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enzymes. The indole-3-acetaldoxime is then converted to indole-3-acetonitrile by another cytochrome P450, CYP71A13. A glutathione conjugate followed by a subsequent unknown enzyme is needed to form dihydrocamalexic acid. A final decarboxylation step by cytochrome P450 CYP71B15, also called
479:
Mucha, Stefanie; Heinzlmeir, Stephanie; Kriechbaumer, Verena; Strickland, Benjamin; Kirchhelle, Charlotte; Choudhary, Manisha; Kowalski, Natalie; Eichmann, Ruth; Hueckelhoven, Ralph; Grill, Erwin; Kuster, Bernhard; Glawischnig, Erich (2019).
737:
Schuhegger, Regina; Nafisi, Majse; Mansourova, Madina; Petersen, Bent Larsen; Olsen, Carl Erik; Svatoš, Aleš; Halkier, Barbara Ann; Glawischnig, Erich (2006).
239:
430:
Nafisi, Majse; Goregaoker, Sameer; Botanga, Christopher J.; Glawischnig, Erich; Olsen, Carl E.; Halkier, Barbara A.; Glazebrook, Jane (2007).
788:
Smith, Basil A.; Neal, Corey L.; Chetram, Mahandranauth; Vo, Baohan; Mezencev, Roman; Hinton, Cimona; Odero-Marah, Valerie A. (2013).
533:"Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis"
204:
641:"Cytosolic γ-Glutamyl Peptidases Process Glutathione Conjugates in the Biosynthesis of Glucosinolates and Camalexin in Arabidopsis"
639:
Geu-Flores, Fernando; Møldrup, Morten Emil; Böttcher, Christoph; Olsen, Carl Erik; Scheel, Dierk; Halkier, Barbara Ann (2011).
848:
432:"Arabidopsis Cytochrome P450 Monooxygenase 71A13 Catalyzes the Conversion of Indole-3-Acetaldoxime in Camalexin Synthesis"
92:
314:
790:"The phytoalexin camalexin mediates cytotoxicity towards aggressive prostate cancer cells via reactive oxygen species"
590:
Su, Tongbing; Xu, Juan; Li, Yuan; Lei, Lei; Zhao, Luo; Yang, Hailian; Feng, Jidong; Liu, Guoqin; Ren, Dongtao (2011).
168:
843:
690:"Arabidopsis PAD3, a Gene Required for Camalexin Biosynthesis, Encodes a Putative Cytochrome P450 Monooxygenase"
130:
367:. The ethanamine moiety attached to the 3 position of the indole ring is subsequently rearranged into a
383:
has not been fully elucidated, most of the enzymes involved in the pathway are known and involved in a
544:
348:
339:
185:
36:
58:
592:"Glutathione-Indole-3-Acetonitrile is Required for Camalexin Biosynthesis in Arabidopsis thaliana"
387:
complex. The pathway starts with a tryptophan precursor which is subsequently oxidized by two
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The base structure of camalexin consists of an indole ring derived from
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phytoalexin deficient4 (PAD3) results in the final product, camalexin.
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23:
531:
Glawischnig, E.; Hansen, B. G.; Olsen, C. E.; Halkier, B. A. (2004).
739:"CYP71B15 (PAD3) Catalyzes the Final Step in Camalexin Biosynthesis"
307:
Except where otherwise noted, data are given for materials in their
213:
InChI=1S/C11H8N2S/c1-2-4-10-8(3-1)9(7-13-10)11-12-5-6-14-11/h1-7,13H
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InChI=1/C11H8N2S/c1-2-4-10-8(3-1)9(7-13-10)11-12-5-6-14-11/h1-7,13H
91:
81:
173:
688:
Zhou, Nan; Tootle, Tina L.; Glazebrook, Jane (1999).
482:"The formation of a camalexin-biosynthetic metabolon"
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537:Proceedings of the National Academy of Sciences
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404:against aggressive prostate cancer cell lines
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355:to deter bacterial and fungal pathogens.
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216:Key: IYODIJVWGPRBGQ-UHFFFAOYSA-N
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379:While the biosynthesis of camalexin
226:Key: IYODIJVWGPRBGQ-UHFFFAOYAV
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14:
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311:(at 25 °C , 100 kPa).
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1:
794:Journal of Natural Medicines
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806:10.1007/s11418-012-0722-3
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235:
200:
51:
35:
30:
21:
558:10.1073/pnas.0305876101
247:c1ccc2c(c1)c(c2)c3nccs3
706:10.1105/tpc.11.12.2419
657:10.1105/tpc.111.083998
608:10.1105/tpc.110.079145
448:10.1105/tpc.107.051383
41:3-(1,3-Thiazol-2-yl)-1
849:2-Thiazolyl compounds
756:10.1104/pp.106.082024
331:3-thiazol-2-yl-indole
499:10.1105/tpc.19.00403
349:secondary metabolite
340:Arabidopsis thaliana
37:Preferred IUPAC name
549:2004PNAS..101.8245G
396:Biological activity
337:found in the plant
301: g·mol
18:
315:Infobox references
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700:(12): 2419–2428.
543:(21): 8245–8250.
492:(11): 2697–2710.
323:Chemical compound
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169:CompTox Dashboard
93:Interactive image
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844:Indole alkaloids
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749:(4): 1248–1254.
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694:The Plant Cell
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645:The Plant Cell
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486:The Plant Cell
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436:The Plant Cell
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125:ECHA InfoCard
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375:Biosynthesis
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52:Identifiers
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353:phytoalexin
256:Properties
131:100.236.489
69:135531-86-1
838:Categories
414:References
365:tryptophan
343:and other
294:Molar mass
104:ChemSpider
80:3D model (
59:CAS Number
17:Camalexin
402:cytotoxic
385:metabolon
381:in planta
359:Structure
345:crucifers
327:Camalexin
824:23179315
775:16766671
724:10590168
675:21712415
626:21239642
577:15148388
518:31511315
466:17573535
407:in vitro
369:thiazole
815:3644009
766:1533948
666:3160024
617:3051237
545:Bibcode
509:6881122
457:1955726
347:. The
144:PubChem
45:-indole
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568:419588
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371:ring.
299:200.26
240:SMILES
157:636970
113:552646
31:Names
205:InChI
82:JSmol
820:PMID
771:PMID
720:PMID
671:PMID
622:PMID
573:PMID
514:PMID
462:PMID
810:PMC
802:doi
761:PMC
751:doi
747:141
710:PMC
702:doi
661:PMC
653:doi
612:PMC
604:doi
563:PMC
553:doi
541:101
504:PMC
494:doi
452:PMC
444:doi
174:EPA
147:CID
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281:N
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275:H
269:C
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43:H
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