280:
191:
545:
24:
655:
580:
581:"Biosynthesis of Germacrene A Carboxylic Acid in Chicory Roots. Demonstration of a Cytochrome P450 (+)-Germacrene A Hydroxylase and NADP+-Dependent Sesquiterpenoid Dehydrogenase(s) Involved in Sesquiterpene Lactone Biosynthesis"
656:"Biosynthesis of Costunolide, Dihydrocostunolide, and Leucodin. Demonstration of Cytochrome P450-Catalyzed Formation of the Lactone Ring Present in Sesquiterpene Lactones of Chicory"
108:
319:
544:
294:
709:
714:
303:
InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1
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633:
279:
190:
84:
385:
128:
680:
703:
605:
514:, germacrene acid. The cytochrome P450 enzyme, (+)-costunolide synthase, which is a
453:
179:
226:
480:
476:
654:
Kraker, J.; Franssen, M.; Joerink, M.; Groot, A.; Bouwmeester, H. (April 2002).
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484:
441:
370:
159:
579:
Kraker, J.; Franssen, M.; Dalm, M.; Groot, A.; Bouwmeester, H. (April 2001).
689:
614:
596:
57:)-6,10-Dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodecafuran-2(3
23:
531:
500:
456:
417:
213:
671:
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Except where otherwise noted, data are given for materials in their
639:. West Sussex, United Kingdom: John Wiley & Sons Ltd. p.
515:
119:
107:
97:
506:, germacra-1(10),4,11(13)-trien-12-ol, through the intermediate
543:
522:
dependent enzyme, then oxidizes germacrene acid to give the
263:
479:. The isoprenyl side chain of (+)-germacrene A is then
510:, germacra-1(10),4,11(13)-trien-12-al to form compound
635:
Medicinal
Natural Products: A Biosynthetic Approach
225:
83:
459:, (+)-germacrene A synthase, to form compound
8:
463:, (+)-germacryl cation. Inside this same
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306:Key: RYLQFBHBWLLLL-AHNJNIBGSA-N
416:roots in 1960. It is also found in
216:
530:, which then cyclizes to form the
14:
555:Biosynthesis of (+)-Costunolide.
327:O=C/1O2/C=C(/CC/C=C(/CC2C\1=C)C)C
548:Biosynthesis of (+)-Costunolide.
440:. The synthesis begins with the
354:
22:
452:(FPP), which is mediated by a
388:(at 25 °C , 100 kPa).
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1:
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406:is a naturally occurring
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631:Dewick, Paul M. (2009).
710:Sesquiterpene lactones
549:
450:farnesyl pyrophosphate
597:10.1104/pp.125.4.1930
547:
495:. NAD(P) dependent
408:sesquiterpene lactone
715:Vinylidene compounds
483:by (+)-germacrene A
410:, first isolated in
37:Preferred IUPAC name
378: g·mol
18:
550:
434:mevalonate pathway
392:Infobox references
16:
672:10.1104/pp.010957
400:Chemical compound
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259:CompTox Dashboard
109:Interactive image
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660:Plant Physiology
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591:(4): 1930–1940.
585:Plant Physiology
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491:enzyme, to form
471:is lost to form
413:Saussurea costus
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343:Chemical formula
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539:(+)-costunolide
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489:cytochrome P450
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404:(+)-Costunolide
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481:hydroxylated
477:germacrene A
472:
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444:of compound
437:
432:through the
427:
411:
403:
402:
149:ChEMBL205612
68:Identifiers
58:
54:
50:
46:
42:
17:Costunolide
666:: 257–258.
497:hydrogenase
485:hydroxylase
442:cyclization
430:synthesized
336:Properties
187:100.208.663
704:Categories
559:References
436:, seen in
371:Molar mass
247:4IK578SA7Z
160:ChemSpider
129:CHEBI:3900
96:3D model (
75:CAS Number
553:Figure 1.
499:(s) then
424:Synthesis
690:12011356
615:11299372
438:Figure 1
85:553-21-9
532:lactone
524:alcohol
501:oxidize
457:cyclase
418:lettuce
376:232.323
227:5281437
214:PubChem
169:4444782
688:
681:155889
678:
613:
603:
475:, (+)-
469:proton
465:enzyme
428:It is
320:SMILES
140:ChEMBL
31:Names
606:88848
518:and O
516:NADPH
295:InChI
120:ChEBI
98:JSmol
61:)-one
686:PMID
611:PMID
467:, a
238:UNII
199:MeSH
53:,11a
676:PMC
668:doi
664:129
641:214
601:PMC
593:doi
589:125
264:EPA
217:CID
49:,10
41:(3a
706::
684:.
674:.
662:.
658:.
623:^
609:.
599:.
587:.
583:.
567:^
541:.
537:,
448:,
420:.
358:20
352:15
45:,6
692:.
670::
643:.
617:.
595::
535:8
528:7
520:2
512:6
508:5
504:4
493:4
473:3
461:2
446:1
364:2
361:O
355:H
349:C
266:)
262:(
100:)
59:H
55:R
51:E
47:E
43:S
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