Naringenin Attenuates Metabolic Disturbances in C-26 Cancer Cachexia Mouse Model

Total Page:16

File Type:pdf, Size:1020Kb

Naringenin Attenuates Metabolic Disturbances in C-26 Cancer Cachexia Mouse Model Naringenin Attenuates Metabolic Disturbances in C-26 Cancer Cachexia Mouse Model: Transitional Study for Human Application Thesis Presented in Partial Fulfillment of the Requirements for the Degree Master of Science in the Graduate School of The Ohio State University By Yuko Nishikawa Graduate Program in Food Science and Technology The Ohio State University 2019 Thesis Committee Dr. Yael Vodovotz, Advisor Dr. Martha A. Belury, Co-Advisor Dr. Steven K. Clinton Dr. Christopher Simons Copyrighted by Yuko Nishikawa 2019 2 Abstract Cancer cachexia is a wasting disease which leads to poor disease prognosis and survival. Cachexia affects about 80% of advanced cancer patients and causes up to one- third of all cancer-related deaths. To date, effective treatment that directly targets cancer cachexia to improve longevity and quality of life is lacking. Metabolic disturbance is the underlying driver of the pathogenesis and progression of cancer cachexia. Common observations in cancer patients presenting cachexia include elevated inflammation, insulin resistance, dyslipidemia, and increased energy expenditure resulting in body weight loss that is irreversible by nutrition therapies. The use of metabolic modulators to improve these metabolic disturbances in some studies successfully slowed cachexia development, suggesting the importance of metabolic regulation in cancer cachexia treatment. Naringenin is a flavonoid found primarily in citrus fruits. Stemming from several epidemiological findings of the inverse associations of consumption of naringenin- containing foods and cancer incidence, a number of studies have explored anticancer activities and other bioactivities of naringenin. Naringenin has shown anti-cancer properties in many human cell lines and has successfully improved the inflammatory status, insulin tolerance, plasma glucose, and lipid profiles in mice. The results of some ii animal studies have suggested that naringenin supplementation during weight loss may help maintain lean body mass while regulating diet-induced metabolic disturbances. These observations have pointed to the potential use of naringenin to combat cachexia, a disease of metabolic disturbance, in cancer population by attenuation of tumor growth and metabolic disturbances, as well as the protection of the lean body mass. The first objective of this study was to determine the effect of dietary naringenin on the well-established C-26 cancer cachexia mouse model. We hypothesized that two- percent dietary naringenin would improve the metabolic disturbances in the C-26 model, slowing the progression of cachexia symptoms. Male CD2F1 mice were provided with either a control diet or a two percent naringenin diet, and each diet group was divided into a tumor and a no-tumor group. To our surprise, naringenin fed tumor mice exhibited weight loss and anorexia earlier than the control diet tumor mice. However, the early onset of anorexia and weight loss was not a predictor of worse outcomes in this study, since naringenin improved the inflammatory status, insulin sensitivity, activity, muscle function, and survival. These results confirmed naringenin's positive metabolism- regulating effects and its favorable impact on the outcomes of disease in the C-26 model. The second objective was to begin to provide a method for translation of the beneficial health effects of naringenin suggested by animal studies to human application. Although the first part of the study observed positive effects of naringenin on metabolic regulation, the concentration of naringenin used in our C-26 study was not directly translatable to the quantity that a human can achieve by consuming regular naringenin- containing foods. We hypothesized that the use of lyophilized naringenin-rich grapefruit iii juice and cyclodextrin in a confection would improve the naringenin bioavailability and increase its concentration. Cyclodextrin is a cyclic compound that has the ability to surround a hydrophobic, poorly soluble compound inside its cavity. By doing so, cyclodextrin encapsulation can improve the solubility and the bioavailability of naringenin. Since there is no universal food-safe complexation method for naringenin and β-cyclodextrin, two different methods were tested to encapsulate naringenin and naringin: the stirring method and the kneading method. The analyses of complexation efficiency by differential scanning calorimetry (DSC) and proton nuclear magnetic resonance (H- NMR) revealed that the stirring method was more efficient for the complexation of β- cyclodextrin with both naringin and naringenin. As a preliminary study for the future bioavailability tests, mice were fed with four different types of confections (sucrose, grapefruit confection (GFC), GFC with three percent naringenin, GFC with naringin equivalent to three percent naringenin) after a 12- hour fast and monitored for 2.5 hours. None of the mice finished consuming 1.6 grams of confection in 2.5 hours, and voluntary ingestion of the confection was found to be not suitable for a bioavailability studies, suggesting the need to oral gavage mice or to utilize a larger animal model. iv Acknowledgments I would like to thank my advisor, Dr. Vodovotz for allowing me to join such an exciting research environment, further allowing me to explore the area of my interest, and providing me with the opportunity to connect with researchers in other fields by introducing me to the Belury lab. I would also like to thank former and current Vodovotz lab members and officemates for giving me opportunities to learn important life skills. I would also like to express sincere gratitude to Dr. Belury for guiding me through the last half of my academic life as a master’s student in the nutrition field. I want to thank Deena, Austin, Rachel, Taylor, and other Belury lab members for sparing their precious time to help me with this study and for providing me with emotional support. I am grateful to the other members of my committee, Dr. Clinton and Dr. Simons, for giving me the motivation to challenge myself academically with their expertise. Support from Wes, Amanda, Emily, and my mentor, Dr. Parkin, has helped me propel through my academic life by restoring my energy and fueling my passion for food science. v Vita 2008………………………………………… B.A. Arts and Science, Kwansei Gakuin University, Hyogo, Japan 2009 to 2013………………………………… School Teacher, Hyogo Prefectural Board of Education, Hyogo, Japan 2017…………………………………………. B.S. Food Science, University of Wisconsin-Madison, Madison, WI 2017 to Present………………………………. Graduate Research Associate, Department of Food Science and Technology, The Ohio State University, Columbus OH Fields of Study Major Field: Food Science and Technology vi Table of Contents Abstract ............................................................................................................................... ii Acknowledgments............................................................................................................... v Vita ..................................................................................................................................... vi Table of Contents .............................................................................................................. vii List of Tables ...................................................................................................................... x List of Figures .................................................................................................................... xi Chapter 1. Literature Review .............................................................................................. 1 1.1 Cancer Cachexia ................................................................................................... 1 1.1.1 Definition, Prevalence, and Impact of Cancer Cachexia .............................. 1 1.1.2 Metabolic Disturbance and Cancer Cachexia ............................................... 3 1.1.3 Multi-organ Symptoms of Cancer Cachexia and Brain Function ............... 11 1.1.4 Suggested Mechanisms of Muscle Wasting in Cancer Cachexia ............... 15 1.1.5 Traditional Treatment for Cancer Cachexia ............................................... 19 1.1.6 C-26 Mouse Model for Human Cancer Cachexia Study ............................ 23 1.2 Naringenin .......................................................................................................... 27 1.2.1 Flavonoids and Bioactivities ....................................................................... 27 1.2.2 Food Sources of Naringenin ....................................................................... 32 1.2.3 Metabolism and Bioavailability of Naringenin Species ............................. 33 1.2.4 Naringenin and Inflammation ..................................................................... 35 1.2.5 Naringenin and Glucose Metabolism.......................................................... 36 1.2.6 Naringenin and Lipid Metabolism .............................................................. 37 1.2.7 Naringenin and Energy Expenditure ........................................................... 38 1.2.8 Naringenin and Brain Functions ................................................................. 38 1.2.9 Naringenin and Cancer ............................................................................... 40 1.3 Cyclodextrin ....................................................................................................... 42 vii 1.3.1 Cyclodextrin
Recommended publications
  • Chemical Profiles and Simultaneous Quantification of Aurantii Fructus By
    molecules Article Chemical Profiles and Simultaneous Quantification of Aurantii fructus by Use of HPLC-Q-TOF-MS Combined with GC-MS and HPLC Methods Yingjie He 1,2,† ID , Zongkai Li 3,†, Wei Wang 2, Suren R. Sooranna 4 ID , Yiting Shi 2, Yun Chen 2, Changqiao Wu 2, Jianguo Zeng 1,2, Qi Tang 1,2,* and Hongqi Xie 1,2,* 1 Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha 410128, China; [email protected] (Y.H.); [email protected] (J.Z.) 2 National and Local Union Engineering Research Center for the Veterinary Herbal Medicine Resources and Initiative, Hunan Agricultural University, Changsha 410128, China; [email protected] (W.W.); [email protected] (Y.S.); [email protected] (Y.C.); [email protected] (C.W.) 3 School of Medicine, Guangxi University of Science and Technology, Liuzhou 565006, China; [email protected] 4 Department of Surgery and Cancer, Chelsea and Westminster Hospital, Imperial College London, London SW10 9NH, UK; [email protected] * Correspondence: [email protected] (Q.T.); [email protected] (H.X.); Fax: +86-0731-8461-5293 (H.X.) † These authors contributed equally to this work. Received: 1 August 2018; Accepted: 29 August 2018; Published: 30 August 2018 Abstract: Aurantii fructus (AF) is a traditional Chinese medicine that has been used to improve gastrointestinal motility disorders for over a thousand years, but there is no exhaustive identification of the basic chemical components and comprehensive quality control of this herb. In this study, high-performance liquid chromatography coupled with quadrupole time of flight mass spectrometry (HPLC-Q-TOF-MS) and gas chromatography coupled mass spectrometry (GC-MS) were employed to identify the basic chemical compounds, and high-performance liquid chromatography (HPLC) was developed to determine the major biochemical markers from AF extract.
    [Show full text]
  • Their Antioxidant and Enzyme Inhibitory Activities
    antioxidants Article Semi-Continuous Subcritical Water Extraction of Flavonoids from Citrus unshiu Peel: Their Antioxidant and Enzyme Inhibitory Activities Dong-Shin Kim and Sang-Bin Lim * Department of Food Bioengineering, Jeju National University, Jeju 63243, Korea; [email protected] * Correspondence: [email protected] Received: 9 April 2020; Accepted: 24 April 2020; Published: 25 April 2020 Abstract: We extracted and hydrolyzed bioactive flavonoids from C. unshiu peel using subcritical water (SW) in a semi-continuous mode. The individual flavonoid yields, antioxidant and enzyme inhibitory activities of the SW extracts were analyzed. The extraction yields of hesperidin and narirutin increased with increasing temperature from 145 ◦C to 165 ◦C. Hydrothermal hydrolysis products (HHP), such as monoglucosides (hesperetin-7-O-glucoside and prunin) and aglycones (hesperetin and naringenin) were obtained in the SW extracts at temperatures above 160 ◦C. The sum of hesperidin and its HHP in the SW extracts was strongly correlated with antioxidant activities, whereas the contents of hesperetin and naringenin were strongly correlated with enzyme inhibitory activities. Hesperetin exhibited the highest antioxidant activities (2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, ferric-reducing antioxidant power, and oxygen radical absorbance capacity), whereas hesperetin-7-O-glucoside exhibited the highest enzyme inhibitory activities (angiotensin-I converting enzyme (ACE) and pancreatic lipase (PL)). Naringenin exhibited the highest enzyme inhibitory activities (xanthine oxidase and α-glucosidase). PMFs (sinensetin, nobiletin, and tangeretin) also exhibited relatively high inhibitory activities against ACE and PL. This study confirms the potential of SW for extracting and hydrolyzing bioactive flavonoids from C. unshiu peel using an environmentally friendly solvent (water) and a shorter extraction time.
    [Show full text]
  • Antifungal Activity of Natural and Enzymatically-Modified Flavonoids
    Food Chemistry 124 (2011) 1411–1415 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Antifungal activity of natural and enzymatically-modified flavonoids isolated from citrus species Maria Paula Salas a,b,*, Gustavo Céliz c, Hugo Geronazzo c, Mirta Daz c, Silvia Liliana Resnik b,d a Agencia Nacional de Promoción Científica y Tecnológica (ANCYPT), Argentina b Departamento de Industrias, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, 1428, Ciudad Autónoma de Buenos Aires, Argentina c Instituto de Investigaciones para la Industria Química (CONICET) and Facultad de Ciencias Exactas, Universidad Nacional de Salta, Avenida Bolivia 5150, Salta, Argentina d Comisión Científica de Investigaciones, Calle 526 entre 10 y 11, La Plata, Buenos Aires, Argentina article info abstract Article history: The antifungal activity of isolated flavonoids from Citrus species, such as naringin, hesperidin and neohes- Received 2 November 2009 peridin, and enzymatically-modified derivatives of these compounds, was studied on four fungi often Received in revised form 17 June 2010 found as food contaminants: Aspergillus parasiticus, Aspergillus flavus, Fusarium semitectum and Penicillium Accepted 27 July 2010 expansum. Although all the flavonoids showed antifungal activity, the intensity of this activity depended on the type of fungus and compound used. The hesperetin glucoside laurate strongly inhibited the myce- lial growth of P. expansum, while prunin decanoate was the most inhibiting flavonoid for A. flavus, A. par- Keywords: asiticus, and F. semitectum. Flavonoids The flavonoids naringin, hesperidin and neohesperidin, obtained as byproducts at low cost from the Mycelial growth Fungal growth residues of the citrus industries, present an interesting option for these industries.
    [Show full text]
  • The Phytochemistry of Cherokee Aromatic Medicinal Plants
    medicines Review The Phytochemistry of Cherokee Aromatic Medicinal Plants William N. Setzer 1,2 1 Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA; [email protected]; Tel.: +1-256-824-6519 2 Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA Received: 25 October 2018; Accepted: 8 November 2018; Published: 12 November 2018 Abstract: Background: Native Americans have had a rich ethnobotanical heritage for treating diseases, ailments, and injuries. Cherokee traditional medicine has provided numerous aromatic and medicinal plants that not only were used by the Cherokee people, but were also adopted for use by European settlers in North America. Methods: The aim of this review was to examine the Cherokee ethnobotanical literature and the published phytochemical investigations on Cherokee medicinal plants and to correlate phytochemical constituents with traditional uses and biological activities. Results: Several Cherokee medicinal plants are still in use today as herbal medicines, including, for example, yarrow (Achillea millefolium), black cohosh (Cimicifuga racemosa), American ginseng (Panax quinquefolius), and blue skullcap (Scutellaria lateriflora). This review presents a summary of the traditional uses, phytochemical constituents, and biological activities of Cherokee aromatic and medicinal plants. Conclusions: The list is not complete, however, as there is still much work needed in phytochemical investigation and pharmacological evaluation of many traditional herbal medicines. Keywords: Cherokee; Native American; traditional herbal medicine; chemical constituents; pharmacology 1. Introduction Natural products have been an important source of medicinal agents throughout history and modern medicine continues to rely on traditional knowledge for treatment of human maladies [1]. Traditional medicines such as Traditional Chinese Medicine [2], Ayurvedic [3], and medicinal plants from Latin America [4] have proven to be rich resources of biologically active compounds and potential new drugs.
    [Show full text]
  • (Piper Nigrum L.) Products Based on LC-MS/MS Analysis
    molecules Article Nontargeted Metabolomics for Phenolic and Polyhydroxy Compounds Profile of Pepper (Piper nigrum L.) Products Based on LC-MS/MS Analysis Fenglin Gu 1,2,3,*, Guiping Wu 1,2,3, Yiming Fang 1,2,3 and Hongying Zhu 1,2,3,* 1 Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning 571533, China; [email protected] (G.W.); [email protected] (Y.F.) 2 National Center of Important Tropical Crops Engineering and Technology Research, Wanning 571533, China 3 Key Laboratory of Genetic Resources Utilization of Spice and Beverage Crops, Ministry of Agriculture, Wanning 571533, China * Correspondence: [email protected] (F.G.); [email protected] (H.Z.); Tel.: +86-898-6255-3687 (F.G.); +86-898-6255-6090 (H.Z.); Fax: +86-898-6256-1083 (F.G. & H.Z.) Received: 16 July 2018; Accepted: 7 August 2018; Published: 9 August 2018 Abstract: In the present study, nontargeted metabolomics was used to screen the phenolic and polyhydroxy compounds in pepper products. A total of 186 phenolic and polyhydroxy compounds, including anthocyanins, proanthocyanidins, catechin derivatives, flavanones, flavones, flavonols, isoflavones and 3-O-p-coumaroyl quinic acid O-hexoside, quinic acid (polyhydroxy compounds), etc. For the selected 50 types of phenolic compound, except malvidin 3,5-diglucoside (malvin), 0 L-epicatechin and 4 -hydroxy-5,7-dimethoxyflavanone, other compound contents were present in high contents in freeze-dried pepper berries, and pinocembrin was relatively abundant in two kinds of pepper products. The score plots of principal component analysis indicated that the pepper samples can be classified into four groups on the basis of the type pepper processing.
    [Show full text]
  • Survey of Phenolic Compounds Produced in Citrus
    USDA ??:-Z7 S rveyof Phenolic United States Department of Agriculture C mpounds Produced IliIIiI Agricultural Research In Citrus Service Technical Bulletin Number 1856 December 1998 United States Department of Agriculture Survey of Phenolic Compounds Agricultural Produced in Citrus Research Service Mark Berhow, Brent Tisserat, Katherine Kanes, and Carl Vandercook Technical Bulletin Number 1856 December 1998 This research project was conducted at USDA, Agricultural Research Service, Fruit and Vegetable Chem­ istry laboratory, Pasadena, California, where Berhow was a research chemist, TIsserat was a research geneticist, Kanes was a research associate, and Vandercook, now retired, was a research chemist. Berhow and Tisserat now work at the USDA-ARS National Center for AgriCUltural Utilization Research, Peoria, Illinois, where Berhow is a research chemist and Tisserat is a research geneticist. Abstract Berhow, M., B. Tisserat, K. Kanes, and C. Vandercook. 1998. Survey of Mention of trade names or companies in this publication is solely for the Phenolic Compounds Produced in Citrus. U.S. Department ofAgriculture, purpose of providing specific information and does not imply recommenda­ Agricultural Research Service, Technical Bulletin No. 1856, 158 pp. tion or endorsement by the U. S. Department ofAgriculture over others not mentioned. A survey of phenolic compounds, especially flavanones and flavone and flavonol compounds, using high pressure liquid chromatography was While supplies last, single copies of this publication may be obtained at no performed in Rutaceae, subfamily Aurantioideae, representing 5 genera, cost from- 35 species, and 114 cultivars. The average number of peaks, or phenolic USDA, ARS, National Center for Agricultural Utilization Research compounds, occurring in citrus leaf, flavedo, albedo, and juice vesicles 1815 North University Street were 21, 17, 15, and 9.3, respectively.
    [Show full text]
  • Studies on the Extraction and Characterization of Pectin and Bitter
    Copyright is owned by the Author of the thesis. Permission is given for a copy to be downloaded by an individual for the purpose of research and private study only. The thesis may not be reproduced elsewhere without the permission of the Author. STUDIES ON THE EXTRACTION AND CHARACTERIZATION OF' PECTIN AND BITTER PRINCIPLES FROM NEW ZEALAND GRAPEFRUIT AND PHILIPPINE CALAMANSI A thesis presented in partial fulfilment of the requirements for the d egr ee of Master of Technology in Food Technology at Massey University MYRNA ORDONA NISPEROS 1981 ii ABSTRACT A study was conducted to determine the presence of bitter components in NZ grapefruit and Philippine ca.lamansi; describe the effect of maturity on the bitter components and other chemical constituents of grapefruit; reduce the bitterness of grapefruit juice by adsorption on polyvinylpyrrolidone; and to extract and characterize pectin from grapefruit peel. Naringin (995 ppm), narirutin (187 ppm), and limonoids (7.9 ppm) were detected in NZ grapefruit juice concentrate (27° Brix). Naringin was not detected in the calamansi juice, and limonin was detected at the level of 10.5 ppm in juice containing 5% crushed seeds. Maturation of the grapefruit caused an increase in pH from J.00 to J.50, an increase in total soluble solids from 10.8 to 14.4 with a decline to 13.5° Brix later in the season, a steady fall in acidity from 2.50 to 1.31 g citric acid/100 mL, and a continuous rise in the Brix/acid ratio from 4.2 to 10.J. Juice yield fluctuated throughout the season.
    [Show full text]
  • Insecticidal and Antifungal Chemicals Produced by Plants
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Archive Ouverte en Sciences de l'Information et de la Communication Insecticidal and antifungal chemicals produced by plants: a review Isabelle Boulogne, Philippe Petit, Harry Ozier-Lafontaine, Lucienne Desfontaines, Gladys Loranger-Merciris To cite this version: Isabelle Boulogne, Philippe Petit, Harry Ozier-Lafontaine, Lucienne Desfontaines, Gladys Loranger- Merciris. Insecticidal and antifungal chemicals produced by plants: a review. Environmental Chem- istry Letters, Springer Verlag, 2012, 10 (4), pp.325 - 347. 10.1007/s10311-012-0359-1. hal-01767269 HAL Id: hal-01767269 https://hal-normandie-univ.archives-ouvertes.fr/hal-01767269 Submitted on 29 May 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Distributed under a Creative Commons Attribution - NonCommercial| 4.0 International License Version définitive du manuscrit publié dans / Final version of the manuscript published in : Environmental Chemistry Letters, 2012, n°10(4), 325-347 The final publication is available at www.springerlink.com : http://dx.doi.org/10.1007/s10311-012-0359-1 Insecticidal and antifungal chemicals produced by plants. A review Isabelle Boulogne 1,2* , Philippe Petit 3, Harry Ozier-Lafontaine 2, Lucienne Desfontaines 2, Gladys Loranger-Merciris 1,2 1 Université des Antilles et de la Guyane, UFR Sciences exactes et naturelles, Campus de Fouillole, F- 97157, Pointe-à-Pitre Cedex (Guadeloupe), France.
    [Show full text]
  • United States Patent (10 ) Patent No.: US 10,538,797 B2 Thomsen Et Al
    US010538797B2 United States Patent (10 ) Patent No.: US 10,538,797 B2 Thomsen et al. (45 ) Date of Patent : Jan. 21 , 2020 (54 ) METHOD FOR THE BIOTECHNOLOGICAL ( 56 ) References Cited PRODUCTION OF FLAVONE GLYCOSIDE DIHYDROCHALCONES U.S. PATENT DOCUMENTS 9,359,622 B2 * 6/2016 Hilmer C12Y 505/01006 (71 ) Applicant: SYMRISE AG , Holzminden (DE ) 2014/0045233 A1 * 2/2014 Hilmer C12Y 505/01006 435/148 ( 72 ) Inventors : Maren Thomsen , Greifswald (DE ) ; Jakob Ley , Holzminden ( DE ) ; Egon FOREIGN PATENT DOCUMENTS Gross , Holzminden (DE ); Winfried Hinrichs , Greifswald (DE ) ; Uwe EP 2 692 729 A1 2/2014 Bornscheuer, Greifswald (DE ) OTHER PUBLICATIONS ( 73 ) Assignee : SYMRISE AG , Holzminden (DE ) Accession V9P0A9 . Mar. 19 , 2014. Alignment to SEQ ID No. 2 ( Year: 2014 ). * ( * ) Notice : Subject to any disclaimer, the term of this Accession V9P0A9 . Mar. 19 , 2014. Alignment to SEQ ID No. 4 ( Year: 2014 ). * patent is extended or adjusted under 35 Accession KF154734 . Dec. 31, 2013. Alignment to SEQ ID No. 1 . U.S.C. 154 ( b ) by 16 days . ( Year: 2013 ) . * Accession KF154734 . Dec. 31, 2013. Alignment to SEQ ID No. 3 . ( 21 ) Appl. No.: 15 /322,768 ( Year : 2013 ) . * Chica et al. Curr Opin Biotechnol . Aug. 2005; 16 ( 4 ): 378-84 . ( Year : 2005 ) . * ( 22 ) PCT Filed : Jun . 27 , 2015 Singh et al . Curr Protein Pept Sci. 2017 , 18 , 1-11 ( Year: 2017) . * Bornscheuer et al. Curr Protoc Protein Sci. Nov. 2011; Chapter PCT No .: PCT/ EP2015 / 064626 26 :Unit26.7 . ( Year: 2011 ). * ( 86 ) Gall et al, “ Enzymatische Umsetzung von Flavonoiden mit einer $ 371 ( c ) ( 1 ) , backteriellen Chalconisomerase und einer Enoatreduktase ,” Angewandte ( 2 ) Date : Apr.
    [Show full text]
  • Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: a Review
    Int. J. Mol. Sci. 2014, 15, 19369-19388; doi:10.3390/ijms151119369 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 www.mdpi.com/journal/ijms Review Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review Nguyen Thai Huynh 1,2,3,4, John Van Camp 2, Guy Smagghe 3 and Katleen Raes 1,* 1 Department of Industrial Biological Sciences, Faculty of Bioscience Engineering, Ghent University—Campus Kortrijk, Graaf Karel de Goedelaan 5, 8500 Kortrijk, Belgium; E-Mail: [email protected] 2 Department of Food Safety and Food Quality, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium; E-Mail: [email protected] 3 Department of Crop Protection, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium; E-Mail: [email protected] 4 Faculty of Food Technology, Ho Chi Minh City University of Food Industry, 140 Le Trong Tan, Tay Thanh Ward, Tan Phu District, 700000 Ho Chi Minh City, Vietnam * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +32-56-241-255; Fax: +32-56-241-224. External Editor: Antonio Segura-Carretero Received: 9 September 2014; in revised form: 16 October 2014 / Accepted: 20 October 2014 / Published: 24 October 2014 Abstract: This paper provides an overview on steered fermentation processes to release phenolic compounds from plant-based matrices, as well as on their potential application to convert phenolic compounds into unique metabolites. The ability of fermentation to improve the yield and to change the profile of phenolic compounds is mainly due to the release of bound phenolic compounds, as a consequence of the degradation of the cell wall structure by microbial enzymes produced during fermentation.
    [Show full text]
  • S1 of S77 Supplementary Materials: Discovery of a New Class of Cathepsin Kinhibitors in Rhizoma Drynariaeas Potential Candidates for the Treatment of Osteoporosis
    Int. J. Mol. Sci.2016, 17, 2116; doi:10.3390/ijms17122116 S1 of S77 Supplementary Materials: Discovery of a New Class of Cathepsin KInhibitors in Rhizoma Drynariaeas Potential Candidates for the Treatment of Osteoporosis Zuo-Cheng Qiu, Xiao-Li Dong, Yi Dai, Gao-Keng Xiao, Xin-Luan Wang, Ka-Chun Wong, Man-Sau Wong and Xin-Sheng Yao Table S1. Compounds identified from Drynariae rhizome (DR). No. Compound Name Chemical Structure 1 Naringin 5,7,3′,5′-Tetrahydroxy-flavanone 2 7-O-neohesperidoside 3 Narigenin-7-O-β-D-glucoside 5,7,3′,5′-Tetrahydroxy-flavanone 4 7-O-β-D-glucopyranoside 5 Naringenin 6 5,7,3′,5′-Tetrahydroxyflavanone 7 Kushennol F 8 Sophoraflavanone G 9 Kurarinone Int. J. Mol. Sci.2016, 17, 2116; doi:10.3390/ijms17122116 S2 of S77 Table S1. Cont. No. Compound Name Chemical Structure 10 Leachianone A 11 Luteolin-7-O-neohesperidoside 12 Luteolin-5-O-neohesperidoside 13 Kaempferol-7-O-α-L-arabinofuranoside 14 8-Prenylapigenin 15 Apigenine 16 Kaempferol-3-O-α-L-rhamnopyranoside OH HO O 17 Astragalin O OH OH O O OH OH OH 18 3-O-β-D-Glucopyranoside-7-O-α-L-arabinofuranoside OH HO O HO O O 19 5,7-Dihydroxychromone-7-O-β-D-glucopyranoside OH OH O Int. J. Mol. Sci.2016, 17, 2116; doi:10.3390/ijms17122116 S3 of S77 Table S1. Cont. No. Compound Name Chemical Structure 20 5,7-Dihydroxychromone-7-O-neohesperidoside Kaempferol 21 3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside 22 Xanthohumol OH HO O 23 Epicatechin OH OH OH 24 (E)-4-O-β-D-Glucopyranosyl caffeic acid 25 β-D-Glucopyranosyl sinapoic acid 26 4-O-β-D-Glucopyranosyl ferulic acid 27 Trans-caffeic acid 28 4-O-β-D-Glucopyranosyl coumaric acid 29 Dihydrocaffeic acid methyl ester 30 Dihydrocaffeic acid 31 3,4-Dihydroxyl benzoic acid 32 4-O-D-Glucosyl vanillic acid Int.
    [Show full text]
  • Evaluation of Antiaggregatory Activity of Flavonoid Aglycone Series Mirza Bojić1, Željko Debeljak1,2, Maja Tomičić3, Marica Medić-Šarić1* and Siniša Tomić4
    Bojić et al. Nutrition Journal 2011, 10:73 http://www.nutritionj.com/content/10/1/73 RESEARCH Open Access Evaluation of antiaggregatory activity of flavonoid aglycone series Mirza Bojić1, Željko Debeljak1,2, Maja Tomičić3, Marica Medić-Šarić1* and Siniša Tomić4 Abstract Background: Among natural compounds, present in every day diet, flavonoids have shown beneficial effect in prevention of cardiovascular diseases that can be attributed, at least partially to the described antiaggregatory activity i.e. antiplatelet effects of flavonoids. Due to the ever increasing pharmacological interest in antiplatelet agents a systematic experimental evaluation of large flavonoid series is needed. Methods: A set of thirty flavonoid aglycones has been selected for the evaluation. All measurements of aggregation were done under standardized and firmly controlled in vitro conditions. The whole blood samples, multiple platelet functional analyzer and adenosine diphosphate (ADP) as a weak agonist of aggregation were selected for this purpose. Results: The results were expressed as minimal concentration of flavonoid that can significantly lower the platelet aggregation compared to the corresponding untreated sample (minimal antiaggregatory concentration - MINaAC). All analyzed flavonoids exhibited antiaggregatory activity MINaAC ranging from 0.119 μM to 122 μM, while the most potent representatives were 3,6-dihydroxyflavone (0.119 μM) and syringetin (0.119 μM). Conclusions: Measurable antiplatelet activity established at submicromolar flavonoid concentrations suggests that even a dietary consumption of some flavonoids can make an impact on in vivo aggregation of platelets. These findings also point out a therapeutical potential of some flavonoids. Background Flavonoid antiplatelet activity can be attributed to the In the developed countries most of the older population increased production of prostacyclin by endothelian is affected by cardiovascular diseases.
    [Show full text]