1,2-Disinapoylgentiobiose

Metabolomics Combined with Sensory Analysis Reveals the Impact of Different Extraction Methods on Coffee Beverages from Coffea arabica and Coffea canephora var. Robusta.[Pubmed:35327231]

Foods. 2022 Mar 11;11(6):807.

An untargeted metabolomics approach combined with sensory analysis was used to depict the impact of different traditional Italian extraction methods (i.e., Espresso, Neapolitan, Moka) along with Filter, on Coffea arabica and Coffea canephora var. robusta beverages. To this aim, polyphenols, Maillard reaction products, and coffee metabolites were screened by high resolution mass spectrometry and elaborated through both unsupervised and supervised multivariate statistical approaches. Multivariate statistics showed a distinctive chemical profile for Espresso preparation, while Moka and Neapolitan were very similar. The orthogonal projection to latent structures and discriminant analysis allowed the identification of 86 compounds showing a high VIP discrimination score (i.e., > 0.8). The 2,5-dimethyl-3-(methyldithio)-furan was a marker for the Filter preparation, while 1,2-Disinapoylgentiobiose characterized both Filter and Neapolitan extractions. Caffeine (known to be a bitter compound) accumulated highly in Filter vs. Espresso, although at the sensory profile, bitterness was more perceived in Espresso. Vegetal aroma carried by pyrazines, pyridines, and phenolic acids were markers of Espresso, with Robusta showing higher values than Arabica. Notwithstanding, our findings showed that the extraction process played a hierarchically higher role in driving the chemical composition of the beverages when compared to coffee species.

Plants as Biofactories: Postharvest Stress-Induced Accumulation of Phenolic Compounds and Glucosinolates in Broccoli Subjected to Wounding Stress and Exogenous Phytohormones.[Pubmed:26904036]

Front Plant Sci. 2016 Feb 10;7:45.

Broccoli contains high levels of bioactive molecules and is considered a functional food. In this study, postharvest treatments to enhance the concentration of glucosinolates and phenolic compounds were evaluated. Broccoli whole heads were wounded to obtain florets and wounded florets (florets cut into four even pieces) and stored for 24 h at 20 degrees C with or without exogenous ethylene (ET, 1000 ppm) or methyl jasmonate (MeJA, 250 ppm). Whole heads were used as a control for wounding treatments. Regarding glucosinolate accumulation, ET selectively induced the 4-hydroxylation of glucobrassicin in whole heads, resulting in approximately 223% higher 4-hydroxyglucobrassicin than time 0 h samples. Additionally, glucoraphanin was increased by approximately 53% in whole heads treated with ET, while neoglucobrassicin was greatly accumulated in wounded florets treated with ET or MeJA, showing increases of approximately 193 and approximately 286%, respectively. On the other hand, although only whole heads stored without phytohormones showed higher concentrations of phenolic compounds, which was reflected in approximately 33, approximately 30, and approximately 46% higher levels of 1,2,2-trisinapoylgentiobose, 1,2-diferulolylgentiobiose, and 1,2-disinapoyl-2-ferulolylgentiobiose, respectively; broccoli florets stored under air control conditions showed enhanced concentrations of 3-O-caffeoylquinic acid, 1,2-Disinapoylgentiobiose, and 1,2-disinapoyl-2-ferulolylgentiobiose ( approximately 22, approximately 185, and approximately 65% more, respectively). Furthermore, exogenous ET and MeJA impeded individual phenolics accumulation. Results allowed the elucidation of simple and effective postharvest treatment to enhance the content of individual glucosinolates and phenolic compounds in broccoli. The stressed-broccoli tissue could be subjected to downstream processing in order to extract and purify bioactive molecules with applications in the dietary supplements, agrochemical and cosmetics markets.

RNAi-mediated suppression of DET1 alters the levels of carotenoids and sinapate esters in seeds of Brassica napus.[Pubmed:19459679]

J Agric Food Chem. 2009 Jun 24;57(12):5326-33.

Carotenoids and sinapate esters in Brassica napus affect the nutritional value of the seed. In this study, the B. napus regulatory gene DE-ETIOLATED1 (DET1), which is a negative regulator of light-mediated responses in plants and affects carotenoid and flavonoid pathways in tomato, was suppressed both constitutively and in a seed-specific manner by RNAi. Constitutive silencing of DET1 resulted in transgenic seeds with substantially elevated levels of lutein, beta-carotene, and zeaxanthin relative to nontransgenic seeds. Levels of these carotenoids were also enhanced but to a lesser extent in seeds of transgenic plants with seed-specific silencing of DET1. Moreover, sinapate esters 1,2-Disinapoylgentiobiose and 1,2-di-O-sinapoylglucose were identified in the seeds using 1D and 2D NMR, as well as ESI-MS spectrum analyses. The levels of 1,2-di-O-sinapoylglucose in seeds in both sets of transgenic plants were lower compared to nontransgenic seeds. The results revealed that DET1 suppression in B. napus can increase the levels of carotenoids and reduce the levels of sinapate esters simultaneously in the seeds, thus enhancing their overall nutritional value.

Influence of two fertilization regimens on the amounts of organic acids and phenolic compounds of tronchuda cabbage (Brassica oleracea L. Var. costata DC).[Pubmed:16277412]

J Agric Food Chem. 2005 Nov 16;53(23):9128-32.

A phytochemical study was undertaken on tronchuda cabbage (Brassica oleracea L. var. costata DC) cultivated under conventional and organic practices and collected at different times. Six organic acids (aconitic, citric, ascorbic, malic, shikimic, and fumaric acids) were identified and quantified by HPLC-UV. Qualitative and quantitative differences were noted between internal and external leaves. Analysis of the phenolics of the internal leaves was achieved by HPLC-DAD, and the phenolic profile obtained was revealed to be distinct from that of the external leaves. By this means were identified and quantified 11 compounds: 3-p-coumaroylquinic acid, kaempferol 3-O-sophoroside-7-O-glucoside, kaempferol 3-O-(caffeoyl)sophoroside-7-O-glucoside, kaempferol 3-O-(sinapoyl)sophoroside-7-O-glucoside, kaempferol 3-O-(feruloyl)sophoroside-7-O-glucoside, kaempferol 3-O-sophoroside, two isomeric forms of 1,2-Disinapoylgentiobiose, 1-sinapoyl-2-feruloylgentiobiose, 1,2,2'-trisinapoylgentiobiose, and 1,2'-disinapoyl-2-feruloylgentiobiose. In general, internal leaves exhibited more constant chemical profiles.

Protective effects of broccoli (Brassica oleracea) and its active components against radical-induced oxidative damage.[Pubmed:16161763]

J Nutr Sci Vitaminol (Tokyo). 2005 Jun;51(3):142-7.

The radical scavenging effect and protective potential from oxidative damage by radical generator, 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPH), in renal epithelial LLC-PK1 cell of broccoli (Brassica oleracea) were investigated and identified the active components under the bioassay-linked fractionation method. The MeOH extract, and fractions of CH2Cl2, BuOH and H2O from broccoli showed the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging effect in a dose-dependent manner. In addition, they exerted the protective effect against LLC-PK1 cellular damage induced by AAPH dose-dependently. In particular, the BuOH fraction was evaluated as the most active fraction, indicating that the BuOH fraction contains the active components with antioxidative capacity. Employing a bioassay-linked fractionation method, the active principles were isolated and characterized as 1,2-Disinapoylgentiobiose and 1-sinapoyl-2-feruloylgentiobiose from the BuOH fraction. These two compounds from broccoli displayed potent antioxidant effects against the DPPH radical, showing the IC50 values of 5.18 and 7.52 microg/mL, respectively. Moreover, the compounds significantly and dose-dependently recovered cell viability lowered by AAPH treatment, suggesting the protective roles from cellular oxidative damage. The present study suggests that broccoli has excellent antioxidative potential and the hydroxycinamic acid esters from broccoli, 1,2-Disinapoylgentiobiose and 1-sinapoyl-2-feruloylgentiobiose, are considered as the active components with antioxidative effect.