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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c5cc09822j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Unveiling fungal detoxification pathways of the cruciferous phytoalexin rapalexin A: Sequential L-cysteine conjugation, acetylation and oxidative cyclization mediated by Colletotrichum spp.
Phytochemistry
January 2020
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9, Canada.
The metabolism of the phytoalexin rapalexin A, a unique indole isothiocyanate (ITC) produced by crucifers (family Brassicaceae), was investigated. Three phytopathogenic fungal species were examined: Colletotrichum dematium (Pers.:Fr.
View Article and Find Full Text PDFBiotransformation of rutabaga phytoalexins by the fungus Alternaria brassicicola: Unveiling the first hybrid metabolite derived from a phytoalexin and a fungal polyketide.
Bioorg Med Chem
January 2017
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
The biotransformations of the rutabaga phytoalexins rutalexin, brassicanate A, isalexin and rapalexin A by the plant pathogenic fungus Alternaria brassicicola are reported. While the biotransformations of rutalexin, brassicanate A, and isalexin are fast, rapalexin A is resistant to fungal transformation. Unexpectedly, biotransformation of rutalexin yields a hybrid metabolite named rutapyrone, derived from rutalexin metabolism and phomapyrone G, a fungal metabolite produced by A.
View Article and Find Full Text PDFDivergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle.
Chem Commun (Camb)
February 2016
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
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.
View Article and Find Full Text PDFDissecting metabolic puzzles through isotope feeding: a novel amino acid in the biosynthetic pathway of the cruciferous phytoalexins rapalexin A and isocyalexin A.
Org Biomol Chem
February 2013
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon SK S7N 5C9, Canada.
Understanding defence pathways of plants is crucial to develop disease-resistant agronomic crops, an important element of sustainable agriculture. For this reason, natural plant defenses such as phytoalexins, involved in protecting plants against microbial pathogens, have enormous biotechnological appeal. Crucifers are economically important plants, with worldwide impact as oilseeds, vegetables of great dietetic value and even nutraceuticals.
View Article and Find Full Text PDFThe cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: chemistry and metabolism in Leptosphaeria maculans.
Bioorg Med Chem
July 2012
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, Canada S7N 5C9.
The interactions of the cruciferous phytoalexins rapalexin A (1), brussalexin A (2) and erucalexin (3) with the fungal plant pathogen Leptosphaeria maculans were analyzed and their inhibitory activities against this pathogen were determined. The reaction of L. maculans to N-methyl S-(indolyl-3-methyl)carbamodithioate, an analogue of brussalexin A, was also investigated.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!