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Terpenoid

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D'Ambro, Emma L.; Schobesberger, Siegfried; Gaston, Cassandra J.; Lopez-Hilfiker, Felipe D.; Lee, Ben H.; Liu, Jiumeng; Zelenyuk, Alla; Bell, David; Cappa, Christopher D.; Helgestad, Taylor; Li, Ziyue (2019-09-05).
47:, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known 619:
Terpenoids can also be classified according to the type and number of cyclic structures they contain: linear, acyclic, monocyclic, bicyclic, tricyclic, tetracyclic, pentacyclic, or macrocyclic. The
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atoms added. Some authors use the term "terpene" more broadly, to include the terpenoids. Just like terpenes, the terpenoids can be classified according to the number of
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in Australia are noted for having a bluish color when seen from a distance. Trees put the "blue" in Blue Ridge, from their terpeenoids released into the atmosphere.
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Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of
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Terpenoids, at least those containing an alcohol functional group, often arise by hydrolysis of carbocationic intermediates produced from
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Ashour, Mohamed; Wink, Michael; Gershenzon, Jonathan (2010). "Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes and Diterpenes".
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Davis, Edward M.; Croteau, Rodney (2000). "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes".
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in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to
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formation. Secondary organic aerosols formed from this pathway may have atmospheric impacts.
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Ludwiczuk, A.; Skalicka-Woźniak, K.; Georgiev, M.I. (2017). "Terpenoids".
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bioactivity and are therefore of interest to medicinal chemists.
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In air, terpenoids are converted into various species, such as
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Organic Carbon Compounds Emitted By Trees Affect Air Quality
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Terpene synthase enzymes (many), having in common a
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IUPAC Subcommittee on Gas Kinetic Data Evaluation –
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Chemistry, International Union of Pure and Applied.
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can be used to identify the presence of terpenoids.
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Class of aromatic organic chemicals found in plants
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The provitamin 14: 1261:Atmospheric Chemistry and Physics 828:Blue Mountains of New South Wales 641:is a diterpenoid anticancer drug. 157:for the predators of herbivores. 126:is a terpene derivative called a 1338:blue mountains chemical terpene. 1000:Specter M (September 28, 2009). 729: 710: 691: 676: 661: 646: 631: 82:. Well-known terpenoids include 1353:. National Park Service. 2007. 1318:Invitation To Organic Chemistry 903:Christianson, David W. (2017). 173:have been moved or removed, or 1404:IUPAC definition of terpenoids 845:List of phytochemicals in food 1: 1244:, ScienceNews, August 6, 2009 2094:Geranylgeranyl pyrophosphate 1219:, ScienceDaily, Aug. 7, 2009 840:List of antioxidants in food 807:) and to a lesser extent by 773:geranylgeranyl pyrophosphate 161:Structure and classification 2644:Dimethylallyl pyrophosphate 1182:Topics in Current Chemistry 921:10.1021/acs.chemrev.7b00287 755:Terpene § Biosynthesis 35:and its derivatives called 2687: 1550:Geranylgeranyl diphosphate 752: 2638:Isopentenyl pyrophosphate 2592:Norisoprenoids (modified) 1282:10.5194/acp-19-11253-2019 1039:10.1007/s13205-014-0220-2 977:10.1002/9781444320503.ch5 245:isopentenyl pyrophosphate 2631:Activated isoprene forms 2432:Sesquarterpenes/oids (7) 1681:Monocyclic (single ring) 795:, organic nitrates, and 165:Terpenoids are modified 2666:Terpenes and terpenoids 2254:Secodehydroabietic acid 1194:10.1007/3-540-48146-X_2 1156:10.4314/tjpr.v7i3.14686 890:10.1351/goldbook.T06279 203:Number of carbon atoms 78:, and the red color in 2049:Farnesyl pyrophosphate 765:farnesyl pyrophosphate 701:is a monoterpenoid, a 74:, the yellow color in 2251:Sandaracopimaric acid 1896:Geranyl pyrophosphate 1440:Secondary metabolites 860:Secondary metabolites 761:geranyl pyrophosphate 753:Further information: 2441:Tetraprenylcurcumene 1922:Grapefruit mercaptan 971:. pp. 258–303. 824:Blue Ridge Mountains 724:, is a triterpenoid. 2671:Plant communication 2224:Dehydroabietic acid 1690:(cyclopentane ring) 1522:Geranyl diphosphate 1314:Johnson AW (1998). 1273:2019ACP....1911253D 1267:(17): 11253–11265. 1002:"A Life of Its Own" 915:(17): 11570–11648. 656:are monoterpenoids. 627:Selected terpenoids 149:; this is known as 1684:Bicyclic (2 rings) 1230:Data Sheet Ox_VOC7 1137:Ayoola GA (2008). 956:. Oxford: Biology. 954:Nature's Chemicals 822:As an example the 783:Impact on aerosols 2653: 2652: 2601:7,8-dihydroionone 2560: 2559: 2427: 2426: 2264: 2263: 2232:Lambertianic acid 2006: 2005: 1855: 1854: 1670:Acyclic (linear, 1613: 1612: 1603:←Enzyme cofactors 1333:978-0-7637-0432-2 1203:978-3-540-66573-1 1078:Houghton, Isaac. 686:is a diterpenoid. 617: 616: 62:, the flavors of 45:functional groups 29:organic chemicals 2678: 2461: 2293: 2270:Sesterterpenoids 2236:Levopimaric acid 2098:Geranyl-linalool 2079: 2012:Sesquiterpenoids 1952:Perillyl alcohol 1866: 1761: 1640: 1633: 1626: 1617: 1433: 1426: 1419: 1410: 1392: 1391: 1389: 1388: 1373: 1367: 1366: 1364: 1362: 1347: 1341: 1340: 1321: 1311: 1305: 1304: 1294: 1284: 1251: 1245: 1242:A source of haze 1239: 1233: 1226: 1220: 1214: 1208: 1207: 1177: 1171: 1170: 1168: 1158: 1149:(3): 1019–1024. 1134: 1128: 1127: 1101: 1092: 1091: 1089: 1087: 1075: 1069: 1068: 1058: 1016: 1010: 1009: 997: 991: 990: 964: 958: 957: 949: 943: 942: 932: 909:Chemical Reviews 900: 894: 893: 875: 826:in the U.S. and 805:hydroxyl radical 769:sesquiterpenoids 733: 714: 695: 680: 665: 650: 635: 451:Sesterterpenoids 353:Sesquiterpenoids 206:General formula 184: 101:Salvia divinorum 49:natural products 23:, also known as 2686: 2685: 2681: 2680: 2679: 2677: 2676: 2675: 2656: 2655: 2654: 2649: 2626: 2604: 2587: 2556: 2512: 2452: 2450:Tetraterpenoids 2444: 2423: 2364: 2355:Cholecalciferol 2281: 2278:Geranylfarnesol 2260: 2243:Neoabietic acid 2228:Isopimaric acid 2203: 2177: 2147: 2122: 2101: 2067: 2002: 1961: 1910: 1861: 1860:Monoterpenoids 1851: 1806: 1780: 1756: 1752: 1748: 1740: 1736:Isovaleric acid 1726: 1722: 1702: 1659: 1644: 1614: 1609: 1597: 1569: 1536: 1508: 1496:Natural phenols 1490: 1452: 1442: 1437: 1400: 1395: 1386: 1384: 1375: 1374: 1370: 1360: 1358: 1349: 1348: 1344: 1334: 1313: 1312: 1308: 1253: 1252: 1248: 1240: 1236: 1227: 1223: 1215: 1211: 1204: 1179: 1178: 1174: 1136: 1135: 1131: 1124: 1103: 1102: 1095: 1085: 1083: 1082:. Elliot Barker 1077: 1076: 1072: 1018: 1017: 1013: 999: 998: 994: 987: 966: 965: 961: 952:Firn R (2010). 951: 950: 946: 902: 901: 897: 877: 876: 872: 868: 836: 799:by short-lived 785: 757: 751: 744: 741:sesquiterpenoid 734: 725: 715: 706: 696: 687: 681: 672: 666: 657: 651: 642: 636: 604: 600: 596: 567: 563: 545:Tetraterpenoids 510: 506: 473: 469: 416: 412: 375: 371: 294: 290: 257:isovaleric acid 237: 233: 163: 53:pharmacological 17: 12: 11: 5: 2684: 2682: 2674: 2673: 2668: 2658: 2657: 2651: 2650: 2648: 2647: 2641: 2634: 2632: 2628: 2627: 2625: 2624: 2621:protein domain 2612: 2610: 2606: 2605: 2603: 2602: 2599: 2595: 2593: 2589: 2588: 2586: 2585: 2582: 2577: 2575:Natural rubber 2571: 2569: 2566:Polyterpenoids 2562: 2561: 2558: 2557: 2555: 2554: 2549: 2544: 2539: 2534: 2529: 2523: 2521: 2514: 2513: 2511: 2510: 2505: 2500: 2495: 2490: 2488:Delta-Carotene 2485: 2483:Gamma-Carotene 2480: 2475: 2473:Alpha-Carotene 2469: 2467: 2458: 2446: 2445: 2443: 2442: 2439: 2435: 2433: 2429: 2428: 2425: 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Retrieved 1073: 1030: 1024: 1014: 1005: 995: 968: 962: 953: 947: 912: 908: 898: 880: 873: 821: 786: 777:diterpenoids 758: 749:Biosynthesis 618: 608:Gutta-percha 583:Polyterpenes 538:ursolic acid 436:salvinorin A 420:Abietic acid 394:Diterpenoids 277:Monoterpenes 164: 132: 120:cannabinoids 113: 99: 96:salvinorin A 57: 24: 20: 18: 2552:Rubixanthin 2542:Astaxanthin 2503:Phytofluene 2455:Carotenoids 2345:Cholesterol 2340:Tocopherols 2310:Campesterol 2209:Resin acids 2194:Gibberellin 2189:Aphidicolin 2182:Tetracyclic 2057:Longifolene 2021:Artemisinin 1998:Umbellulone 1886:Citronellol 1876:Citronellal 1575:Antibiotics 1565:Pimaradiene 1560:Aphidicolin 1504:Polyphenols 1108:: 233–266. 720:, a common 705:derivative. 571:Carotenoids 493:Triterpenes 477:Andrastin A 424:ginkgolides 318:citronellol 314:citronellal 187:Terpenoids 155:attractants 25:isoprenoids 2660:Categories 2537:Zeaxanthin 2381:Lanosterol 2328:Sitosterol 2323:Sitostanol 2199:Paclitaxel 2106:Monocyclic 1993:Ascaridole 1988:Eucalyptol 1941:Hinokitiol 1915:Monocyclic 1785:Monocyclic 1652:terpenoids 1583:Penicillin 1387:2023-12-10 1166:1807/60332 866:References 803:(like the 699:Hinokitiol 654:Terpineols 639:Paclitaxel 428:paclitaxel 399:Diterpenes 330:hinokitiol 326:eucalyptol 196:Number of 169:, wherein 128:carotenoid 110:bilobalide 106:ginkgolide 76:sunflowers 60:eucalyptus 41:diterpenes 21:terpenoids 2609:Synthesis 2465:Carotenes 2360:Ecdysones 2164:Forskolin 2152:Tricyclic 2139:Epimanool 2064:Nootkatin 2061:Muurolene 2053:Juniperol 2045:Chanootin 2026:Bisabolol 1957:Carvacrol 1797:Terpinene 1699:(4 rings) 1646:Types of 1458:Alkaloids 1301:1680-7316 1188:: 53–95. 1047:2190-572X 1026:3 Biotech 884:. IUPAC. 850:Nutrition 789:aldehydes 703:tropolone 669:Humulones 522:limonoids 481:manoalide 249:isoprenol 209:Examples 190:Analogue 112:found in 2508:Phytoene 2493:Lycopene 2394:Squalane 2386:Saponins 2297:Steroids 2159:Cembrene 2136:-Abienol 2127:Bicyclic 2031:Cadinene 1966:Bicyclic 1932:p-Cymene 1906:Linalool 1891:Geraniol 1842:Sabinene 1832:Camphene 1811:Bicyclic 1792:Limonene 1776:Myrcenes 1717:Isoprene 1697:Steroids 1688:Iridoids 1656:isoprene 1648:terpenes 1527:Limonene 1486:Atropine 1471:Morphine 1355:Archived 1065:28324581 939:28841019 834:See also 797:epoxides 722:limonoid 534:squalene 440:sclareol 387:humulone 379:Farnesol 338:linalool 334:iridoids 322:geraniol 220:Isoprene 198:isoprene 192:terpenes 179:isoprene 167:terpenes 143:proteins 135:steroids 118:and the 80:tomatoes 64:cinnamon 37:terpenes 33:isoprene 2646:(DMAPP) 2376:Betulin 2174:Pimarol 2171:Pimaral 2118:Retinal 2113:Retinol 2082:Acyclic 2041:Cedrene 2036:Cadinol 1978:Borneol 1973:Camphor 1927:Menthol 1901:Halomon 1869:Acyclic 1837:Thujene 1771:Ocimene 1764:Acyclic 1476:Cocaine 1466:Codeine 1447:General 1376:CSIRO. 1269:Bibcode 1056:4362742 930:5599884 813:aerosol 779:, etc. 737:Geosmin 718:Limonin 684:Retinol 590:>40 530:sterols 444:steviol 432:retinol 383:geosmin 342:menthol 306:carvone 302:camphor 139:sterols 92:camphor 88:menthol 2568:(many) 2547:Lutein 2398:Acids 2089:Phytol 1947:Thymol 1881:Citral 1847:Carene 1818:Pinene 1731:Prenol 1678:forms) 1658:units) 1654:(# of 1608:  1532:Pinene 1451:  1330:  1299:  1232:, 2007 1200:  1120:  1063:  1053:  1045:  983:  937:  927:  775:gives 767:gives 587:>8 514:Amyrin 346:thymol 310:citral 265:prenol 200:units 175:oxygen 84:citral 72:ginger 70:, and 68:cloves 2640:(IPP) 2457:) (8) 2369:Other 1676:trans 1555:Taxol 1086:3 May 809:ozone 739:is a 261:HMBPP 241:DMAPP 1824:and 1757:)(2) 1674:and 1650:and 1363:2007 1328:ISBN 1297:ISSN 1198:ISBN 1118:ISBN 1088:2016 1061:PMID 1043:ISSN 981:ISBN 935:PMID 817:haze 815:and 137:and 133:The 108:and 19:The 2289:(6) 2272:(5) 2134:cis 2075:(4) 2014:(3) 1710:(1) 1672:cis 1324:261 1287:hdl 1277:doi 1190:doi 1186:209 1161:hdl 1151:doi 1110:doi 1051:PMC 1035:doi 973:doi 925:PMC 917:doi 913:117 886:doi 557:40 500:30 463:25 406:20 365:15 284:10 2662:: 1755:16 1751:10 1749:(C 1719:(C 1380:. 1336:. 1326:. 1295:. 1285:. 1275:. 1265:19 1263:. 1259:. 1196:. 1184:. 1159:. 1145:. 1141:. 1116:. 1096:^ 1059:. 1049:. 1041:. 1029:. 1023:. 1004:. 979:. 933:. 923:. 911:. 907:. 791:, 610:, 593:(C 566:64 562:40 554:8 536:, 532:, 528:, 524:, 520:, 516:, 509:48 505:30 497:6 479:, 472:40 468:25 460:5 442:, 438:, 434:, 430:, 426:, 422:, 415:32 411:20 403:4 385:, 381:, 374:24 370:15 362:3 344:, 340:, 336:, 332:, 328:, 324:, 320:, 316:, 312:, 308:, 304:, 300:, 293:16 289:10 281:2 263:, 259:, 255:, 251:, 247:, 243:, 227:5 224:1 130:. 104:, 94:, 90:, 86:, 66:, 39:, 2623:) 2619:( 2520:: 2453:( 1943:) 1939:( 1828:) 1826:β 1822:α 1820:( 1753:H 1727:) 1725:8 1723:H 1721:5 1639:e 1632:t 1625:v 1432:e 1425:t 1418:v 1390:. 1365:. 1303:. 1289:: 1279:: 1271:: 1206:. 1192:: 1169:. 1163:: 1153:: 1147:7 1126:. 1112:: 1090:. 1067:. 1037:: 1031:5 1008:. 989:. 975:: 941:. 919:: 892:. 888:: 743:. 603:n 601:) 599:8 597:H 595:5 564:H 560:C 507:H 503:C 470:H 466:C 413:H 409:C 372:H 368:C 291:H 287:C 236:8 234:H 232:5 230:C

Index

organic chemicals
isoprene
terpenes
diterpenes
functional groups
natural products
pharmacological
eucalyptus
cinnamon
cloves
ginger
sunflowers
tomatoes
citral
menthol
camphor
salvinorin A
Salvia divinorum
ginkgolide
bilobalide
Ginkgo biloba
cannabinoids
beta carotene
carotenoid
steroids
sterols
proteins
cell membrane
isoprenylation
attractants

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