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Singh SK, Sasmal S, Kumar Y. Therapeutic Potential of HMF and Its Derivatives: a Computational Study. Appl Biochem Biotechnol 2024; 196:841-877. [PMID: 37223872 PMCID: PMC10206368 DOI: 10.1007/s12010-023-04547-1] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Accepted: 04/12/2023] [Indexed: 05/25/2023]
Abstract
Over the past century, chemicals and energy have increasingly been derived from non-renewable resources. The growing demand for essential chemicals and shrinking inventory make reliable, sustainable sources essential. Carbohydrates offer by far the greatest carbon supply. Furan compounds, a particular family of dehydration products, are believed to offer high chemical potential. Here, we analyze 5-HMF (5, hydroxymethylfurfural) and some of its derivatives in particular, a furan-type platform chemical. To analyze the therapeutic potential of HMF and its derivatives, this study utilized cutting-edge technologies such as computer-aided drug design, virtual screening, molecular docking, and molecular dynamic simulation. We conducted 189 docking simulations and examined some of the most promising dock poses using the molecular dynamic simulator. As for the receptors for our compounds, the leading candidates are human acetylcholinesterase, beta-lactamases, P. aeruginosa LasR, and S. aureus tyrosyl-tRNA synthetases. Out of all derivatives considered in this study, 2,5-furandicarboxylic acid (FCA) performed best.
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Affiliation(s)
- Shashank Kumar Singh
- Department of Biological Sciences and Engineering (BSE), Netaji Subhas University of Technology, Dwarka Sector-3, New Delhi, 110078, India
| | - Soumya Sasmal
- Department of Biotechnology, Visva Bharati, Santiniketan, West Bengal, 731235, India
| | - Yatender Kumar
- Department of Biological Sciences and Engineering (BSE), Netaji Subhas University of Technology, Dwarka Sector-3, New Delhi, 110078, India.
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Bakr AF, Shao P, Farag MA. Recent advances in glycyrrhizin metabolism, health benefits, clinical effects and drug delivery systems for efficacy improvement; a comprehensive review. PHYTOMEDICINE : INTERNATIONAL JOURNAL OF PHYTOTHERAPY AND PHYTOPHARMACOLOGY 2022; 99:153999. [PMID: 35220130 DOI: 10.1016/j.phymed.2022.153999] [Citation(s) in RCA: 14] [Impact Index Per Article: 4.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 12/23/2021] [Revised: 02/06/2022] [Accepted: 02/15/2022] [Indexed: 06/14/2023]
Abstract
BACKGROUND Glycyrrhizin (GL) is a major active constituent of licorice root (Glycyrrhiza glabra) that is considered one of the oldest and most frequently employed botanicals in Chinese medicine and worldwide, with most effects attributed to its rich GL content. Structurally, GL a triterpene saponin that is widely used as a flavoring agent in foodstuffs and cosmetics, and also proposed for various clinical applications with a myriad of health benefits. Pharmacological and biological activities of GL include antiviral, anti-inflammatory, antioxidant, and anticancer activities (in vitro and in vivo). Currently, there is no comprehensive review on GL biological effects and its action mechanisms. PURPOSE This review summarizes GL pharmacological actions from a molecular biology perception, presented on its metabolism and side effects based on in vitro, in vitro and clinical studies. Moreover, the potential of GL as a nanomedicine delivery system is also summarized. The progress in drug delivery research using GL presented herein is expected to provide a theoretical basis for developing other novel drugs formulations. METHODS A systematic review was carried out in several electronic databases (Science Direct, SpringerLink, CNKI, PubMed, Web of Science, Elsevier, and Scopus), using the following key words: glycyrrhizin "AND" bioactivity "OR" clinic "OR" therapeutic "OR" drug delivery. This search included manuscripts published between 1989 and 2021. RESULTS 126 researches were selected and summarized in this review. The analysis of these studies indicated that GL has antiviral activity against different viruses. Further, GL efficiently suppressed the respiratory manifestations associated with COVID-19 by reducing the expression of angiotensin converting enzyme 2 (ACE2) that employed by the virus as an entry point. Otherwise, GL was found to induce antioxidant, anti-inflammatory, immune-modulatory, and anticancer activity. Besides, diminution the particle size of GL to nanometer size significantly augments their action and biodistribution. CONCLUSION This article summarizes the pharmacological actions of GL. The potential of GL as a nanomedicine delivery system is also presented. Nevertheless, most studies reported provide no deep insight of GL health effects warranting for more future studies to elucidate its action mechanism and potential therapeutic benefits through preclinical and clinical trials.
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Affiliation(s)
- Alaa F Bakr
- Pathology Department, Faculty of Veterinary Medicine, Cairo University, Gamaa St., Giza 12211, Egypt
| | - Ping Shao
- Department of Food Science and Technology, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China; Key Laboratory of Food Macromolecular Resources Processing Technology Research, China National Light Industry, China.
| | - Mohamed A Farag
- Pharmacognosy Department, College of Pharmacy, Cairo University, Kasr el Aini St., P.B. 11562, Cairo, Egypt.
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Wang S, Wang Q, Yin X, Chen B, Liu X. Simultaneous Determination of Iridoid Glycosides, Phenylpropanoid Glycosides, Organic Acids, Nucleosides and Amino Acids in Scrophulariae Radix Processed by Different Processing Methods by HPLC-QTRAP-MS/MS. J Chromatogr Sci 2021; 60:232-242. [PMID: 34100538 DOI: 10.1093/chromsci/bmab056] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/18/2019] [Indexed: 11/14/2022]
Abstract
Scrophulariae Radix is one of the widely used traditional Chinese medicines. In this study, a high-performance liquid chromatography coupled with triple quadrupole-linear ion trap mass spectrometry method was established for the simultaneous determination of multiple bioactive constituents including four iridoid glycosides, two phenylpropanoid glycosides, six organic acids, 11 nucleosides and 16 amino acids in Scrophulariae Radix. The validated method was used to analyze nine Scrophulariae Radix samples processed by different processing methods. In addition, Grey relational analysis and DTOPSIS were used to evaluate the samples according to the content of 39 ayalytes. The results showed that the quality of Scrophulariae Radix processed by cutting into slices, sun drying and "sweating" methods were better. All the results proved that the developed method was available and could be used to evaluate the quality of Scrophulariae Radix.
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Affiliation(s)
- Shengnan Wang
- Department of Pharmacy, Affiliated Hospital of Nantong University, Nantong 226001, China
| | - Qin Wang
- Department of Pharmacy, Affiliated Hospital of Nantong University, Nantong 226001, China
| | - Xiaoqin Yin
- Department of Pharmacy, Affiliated Hospital of Nantong University, Nantong 226001, China
| | - Bohua Chen
- Department of Pharmacy, Affiliated Hospital of Nantong University, Nantong 226001, China
| | - Xunhong Liu
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
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Wang S, Hua Y, Zou L, Liu X, Yan Y, Zhao H, Luo Y, Liu J. Comparison of Chemical Constituents in Scrophulariae Radix Processed by Different Methods based on UFLC-MS Combined with Multivariate Statistical Analysis. J Chromatogr Sci 2017; 56:122-130. [DOI: 10.1093/chromsci/bmx090] [Citation(s) in RCA: 13] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/22/2016] [Indexed: 11/13/2022]
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Wang S, Hua Y, Lin Y, Zou L, Liu X, Yan Y, Zhao H, Luo Y, Liu J. Dynamic changes of metabolite accumulation in Scrophulariae Radix based on liquid chromatography-tandem mass spectrometry combined with multivariate statistical analysis. J Sep Sci 2017; 40:2883-2894. [PMID: 28493542 DOI: 10.1002/jssc.201700129] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/03/2017] [Revised: 04/09/2017] [Accepted: 05/03/2017] [Indexed: 11/10/2022]
Abstract
Scrophulariae Radix is one of the most popular traditional Chinese medicines. The harvesting time of Scrophulariae Radix is closely related to the quality of products in this traditional Chinese medicine. The goal of the study is to analyze the dynamic changes of metabolite accumulation in Scrophulariae Radix. The difference of constituents in Scrophulariae Radix harvested at different times was analyzed by liquid chromatography with triple quadrupole-time of flight tandem mass spectrometry coupled with principal component analysis and partial least-square discriminant analysis. According to the accurate mass of molecular and product ions provided by triple quadrupole-time of flight tandem mass spectrometry, a total of 30 differential constituents were identified. Furthermore, the contents of ten index differential constituents in Scrophulariae Radix were simultaneously determined by liquid chromatography coupled with triple quadrupole-linear ion trap tandem mass spectrometry. Gray relational analysis was performed to evaluate the samples harvested at different times according to the contents of ten constituents. All of the results demonstrated that the quality of Scrophulariae Radix collected at traditional harvest time was better. This study will provide the basic information for revealing the dynamic change law of metabolite accumulation of Scrophulariae Radix and exploring its quality forming mechanism.
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Affiliation(s)
- Shengnan Wang
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Yujiao Hua
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Ying Lin
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Lisi Zou
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Xunhong Liu
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Ying Yan
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Hui Zhao
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Yiyuan Luo
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
| | - Juanxiu Liu
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China
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Wang S, Hua Y, Xu L, Zou L, Liu X, Luo Y, Liu J, Yan Y. Quality Evaluation of Scrophulariae Radix Processed by Different 'Sweating' Methods Based on Simultaneous Determination of Multiple Bioactive Constituents Combined with Grey Relational Analysis. Molecules 2016; 21:molecules21070850. [PMID: 27367656 PMCID: PMC6273517 DOI: 10.3390/molecules21070850] [Citation(s) in RCA: 15] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/19/2016] [Revised: 06/22/2016] [Accepted: 06/24/2016] [Indexed: 11/24/2022] Open
Abstract
Scrophulariae Radix is one of the most popular traditional Chinese medicines (TCMs), which needs to be processed by ‘sweating’ methods. Primary processing of Scrophulariae Radix is an important link which closely relates to the quality of products in this TCM. To facilitate selection of the suitable ‘sweating’ processing method for Scrophulariae Radix, in this study the quality of Scrophulariae Radix processed by different ‘sweating’ methods was evaluated based on simultaneous determination of multiple bioactive constituents combined with grey relational analysis. The contents of iridoid glycosides, phenylpropanoid glycosides, and organic acids in Scrophulariae Radix processed by different ‘sweating’ methods were simultaneously determined using ultra high performance liquid chromatography coupled with triple quadrupole-linear ion trap mass spectrometry (UPLC-QTRAP-MS/MS). Furthermore, grey relational analysis (GRA) was performed to evaluate the ‘sweating’ processed samples according to the contents of twelve constituents. All of the results demonstrated that the quality of Scrophulariae Radix processed by oven drying at 35 °C and ‘sweating’ for three days was better. The developed method was useful for the overall assessment on quality of Scrophulariae Radix, and this study may provide the foundation and support for ‘sweating’ processing of Scrophulariae Radix in normalization and standardization.
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Affiliation(s)
- Shengnan Wang
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
| | - Yujiao Hua
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
| | - Li Xu
- Yangzhou Institute for Drug Control, Yangzhou 225100, China.
| | - Lisi Zou
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
| | - Xunhong Liu
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
| | - Yiyuan Luo
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
| | - Juanxiu Liu
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
| | - Ying Yan
- College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
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Chirumbolo S. Commentary: The antiviral and antimicrobial activities of licorice, a widely-used Chinese herb. Front Microbiol 2016; 7:531. [PMID: 27148220 PMCID: PMC4834445 DOI: 10.3389/fmicb.2016.00531] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Key Words] [Track Full Text] [Download PDF] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/20/2015] [Accepted: 03/31/2016] [Indexed: 01/09/2023] Open
Affiliation(s)
- Salvatore Chirumbolo
- Department of Medicine-Unit of Geriatry, University Laboratories for Medical Research, University of Verona Verona, Italy
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Scientific Opinion on the safety and efficacy of glycyrrhizic acid ammoniated (chemical group 30, miscellaneous substances) when used as a flavouring for all animal species. EFSA J 2015. [DOI: 10.2903/j.efsa.2015.3971] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/11/2022] Open
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Evaluation of the antioxidant, anti-inflammatory, and anticancer activities of Euphorbia hirta ethanolic extract. Molecules 2014; 19:14567-81. [PMID: 25225720 PMCID: PMC6271915 DOI: 10.3390/molecules190914567] [Citation(s) in RCA: 35] [Impact Index Per Article: 3.2] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/09/2014] [Accepted: 09/04/2014] [Indexed: 11/20/2022] Open
Abstract
This study evaluated the chemical composition, antioxidant, anti-inflammatory and anticancer activities of a Euphorbia hirta L. extract. The antioxidant activities of whole E. hirta ethanol extract were determined by electron spin resonance spectrophotometric analysis of 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl, and alkyl radical levels and by using an online high-performance liquid chromatography (HPLC)-2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) assay. The E. hirta ethanol extract (0.5 mg/mL) exhibited DPPH-scavenging activity of 61.19% ± 0.22%, while the positive control (0.5 mg/mL ascorbic acid) had 100% ± 0.22% activity. The concentration of the extract required to trap 50% of DPPH (IC50) was 0.205 mg/mL. Online HPLC analysis of the extract also showed strong antioxidant activity. The anti-inflammatory activity of the E. hirta extract was assessed in lipopolysaccharide-induced RAW 264.7 macrophages. The anti-inflammatory activity was highest in the presence of 200 µg/mL E. hirta extract, and nitric oxide production was decreased significantly (p < 0.05). The extract also showed selective anticancer activity at a concentration of 100 µg/mL (p < 0.05). These results indicated that E. hirta may warrant further investigation for the development of antioxidant, anti-inflammatory, and anticancer herbal medications.
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CAO G, CONG XD, CAI H, LI XM, JI JY, ZHANG Y, CAI BC. Simultaneous quantitation of eight active components in crude and processed Radix Scrophulariae extracts by high performance liquid chromatography with diode array detector. Chin J Nat Med 2012. [DOI: 10.3724/sp.j.1009.2012.00213] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/25/2022]
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Matzi V, Lindenmann J, Muench A, Greilberger J, Juan H, Wintersteiger R, Maier A, Smolle-Juettner FM. The impact of preoperative micronutrient supplementation in lung surgery. A prospective randomized trial of oral supplementation of combined alpha-ketoglutaric acid and 5-hydroxymethylfurfural. Eur J Cardiothorac Surg 2007; 32:776-82. [PMID: 17768058 DOI: 10.1016/j.ejcts.2007.07.016] [Citation(s) in RCA: 39] [Impact Index Per Article: 2.2] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 02/28/2007] [Revised: 06/28/2007] [Accepted: 07/13/2007] [Indexed: 10/22/2022] Open
Abstract
OBJECTIVE Preoperative micronutrient supplementation in fast-track surgery programs have shown to reduce complications, shorten recovery, and thereby lower costs. In a prospective randomized study, the metabolic effects of a combination of alpha-ketoglutaric acid (alpha-KG) and 5-hydroxymethylfurfural (5-HMF) were evaluated concerning their impact on improvement of exercise capacity and reduction of oxidative stress in lung surgery. METHODS Thirty-two consecutive patients admitted for lung resection due to NSCLC were randomized to the study protocol. All patients received preoperative nutritional guidelines according to general recommendations. In 16 (study group), a supplementation of 7.2g alpha-KG and 720 mg 5-HMF/day (SANOPAL) was administered from days 1 to 10. Spiroergometric evaluation was carried out at baseline and day 10 after micronutrient supplementation. Blood samples for the determination of oxidative stress, i.e. carbonyl proteins (CPs) and isoprostanes (IPs) were taken on at baseline, in the operating room just before resection treatment, and 25 min after single lung ventilation (SLV). RESULTS Spiroergometric re-evaluation showed a significant increase of VO2max (p=0.0108) and Watt's (p=0.011) in favor of the study group. Determination of oxidative stress showed a significant reduction of CPs before (p=0.048) and after SLV (p=0.0001) for the study group compared to the control group. The same is true for IPs before (p=0.003) and after SLV (p=0.02). Hospitalization and intensive care unit (ICU) of the study group showed a significant reduction compared to the control group (p=0.03 and p=0.02, respectively). CONCLUSIONS Simple oral supplementation using a combination of alpha-KG and 5-HMF of preoperative micronutrition may therefore be one further step in a multimodality approach of fast-track surgery programs also in lung surgery.
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Affiliation(s)
- Veronika Matzi
- Department of Surgery, Division of Thoracic and Hyperbaric Surgery, Medical University Graz, Graz, Austria
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Xu Q, Li YH, Lü XY. Investigation on influencing factors of 5-HMF content in Schisandra. J Zhejiang Univ Sci B 2007; 8:439-45. [PMID: 17565516 PMCID: PMC1879164 DOI: 10.1631/jzus.2007.b0439] [Citation(s) in RCA: 18] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/21/2006] [Accepted: 12/07/2006] [Indexed: 11/11/2022]
Abstract
In order to investigate the influencing factors of 5-hydroxymethyl-2-furaldehyde (5-HMF) content in Schisandra, confirm the theory of 5-HMF deriving mainly from Schisandra processing course, and give some suggestions about the Schisandra processing method, the 5-HMF contents in decoctions of Schisandra under different heating temperature, decocting time, soaking time, processing methods and treatment with different solvents before decocting the Schisandra were measured by RP-HPLC method. The results showed that there is great difference of 5-HMF level in decoctions from differently processed Schisandra and unprocessed Schisandra; decocting time of 60 min has some effects on 5-HMF level in decoctions and there is certain quantity 5-HMF in processed Schisandra itself and very little 5-HMF in unprocessed Schisandra. Heating time, heating temperature and treating solvents all have effect on 5-HMF level in decoction of Schisandra. 5-HMF in Schisandra was mainly from processing course. Both long heating time and high heating temperature can increase 5-HMF level in Schisandra. The production of 5-HMF in Schisandra may have some relationships with some polar components, which can dissolve in water, ethanol and acetone, especially in ethanol. To control processing temperature, processing time and treatment with some solvent is very important for controlling 5-HMF level in Schisandra.
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Affiliation(s)
- Qing Xu
- Institute of Pharmaceutical Engineering, Zhejiang University, Hangzhou 310027, China
- Department of Internal Medicine, Hospital of Zhejiang University, Hangzhou 310027, China
| | - Ying-hua Li
- Institute of Pharmaceutical Engineering, Zhejiang University, Hangzhou 310027, China
| | - Xiu-yang Lü
- Institute of Pharmaceutical Engineering, Zhejiang University, Hangzhou 310027, China
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Kaliora AC, Stathopoulou MG, Triantafillidis JK, Dedoussis GVZ, Andrikopoulos NK. Chios mastic treatment of patients with active Crohn’s disease. World J Gastroenterol 2007; 13:748-53. [PMID: 17278198 PMCID: PMC4066008 DOI: 10.3748/wjg.v13.i5.748] [Citation(s) in RCA: 65] [Impact Index Per Article: 3.6] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Indexed: 02/06/2023] Open
Abstract
AIM: To evaluate the effectiveness of mastic administration on the clinical course and plasma inflammatory mediators of patients with active Crohn’s disease (CD).
METHODS: This pilot study was conducted in patients with established mild to moderately active CD, attending the outpatient clinics of the hospital, and in healthy controls. Ten patients and 8 controls were recruited for a 4-wk treatment with mastic caps (6 caps/d, 0.37 g/cap). All patients successfully completed the protocol. CD Activity Index (CDAI), Nutritional Risk Index (NRI), C-reactive protein (CRP), interleukin-6 (IL-6), tumor necrosis factor-alpha (TNF-α), monocyte chemotactic protein-1 (MCP-1), and total antioxidant potential (TAP) were evaluated in the plasma at baseline and at the end of the treatment period. Results were expressed as mean values ± SE and P < 0.05 was considered to indicate statistical significance.
RESULTS: Patients exhibited significant reduction of CDAI (222.9 ± 18.7 vs 136.3 ± 12.3, P = 0.05) as compared to pretreament values. Plasma IL-6 was significantly decreased (21.2 ± 9.3 pg/mL vs 7.2 ± 2.8 pg/ mL, P = 0.027), and so did CRP (40.3 ± 13.1 mg/mL vs 19.7 ± 5.5, P = 0.028). TAP was significantly increased (0.15 ± 0.09 vs 0.57 ± 0.15 mmol/L uric acid, P = 0.036). No patient or control exhibited any kind of side effects.
CONCLUSION: The results suggest that mastic significantly decreased the activity index and the plasma levels of IL-6 and CRP in patients with mildly to moderately active CD. Further double-blind, placebo-controlled studies in a larger number of patients are required to clarify the role of this natural product in the treatment of patients with CD.
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Affiliation(s)
- Andriana C Kaliora
- Department of Science of Dietetics-Nutrition, Harokopio University of Athens, 70 El. Venizelou ave., Kallithea 17671, Athens, Greece.
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