Camalexin

Names

[ Name ]:
Camalexin

[Synonym ]:
2-(1H-indol-3-yl)thiazole
3-Thiazol-2-yl-1H-indole
Camalexin

Biological Activity

[Description]:

Camalexin is a phytoalexin isolated from Camelina sativa and Arabidopsis (Cruciferae) with antibacterial, antifungal, antiproliferative and anticancer activities. Camalexin can induce reactive oxygen species (ROS) production[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Reactive oxygen species (ROS)[1][2]

[In Vitro]

Camalexin shows antiproliferative activity against a human breast cancer cell line[2]. For the oomycetes Phytophthora and Pythium Nep1-like proteins (necrosis and ethylene-inducing peptide 1-like proteins) are the initial triggers of Camalexin synthesis and formation of reactive oxygen species (ROS). ROS appear to be of general relevance for Camalexin formation. Chemical induction of ROS, such as by application of acifluorfen, coincided with Camalexin synthesis. In a screen for enhanced susceptibility to Alternaria brassicicola the esa1 mutant is identified, which shows delayed Camalexin induction. Particularly in response to ROS inducing agents reduced Camalexin levels are synthesized. This crucial role for ESA1 is confirmed by the inability of esa1 mutants to synthesize Camalexin in response to Leptosphaeria maculans. An additional mutant that exhibits greatly reduced Camalexin accumulation is ups1, which is isolated on the basis of diminished expression of a tryptophan biosynthetic enzyme[2].

[References]

[1]. William A.Ayer, et al. Synthesis of camalexin and related phytoalexins. Tetrahedron. Volume 48, Issue 14, 1992, Pages 2919-2924.

[2]. Glawischnig E. Camalexin. Phytochemistry. 2007 Feb;68(4):401-6.

[3]. Mezencev R, et al. Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers. Neoplasma. 2003;50(4):239-45.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₁H₈N₂S

[ Molecular Weight ]:
200.26000

[ Exact Mass ]:
200.04100

[ PSA ]:
56.92000

[ LogP ]:
3.29140

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Articles

TRANSCRIPTION ACTIVATOR-LIKE EFFECTOR NUCLEASE-Mediated Generation and Metabolic Analysis of Camalexin-Deficient cyp71a12 cyp71a13 Double Knockout Lines.

Plant Physiol. 168 , 849-58, (2015)

In Arabidopsis (Arabidopsis thaliana), a number of defense-related metabolites are synthesized via indole-3-acetonitrile (IAN), including camalexin and indole-3-carboxylic acid (ICOOH) derivatives. Cy...

Identification of Multiple Phytotoxins Produced by Fusarium virguliforme Including a Phytotoxic Effector (FvNIS1) Associated With Sudden Death Syndrome Foliar Symptoms.

Mol. Plant Microbe Interact. 29 , 96-108, (2016)

Sudden death syndrome (SDS) of soybean is caused by a soilborne pathogen, Fusarium virguliforme. Phytotoxins produced by F. virguliforme are translocated from infected roots to leaves, in which they c...

Analysis of the Molecular Dialogue Between Gray Mold (Botrytis cinerea) and Grapevine (Vitis vinifera) Reveals a Clear Shift in Defense Mechanisms During Berry Ripening.

Mol. Plant Microbe Interact. 28 , 1167-80, (2015)

Mature grapevine berries at the harvesting stage (MB) are very susceptible to the gray mold fungus Botrytis cinerea, while veraison berries (VB) are not. We conducted simultaneous microscopic and tran...

Related Compounds

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