Dataset Information

Fast and Highly Selective Continuous-Flow Catalytic Hydrogenation of a Cafestol-Kahweol Mixture Obtained from Green Coffee Beans.

ABSTRACT: This work investigates batch and continuous-flow heterogeneous catalytic hydrogenation of a mixture of cafestol and kahweol (C&K) to obtain pure cafestol. These diterpenes were extracted from green coffee beans, and hydrogenation was performed using well-established palladium catalysts (Pd/C, Pd/CaCO3, Pd/BaSO4, and Pd/Al2O3) and a carbon black-supported Pd catalyst coated by a covalently tethered SiO2 shell with mesoporous texture (Pd/CB@SiO2), all partially deactivated with quinoline. Pd/C 10% poisoned with 1 wt % quinoline gave the best result for batch reaction, producing cafestol from kahweol with high selectivity (>99%) after 10 min. Excellent selectivity was also obtained with the catalyst Pd/CB@SiO2 with only 1% Pd. In addition, Pd/C-quinoline adapted for continuous-flow experiments exhibited the best catalytic activity, also providing cafestol with excellent selectivity (>99%) after 9.8 s.

SUBMITTER: Lima FA

PROVIDER: S-EPMC7557226 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Fast and Highly Selective Continuous-Flow Catalytic Hydrogenation of a Cafestol-Kahweol Mixture Obtained from Green Coffee Beans.

Lima Fernanda Alves FA Bezerra Marco A M MAM Souza Rodrigo R Itabaiana Ivaldo I Haynes Tommy T Hermans Sophie S Wojcieszak Robert R Novaes Fábio Junior M FJM Rezende Claudia Moraes CM

ACS omega 20200928 40

This work investigates batch and continuous-flow heterogeneous catalytic hydrogenation of a mixture of cafestol and kahweol (C&K) to obtain pure cafestol. These diterpenes were extracted from green coffee beans, and hydrogenation was performed using well-established palladium catalysts (Pd/C, Pd/CaCO3, Pd/BaSO4, and Pd/Al2O3) and a carbon black-supported Pd catalyst coated by a covalently tethered SiO2 shell with mesoporous texture (Pd/CB@Si ...[more]

PMID: 33073097

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Project description:The current study investigates the phytochemical composition of coffee plant organs and their corresponding antioxidant capacities compared to green and roasted coffee beans. HPLC analysis indicated that the investigated compounds were present in all organs except mangiferin, which was absent in roots, stems and seeds, and caffeine, which was absent in stems and roots. Total phytochemicals were highest in the green beans (GB) at 9.70 mg g-1 dry weight (DW), while roasting caused a 66% decline in the roasted beans (RB). This decline resulted more from 5-CQA and sucrose decomposition by 68% and 97%, respectively, while caffeine and trigonelline were not significantly thermally affected. Roasting increased the total phenolic content (TPC) by 20.8% which was associated with an increase of 68.8%, 47.5% and 13.4% in the antioxidant capacity (TEAC) determined by 2,2-diphenyl-1-picryl hydrazyl radical (DPPH), 2,2-azino bis (3-ethyl benzothiazoline-6-sulphonic acid) radical (ABTS) and Ferric ion reducing antioxidant power (FRAP) assays, respectively. Amongst the leaves, the youngest (L1) contained the highest content at 8.23 mg g-1 DW, which gradually reduced with leaf age to 5.57 mg g-1 DW in the oldest (L6). Leaves also contained the highest TPC (over 60 mg g-1 GAE) and exhibited high TEAC, the latter being highest in L1 at 328.0, 345.7 and 1097.4, and least in L6 at 304.6, 294.5 and 755.1 µmol Trolox g-1 sample for the respective assays. Phytochemical accumulation, TPC and TEAC were least in woody stem (WS) at 1.42 mg g-1 DW; 8.7 mg g-1 GAE; 21.9, 24.9 and 110.0 µmol Trolox g-1 sample; while herbaceous stem (HS) contained up to 4.37 mg g-1 DW; 27.8 mg g-1 GAE; 110.9, 124.8 and 469.7 µmol Trolox g-1 sample, respectively. Roots contained up to 1.85 mg g-1 DW, 15.8 mg-1 GAE and TEAC of 36.8, 41.5 and 156.7 µmol Trolox g-1 sample. Amongst the organs, therefore, coffee leaves possessed higher values than roasted beans on the basis of phytochemicals, TPC and TEAC. Leaves also contain carotenoids and chlorophylls pigments with potent health benefits. With appropriate processing methods, a beverage prepared from leaves (coffee leaf tea) could be a rich source of phytochemicals and antioxidants with therapeutic and pharmacological values for human health.

Project description:The objectives of the present study consisted of identifying the impact of extraction methods and parameters held over the phytochemistry and biological activities of green coffee beans. Extraction processes belonging to two categories were performed: classical methods-maceration, Soxhlet extraction, and such innovative methods as turboextraction, ultrasound-assisted extraction, and a combination of the latter two. Total polyphenolic and flavonoid content, as well as in vitro antioxidant activity of the resulted extracts were spectrophotometrically determined. Extracts displaying the highest yields of bioactive compounds were subjected to High Performance Liquid Chromatography-Mass Spectrometry analysis. The extracts with the best phytochemical profiles were selected for biological activity assessment. In vivo, a model of plantar inflammation in Wistar rats was used to determine antioxidant activity, by evaluating the oxidative stress reduction potential, and anti-inflammatory activity. In vitro antimicrobial activity was also determined. The Soxhlet extraction and ultrasound-assisted extraction gave the highest bioactive compound yields. The highest total polyphenolic content was 2.691 mg/mL gallic acid equivalents and total flavonoid content was 0.487 mM quercetin equivalents for the Soxhlet extract subjected to 60 min extraction time. Regarding the antioxidant activity, ultrasound-assisted extraction reached the highest levels, i.e., 9.160 mg/mL Trolox equivalents in the DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) assay and 26.676 mM Trolox equivalents in the FRAP (Ferric Reducing Antioxidant Power) assay, at a 30 min extraction time and 50 °C extraction temperature. The 60 min Soxhlet extract reached the highest level for the ABTS+ (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) assay, 16.136 mM Trolox equivalents, respectively. Chlorogenic acid was present in the highest concentration in the same Soxhlet extract, 1657.179 µg/mL extract, respectively. Sterolic compounds were found in high concentrations throughout all the analyzed extracts. A proportional increase between yields and extraction parameter values was observed. Increased inhibition of Gram-negative bacteria was observed. The finally selected Soxhlet extract, that of 60 min extraction time, presented a significant in vivo antioxidant activity, with a slight anti-inflammatory activity. Antioxidant levels were elevated after 2 h of extract administration. Pro-inflammatory cytokine secretion was not influenced by the administration of the extract.

Dataset Information

Fast and Highly Selective Continuous-Flow Catalytic Hydrogenation of a Cafestol-Kahweol Mixture Obtained from Green Coffee Beans.

Publications

Fast and Highly Selective Continuous-Flow Catalytic Hydrogenation of a Cafestol-Kahweol Mixture Obtained from Green Coffee Beans.

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