2086-86-4Relevant academic research and scientific papers
Sinalexin, a phytoalexin from white mustard elicited by destruxin B and Alternaria brassicae
Soledade,Pedras,Smith, Kevin C.
, p. 833 - 837 (2007/10/03)
Determination of the structure of sinalexin, a phytoalexin produced by white mustard (Sinapis alba) under biotic or abiotic elicitation, is described. Additionally, the isolation and synthesis of 4- hydroxybenzylisothiocyanate, the major antifungal component isolated from extracts of white mustard, and optimized conditions for the isolation of the phytotoxin destruxin B are described.
Inter- and intramolecular isotopic correlations in some cyanogenic glycosides and glucosinolates and their practical importance
Butzenlechner, Maria,Thimet, Susanne,Kempe, Klaus,Kexel, Hugo,Schmidt, Hanns-Ludwig
, p. 585 - 592 (2007/10/03)
Sinalbin is a complex organic salt from white mustard. The δ 13C- values of the aromatic parts of the anion glucosinalbin (p- hydroxyphenylacetic acid) and of the cation sinapin (sinapic acid) are identical (-32.2‰) and both aromatic compounds are depleted by 6.4‰ with respect to the glucose moiety (-25.8‰) bound in glucosinalbin. The δ 13C value of the choline part of the molecule can be correlated to its metabolic origin from glucose. However, there is an unexpected dramatic 13C- enrichment in the first C atom of glucosinalbin, originally the C-2 of tyrosine. This enrichment of approximately 11% relative to the mean value of the aglycone is found in the same position of four other glucosinolates and cyanogenic glycosides derived from phenylalanine or tyrosine. An isotope effect on the phenylalanine-ammonia-lyase reaction is discussed as the most probable cause for this finding. In contrast, sinigrin, the glucosinolate from black mustard, shows a relative 13C-depletion of 6.5‰ in the corresponding first C-atom of the aglycone allyl mustard oil. The proposed reason for this depletion is an isotope effect on an aldol reaction during the biosynthetic introduction of this C-atom into the aglycone skeleton. Synthetic allyl mustard oil is depleted by 14% in the same position relative to the δ 13C-value of the whole molecule, probably owing to an isotope effect on the first step of its chemical synthesis, the binding of allyl amine to CS2. This difference can be used to detect adulterations of mustard.
