393:
318:
135:
126:
22:
576:
1309:. Highest values may be seen in the top sections of the sediment, which decrease with depth. However, the cholesterol behaves in a similar manner, and the ratio brassicasterol/cholesterol is fairly uniform at all depths, indicating either a comparable degradation rate with no change in source or different degradation rates and a change in source.
1296:
1353:
1357:
The location of brassicasterol in this figure (shown in red) indicates that the distribution of this compound is similar to that of the short-chain fatty acids and alcohols, which are known to be of marine origin. The terrestrially derived biomarkers such as β-sitosterol are on the opposite side of
774:
255:
1285:
The principal source of brassicasterol in the environment is from marine algae. Its relatively high concentration and stability allows it to be used in the assessment of the origin of organic matter in samples, especially sediments.
1295:
1374:
Vanmierlo, T.; Popp, J.; Kölsch, H.; Friedrichs, S.; Jessen, F.; Stoffel-Wagner, B.; Bertsch, T.; Hartmann, T.; Maier, W.; von
Bergmann, K.; Steinbusch, H.; Mulder, M.; Lütjohann, D. (September 2011).
1352:
416:
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
426:
InChI=1/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
1317:
1620:
773:
1424:
1958:
1909:
1904:
1834:
1547:
1613:
2118:
1577:
1340:) enable identification of compounds that have similar origins or behaviour. An example can be seen in the loadings plot for sediment samples from the
690:
sediments and soils, brassicasterol is stable for many hundreds of years, enabling it to be used as an indicator of past algal production (see below).
589:
1572:
2048:
1844:
1587:
1516:
1839:
1606:
1567:
739:
1914:
1931:
1506:
442:
809:
as an intermediate. A list of the algae in which brassicasterol has been identified is shown below together with approximate composition.
1420:
Constituents of
Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (
1421:
1829:
1467:
86:
1672:
58:
584:
1677:
675:
1376:"The plant sterol brassicasterol as additional CSF biomarker in Alzheimer's disease: Plant sterols as biomarker in AD"
65:
407:
105:
1824:
596:
642:
39:
2006:
72:
1819:
43:
157:
1770:
1321:
350:
313:
54:
678:. This means that, in most environmental systems, brassicasterol will be associated with the solid phase.
1854:
1749:
1721:
371:
1460:
1375:
2083:
2016:
1849:
1744:
1739:
759:
388:
1710:
1598:
1788:
687:
32:
1997:
1877:
1807:
1636:
654:
2058:
2158:
1765:
1734:
1453:
295:
147:
750:(bis-trimethyl silyl trifluoroacetamide) to replace the hydrogen with the less exchangeable
653:). There is some evidence to suggest that it may also be a relevant additional biomarker in
79:
2153:
2068:
1963:
1941:
359:
8:
392:
317:
231:
221:
125:
1644:
1403:
275:
1887:
1395:
1391:
1131:
763:
755:
1407:
339:
1705:
1387:
786:
465:
1667:
1542:
1428:
814:
550:
2128:
2113:
2095:
1729:
1511:
1337:
751:
567:
134:
2147:
2063:
1692:
1537:
767:
626:
511:
306:
2053:
2043:
1582:
1562:
1399:
1302:
1265:
630:
558:
2079:
1984:
1973:
1968:
1946:
1936:
1869:
1629:
1557:
1532:
1495:
1476:
1243:
1237:
1060:
806:
619:
554:
546:
526:
190:)-1--9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1
2123:
2103:
2073:
2035:
1953:
1926:
1919:
1899:
1892:
1780:
1662:
1552:
1500:
1333:
1274:
1249:
799:
746:. Prior to analysis, the hydroxyl group is frequently derivatised with
671:
490:
286:
2108:
638:
634:
566:
Except where otherwise noted, data are given for materials in their
21:
1882:
1793:
1628:
1341:
1306:
802:
731:
727:
719:
711:
703:
699:
650:
254:
1989:
1700:
1682:
1654:
1633:
735:
326:
1445:
743:
715:
707:
615:
612:
770:
for the TMS ether of brassicasterol can be seen in the figure.
754:(TMS) group. Instrumental analysis is frequently conducted on
1373:
1345:
1325:
747:
723:
622:
266:
244:
376:
646:
516:
150 to 151 °C (302 to 304 °F; 423 to 424 K)
1301:
The concentration of brassicasterol in a core sample from
714:; most analytical methods, therefore, utilise a strong
1289:
1280:
46:. Unsourced material may be challenged and removed.
742:by partitioning into a less polar solvent such as
637:for the presence of (marine) algal matter in the
2145:
450:O4C/C3=C/C1(CC2((CC12)(/C=C/(C)C(C)C)C)C)3(C)CC4
338:
230:
633:. This compound has frequently been used as a
1614:
1461:
706:(-OH) group, it is frequently bound to other
798:Brassicasterol is formed in plants from the
779:
611:(24-methyl cholest-5,22-dien-3β-ol) is a 28-
1621:
1607:
1468:
1454:
391:
316:
294:
817:(as percentage). Data from Volkman, 1986
358:
106:Learn how and when to remove this message
1312:
1358:the figure and are mutually exclusive.
387:
2146:
660:
307:
207:24β-methylcholesta-5,22-dien-3 beta-ol
1602:
1449:
419:Key: OILXMJHPFNGGTO-ZAUYPBDWSA-N
274:
1440:Data from a review by Volkman, 1986
693:
629:) and some terrestrial plants, like
44:adding citations to reliable sources
15:
676:octanol-water partition coefficient
641:, and is one of the ingredients in
429:Key: OILXMJHPFNGGTO-ZAUYPBDWBS
329:
13:
1290:Brassicasterol / cholesterol ratio
14:
2170:
1318:Multivariate statistical analyses
209:24-methyl cholest-5,22-dien-3β-ol
1475:
1392:10.1111/j.1600-0447.2011.01713.x
1351:
1294:
1281:Use as a tracer for marine algae
793:
772:
574:
477:
133:
124:
20:
670:Brassicasterol has a low water
643:stigmasterol-rich plant sterols
570:(at 25 °C , 100 kPa).
205:(3β,22E)-ergosta-5,22-dien-3-ol
31:needs additional citations for
1434:
1414:
1380:Acta Psychiatrica Scandinavica
1367:
1254:D = 22-dehydrocholesterol ((22
681:
674:and, as a consequence, a high
483:
471:
1:
1361:
726:linkages. Typical extraction
665:
1771:Geranylgeranyl pyrophosphate
1322:principal component analysis
1270:G = 24-methylene cholesterol
738:are then separated from the
7:
1750:Dimethylallyl pyrophosphate
1258:)-cholesta-5,22-dien-3β-ol)
813:Sterol content of selected
194:-cyclopentaphenanthren-7-ol
10:
2175:
2093:
2033:
2026:
1982:
1867:
1815:
1806:
1779:
1758:
1745:Isopentenyl pyrophosphate
1740:5-Diphosphomevalonic acid
1719:
1691:
1652:
1643:
1525:
1483:
780:Formation and occurrences
760:flame ionisation detector
651:European numbering system
564:
535:
520:
458:
438:
403:
214:
200:
156:
146:
141:
132:
123:
1959:Cholesta-7,24-dien-3-ol
1910:4alpha-Methylzymosterol
1789:Prephytoene diphosphate
1637:metabolic intermediates
618:synthesised by several
151:Ergosta-5,22-dien-3β-ol
1878:Farnesyl pyrophosphate
1808:Non-mevalonate pathway
2011:-Dihydroxycholesterol
1905:14-demethyllanosterol
1766:Geranyl pyrophosphate
1735:Phosphomevalonic acid
1711:β-Hydroxybutyric acid
1313:Multivariate analysis
1201:Prorocentrum cordatum
158:Systematic IUPAC name
2069:24-Methylenelophenol
1964:7-Dehydrodesmosterol
1942:7-Dehydrocholesterol
1026:Gonyaulax polygramma
924:Peridinium foliaceum
890:Peridinium foliaceum
40:improve this article
2059:4α-methylfecosterol
2002:-Hydroxycholesterol
1167:Gymnodinium simplex
958:Gonyaulax diegensis
818:
784:It can be found in
758:(GC) with either a
661:Chemical properties
655:Alzheimer's disease
498: g·mol
120:
1645:Mevalonate pathway
1427:2014-01-04 at the
1261:E = brassicasterol
1097:Glenodinium hallii
812:
730:include 6% KOH in
597:Infobox references
536:Related compounds
118:
2141:
2140:
2137:
2136:
1888:2,3-Oxidosqualene
1863:
1862:
1802:
1801:
1596:
1595:
1332:, other sterols,
1233:
1232:
1132:Noctiluca milaris
992:Pyrocystis lunula
764:mass spectrometer
756:gas chromatograph
718:(KOH or NaOH) to
694:Chemical analysis
605:Chemical compound
603:
602:
372:CompTox Dashboard
256:Interactive image
116:
115:
108:
90:
2166:
2119:Ergostatetraenol
2031:
2030:
1990:Steroid hormones
1813:
1812:
1706:Acetoacetic acid
1650:
1649:
1623:
1616:
1609:
1600:
1599:
1578:Stigmastadienone
1548:δ-7-stigmasterol
1470:
1463:
1456:
1447:
1446:
1441:
1438:
1432:
1418:
1412:
1411:
1371:
1355:
1298:
819:
811:
787:Mirabilis jalapa
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587:
581:
578:
577:
497:
485:
479:
473:
466:Chemical formula
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395:
380:
378:
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342:
331:
320:
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298:
278:
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234:
137:
128:
121:
117:
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100:
97:
91:
89:
55:"Brassicasterol"
48:
24:
16:
2174:
2173:
2169:
2168:
2167:
2165:
2164:
2163:
2144:
2143:
2142:
2133:
2089:
2022:
1987:
1978:
1859:
1798:
1775:
1754:
1715:
1687:
1668:Acetoacetyl-CoA
1639:
1627:
1597:
1592:
1573:Stigmastadienol
1538:δ-5-avenasterol
1533:δ-7-avenasterol
1521:
1479:
1474:
1444:
1439:
1435:
1429:Wayback Machine
1419:
1415:
1372:
1368:
1364:
1356:
1315:
1292:
1283:
815:dinoflagellates
796:
782:
771:
696:
684:
668:
663:
606:
599:
594:
593:
592: ?)
583:
579:
575:
571:
557:
553:
549:
543:
542:Related Sterols
495:
482:
476:
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454:
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417:
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365:
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332:
301:
281:
261:
248:
237:
224:
210:
208:
206:
204:
196:
195:
152:
119:Brassicasterol
112:
101:
95:
92:
49:
47:
37:
25:
12:
11:
5:
2172:
2162:
2161:
2156:
2139:
2138:
2135:
2134:
2132:
2131:
2129:Ergocalciferol
2126:
2121:
2116:
2114:Ergostatrienol
2111:
2106:
2100:
2098:
2096:Ergocalciferol
2091:
2090:
2088:
2087:
2076:
2071:
2066:
2061:
2056:
2051:
2049:Cycloeucalenol
2046:
2040:
2038:
2028:
2024:
2023:
2021:
2020:
2013:
2004:
1994:
1992:
1980:
1979:
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1902:
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1791:
1785:
1783:
1777:
1776:
1774:
1773:
1768:
1762:
1760:
1756:
1755:
1753:
1752:
1747:
1742:
1737:
1732:
1730:Mevalonic acid
1726:
1724:
1717:
1716:
1714:
1713:
1708:
1703:
1697:
1695:
1689:
1688:
1686:
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1550:
1545:
1540:
1535:
1529:
1527:
1523:
1522:
1520:
1519:
1514:
1512:Ergostatrienol
1509:
1504:
1498:
1493:
1491:Brassicasterol
1487:
1485:
1481:
1480:
1473:
1472:
1465:
1458:
1450:
1443:
1442:
1433:
1413:
1386:(3): 184–192.
1365:
1363:
1360:
1338:fatty alcohols
1324:of a range of
1314:
1311:
1291:
1288:
1282:
1279:
1278:
1277:
1271:
1268:
1262:
1259:
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1224:
1221:
1218:
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1206:
1203:
1197:
1196:
1193:
1190:
1187:
1184:
1181:
1178:
1175:
1172:
1169:
1163:
1162:
1159:
1156:
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1150:
1147:
1144:
1141:
1138:
1135:
1127:
1126:
1123:
1120:
1117:
1114:
1111:
1108:
1105:
1102:
1099:
1093:
1092:
1089:
1086:
1083:
1080:
1077:
1074:
1071:
1068:
1065:
1056:
1055:
1052:
1049:
1046:
1043:
1040:
1037:
1034:
1031:
1028:
1022:
1021:
1018:
1015:
1012:
1009:
1006:
1003:
1000:
997:
994:
988:
987:
984:
981:
978:
975:
972:
969:
966:
963:
960:
954:
953:
950:
947:
944:
941:
938:
935:
932:
929:
926:
920:
919:
916:
913:
910:
907:
904:
901:
898:
895:
892:
886:
885:
882:
879:
876:
873:
870:
867:
864:
861:
858:
851:
850:
847:
844:
841:
838:
835:
832:
829:
826:
823:
795:
792:
781:
778:
752:trimethylsilyl
695:
692:
683:
680:
667:
664:
662:
659:
609:Brassicasterol
604:
601:
600:
595:
573:
572:
568:standard state
565:
562:
561:
544:
541:
538:
537:
533:
532:
531:Non-flammable
529:
523:
522:
518:
517:
514:
508:
507:
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500:
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493:
487:
486:
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474:
469:
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460:
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441:
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428:
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422:
418:
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414:
406:
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404:
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398:
397:
389:DTXSID80197124
384:
382:
370:
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363:
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346:
344:
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335:
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251:
249:
242:
239:
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236:
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225:
220:
217:
216:
212:
211:
203:brassicasterol
202:
198:
197:
161:
160:
154:
153:
150:
144:
143:
139:
138:
130:
129:
114:
113:
28:
26:
19:
9:
6:
4:
3:
2:
2171:
2160:
2157:
2155:
2152:
2151:
2149:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2101:
2099:
2097:
2092:
2085:
2081:
2077:
2075:
2072:
2070:
2067:
2065:
2064:Isofucosterol
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2041:
2039:
2037:
2032:
2029:
2025:
2018:
2014:
2012:
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2003:
2001:
1996:
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1991:
1986:
1981:
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1908:
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1903:
1901:
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1897:
1894:
1891:
1889:
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1884:
1881:
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1873:
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1848:
1846:
1843:
1841:
1838:
1836:
1833:
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1828:
1826:
1823:
1821:
1818:
1817:
1814:
1811:
1809:
1805:
1795:
1792:
1790:
1787:
1786:
1784:
1782:
1778:
1772:
1769:
1767:
1764:
1763:
1761:
1757:
1751:
1748:
1746:
1743:
1741:
1738:
1736:
1733:
1731:
1728:
1727:
1725:
1723:
1718:
1712:
1709:
1707:
1704:
1702:
1699:
1698:
1696:
1694:
1693:Ketone bodies
1690:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1666:
1664:
1661:
1660:
1658:
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1651:
1648:
1646:
1642:
1638:
1635:
1631:
1624:
1619:
1617:
1612:
1610:
1605:
1604:
1601:
1589:
1588:Stigmastenone
1586:
1584:
1581:
1579:
1576:
1574:
1571:
1569:
1566:
1564:
1561:
1559:
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1530:
1528:
1524:
1518:
1517:Ergostadienol
1515:
1513:
1510:
1508:
1505:
1502:
1499:
1497:
1494:
1492:
1489:
1488:
1486:
1482:
1478:
1471:
1466:
1464:
1459:
1457:
1452:
1451:
1448:
1437:
1430:
1426:
1423:
1417:
1409:
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794:Algal sources
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512:Melting point
510:
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308:ECHA InfoCard
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57: –
56:
52:
51:Find sources:
45:
41:
35:
34:
29:This article
27:
23:
18:
17:
2159:Phytosterols
2080:Phytosterols
2054:Obtusifoliol
2044:Cycloartenol
2008:
1999:
1583:Stigmasterol
1568:Stigmastenol
1563:Stigmastanol
1543:β-Sitosterol
1503:(Vitamin D2)
1490:
1477:Phytosterols
1436:
1416:
1383:
1379:
1369:
1350:
1329:
1328:biomarkers (
1316:
1303:Loch Striven
1300:
1293:
1284:
1266:stigmasterol
1255:
1200:
1166:
1130:
1096:
1059:
1025:
991:
957:
923:
889:
854:
797:
785:
783:
740:polar lipids
697:
685:
669:
608:
607:
559:stigmasterol
551:β-sitosterol
506:White solid
215:Identifiers
201:Other names
191:
187:
183:
179:
175:
171:
167:
163:
102:
93:
83:
76:
69:
62:
50:
38:Please help
33:verification
30:
2154:Cholestanes
1985:Cholesterol
1974:Cholesterol
1969:Desmosterol
1947:Cholesterol
1937:Lathosterol
1915:Zymosterone
1870:Cholesterol
1630:Cholesterol
1558:Spinasterol
1496:Campesterol
1334:fatty acids
1244:campesterol
1238:cholesterol
1061:Gymnodinium
807:campesterol
734:. The free
682:Degradation
639:environment
620:unicellular
555:campesterol
547:cholesterol
527:Flash point
503:Appearance
459:Properties
314:100.006.807
2148:Categories
2124:Ergosterol
2104:Fecosterol
2074:Sitosterol
2036:Sitosterol
1954:Zymosterol
1932:Zymostenol
1927:Zymosterol
1920:Zymosterol
1900:Lanosterol
1893:Lanosterol
1781:Carotenoid
1663:Acetyl-CoA
1553:Momordenol
1507:Ergostenol
1501:Ergosterol
1362:References
1275:fucosterol
1250:sitosterol
800:isoprenoid
766:(MS). The
710:including
698:Since the
672:solubility
666:Solubility
491:Molar mass
360:2B0KG2XFOF
287:ChemSpider
276:CHEBI:3168
243:3D model (
222:CAS Number
148:IUPAC name
66:newspapers
2109:Episterol
1344:Estuary,
855:Gonyaulax
762:(FID) or
712:glycerols
688:anaerobic
635:biomarker
96:June 2018
2086:instead.
2027:Nonhuman
2019:instead.
1883:Squalene
1794:Phytoene
1759:Geranyl-
1425:Archived
1422:abstract
1408:25346711
1400:21585343
1342:Mawddach
1320:such as
1307:Scotland
1063:wilczeki
822:Species
805:through
803:squalene
732:methanol
728:solvents
720:saponify
704:hydroxyl
700:molecule
645:(Number
521:Hazards
232:474-67-9
1835:CDP-MEP
1701:Acetone
1683:HMG-CoA
1678:HMB-CoA
1655:HMG-CoA
1634:steroid
849:others
736:sterols
649:in the
590:what is
588: (
496:398.675
340:6432458
327:PubChem
296:4444704
80:scholar
2007:20α,22
1845:HMB-PP
1830:CDP-ME
1406:
1398:
1336:, and
744:hexane
716:alkali
708:lipids
702:has a
616:sterol
613:carbon
585:verify
582:
443:SMILES
142:Names
82:
75:
68:
61:
53:
2078:More
1983:From
1855:DMAPP
1840:MEcPP
1722:DMAPP
1404:S2CID
1346:Wales
1326:lipid
748:BSTFA
724:ester
623:algae
408:InChI
267:ChEBI
245:JSmol
87:JSTOR
73:books
2084:here
2082:see
2017:here
2015:See
1820:DOXP
1632:and
1396:PMID
1330:e.g.
1273:H =
1264:F =
1248:C =
1242:B =
1236:A =
722:the
647:E499
631:rape
351:UNII
186:,11a
59:news
2094:To
2034:To
1988:to
1868:To
1850:IPP
1825:MEP
1720:to
1673:HMB
1653:to
1526:C29
1484:C28
1388:doi
1384:124
1229:25
1195:47
1161:14
1054:47
1020:15
986:32
894:100
860:100
857:spp
686:In
377:EPA
330:CID
182:,9b
178:,9a
170:,3b
166:,3a
42:by
2150::
1998:22
1402:.
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1382:.
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1223:63
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1125:0
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884:0
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843:G
840:F
837:E
834:D
831:C
828:B
825:A
790:.
657:.
481:46
475:28
174:,7
162:(1
2009:R
2000:R
1622:e
1615:t
1608:v
1469:e
1462:t
1455:v
1431:)
1410:.
1390::
1256:E
1226:0
1220:0
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1214:0
1211:0
1208:0
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1192:0
1189:0
1186:0
1180:0
1177:0
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1158:0
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1146:5
1143:1
1140:1
1137:0
1122:0
1119:0
1113:0
1110:0
1107:0
1101:8
1088:0
1085:0
1082:0
1079:1
1073:0
1051:0
1048:0
1045:0
1042:7
1039:9
1036:0
1033:1
1017:0
1014:0
1011:0
1008:1
1005:2
1002:0
999:6
980:0
977:0
974:0
971:0
968:0
965:0
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946:0
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940:0
937:0
934:0
915:0
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909:0
906:0
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881:0
878:0
875:0
872:0
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625:(
580:N
484:O
478:H
472:C
379:)
375:(
247:)
192:H
188:R
184:S
180:R
176:S
172:S
168:S
164:R
109:)
103:(
98:)
94:(
84:·
77:·
70:·
63:·
36:.
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