the original
1080:
1039:
1035:
1025:
984:
980:
927:
923:
913:
880:
876:
866:
833:
829:
783:
779:
737:
727:
713:
709:
706:Cupressaceae
705:
697:
693:
690:Cupressaceae
689:
685:3C-CPMAS-NMR
658:
630:
621:
608:
604:
602:
583:
572:
568:
565:
559:
544:
540:
525:
522:Preservation
515:Cupressaceae
513:
506:
499:
498:the ancient
492:
486:
476:
460:
456:Cupressaceae
454:
446:
418:
417:
147:ChEMBL197308
66:Identifiers
56:
52:
599:Bioactivity
550:Measurement
532:simonellite
488:Verbenaceae
311:Properties
127:CHEBI:78274
17:Ferruginol
1490:Diterpenes
1484:Categories
1400:(7): 308.
987:: 102413.
720:References
618:cell lines
614:anti-tumor
473:Background
419:Ferruginol
343:Molar mass
212:N2CMM6X37M
158:ChemSpider
94:3D model (
73:CAS Number
37:IUPAC name
1455:0022-3573
1416:2221-1691
1332:0300-9084
1312:Biochimie
1288:retracted
1280:retracted
1246:1791-2997
1056:1432-2048
1017:210270723
1009:0895-9811
946:1934-578X
905:0146-6380
858:0166-5162
808:0146-6380
754:0368-1769
704:excluded
633:apoptosis
467:biomarker
443:Miro tree
431:diterpene
427:terpenoid
370:56-57 °C
1463:18237473
1375:15808460
1340:18294971
1273:33537814
1254:28901510
1197:18237473
1064:15856284
954:22799077
626:oncogene
622:In vitro
610:in vitro
560:Taxodium
435:abietane
83:514-62-5
1471:9928974
1205:9928974
1072:6298474
989:Bibcode
885:Bibcode
838:Bibcode
788:Bibcode
667:in the
605:Sequoia
465:. As a
451:conifer
441:of the
433:of the
425:with a
400:what is
398: (
356:Density
348:286.459
179:PubChem
1469:
1461:
1453:
1414:
1373:
1338:
1330:
1271:
1267:,
1252:
1244:
1203:
1195:
1070:
1062:
1054:
1036:Planta
1015:
1007:
952:
944:
903:
856:
806:
752:
536:retene
423:phenol
395:verify
392:
295:SMILES
192:442027
167:390582
138:ChEMBL
31:Names
1467:S2CID
1284:with
1201:S2CID
1143:(1).
1097:(PDF)
1090:(PDF)
1068:S2CID
1013:S2CID
607:have
439:resin
260:InChI
118:ChEBI
96:JSmol
1459:PMID
1451:ISSN
1412:ISSN
1371:PMID
1336:PMID
1328:ISSN
1269:PMID
1250:PMID
1242:ISSN
1193:PMID
1118:help
1060:PMID
1052:ISSN
1005:ISSN
950:PMID
942:ISSN
901:ISSN
854:ISSN
804:ISSN
750:ISSN
712:and
696:and
659:The
534:and
459:and
203:UNII
1443:doi
1402:doi
1363:doi
1320:doi
1261:doi
1232:doi
1183:hdl
1175:doi
1145:doi
1044:doi
1040:221
997:doi
932:doi
893:doi
846:doi
796:doi
742:doi
229:EPA
182:CID
55:,8a
51:(4b
1486::
1465:.
1457:.
1449:.
1439:60
1437:.
1433:.
1410:.
1398:10
1396:.
1392:.
1369:.
1359:15
1357:.
1334:.
1326:.
1316:90
1314:.
1310:.
1248:.
1240:.
1228:16
1226:.
1222:.
1199:.
1191:.
1181:.
1171:60
1169:.
1141:46
1139:.
1135:.
1109::
1107:}}
1103:{{
1066:.
1058:.
1050:.
1038:.
1034:.
1011:.
1003:.
995:.
985:98
983:.
979:.
962:^
948:.
940:.
926:.
922:.
899:.
891:.
881:26
879:.
875:.
852:.
844:.
834:75
832:.
828:.
816:^
802:.
794:.
784:36
782:.
778:.
762:^
748:.
736:.
692:,
620:.
483:30
479:20
333:30
327:20
1473:.
1445::
1418:.
1404::
1377:.
1365::
1342:.
1322::
1294:)
1292:.
1263::
1256:.
1234::
1207:.
1185::
1177::
1153:.
1147::
1120:)
1116:(
1074:.
1046::
1019:.
999::
991::
956:.
934::
928:7
907:.
895::
887::
860:.
848::
840::
810:.
798::
790::
756:.
744::
573:O
571:,
569:N
510:.
503:,
496:,
481:H
445:(
390:N
336:O
330:H
324:C
231:)
227:(
98:)
57:S
53:S
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
