1092:
875:
832:
786:
279:
26:
180:
1615:
Koolen HH, Soares ER, Silva FM, Souza AQ, Medeiros LS, Filho ER, Almeida RA, Ribeiro IA, Pessoa Cdo Ó, Morais MO, Costa PM, Souza AD (2012). "An antimicrobial diketopiperazine alkaloid and co-metabolites from an endophytic strain of
461:. These characteristics facilitated its purification, and they were able to obtain 10 grams (0.35 oz) of cerevisterol from 4,500 kilograms (9,900 lb) of dry yeast. The following year, they determined its
1810:
Mizushina Y, Takahashi N, Hanashima L, Koshino H, Esumi Y, Uzawa JJ, Sugawara F, Sakaguchi K (1999). "Lucidenic acid O and lactone, new terpene inhibitors of eukaryotic DNA polymerases from a basidiomycete,
488:
Its structure was determined in 1954 by comparison with a sample that was chemically synthesized from ergosterol. Purified cerevisterol has the form of a white amorphous solid. When crystallized in
1724:
Liu TF, Lu X, Tang H, Zhang MM, Wang P, Sun P, Liu ZY, Wang ZL, Li L, Rui YC, Li TJ, Zhang W (2013). "3β,5α,6β-Oxygenated sterols from the South China Sea gorgonian
293:
1034:
Mallavadhani UV, Sudhakar AV, Satyanarayana KV, Mahapatra A, Li W, van
Breemen RB (2006). "Chemical and analytical screening of some edible mushrooms".
453:. Chemists Edna M. Honeywell and Charles E. Bills purified the compound and reported some of its properties in a 1932 publication. They noted its high
1674:
Li DH, Cai SX, Tian L, Lin ZJ, Zhu TJ, Fang YC, Liu PP, Gu QQ, Zhu WM (2007). "Two new metabolites with cytotoxicities from deep-sea fungus
501:
1276:
Koyama K, Akiba M, Imaizumi T, Kinoshite K, Takahashi K, Suzuki A, Yano S, Horie S, Watanabe K (2002). "Antinociceptive constituents of
714:
385:
236:
1323:
Zhang P, Li M, Li N, Xu J, Li ZL, Wang Y, Wang JH (2005). "Antibacterial constituents from fruit bodies of ascomycete
257:
1062:
1860:
445:
406:
1771:
Kong WW, Shao CL, Wang CY, Xu Y, Qian PY, Chen AN, Huang H (2012). "Diterpneoids and steroids from gorgonian
515:, showing no discoloration or change in melting point even after several weeks of exposure to light and air.
633:
504:
1091:
888:
Alt GN, Barton DH (1954). "The action of perphthalic acid on 5-dihydroergosteryl and ergosteryl acetates".
874:
831:
785:
661:
624:
588:
618:
1191:
Gao JM, Wang M, Wei GH, Zhang AL, Draghici C, Konishi Y (2007). "Ergosterol peroxides as phospholipase A
651:
612:
606:
554:
536:
48:
38:
1406:
1144:
Leon F, Brouard I, Torres F, Quintana J, Rivera A, Estevez F, Bermejo J (2008). "A new ceramide from
600:
542:
274:
569:
548:
424:
146:
1792:
1753:
1703:
1653:
1551:
1502:
1352:
1305:
1258:
1173:
1126:
1016:
939:
733:
683:
639:
594:
565:
512:
1832:
1745:
1695:
1645:
1597:
1494:
1344:
1297:
1216:
1165:
1008:
966:
706:
666:
200:
1855:
1824:
1784:
1737:
1687:
1637:
1589:
1541:
1533:
1486:
1453:
1414:
1393:
Ceccherelli P, Fringuelli R, Madruzza GF (1975). "Cerevisterol and ergosterol peroxide from
1336:
1289:
1250:
1208:
1157:
1118:
1078:
1043:
1000:
931:
893:
861:
818:
772:
578:
462:
415:
316:
245:
1520:
Gonzalez AG, Perez EM, Padron CE, Barrera JB (1992). "Chemical constituents of the lichen
1473:
Gonzalez AG, Barrera JB, Perez EM, Padron CE (1992). "Chemical constituents of the lichen
987:
Kim JA, Tay D, de Blanco EC (2008). "NF-κB inhibitory activity of compounds isolated from
532:
482:
278:
1570:
156:
1410:
1569:
Wang QX, Li SF, Zhao F, Dai HQ, Bao L, Ding R, Gao H, Zhang LX, Wen HA, Liu HW (2011).
560:
379:
1828:
1418:
866:
823:
777:
1849:
1796:
1506:
1309:
524:
497:
489:
454:
367:
225:
1707:
1657:
1555:
1458:
1433:
1356:
1262:
1177:
1130:
1083:
1020:
943:
758:"Antiricketic substances. VII. Studies on highly purified ergosterol and its esters"
1757:
1741:
1047:
957:
Cherotch YP, Shivrina AN (1973). "Cerevisterol in mushrooms of family
Boletaceae".
847:"Cerevisterol: New notes on composition, properties, and relation to other sterols"
803:
757:
737:
574:
478:
457:(265.3 °C) relative to other sterols, and insolubility in the organic solvent
1728:
and their tumor cell growth inhibitory activity and apoptosis-inducing function".
1641:
1593:
1212:
846:
693:
645:
1788:
1254:
1122:
935:
718:
710:
583:
528:
450:
344:
191:
1370:
Zhan ZJ, Sun HD, Wu HM, Yue JM (2003). "Chemical components from the fungus
729:
688:
656:
629:
508:
432:
428:
1836:
1749:
1699:
1649:
1601:
1537:
1498:
1348:
1301:
1220:
1169:
1161:
1012:
1490:
970:
523:
Cerevisterol is widely distributed in the fungal kingdom. In the division
25:
1293:
897:
725:
443:
Cerevisterol was first discovered in 1928 as a component of crude yeast (
420:
1691:
1546:
1340:
1105:
Coy ED, Nieto IJ (2009). "Sterol composition of the macromycete fungus
493:
357:
212:
1004:
458:
401:
378:
Except where otherwise noted, data are given for materials in their
411:
179:
169:
1063:"Triterpenoids and fatty acids identified in the edible mushroom
85:)-1--9a,11a-dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1
722:
262:
1237:
Yaoita Y, Satoh Y, Kikuchi M (2007). "A new ceramide from
1148:
and its cytotoxic activity against human melanoma cells".
655:. In 2013, the sterol was reported in the South China Sea
804:"Cerevisterol, a sterol accompanying ergosterol in yeast"
449:) sterols remaining from the manufacture of the related
492:, it forms elongated prisms, while crystallization in
301:
O1C=C23()CC(3(CC2()4(C)CC(C14O)O)C)()(C)/C=C/(C(C)C)C
527:, it occurs in several members of the fungal family
481:, and with two of the oxygen molecules occurring in
1438:, an endophytic fungus isolated from the fruits of
404:. Originally described in the 1930s from the yeast
681:)-cerevisterol, has been reported from the coral
797:
795:
224:
134:)-24-Methyl-5α-cholesta-7,22-diene-3β,5,6β-triol
924:World Journal of Microbiology and Biotechnology
155:
1571:"Chemical constituents from endophytic fungus
1232:
1230:
721:activation. The sterol is cytotoxic to mouse
8:
1432:Marinho AM, Marinho PS, Rodrigues E (2009).
372:265.3 °C (509.5 °F; 538.5 K)
1719:
1717:
410:, it has since been found in several other
400:(5α-ergosta-7,22-diene-3β,5,6β-triol) is a
1669:
1667:
982:
980:
914:Gu W. (2009). "Bioactive metabolites from
277:
199:
126:)-5α-Ergosta-7,22-diene-3β,5,6β-triol; (22
110:)-5α-Ergosta-7,22-diene-3β,5,6β-triol; (22
17:
1545:
1457:
1082:
918:ML-P08, an endophytic fungus residing in
909:
907:
865:
822:
776:
673:. A modified version of the compound, (22
244:
118:)-Ergosta-7,22-diene-3β,5α,6β-triol; (22
106:)-Ergosta-7,22-diene-3β,5α,6β-triol; (22
1071:Journal of the Chilean Chemical Society
748:
717:, and it is also a potent inhibitor of
298:
273:
500:produces broad hexagonal prisms. Its
7:
1817:Bioorganic & Medicinal Chemistry
215:
42:5α-Ergosta-7,22-diene-3β,5,6β-triol
507:shows a maximum at about 248
14:
1526:Zeitschrift für Naturforschung C
1090:
873:
830:
784:
687:. It was shown to be moderately
628:. It has also been found in the
328:
89:-cyclopentaphenanthrene-5,5a,7(5
24:
1459:10.1590/s0100-40422009000700005
1084:10.4067/S0717-97072008000200015
890:Journal of the Chemical Society
854:Journal of Biological Chemistry
845:Honeywell EM, Bills CE (1933).
811:Journal of Biological Chemistry
802:Honeywell EM, Bills CE (1932).
765:Journal of Biological Chemistry
756:Bills CE, Honeywell EM (1928).
382:(at 25 °C , 100 kPa).
1777:Chemistry of Natural Compounds
1742:10.1016/j.steroids.2012.10.003
1680:Archives of Pharmacal Research
1329:Archives of Pharmacal Research
1111:Chemistry of Natural Compounds
1048:10.1016/j.foodchem.2004.12.018
334:
322:
1:
1829:10.1016/S0968-0896(99)00121-2
1419:10.1016/S0031-9422(00)98646-1
867:10.1016/S0021-9258(18)75830-4
824:10.1016/S0021-9258(18)76066-3
778:10.1016/S0021-9258(18)83902-3
669:of cerevisterol was found in
1642:10.1080/14786419.2011.639070
1594:10.1016/j.fitote.2011.04.002
1213:10.1016/j.phymed.2006.12.006
1061:Nieto IJ, Chegwin C (2008).
691:to embryos of the zebrafish
1243:Journal of Natural Medicine
1195:inhibitors from the fungus
1877:
1150:Chemistry and Biodiversity
959:Doklady Akademii Nauk SSSR
736:epithelial cells grown in
649:, and the deep-sea fungus
586:, it has been reported in
1789:10.1007/s10600-012-0294-1
1255:10.1007/s11418-006-0121-8
1123:10.1007/s10600-009-9301-6
936:10.1007/s11274-009-0062-y
616:, as well as the lichens
376:
309:
289:
139:
99:
47:
37:
32:
23:
1630:Natural Product Research
446:Saccharomyces cerevisiae
439:Discovery and properties
418:. Cerevisterol has some
407:Saccharomyces cerevisiae
916:Alternaria brassicicola
634:Alternaria brassicicola
1538:10.1515/znc-1992-7-802
1434:"Steroids produced by
1278:Auricularia polytricha
1162:10.1002/cbdv.200890002
589:Auricularia polytricha
427:properties, including
1491:10.1055/s-2006-961433
1107:Laetiporus sulphureus
993:Phytotherapy Research
989:Cantharellus cibarius
555:Laetiporus sulphureus
537:Cantharellus cibarius
49:Systematic IUPAC name
1376:Acta Botanica Sinica
1372:Engleromyces goetzei
1294:10.1055/s-2002-23141
1065:Pleurotus sajor-cajú
898:10.1039/JR9540001356
715:DNA polymerase alpha
662:Muriceoopsis flavida
625:Stereocaulon azoreum
601:Engleromyces goetzei
549:Pleurotus sajor-caju
543:Volvariella volvacea
511:. Cerevisterol is a
1726:Muriceopsis flavida
1522:Sterocaulon azoreum
1475:Ramalina hierrensis
1436:Penicillium herquei
1411:1975PChem..14.1434C
1197:Lactarius hatsudake
665:. A 9-hydroxylated
619:Ramalina hierrensis
570:Lactarius hatsudake
505:absorption spectrum
352: g·mol
20:
1773:Subergorgia mollis
1692:10.1007/BF02980236
1676:Aspergillus sydowi
1573:Fusarium oxysporum
1395:Acremonium luzulae
1341:10.1007/BF02973872
1325:Bulgaria inquinans
684:Subergorgia mollis
652:Aspergillus sydowi
643:, and a strain of
640:Fusarium oxysporum
613:Pencillium herquei
607:Acremonium luzulae
595:Bulgaria inquinans
582:. In the division
431:to some mammalian
414:and, recently, in
386:Infobox references
18:
1813:Ganoderma lucidum
1448:(in Portuguese).
1241:(Pers.) Ricken".
394:Chemical compound
392:
391:
258:CompTox Dashboard
181:Interactive image
1868:
1861:Natural products
1841:
1840:
1807:
1801:
1800:
1768:
1762:
1761:
1721:
1712:
1711:
1671:
1662:
1661:
1612:
1606:
1605:
1579:
1566:
1560:
1559:
1549:
1517:
1511:
1510:
1470:
1464:
1463:
1461:
1429:
1423:
1422:
1390:
1384:
1383:
1367:
1361:
1360:
1320:
1314:
1313:
1273:
1267:
1266:
1239:Ramaria botrytis
1234:
1225:
1224:
1188:
1182:
1181:
1141:
1135:
1134:
1102:
1096:
1095:
1094:
1088:
1086:
1058:
1052:
1051:
1031:
1025:
1024:
1005:10.1002/ptr.2467
984:
975:
974:
954:
948:
947:
911:
902:
901:
885:
879:
878:
877:
871:
869:
851:
842:
836:
835:
834:
828:
826:
808:
799:
790:
789:
788:
782:
780:
762:
753:
671:R. botrytis
579:Ramaria botrytis
533:edible mushrooms
463:chemical formula
416:deep water coral
351:
336:
330:
324:
317:Chemical formula
282:
281:
266:
264:
248:
228:
217:
203:
183:
159:
28:
21:
1876:
1875:
1871:
1870:
1869:
1867:
1866:
1865:
1846:
1845:
1844:
1809:
1808:
1804:
1770:
1769:
1765:
1723:
1722:
1715:
1673:
1672:
1665:
1614:
1613:
1609:
1577:
1568:
1567:
1563:
1519:
1518:
1514:
1472:
1471:
1467:
1440:Melia azedarach
1431:
1430:
1426:
1392:
1391:
1387:
1369:
1368:
1364:
1322:
1321:
1317:
1275:
1274:
1270:
1236:
1235:
1228:
1194:
1190:
1189:
1185:
1143:
1142:
1138:
1104:
1103:
1099:
1089:
1060:
1059:
1055:
1033:
1032:
1028:
986:
985:
978:
956:
955:
951:
913:
912:
905:
887:
886:
882:
872:
849:
844:
843:
839:
829:
806:
801:
800:
793:
783:
760:
755:
754:
750:
746:
703:
521:
513:stable molecule
483:hydroxyl groups
476:
472:
468:
441:
395:
388:
383:
349:
339:
333:
327:
319:
305:
302:
297:
296:
285:
275:DTXSID001045318
267:
260:
251:
231:
218:
206:
186:
173:
162:
149:
135:
95:
94:
43:
12:
11:
5:
1874:
1872:
1864:
1863:
1858:
1848:
1847:
1843:
1842:
1823:(9): 2047–52.
1802:
1763:
1713:
1663:
1636:(21): 2013–9.
1620:isolated from
1607:
1561:
1532:(7–8): 503–7.
1512:
1465:
1424:
1399:Phytochemistry
1385:
1362:
1315:
1268:
1226:
1192:
1183:
1146:Suillus luteus
1136:
1097:
1053:
1036:Food Chemistry
1026:
976:
961:(in Russian).
949:
930:(9): 1677–83.
920:Malus halliana
903:
880:
837:
791:
747:
745:
742:
702:
699:
561:Suillus luteus
520:
517:
474:
470:
466:
440:
437:
393:
390:
389:
384:
380:standard state
377:
374:
373:
370:
364:
363:
360:
354:
353:
347:
341:
340:
337:
331:
325:
320:
315:
312:
311:
307:
306:
304:
303:
300:
292:
291:
290:
287:
286:
284:
283:
270:
268:
256:
253:
252:
250:
249:
241:
239:
233:
232:
230:
229:
221:
219:
211:
208:
207:
205:
204:
196:
194:
188:
187:
185:
184:
176:
174:
167:
164:
163:
161:
160:
152:
150:
145:
142:
141:
137:
136:
101:
97:
96:
52:
51:
45:
44:
41:
35:
34:
30:
29:
13:
10:
9:
6:
4:
3:
2:
1873:
1862:
1859:
1857:
1854:
1853:
1851:
1838:
1834:
1830:
1826:
1822:
1818:
1814:
1806:
1803:
1798:
1794:
1790:
1786:
1782:
1778:
1774:
1767:
1764:
1759:
1755:
1751:
1747:
1743:
1739:
1736:(1): 108–14.
1735:
1731:
1727:
1720:
1718:
1714:
1709:
1705:
1701:
1697:
1693:
1689:
1686:(9): 1051–4.
1685:
1681:
1677:
1670:
1668:
1664:
1659:
1655:
1651:
1647:
1643:
1639:
1635:
1631:
1627:
1623:
1619:
1611:
1608:
1603:
1599:
1595:
1591:
1588:(5): 777–81.
1587:
1583:
1576:
1574:
1565:
1562:
1557:
1553:
1548:
1543:
1539:
1535:
1531:
1527:
1523:
1516:
1513:
1508:
1504:
1500:
1496:
1492:
1488:
1484:
1480:
1479:Planta Medica
1476:
1469:
1466:
1460:
1455:
1452:(7): 1710–2.
1451:
1447:
1443:
1441:
1437:
1428:
1425:
1420:
1416:
1412:
1408:
1405:(5–6): 1434.
1404:
1400:
1396:
1389:
1386:
1381:
1377:
1373:
1366:
1363:
1358:
1354:
1350:
1346:
1342:
1338:
1335:(8): 889–91.
1334:
1330:
1326:
1319:
1316:
1311:
1307:
1303:
1299:
1295:
1291:
1287:
1283:
1282:Planta Medica
1279:
1272:
1269:
1264:
1260:
1256:
1252:
1248:
1244:
1240:
1233:
1231:
1227:
1222:
1218:
1214:
1210:
1207:(12): 821–4.
1206:
1202:
1201:Phytomedicine
1198:
1187:
1184:
1179:
1175:
1171:
1167:
1163:
1159:
1155:
1151:
1147:
1140:
1137:
1132:
1128:
1124:
1120:
1116:
1112:
1108:
1101:
1098:
1093:
1085:
1080:
1077:(2): 1515–7.
1076:
1072:
1068:
1066:
1057:
1054:
1049:
1045:
1041:
1037:
1030:
1027:
1022:
1018:
1014:
1010:
1006:
1002:
999:(8): 1104–6.
998:
994:
990:
983:
981:
977:
972:
968:
965:(4): 1015–6.
964:
960:
953:
950:
945:
941:
937:
933:
929:
925:
921:
917:
910:
908:
904:
899:
895:
891:
884:
881:
876:
868:
863:
860:(2): 515–20.
859:
855:
848:
841:
838:
833:
825:
820:
816:
812:
805:
798:
796:
792:
787:
779:
774:
770:
766:
759:
752:
749:
743:
741:
739:
735:
731:
727:
724:
720:
716:
712:
708:
705:Cerevisterol
700:
698:
696:
695:
690:
686:
685:
680:
676:
672:
668:
664:
663:
658:
654:
653:
648:
647:
642:
641:
636:
635:
631:
627:
626:
621:
620:
615:
614:
609:
608:
603:
602:
597:
596:
591:
590:
585:
581:
580:
576:
572:
571:
567:
566:milk mushroom
563:
562:
557:
556:
551:
550:
545:
544:
539:
538:
534:
530:
526:
525:Basidiomycota
518:
516:
514:
510:
506:
503:
499:
498:ethyl acetate
495:
491:
490:ethyl alcohol
486:
484:
480:
464:
460:
456:
455:melting point
452:
448:
447:
438:
436:
434:
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368:Melting point
366:
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348:
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40:
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27:
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19:Cerevisterol
16:
1820:
1816:
1812:
1805:
1783:(3): 512–5.
1780:
1776:
1772:
1766:
1733:
1729:
1725:
1683:
1679:
1675:
1633:
1629:
1625:
1621:
1617:
1610:
1585:
1581:
1572:
1564:
1529:
1525:
1521:
1515:
1485:(2): 214–8.
1482:
1478:
1474:
1468:
1449:
1446:Química Nova
1445:
1442:(Meliaceae)"
1439:
1435:
1427:
1402:
1398:
1394:
1388:
1382:(2): 248–52.
1379:
1375:
1371:
1365:
1332:
1328:
1324:
1318:
1288:(3): 284–5.
1285:
1281:
1277:
1271:
1249:(2): 205–7.
1246:
1242:
1238:
1204:
1200:
1196:
1186:
1156:(1): 120–5.
1153:
1149:
1145:
1139:
1117:(2): 193–6.
1114:
1110:
1106:
1100:
1074:
1070:
1064:
1056:
1042:(1): 58–64.
1039:
1035:
1029:
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927:
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575:coral fungus
568:
559:
553:
547:
541:
535:
522:
487:
479:double bonds
444:
442:
429:cytotoxicity
419:
405:
398:Cerevisterol
397:
396:
140:Identifiers
131:
127:
123:
119:
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111:
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103:
100:Other names
90:
86:
82:
78:
74:
70:
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62:
58:
54:
15:
1618:Gliocladium
1582:Fitoterapia
1547:10261/18129
892:: 1356–61.
701:Bioactivity
694:Danio rerio
646:Gliocladium
477:, with two
362:1.086 g/ml
310:Properties
1850:Categories
744:References
728:cells and
719:NF-kappa B
711:eukaryotic
630:endophytes
584:Ascomycota
573:, and the
529:Boletaceae
519:Occurrence
451:ergosterol
433:cell lines
345:Molar mass
246:6MHQ9J8E6J
192:ChemSpider
168:3D model (
147:CAS Number
39:IUPAC name
1797:254423023
1678:YH11-2".
1622:Strychnos
1507:260248348
1310:260248916
771:: 15–23.
689:cytotoxic
657:gorgonian
564:, in the
425:bioactive
1837:10530954
1750:23123740
1730:Steroids
1708:34701088
1700:17958319
1658:30434549
1650:22117164
1626:toxifera
1602:21497643
1556:13255580
1499:17226459
1357:46339708
1349:16178412
1302:11914973
1263:35556659
1221:17292597
1178:12772225
1170:18205114
1131:29177512
1021:41177917
1013:18570270
944:84956891
817:: 71–8.
734:alveolar
726:leukemia
707:inhibits
667:analogue
421:in vitro
226:10181133
157:516-37-0
1856:Sterols
1758:6620696
1407:Bibcode
971:4796271
738:culture
713:enzyme
494:acetone
465:to be C
358:Density
350:430.673
213:PubChem
201:8356635
93:)-triol
1835:
1795:
1756:
1748:
1706:
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1355:
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1019:
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969:
942:
732:human
659:coral
610:, and
558:, and
531:, the
459:hexane
402:sterol
294:SMILES
33:Names
1793:S2CID
1754:S2CID
1704:S2CID
1654:S2CID
1578:(PDF)
1552:S2CID
1503:S2CID
1353:S2CID
1306:S2CID
1259:S2CID
1174:S2CID
1127:S2CID
1017:S2CID
940:S2CID
850:(PDF)
807:(PDF)
761:(PDF)
412:fungi
170:JSmol
1833:PMID
1746:PMID
1696:PMID
1646:PMID
1624:cf.
1598:PMID
1495:PMID
1345:PMID
1298:PMID
1217:PMID
1166:PMID
1009:PMID
967:PMID
730:A549
723:P388
709:the
677:, 24
622:and
237:UNII
81:,11a
1825:doi
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1785:doi
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1738:doi
1688:doi
1638:doi
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1590:doi
1542:hdl
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1487:doi
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1337:doi
1327:".
1290:doi
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1251:doi
1209:doi
1199:".
1158:doi
1119:doi
1109:".
1079:doi
1044:doi
1001:doi
991:".
963:212
932:doi
922:".
894:doi
862:doi
858:103
819:doi
773:doi
496:or
263:EPA
216:CID
130:,24
122:,24
114:,24
102:(22
77:,9b
73:,9a
65:,5a
57:,3a
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509:nm
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132:R
128:E
124:R
120:E
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112:E
108:E
104:E
91:H
87:H
83:R
79:S
75:R
71:S
67:R
63:R
59:R
55:R
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