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(Coffea Arabica) Beans: Chlorogenic Acid As a Potential Bioactive Compound

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(Coffea Arabica) Beans: Chlorogenic Acid As a Potential Bioactive Compound molecules Article Decaffeination and Neuraminidase Inhibitory Activity of Arabica Green Coffee (Coffea arabica) Beans: Chlorogenic Acid as a Potential Bioactive Compound Muchtaridi Muchtaridi 1,2,* , Dwintha Lestari 2, Nur Kusaira Khairul Ikram 3,4 , Amirah Mohd Gazzali 5 , Maywan Hariono 6 and Habibah A. Wahab 5 1 Department of Pharmaceutical Analysis and Medicinal Chemistry, Faculty of Pharmacy, Universitas Padjadjaran, Jl. Bandung-Sumedang KM 21, Jatinangor 45363, Indonesia 2 Department of Pharmacy, Faculty of Science and Technology, Universitas Muhammadiyah Bandung, Jl. Soekarno-Hatta No. 752, Bandung 40614, Indonesia; [email protected] 3 Institute of Biological Sciences, Faculty of Science, Universiti Malaya, Kuala Lumpur 50603, Malaysia; [email protected] 4 Centre for Research in Biotechnology for Agriculture (CEBAR), Kuala Lumpur 50603, Malaysia 5 School of Pharmaceutical Sciences, Universiti Sains Malaysia, USM, Penang 11800, Malaysia; [email protected] (A.M.G.); [email protected] (H.A.W.) 6 Faculty of Pharmacy, Campus III, Sanata Dharma University, Paingan, Maguwoharjo, Depok, Sleman, Yogyakarta 55282, Indonesia; [email protected] * Correspondence: [email protected]; Tel.: +62-22-8784288888 (ext. 3210) Abstract: Coffee has been studied for its health benefits, including prevention of several chronic Citation: Muchtaridi, M.; Lestari, D.; diseases, such as type 2 diabetes mellitus, cancer, Parkinson’s, and liver diseases. Chlorogenic acid Khairul Ikram, N.K.; Gazzali, A.M.; (CGA), an important component in coffee beans, was shown to possess antiviral activity against Hariono, M.; Wahab, H.A. viruses. However, the presence of caffeine in coffee beans may also cause insomnia and stomach Decaffeination and Neuraminidase irritation, and increase heart rate and respiration rate. These unwanted effects may be reduced by Inhibitory Activity of Arabica Green decaffeination of green bean Arabica coffee (GBAC) by treatment with dichloromethane, followed Coffea arabica Coffee ( ) Beans: by solid-phase extraction using methanol. In this study, the caffeine and chlorogenic acid (CGA) Chlorogenic Acid as a Potential level in the coffee bean from three different areas in West Java, before and after decaffeination, Bioactive Compound. Molecules 2021, was determined and validated using HPLC. The results showed that the levels of caffeine were 26, 3402. https://doi.org/10.3390/ molecules26113402 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 Academic Editor: Francesca Masino 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 Received: 1 May 2021 subjected to the H5N1 neuraminidase (NA) binding assay to determine its bioactivity as an anti- Accepted: 2 June 2021 influenza agent. The results show that samples from Tasikmalaya, Pangalengan, and Garut possess Published: 4 June 2021 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 Publisher’s Note: MDPI stays neutral the Garut samples. Therefore, the level of caffeine and CGA influenced the level of NA inhibitory with regard to jurisdictional claims in activity. This is supported by the validation of CGA-NA binding interaction via molecular docking published maps and institutional affil- and pharmacophore modeling; hence, CGA could potentially serve as a bioactive compound for iations. neuraminidase activity in GBAC. Keywords: decaffeination; chlorogenic acid; caffeine; green coffee; HPLC Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article 1. Introduction distributed under the terms and conditions of the Creative Commons Indonesia produces at least 10,500.00 bags (60 kg/bags) of coffee per year [1], which Attribution (CC BY) license (https:// contributed to around 6.6% of total coffee production worldwide in 2012 [2]. The con- creativecommons.org/licenses/by/ sumption of processed coffee-based products in Indonesia increases by approximately 7.5% 4.0/). Molecules 2021, 26, 3402. https://doi.org/10.3390/molecules26113402 https://www.mdpi.com/journal/molecules Molecules 2021, 26, 3402 2 of 11 every year. In addition, Indonesia produces 700 kg of robusta coffee beans/ha/year and 800 kg of Arabica coffee beans/ha/year. Previous studies have suggested that coffee partially provides health benefits to treat certain diseases, such as type 2 diabetes mellitus [3], besides having antioxidant [4], anti- inflammatory [5], and antibacterial activities [6]. In particular, Van Dam (2005) reported that regular consumption of coffee can reduce the risk of type 2 diabetes mellitus [7], whilst O’Keefe et al. (2013) suggested that it may reduce the risk of death caused by cardiovascular diseases [8]. It is known that coffee contains caffeine at different levels, depending on the seeds, cultivation area, and process. For example, robusta coffee contains 1.7–4.0% of caffeine, which is almost twice the content of Arabica coffee (0.8–1.4%) [9–12]. Caffeine is reported to cause side effects, such as insomnia, palpitations, an increase in the frequency of urination, headaches, and other symptoms—this is in addition to its main pharmacological effect as a stimulant [13–17]. Decaffeination (decaf) has been well studied as an effort to reduce the adverse effects of caffeine by minimizing its concentration in coffee. This technique is carried out using alcohol or a certain solvent, such as cyclohexane. However, during decaf, the caffeine level in green bean extract of Coffea arabica, which is approximately 34.1–38.5 g kg−1, is reduced by only 0.4%; hence, decaffeination could not significantly reduce the content of caffeine [18]. However, in general, the chlorogenic acid (CGA) derivatives level in decaf- feinated coffee is higher than non-decaf. The 3-chlorogenic acid (3-CGA) and 4-chlorogenic acid (4-CGA) levels in decaffeinated coffee probably increase due to the lixiviation process that occurs during decaf [19]. Interestingly, another study reported that decaf reduced CGA by 10% [20]. The inconsistency of data available in the literature prompted us to conduct this current study, to evaluate the level of chlorogenic acid available in coffee bean extracts before and after the decaffeination process. Chlorogenic acid is shown to exhibit high activity against the neuraminidase enzyme, which is important in the replication of influenza viruses, such as H5N1 and H1N1 [21]. The intravenous administration of 100 mg/kg/d chlorogenic acid was reported to effectively inhibit H1N1 and H3N2 infections in mice [22]. Based on the reports from previous studies, it is paramount to determine the influence of the decaf process on neuraminidase (NA) inhibition activity as a potentially effective source of anti-influenza in preventing and reducing influenza virus A infection. In this present study, high performance liquid chromatography (HPLC) is used to determine the level of both caffeine and chlorogenic acid in the crude Coffea arabica bean extracts, before and after decaffeination. The coffee beans were collected from three different areas in West Java, Indonesia. The coffee samples were then evaluated for their inhibitory effects against the neuraminidase enzyme (NA) of the H5N1 influenza virus. 2. Materials and Methods 2.1. Plants Material Crude Arabica coffee (Coffea arabica L.) beans were collected from Garut, Pangalengan, and Tasikmalaya in West Java Province, Indonesia, and the specimens were identified in the Laboratory of Plant Taxonomy Herbarium Department of Biology, Faculty of Mathematics and Natural Sciences, University of Padjadjaran (Bandung, Indonesia). 2.2. Chemicals and Reagents Methanol, ethanol, double distilled water, iron (III) chloride, gelatin, ammonia, chlo- roform, hydrochloric acid, Mayer’s reagent, Dragendorff’s reagent, magnesium, amyl alcohol, ether, vanillin-sulfuric acid reagent, sodium hydroxide, and Liebermann–Burchard reagent were purchased from Merck (Kenilworth, NJ, USA), without further purifications. Molecules 2021, 26, 3402 3 of 11 2.3. For the Enzymatic Inhibition Assay H5N1 neuraminidase (SINOBIO, Beijing, China), MUNANA [202-(4-methylumbelliferyl)- a-D-N-acetylneuraminic acid sodium salt hydrate] (Sigma, St. Louis, MO, USA), MES [2-(N-morpholino) ethanesulfonic acid] (Sigma, St. Louis, MO, USA), and DANA [2,3- didehydro-2- deoxy-N-acetylneuraminic acid] (Sigma, St. Louis, MO, USA). 2.4. Extraction Coffee beans (20 g) from Pangalengan, Garut, and Tasikmalaya were pulverized and extracted using the digestion method by soaking and stirring in 250 mL of double distilled water at 40–50 ◦C for 30 min [23]. The mixture was cooled down at room temperature and then filtered out. 2.5. Phytochemical Screening Phytochemical screening was performed to identify phytochemical substances con- tained in the crude extract such as alkaloids, flavonoids, tannins, polyphenols, saponins, steroids, and quinone. This screening was carried out based on Farnsworth method [24]. 2.6. Decaffeination of Coffee Extract The decaf process was conducted using liquid–liquid extraction by mixing the coffee powder in dichloromethane with a ratio of 1:1. The process was repeated three times and stirred for 10 min at room temperature [25]. Dichloromethane
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