Decaffeination and Neuraminidase Inhibitory Activity of Arabica Green Coffee (Coffea arabica) Beans: Chlorogenic Acid as a Potential Bioactive Compound

Abstract

Coffee has been studied for its health benefits, including prevention of several chronic diseases, such as type 2 diabetes mellitus, cancer, Parkinson’s, and liver diseases. Chlorogenic acid (CGA), an important component in coffee beans, was shown to possess antiviral activity against viruses. However, the presence of caffeine in coffee beans may also cause insomnia and stomach irritation, and increase heart rate and respiration rate. These unwanted effects may be reduced by decaffeination of green bean Arabica coffee (GBAC) by treatment with dichloromethane, followed by solid-phase extraction using methanol. In this study, the caffeine and chlorogenic acid (CGA) level in the coffee bean from three different areas in West Java, before and after decaffeination, was determined and validated using HPLC. The results showed that the levels of caffeine were reduced significantly, with an order as follows: Tasikmalaya (2.28% to 0.097% (97 ppm), Pangalengan (1.57% to 0.049% (495 ppm), and Garut (1.45% to 0.00002% (0.2 ppm). The CGA levels in the GBAC were also reduced as follows: Tasikmalaya (0.54% to 0.001% (118 ppm), Pangalengan (0.97% to 0.0047% (388 ppm)), and Garut (0.81% to 0.029% (282 ppm). The decaffeinated samples were then subjected to the H5N1 neuraminidase (NA) binding assay to determine its bioactivity as an anti-influenza agent. The results show that samples from Tasikmalaya, Pangalengan, and Garut possess NA inhibitory activity with IC50 of 69.70, 75.23, and 55.74 μg/mL, respectively. The low level of caffeine with a higher level of CGA correlates with their higher levels of NA inhibitory, as shown in the Garut samples. Therefore, the level of caffeine and CGA influenced the level of NA inhibitory activity. This is supported by the validation of CGA-NA binding interaction via molecular docking and pharmacophore modeling; hence, CGA could potentially serve as a bioactive compound for neuraminidase activity in GBAC.

A study on catalytic and non-catalytic sites of H5N1 and H1N1 neuraminidase as the target for chalcone inhibitors

“…However, upon inspection of the chemical structure, chalcone might not be a favorable scaffold for NA inhibitors which usually belong to the shikimic acid structure. The shikimic acid inhibitors such as oseltamivir and zanamivir bind to the catalytic site of NA, which is a small pocket surrounded by basic sub-pocket, acidic subpocket as well as hydrophobic sub-pocket alongside its conserved amino acid residues [20]. Chalcone is a phenyl ring extended by an α,β-unsaturated carbonyl with various alkyl or aryl moieties next to the carbonyl group, making it too bulky to fit into the NA catalytic site [21].…”

Targeted and Non-Targeted HPLC Analysis of Coffee-Based Products as Effective Tools for Evaluating the Coffee Authenticity

“…Coffee has been valued for years for its stimulating effect on the central nervous system, associated primarily with caffeine [ 23 , 24 , 25 ]. Nevertheless, studies show that consumption of two to three coffee cups a day brings many other potential health benefits, including prevention of cancer, type 2 diabetes, cardiovascular and liver diseases, and Alzheimer’s and Parkinson’s diseases [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. In addition to caffeine, the most important bioactive compounds responsible for these effects are mainly polyphenols [ 21 , 35 , 36 , 37 ], of which esters of caffeic and quinic acids, known as chlorogenic acid isomers, are the most abundant [ 23 , 24 ].…”

“…In addition to caffeine, the most important bioactive compounds responsible for these effects are mainly polyphenols [ 21 , 35 , 36 , 37 ], of which esters of caffeic and quinic acids, known as chlorogenic acid isomers, are the most abundant [ 23 , 24 ]. While caffeic acid has anticancer effects [ 38 ], chlorogenic acids (CGA, Figure 1 ), including the isomers of caffeoylquinic (CafQA), dicaffeoylquinic (diCafQA), feruloylquinic (FQA), and p-coumaroylquinic (pCoQA) acids, exhibit antibacterial, antifungal, antiviral, antioxidant, and chemoprotective properties [ 34 , 39 , 40 ]. Coffee polyphenols, together with caffeine, also balance cholesterol and arrhythmia, reduce lipid oxidation and risk of obesity, hypertension, hyperglycemia, or heart and liver failure [ 30 , 41 , 42 , 43 , 44 , 45 ].…”

The Effect of Green Coffee on Blood Pressure, Liver and Kidney Functions in Obese Model Rats

“…The US's average caffeine consumption of coffee is 2-3 cups of coffee a day or the equivalent of 180-190 mg of caffeine [1]. Meanwhile, coffee consumption in Indonesia increases by 7.5% annually [4].…”

“…Coffee contains anti-inflammatory, anticancer, antifibrotic, and antioxidant [18]. Robusta coffee contains twice as much caffeine as Arabica coffee (1.7-4.0 and 0.8-1.4% caffeine) [4]. GC contains a number of chemical compounds such as caffeine, antioxidants, minerals, carbohydrates, protein, trigonelline, chlorogenic acid (CGA), glycosides, and volatile components [19].…”