Glucoberteroin

Glucosinolates in two endemic plants of the Aurinia genus and their chemotaxonomic significance.[Pubmed:24354202]

Nat Prod Commun. 2013 Oct;8(10):1463-6.

Glucosinolates (GLs) were characterized in the seed and root of Aurinia leucadea (Guss.) C. Koch and A. sinuata (L.) Griseb., and quantified according to the ISO 9167-1 official method based on the HPLC analysis of desulfo-GLs. Glucoalyssin (GAL, 1), glucobrassicanapin (GBN, 2) and Glucoberteroin (GBE, 3) were the major GLs identified in A. leucadea and A. sinuata. GC/MS analysis of the volatile fractions obtained after enzyme hydrolysis showed that they mostly contain isothiocyanates (ITCs) originating from the parent GLs. On this basis and from previous reports, C-5 alkyl GLs 1, 2, and 3 can be considered as chemotaxonomic markers of the Aurinia genus.

Glucosinolate profiling and antimicrobial screening of Aurinia leucadea (Brassicaceae).[Pubmed:22162169]

Chem Biodivers. 2011 Dec;8(12):2310-21.

Glucosinolates (GLs) were characterized in various aerial parts (stems, leaves, and flowers) of Aurinia leucadea (Guss.) C. Koch and quantified according to the ISO 9167-1 official method based on the HPLC analysis of desulfoglucosinolates. Eight GLs, i.e., glucoraphanin (GRA), glucoalyssin (GAL; 1), gluconapin (GNA; 2), glucocochlearin (GCC), glucobrassicanapin (GBN; 3), glucotropaeolin (GTL), glucoerucin (GER), and Glucoberteroin (GBE) were identified. The total GL contents were 57.1, 37.8, and 81.3 mumol/g dry weight in the stems, leaves, and flowers, respectively. The major GL detected in all parts of the plant was 2, followed by 1 and 3. GC/MS Analysis of the volatile fractions extracted from the aerial parts of fresh plant material either by hydrodistillation or CH(2) Cl(2) extraction showed that these fractions mostly contained isothiocyanates (ITCs). The main ITCs were but-3-enyl- (55.6-71.8%), pent-4-enyl- (7.6-15.3%), and 5-(methylsulfinyl)pentyl ITC (0-9.5%), originating from the corresponding GLs 2, 3, and 1, respectively. The antimicrobial activity of the volatile samples was investigated by determining inhibition zones with the disk-diffusion method and minimal inhibitory concentrations (MIC) with the microdilution method. They were found to inhibit a wide range of bacteria and fungi, with MIC values of 2.0-32.0 mug/ml, indicating their promising antimicrobial potential, especially against the fungi Candida albicans and Rhizopus stolonifer as well as against the clinically important pathogen Pseudomonas aeruginosa.

Glucosinolate distribution in aerial parts of Degenia velebitica.[Pubmed:22083920]

Chem Biodivers. 2011 Nov;8(11):2090-6.

The glucosinolates present in the leaf, stem, and seed extracts of Degenia velebitica (Degen) Hayek were characterized and quantified according to the ISO 9167-1 method, which is based on the HPLC analysis of desulfoglucosinolates. The stems contained glucoalyssin (3a) as the major compound as well as Glucoberteroin (1a) and glucoaubrietin (4a). The leaves contained three glucosinolates, the major one being 3a, followed by glucobrassicanapin (2a) and 1a. Glucoberteroin (1a) was the major glucosinolate in the seeds, along with the two minor glucosinolates 3a and glucoerucin (5a). The content of 1a in the whole, non-defatted seeds amounted to 4% (w/w). The compound was characterized as its desulfo counterpart by spectroscopic techniques.

Metabolic responses of Thellungiella halophila/salsuginea to biotic and abiotic stresses: metabolite profiles and quantitative analyses.[Pubmed:20122704]

Phytochemistry. 2010 Apr;71(5-6):581-9.

The metabolite profiles of the model crucifer Thellungiella salsuginea (salt cress) ecotype Shandong subjected to various biotic and abiotic stresses were analyzed using HPLC-DAD-ESI-MS. Two different cruciferous microbial pathogens, Albugo candida, a biotrophic oomycete, and Leptosphaeria maculans, a necrotrophic fungus, elicited formation of the phytoalexins wasalexins A and B without causing visual damage on inoculated leaves. Analyses of non-polar and polar metabolites led to elucidation of the chemical structures of five metabolites: 4'-O-(E)-sinapoyl-7-methoxyisovitexin-2''-O-beta-D-glucopyranoside, 4'-O-(E)-sinapoylisovitexin-2''-O-beta-D-glucopyranoside, 4-O-beta-D-glucopyranosyl-7-hydroxymatairesinol, 5'-O-beta-D-glucopyranosyldihydroneoascorbigen and 3-O-beta-D-glucopyranosylthiane. 3-O-beta-D-glucopyranosylthiane, an unique metabolite for which we suggest the name glucosalsuginin, is proposed to derive from the glucosinolate Glucoberteroin. In addition, the identification of a broad range of polar metabolites identical to those of other crucifers was carried out. Quantification of several metabolites over a period of eight days showed that concentrations of the polar phytoanticipin 4-methoxyglucobrassicin increased substantially in leaves irradiated with UV light (lambda(max) 254 nm) relative to control leaves, but not in leaves subjected to other stresses.

Updated glucosinolate profile of Dithyrea wislizenii.[Pubmed:19334740]

J Nat Prod. 2009 May 22;72(5):889-93.

Fruit extracts of Dithyrea wislizenii were analyzed for desulfoglucosinolates and intact glucosinolates using HPLC-APCI-MS and HPLC-ESI-MS, respectively. 2-Propenylglucosinolate (sinigrin) was shown to be present in the extracts. 6-Methylsulfanylhexyl- (glucolesquerellin 9), 6-methylsulfinylhexyl- (glucohesperin 10), 7-methylsulfanylheptyl- (11), and 5-methylsulfanylpentylglucosinolate (Glucoberteroin 12) were isolated from the extracts and characterized by NMR and MS data. 7-Methoxyglucobrassicin was not detected in D. wislizenii extracts.