Unveiling the first indole-fused thiazepine: structure, synthesis and biosynthesis of cyclonasturlexin, a remarkable cruciferous phytoalexin.
نویسندگان
چکیده
As a mechanism of defense against pathogens and other types of stress, watercress plants produce a variety of elicited chemical defenses generally known as phytoalexins. Herein the chemical structure, synthesis, biosynthesis and antifungal activity of cyclonasturlexin, the most intriguing indolyl phytoalexin isolated to date, are reported.
منابع مشابه
Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle.
Transformation of 1-t-Boc-4-methoxyindole-3-glucosinolate under acidic conditions yielded the potent phytoalexin rapalexin A, providing its first biomimetic synthesis via Lossen type rearrangement, while a novel 1-thioimidocarbonyl-β-d-glucopyranose heterocyclic system was obtained under basic conditions via Neber type rearrangement.
متن کاملThe Biosynthetic Pathway of Indole-3-Carbaldehyde and Indole-3-Carboxylic Acid Derivatives in Arabidopsis.
Indolic secondary metabolites play an important role in pathogen defense in cruciferous plants. In Arabidopsis (Arabidopsis thaliana), in addition to the characteristic phytoalexin camalexin, derivatives of indole-3-carbaldehyde (ICHO) and indole-3-carboxylic acid (ICOOH) are synthesized from tryptophan via the intermediates indole-3-acetaldoxime and indole-3-acetonitrile. Based on feeding expe...
متن کاملThe Biosynthetic Pathway of Indole-3-Carbaldehyde and Indole-3-Carboxylic Acid Derivatives in Arabidopsis1[W]
Indolic secondary metabolites play an important role in pathogen defense in cruciferous plants. In Arabidopsis (Arabidopsis thaliana), in addition to the characteristic phytoalexin camalexin, derivatives of indole-3-carbaldehyde (ICHO) and indole-3carboxylic acid (ICOOH) are synthesized from tryptophan via the intermediates indole-3-acetaldoxime and indole-3-acetonitrile. Based on feeding exper...
متن کاملCamalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis.
Characteristic for cruciferous plants is their production of N- and S-containing indole phytoalexins with disease resistance and cancer-preventive properties, previously proposed to be synthesized from indole independently of tryptophan. We show that camalexin, the indole phytoalexin of Arabidopsis thaliana, is synthesized from tryptophan via indole-3-acetaldoxime (IAOx) in a reaction catalyzed...
متن کاملArabidopsis PAD3, a gene required for camalexin biosynthesis, encodes a putative cytochrome P450 monooxygenase.
Phytoalexins are low molecular weight antimicrobial compounds that are synthesized in response to pathogen attack. The phytoalexin camalexin, an indole derivative, is produced by Arabidopsis in response to infection with the bacterial pathogen Pseudomonas syringae. The phytoalexin deficient 3 (pad3) mutation, which causes a defect in camalexin production, has no effect on resistance to P. syrin...
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عنوان ژورنال:
- Chemical communications
دوره 52 34 شماره
صفحات -
تاریخ انتشار 2016