240:
165:
545:
24:
440:(plus glucose, sulfate, and hydrogen ion), which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants.
366:
492:
The three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. The additional three derivatives appear to be rare in nature. 4-methoxyglucobrassicin was recently reported to be a signal molecule involved in plant defence against bacteria and fungi.
468:
plants, hence the ending of the name. When a second, similar natural product was discovered, it was named neoglucobrassicin. When further derivatives were discovered, a more systematic nomenclature was used. Currently, the following six derivatives are known from plants:
102:
432:, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are
541:) to create a free thiol. A single glucosylation occurs attaching a glucose molecule to the indole hydroximate through a thioether linkage. Finally, the hydroximate itself is sulfated creating glucobrassicin.
672:
Bednarek, P.; Pislewska-Bednarek, M.; Svatos, A.; Schneider, B.; Doubsky, J.; Mansurova, M.; Humphry, M.; Consonni, C.; Panstruga, R.; Sanchez-Vallet, A.; Molina, A.; Schulze-Lefert, P. (2009).
263:
InChI=1S/C16H20N2O9S2/c19-7-11-13(20)14(21)15(22)16(26-11)28-12(18-27-29(23,24)25)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-17,19-22H,5,7H2,(H,23,24,25)/b18-12-/t11-,13-,14+,15-,16+/m1/s1
379:
279:
889:
254:
794:
Mutants in the C–S Lyase of
Glucosinolate Biosynthesis Establish a Critical Role for Indole-3-acetaldoxime in Auxin Homeostasis"
578:
Agerbirk, Niels; Vos, Martin; Kim, Jae Hak; Jander, Georg (2008). "Indole glucosinolate breakdown and its biological effects".
443:
Glucobrassicin is also known to be a highly active egg-laying stimulant of cabbage white butterflies such as the small white (
386:
197:
218:
537:-alkylthiohydroximate derivative, which is then cleaved off by a carbon–sulfur lyase (like the SUR1 enzyme found in
526:
882:
761:
Bender, Judith; Celenza, John L. (2008). "Indolic
Glucosinolates at the Crossroads of Tryptophan Metabolism".
1108:
160:
459:
502:
36:
685:
674:"A Glucosinolate Metabolism Pathway in Living Plant Cells Mediates Broad-Spectrum Antifungal Defense"
625:
235:
875:
68:
544:
501:
The biosynthesis of glucobrassicin begins with tryptophan produced through several steps from the
521:) catalyzes a second subsequent monooxygenase reaction to create a proposed the intermediate 1-
1082:
1028:
815:
738:
703:
651:
433:
142:
1113:
854:
805:
770:
730:
693:
641:
633:
587:
451:
302:
206:
962:
957:
952:
947:
929:
924:
919:
914:
906:
558:
510:
437:
78:
23:
689:
629:
239:
164:
122:
646:
609:
506:
429:
357:
1102:
1050:
1033:
810:
789:
734:
414:
402:
153:
186:
445:
837:
Galletti, Stefania; Barillari, Jessica; Iori, Renato; Venturi, Gianpietro (2006).
1038:
995:
985:
1000:
980:
774:
591:
425:
342:
133:
1087:
1070:
1065:
1060:
1055:
1045:
1023:
990:
972:
898:
698:
673:
637:
819:
742:
707:
655:
462:
of glucobrassicin are known. The compound itself was first isolated from
1015:
1005:
608:
Clay, N. K.; Adio, A. M.; Denoux, C.; Jander, G.; Ausubel, F. M. (2009).
464:
410:
1077:
517:) using NADPH and molecular Oxygen. A separate p450 enzyme (CYP83B1 in
406:
173:
859:
838:
939:
422:
721:
Herrman, Klaus M.; Weaver, Lisa M. (1999). "The
Shikimate Pathway".
356:
Except where otherwise noted, data are given for materials in their
543:
113:
101:
91:
788:
Mikkelsen, Michael; Naur, Peter; Halkier, Barbara (March 2004).
418:
871:
867:
509:. Tryptophan is converted to indole-3-acetaldoxime (IAOx) by
405:
that can be found in almost all cruciferous plants, such as
223:
374:
287:
c1ccc2c(c1)c(c2)C/C(=N/OS(=O)(=O)O)/S3((((O3)CO)O)O)O
1014:
971:
938:
905:
525:-nitro-2-indolyl-ethane. A cysteine is utilized by
756:
754:
752:
421:. As for other glucosinolates, degradation by the
185:
77:
847:Journal of the Science of Food and Agriculture
513:enzymes (the redundant CYP92B3 and CYP79B3 in
883:
843:) leaves by chemical and physical treatments"
533:(GST) in a conjugation process to produce an
8:
610:"Glucosinolate Metabolites Required for an
473:1-Methoxyglucobrassicin (neoglucobrassicin)
890:
876:
868:
667:
665:
238:
163:
141:
15:
858:
809:
723:Annu. Rev. Plant Physiol. Plant Mol. Biol
697:
645:
205:
570:
284:
259:
234:
603:
601:
154:
839:"Glucobrassicin enhancement in woad (
266:Key: DNDNWOWHUWNBCK-PIAXYHQTSA-N
121:
7:
176:
14:
811:10.1111/j.1365-313x.2004.02002.x
735:10.1146/annurev.arplant.50.1.473
364:
320:
314:
22:
360:(at 25 °C , 100 kPa).
548:Biosynthesis of glucobrassicin
332:
326:
308:
1:
56:Indol-3-ylmethylglucosinolate
497:Biosynthesis from tryptophan
488:6′-Isoferuloylglucobrassicin
482:1,4-Dimethoxyglucobrassicin
1130:
428:is expected to produce an
775:10.1007/s11101-008-9111-7
592:10.1007/s11101-008-9098-0
354:
295:
275:
250:
61:
53:
35:
30:
21:
1061:Anthraquinone glycoside
699:10.1126/science.1163732
638:10.1126/science.1164627
614:Innate Immune Response"
479:4-Methoxyglucobrassicin
476:4-Hydroxyglucobrassicin
449:) and the large white (
580:Phytochemistry Reviews
549:
547:
503:shikimic acid pathway
485:1-Sulfoglucobrassicin
1046:Cyanogenic glycoside
515:Arabidopsis thaliana
1071:Flavonoid glycoside
1024:Alcoholic glycoside
690:2009Sci...323..101B
630:2009Sci...323...95C
350: g·mol
18:
1066:Coumarin glycoside
1056:Phenolic glycoside
550:
387:Infobox references
16:
1096:
1095:
1083:Steviol glycoside
1029:Cardiac glycoside
930:C-glycosidic bond
925:S-glycosidic bond
920:N-glycosidic bond
915:O-glycosidic bond
860:10.1002/jsfa.2571
798:The Plant Journal
684:(5910): 101–106.
434:indole-3-carbinol
395:Chemical compound
393:
392:
219:CompTox Dashboard
103:Interactive image
47:
1121:
892:
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869:
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841:Isatis tinctoria
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624:(5910): 95–101.
605:
596:
595:
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452:Pieris brassicae
377:
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303:Chemical formula
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831:Further reading
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559:Gluconasturtiin
555:
511:cytochrome p450
499:
438:thiocyanate ion
396:
389:
384:
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382: ?)
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17:Glucobrassicin
12:
11:
5:
1127:
1125:
1117:
1116:
1111:
1109:Glucosinolates
1101:
1100:
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804:(5): 770–777.
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763:Phytochem. Rev
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507:chorismic acid
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430:isothiocyanate
399:Glucobrassicin
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358:standard state
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48:-glucopyranose
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10:
9:
6:
4:
3:
2:
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1115:
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1088:Thioglycoside
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1057:
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1051:Glycosylamine
1049:
1047:
1044:
1040:
1037:
1035:
1034:Bufadienolide
1032:
1031:
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1027:
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987:
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979:
978:
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964:
963:1,6-Glycoside
961:
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958:1,4-Glycoside
956:
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403:glucosinolate
401:is a type of
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853:(12): 1833.
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531:-transferase
528:
527:glutathione
522:
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463:
457:
450:
446:Pieris rapae
444:
442:
398:
397:
62:Identifiers
54:Other names
41:
1039:Cardenolide
996:Glucuronide
986:Galactoside
953:β-Glycoside
948:α-Glycoside
792:Arabidopsis
729:: 473–503.
612:Arabidopsis
539:Arabidopsis
519:Arabidopsis
460:derivatives
296:Properties
161:100.231.968
123:CHEBI:29028
44:--1-thio-β-
1103:Categories
1001:Rhamnoside
981:Fructoside
899:Glycosides
565:References
505:compound,
426:myrosinase
343:Molar mass
207:EA6EH0IU89
134:ChemSpider
90:3D model (
69:CAS Number
37:IUPAC name
991:Glucoside
769:: 25–37.
79:4356-52-9
1016:Aglycone
1006:Riboside
940:Geometry
820:14871316
743:15012217
708:19095900
656:19095898
553:See also
465:Brassica
458:Several
415:mustards
411:broccoli
407:cabbages
1114:Indoles
1078:Saponin
973:Glycone
686:Bibcode
678:Science
647:2630859
626:Bibcode
618:Science
586:: 101.
380:what is
378: (
187:6602378
174:PubChem
143:5034767
818:
741:
706:
654:
644:
423:enzyme
417:, and
375:verify
372:
348:448.46
280:SMILES
31:Names
255:InChI
114:ChEBI
92:JSmol
907:Bond
816:PMID
739:PMID
704:PMID
652:PMID
436:and
419:woad
198:UNII
855:doi
806:doi
771:doi
731:doi
694:doi
682:323
642:PMC
634:doi
622:323
588:doi
523:aci
455:).
224:EPA
177:CID
1105::
851:86
849:.
845:.
814:.
802:37
800:.
796:.
765:.
751:^
737:.
727:50
725:.
702:.
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680:.
676:.
664:^
650:.
640:.
632:.
620:.
616:.
600:^
582:.
413:,
409:,
318:20
312:16
40:1-
891:e
884:t
877:v
863:.
857::
822:.
808::
790:"
777:.
773::
767:8
745:.
733::
710:.
696::
688::
658:.
636::
628::
594:.
590::
584:8
535:S
529:S
370:N
336:2
333:S
330:9
327:O
324:2
321:N
315:H
309:C
226:)
222:(
94:)
46:D
42:S
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