64:
151:
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20:
175:
345:
Dada, Lubna; Stolzenburg, Dominik; Simon, Mario; Fischer, Lukas; Heinritzi, Martin; Wang, Mingyi; Xiao, Mao; Vogel, Alexander L.; Ahonen, Lauri; Amorim, Antonio; Baalbaki, Rima; Baccarini, Andrea; Baltensperger, Urs; Bianchi, Federico; Daellenbach, Kaspar R. (2023).
158:
Cyclic sesquiterpenes are more common than cyclic monoterpenes because of the increased chain length and additional double bond in the sesquiterpene precursors. In addition to common six-membered ring systems such as the ones found in
190:
286:
The term merosesquiterpenoids was coined in 1968 to describe molecules of this class that have a mixed biosynthetic origin, meaning isoprenoid precursors like isopentenyl pyrophosphate are derived from both the
123:, has identified sesquiterpenes—gaseous hydrocarbons that are released by plants—as potentially playing a major role in cloud formation in relatively pristine regions of the atmosphere.
265:, the volatile compound that gives an earthy taste and musty odor in drinking water and the characteristic odor on a rainy day, is a sesquiterpenoid, produced by bacteria, especially
486:
D’Harlingue, A., Mamdouh, A. M., Malfatti, P., Soulie, M.-C., & Bompeix, G. (1995). Evidence for rishitin biosynthesis in tomato cultures. Phytochemistry, 39(1), 69–70.
464:
Katsui, N.; Murai, A.; Takasugi, M.; Imaizumi, K.; Masamune, T.; Tomiyama, K. (1968). "The structure of rishitin, a new antifungal compound from diseased potato tubers".
261:
The FPP backbone can be rearranged in several different ways and further decorated with different functional groups, hence the large variety of sesquiterpenoids.
283:
ring, hence the name. They are found in many plants and can cause allergic reactions and toxicity if consumed excessively, particularly in grazing livestock.
416:
626:
1605:
395:
Davis, Edward M.; Croteau, Rodney (2000). "Cyclization
Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes".
449:
329:
116:
1082:
554:"Biosynthesis of polyketide-terpenoid (meroterpenoid) metabolites andibenin B and andilesin A in Aspergillus variecolor"
107:, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as
1632:
526:
1626:
136:
619:
598:
269:, that are present in the soils and water supplies. Oxidation of farnesene then provides the sesquiterpenoid
1654:
499:
Izaguirre G, Taylor WD (June 1995). "Geosmin and 2-methylisoborneol production in a major aqueduct system".
1037:
292:
140:
112:
33:
604:
552:
Simpson, Thomas J.; Ahmed, Salman A.; Rupert McIntyre, C.; Scott, Fiona E.; Sadler, Ian H. (1997-03-17).
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With the addition of a third ring, the possible structures become increasingly varied. Examples include
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ring. Rishitin is another example of a cadinene, which is found in potatoes and tomatoes.
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ring, hence the name. These compounds are found in many other plants and can cause
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Chizzola R (2013), "Regular
Monoterpenes and Sesquiterpenes (Essential Oils)",
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143:(FPP), which is an intermediate in the biosynthesis of sesquiterpenes such as
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produce the related sesquiterpenoids. A recent study conducted in the
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such as clove oil, contains a nine-membered ring fused to a
348:"Role of sesquiterpenes in biogenic new particle formation"
527:"Sesquiterpene Lactones and their toxicity to livestock"
279:
are a common class of sesquiterpenoids that contain a
208:
are sesquiterpenoids that give "hoppy" flavor to beer.
76:, Australia, which produces two unique sesquiterpenes
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Terpene synthase enzymes (many), having in common a
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Terpenes: Flavors, Fragrances, Pharmaca, Pheromones
436:, Springer Berlin Heidelberg, pp. 2973–3008,
682:Iridoid glycosides (iridoids bound to a sugar)
312:Eberhard Breitmaier (2006). "Sesquiterpenes".
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36:which are sesquiterpenoids (built from three
8:
488:https://doi.org/10.1016/0031-9422(94)00844-J
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597:at the U.S. National Library of Medicine
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238:are aromatic bicyclic sesquiterpenoids.
304:
52:if consumed in excess, particularly in
216:contain two fused six-membered rings.
7:
197:, one of a family of sesquiterpene.
1606:terpene synthase N terminal domain
14:
117:Cosmics Leaving Outdoor Droplets
181:, a sesquiterpene abundant in
1:
570:10.1016/S0040-4020(97)00015-X
442:10.1007/978-3-642-22144-6_130
1083:Geranylgeranyl pyrophosphate
513:10.1016/0273-1223(95)00454-u
501:Water Science and Technology
1633:Dimethylallyl pyrophosphate
397:Topics in Current Chemistry
1671:
1627:Isopentenyl pyrophosphate
1581:Norisoprenoids (modified)
322:10.1002/9783527609949.ch3
139:results in the 15-carbon
137:isopentenyl pyrophosphate
127:Biosynthesis and examples
91:units and often have the
1620:Activated isoprene forms
1421:Sesquarterpenes/oids (7)
670:Monocyclic (single ring)
599:Medical Subject Headings
1243:Secodehydroabietic acid
466:Chemical Communications
409:10.1007/3-540-48146-X_2
293:non-mevalonate pathways
119:large cloud chamber at
1038:Farnesyl pyrophosphate
364:10.1126/sciadv.adi5297
277:Sesquiterpene lactones
220:, a component of many
209:
198:
186:
155:
154:Farnesyl pyrophosphate
141:farnesyl pyrophosphate
87:that consist of three
77:
60:
34:sesquiterpene lactones
1240:Sandaracopimaric acid
885:Geranyl pyrophosphate
204:
192:
177:
153:
133:geranyl pyrophosphate
66:
40:units) and contain a
22:
1430:Tetraprenylcurcumene
911:Grapefruit mercaptan
533:. Cornell University
474:10.1039/C19680000043
74:Cooktown, Queensland
29:Artemisia tridentata
1213:Dehydroabietic acid
679:(cyclopentane ring)
673:Bicyclic (2 rings)
316:. pp. 24–51.
210:
199:
187:
156:
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69:Phallus indusiatus
61:
46:allergic reactions
1642:
1641:
1590:7,8-dihydroionone
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1415:
1253:
1252:
1221:Lambertianic acid
995:
994:
844:
843:
659:Acyclic (linear,
564:(11): 4013–4034.
418:978-3-540-66573-1
93:molecular formula
16:Class of terpenes
1662:
1450:
1282:
1259:Sesterterpenoids
1225:Levopimaric acid
1087:Geranyl-linalool
1068:
1001:Sesquiterpenoids
941:Perillyl alcohol
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352:Science Advances
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257:Sesquiterpenoids
249:and the alcohol
131:The reaction of
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1439:Tetraterpenoids
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1353:
1344:Cholecalciferol
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1267:Geranylfarnesol
1249:
1232:Neoabietic acid
1217:Isopimaric acid
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849:Monoterpenoids
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1477:Delta-Carotene
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1472:Gamma-Carotene
1469:
1464:
1462:Alpha-Carotene
1458:
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1424:
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1418:
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972:Bornyl acetate
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1229:Mercusic acid
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1573:Gutta-balatá
1569:Gutta percha
1507:Xanthophylls
1487:Neurosporene
1406:Moronic acid
1396:Ursolic acid
1339:Testosterone
1322:Stigmasterol
1307:Cycloartenol
1294:Phytosterols
1236:Pimaric acid
1206:Abietic acid
1157:Manoyl oxide
1132:Salvinorin A
1122:
1062:Diterpenoids
926:Thujaplicins
851:(2,modified)
791:Phellandrene
735:Monoterpenes
664:
660:
653:Basic forms:
561:
557:
547:
537:December 29,
535:. Retrieved
531:Cornell CALS
530:
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468:(1): 43–44.
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67:
27:
1541:Rubixanthin
1531:Astaxanthin
1492:Phytofluene
1444:Carotenoids
1334:Cholesterol
1329:Tocopherols
1299:Campesterol
1198:Resin acids
1183:Gibberellin
1178:Aphidicolin
1171:Tetracyclic
1046:Longifolene
1010:Artemisinin
987:Umbellulone
875:Citronellol
865:Citronellal
558:Tetrahedron
243:longifolene
236:guaiazulene
226:cyclobutane
179:Zingiberene
161:zingiberene
32:) contains
1526:Zeaxanthin
1370:Lanosterol
1317:Sitosterol
1312:Sitostanol
1188:Paclitaxel
1095:Monocyclic
982:Ascaridole
977:Eucalyptol
930:Hinokitiol
904:Monocyclic
774:Monocyclic
641:terpenoids
299:References
289:mevalonate
251:patchoulol
165:bisacurone
1598:Synthesis
1454:Carotenes
1349:Ecdysones
1153:Forskolin
1141:Tricyclic
1128:Epimanool
1053:Nootkatin
1050:Muurolene
1042:Juniperol
1034:Chanootin
1015:Bisabolol
946:Carvacrol
786:Terpinene
688:(4 rings)
635:Types of
578:0040-4020
403:: 53–95.
214:cadinenes
206:Humulones
145:farnesene
109:oxidation
57:livestock
1649:Category
1497:Phytoene
1482:Lycopene
1383:Squalane
1375:Saponins
1286:Steroids
1148:Cembrene
1125:-Abienol
1116:Bicyclic
1020:Cadinene
955:Bicyclic
921:p-Cymene
895:Linalool
880:Geraniol
831:Sabinene
821:Camphene
800:Bicyclic
781:Limonene
765:Myrcenes
706:Isoprene
686:Steroids
677:Iridoids
645:isoprene
637:terpenes
382:37682996
373:10491295
271:farnesol
195:Cadinene
169:humulene
89:isoprene
85:terpenes
50:toxicity
38:isoprene
1635:(DMAPP)
1365:Betulin
1163:Pimarol
1160:Pimaral
1107:Retinal
1102:Retinol
1071:Acyclic
1030:Cedrene
1025:Cadinol
967:Borneol
962:Camphor
916:Menthol
890:Halomon
858:Acyclic
826:Thujene
760:Ocimene
753:Acyclic
281:lactone
263:Geosmin
247:copaene
103:. Like
54:grazing
42:lactone
1557:(many)
1536:Lutein
1387:Acids
1078:Phytol
936:Thymol
870:Citral
836:Carene
807:Pinene
720:Prenol
667:forms)
647:units)
643:(# of
601:(MeSH)
576:
448:
415:
380:
370:
358:(36).
328:
183:ginger
1629:(IPP)
1446:) (8)
1358:Other
665:trans
135:with
72:, in
813:and
746:)(2)
663:and
639:and
574:ISSN
539:2018
446:ISBN
413:ISBN
378:PMID
326:ISBN
291:and
234:and
212:The
163:and
121:CERN
48:and
1278:(6)
1261:(5)
1123:cis
1064:(4)
1003:(3)
699:(1)
661:cis
566:doi
509:doi
470:doi
438:doi
405:doi
401:209
368:PMC
360:doi
318:doi
111:or
1651::
744:16
740:10
738:(C
708:(C
572:.
562:53
560:.
556:.
529:.
505:31
503:.
444:,
411:.
399:.
376:.
366:.
354:.
350:.
324:.
295:.
273:.
253:.
245:,
193:δ-
171:.
147:.
101:24
97:15
1612:)
1608:(
1509::
1442:(
932:)
928:(
817:)
815:β
811:α
809:(
742:H
716:)
714:8
712:H
710:5
628:e
621:t
614:v
580:.
568::
541:.
515:.
511::
476:.
472::
440::
421:.
407::
384:.
362::
356:9
334:.
320::
185:.
99:H
95:C
59:.
26:(
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