Lignan As Interesting Food Components and Their Health Effects
Total Page:16
File Type:pdf, Size:1020Kb
Load more
Recommended publications
-
Serum Enterolactone
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Julkari Annamari Kilkkinen SERUM ENTEROLACTONE D E T E R M I N A N T S A N D A S S O C I A T I O N S W I T H B R E A S T A N D P R O S T A T E C A N C E R S A C A D E M I C D I S S E R T A T I O N To be presented with the permission of the Faculty of Medicine, University of Helsinki, for public examination in Auditorium XII, University Main Building, on June 11th, 2004, at 12 noon. National Public Health Institute, Helsinki, Finland and Department of Public Health, University of Helsinki, Finland Helsinki 2004 P u b l i c a t i o n s o f t h e N a t i o n a l P u b l i c H e a l t h I n s t i t u t e K T L A 1 0 / 2 0 0 4 Copyright National Public Health Institute Julkaisija-Utgivare-Publisher Kansanterveyslaitos (KTL) Mannerheimintie 166 00300 Helsinki Puh. vaihde (09) 474 41, telefax (09) 4744 8408 Folkhälsoinstitutet Mannerheimvägen 166 00300 Helsingfors Tel. växel (09) 474 41, telefax (09) 4744 8408 National Public Health Institute Mannerheimintie 166 FIN-00300 Helsinki, Finland Telephone +358 9 474 41, telefax +358 9 4744 8408 ISBN 951-740-448-4 ISSN 0359-3584 ISBN 951-740-449-2 (pdf) ISSN 1458-6290 (pdf) Hakapaino Oy Helsinki 2004 S u p e r v i s e d b y Professor Pirjo Pietinen Department of Epidemiology and Health Promotion National Public Health Institute, Helsinki, Finland Professor Jarmo Virtamo Department of Epidemiology and Health Promotion National Public Health Institute, Helsinki, Finland R e v i e w e d b y Associate Professor Sari -
Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha
Molecules 2013, 18, 1122-1127; doi:10.3390/molecules18011122 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Communication Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha Jong-Sik Jin 1, Jong-Hyun Lee 2 and Masao Hattori 1,* 1 Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan 2 College of Pharmacy, Dongduk Women’s University, 23-1 Wolgok-Dong, Sungbuk-Gu, Seoul 136-714, Korea * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel./Fax: +81-766-52-4314. Received: 8 October 2012; in revised form: 10 January 2013 / Accepted: 14 January 2013 / Published: 16 January 2013 Abstract: Phytoestrogens are defined as plant-derived compounds with estrogen-like activities according to their chemical structures and activities. Plant lignans are generally categorized as phytoestrogens. It was reported that (−)-arctigenin, the aglycone of arctiin, was demethylated to (−)-dihydroxyenterolactone (DHENL) by Eubacterium (E.) sp. ARC-2. Through stepwise demethylation, E. sp. ARC-2 produced six intermediates, three mono- desmethylarctigenins and three di-desmethylarctigenins. In the present study, ligand binding affinities of (−)-arctigenin and its seven metabolites, including DHENL, were investigated for an estrogen receptor alpha, and found that demethylated metabolites had stronger binding affinities than (−)-arctigenin using a ligand binding screen assay method. The IC50 value of (2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dihydroxybenzyl)- butyrolactone was 7.9 × 10−4 M. Keywords: arctigenin; estrogen receptor alpha; demethylation; ligand binding affinity 1. Introduction Some plant lignans have been categorized as phytoestrogens or their precursors with isoflavones because natural compounds and/or their metabolites act like estrogen [1–3]. -
Phenylpropanoids
Phenylpropanoids The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of cinnamic acid, which is synthesized from phenylalanine in the first step of phenylpropanoid biosynthesis. Phenylpropanoids are found throughout the plant kingdom, where they serve as essential components of a number of structural polymers, provide protection from ultraviolet light, defend against herbivores and pathogens, and mediate plant-pollinator interactions as floral pigments and scent compounds. Concentrations of phenylpropanoids within plants are also altered by changes in resource availability. www.MedChemExpress.com 1 Phenylpropanoids Inhibitors & Modulators (+)-Columbianetin (+)-Columbianetin acetate ((S)-Columbianetin) Cat. No.: HY-N0363 ((S)-Columbianetin acetate) Cat. No.: HY-N0363A (+)-Columbianetin is an isomer of Columbianetin. (S)-Columbianetin acetate is an isomer of Columbianetin is a phytoalexin associated with Columbianetin. Columbianetin is a phytoalexin celery (Apium graveolens) resistance to associated with celery (Apium graveolens) pathogens during storage. Columbianetin exhibits resistance to pathogens during storage. excellent anti-fungal and anti-inflammatory Columbianetin exhibits excellent anti-fungal and activity. anti-inflammatory activity. Purity: >98% Purity: >98% Clinical Data: No Development Reported Clinical Data: No Development Reported Size: 5 mg, 10 mg, 20 mg Size: 5 mg, 10 mg, 20 mg (+)-Guaiacin (+)-Peusedanol Cat. No.: HY-N2247A Cat. No.: HY-N6063 (+)-Guaiacin is a compound extracted of the bark (+)-Peusedanol is a coumarin isolated from of Machilus wangchiana Chun. (Lauraceae). Peucedanumjaponicum. (+)-Guaiacin shows potent in vitro activities against the release of β-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF) . -
Enterolactone Induces Apoptosis in Human Prostate Carcinoma Lncap Cells Via a Mitochondrial-Mediated, Caspase-Dependent Pathway
2581 Enterolactone induces apoptosis in human prostate carcinoma LNCaP cells via a mitochondrial-mediated, caspase-dependent pathway Li-Hua Chen,1 Jing Fang,1 Huaixing Li,1 United States and China (1, 2). Diet is considered a primary Wendy Demark-Wahnefried,2 and Xu Lin1 factor contributing to the huge differential in the preva- lence of prostatic carcinoma (3). Although there are several 1 Institute for Nutritional Sciences, Shanghai Institutes for dietary factors that may be important for this disease, we Biological Sciences, Chinese Academy of Sciences, and Graduate School of the Chinese Academy of Sciences, Shanghai, China; propose a study that specifically focuses on dietary lignans and 2School of Nursing and Department of Surgery, Duke because the traditional plant-based diet in Asia is rich University Medical Center, Durham, North Carolina in lignans as compared with the omnivorous diet of the United States and Northern Europe (4). Moreover, our previous studies suggest an inhibitory effect of this Abstract phytochemical on prostate cancer growth (5). The mammalian lignan enterolactone is a major metabolite Dietary lignans have phytoestrogenic properties (6) and of plant-based lignans that has been shown to inhibit the are broadly available in cereals, legumes, fruits, vegetables, growth and development of prostate cancer. However, and grains, with the highest concentration in flaxseed and little is known about the mechanistic basis for its anti- sesame seeds (7, 8). Plant-based lignans, secoisolariciresinol cancer activity. In this study, we report that enterolactone and matairesinol, are converted by the intestinal microflora selectively suppresses the growth of LNCaP prostate to mammalian lignans of enterodiol and enterolactone, the cancer cells by triggering apoptosis. -
Anticancer Mechanisms of Flaxseed and Its Derived Mammalian
ANTICANCER MECHANISMS OF FLAXSEED AND ITS DERIVED MAMMALIAN LIGNAN ENTEROLACTONE IN LUNG A Dissertation Submitted to the Graduate Faculty of the North Dakota State University of Agriculture and Applied Science By Shireen Chikara In Partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Program: Cellular and Molecular Biology April 2017 Fargo, North Dakota North Dakota State University Graduate School Title ANTICANCER MECHANISMS OF FLAXSEED AND ITS DERIVED MAMMALIAN LIGNAN ENTEROLACTONE IN LUNG By Shireen Chikara The Supervisory Committee certifies that this disquisition complies with North Dakota State University’s regulations and meets the accepted standards for the degree of DOCTOR OF PHILOSOPHY SUPERVISORY COMMITTEE: Dr. Katie Reindl Chair Dr. Jane Schuh Dr. Yeong Rhee Dr. Steven Qian Approved: 04-13-2017 Dr. Jane Schuh Date Department Chair ABSTRACT Whole flaxseed and its derived lignans have shown anti-cancer properties in a variety of malignancies. However, their potential remains uninvestigated in lung cancer, the leading cause of cancer-related deaths worldwide. We investigated the anti-tumor effects of flaxseed-derived mammalian lignan enterolactone (EL) in human lung cancer cell cultures and the chemopreventive potential of 10% whole flaxseed in a mouse model of lung carcinogenesis. We found that EL inhibits in vitro proliferation and motility of a panel of non-small cell lung cancer cell (NSCLC) lines. EL-mediated inhibition in lung cancer cell proliferation was due to a decrease in mRNA and protein expression levels of G1-phase cell cycle promoters and a simultaneous increase in mRNA and protein expression levels of p21WAF1/CIP1, a negative regulator of the G1-phase. -
Chem. Pharm. Bull. 51(4) 378—384 (2003) Vol
378 Chem. Pharm. Bull. 51(4) 378—384 (2003) Vol. 51, No. 4 Transformation of Arctiin to Estrogenic and Antiestrogenic Substances by Human Intestinal Bacteria a a b a Li-Hua XIE, Eun-Mi AHN, Teruaki AKAO, Atef Abdel-Monem ABDEL-HAFEZ, a ,a Norio NAKAMURA, and Masao HATTORI* a Institute of Natural Medicine, Toyama Medical and Pharmaceutical University; 2630 Sugitani, Toyama 930–0194, Japan: and b Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University; 2630 Sugitani, Toyama 930–0194, Japan. Received October 23, 2002; accepted January 18, 2003 After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six -metabolites were formed, and their structures were identified as (؊)-arctigenin (2), (2R,3R)-2-(3,4-dihydroxy -(benzyl)-3-(3؆,4؆-dimethoxybenzyl)butyrolactone (3), (2R,3R)-2-(3-hydroxybenzyl)-3-(3؆,4؆-dimethoxybenzyl butyrolactone (4), (2R,3R)-2-(3-hydroxybenzyl)-3-(3؆-hydroxy-4؆-methoxybenzyl)butyrolactone (5), (2R,3R)-2- -3-hydroxybenzyl)-3-(3؆,4؆-dihydroxybenzyl)butyrolactone (6), and (؊)-enterolactone (7) by various spectro) scopic means including two dimensional (2D)-NMR, mass spectrometry, and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and the time course of the transformation. En- terolactones obtained from the biotransformation of arctiin and secoisolariciresinol diglucoside (SDG, from the (seeds of Linum usitatissium) by human intestinal bacteria were proved to be enantiomers, with the (؊)-(2R,3R and (؉)-(2S,3S) configurations, respectively. Compound 6 showed the most potent proliferative effect on the growth of MCF-7 human breast cancer cells in culture among 1 and six metabolites, while it showed inhibitory activity on estradiol-mediated proliferation of MCF-7 cells at a concentration of 10 mM. -
Urinary and Serum Concentrations of Seven Phytoestrogens in a Human Reference Population Subset
Journal of Exposure Analysis and Environmental Epidemiology (2003) 13, 276–282 r 2003 Nature Publishing Group All rights reserved 1053-4245/03/$25.00 www.nature.com/jea Urinary and serum concentrations of seven phytoestrogens in a human reference population subset LIZA VALENTI´ N-BLASINI, BENJAMIN C. BLOUNT, SAMUEL P. CAUDILL, AND LARRY L. NEEDHAM National Center for Environmental Health, Centers for Disease Control and Prevention, Atlanta, GA 30341, USA Diets rich in naturally occurring plant estrogens (phytoestrogens) are strongly associated with a decreased risk for cancer and heart disease in humans. Phytoestrogens have estrogenic and, in some cases, antiestrogenic and antiandrogenic properties, and may contribute to the protective effect of some diets. However, little information is available about the levels of these phytoestrogens in the general US population. Therefore, levels of phytoestrogenswere determined in urine (N ¼ 199) and serum (N ¼ 208) samples taken from a nonrepresentative subset of adults who participated in NHANES III, 1988– 1994. The phytoestrogens quantified were the lignans (enterolactone, enterodiol, matairesinol); the isoflavones (genistein, daidzein, equol, O- desmethylangolensin); and coumestrol (urine only). Phytoestrogens with the highest mean urinary levels were enterolactone (512 ng/ml), daidzein(317 ng/ ml), and genistein (129 ng/ml). In serum, the concentrations were much less and the relative order was reversed, with genistein having the highest mean level (4.7 ng/ml), followed by daidzein (3.9 ng/ml) and enterolactone (3.6 ng/ml). Highly significant correlations of phytoestrogen levels in urineand serum samples from the same persons were observed for enterolactone, enterodiol, genistein, and daidzein. Determination of phytoestrogen concentrations in large study populations will give a better insight into the actual dietary exposure to these biologically active compounds in the US population. -
Overview of the Anti-Inflammatory Effects, Pharmacokinetic Properties
Acta Pharmacologica Sinica (2018) 39: 787–801 © 2018 CPS and SIMM All rights reserved 1671-4083/18 www.nature.com/aps Review Article Overview of the anti-inflammatory effects, pharmacokinetic properties and clinical efficacies of arctigenin and arctiin from Arctium lappa L Qiong GAO, Mengbi YANG, Zhong ZUO* School of Pharmacy, Faculty of Medicine, The Chinese University of Hong Kong, Hong Kong SAR, China Abstract Arctigenin (AR) and its glycoside, arctiin, are two major active ingredients of Arctium lappa L (A lappa), a popular medicinal herb and health supplement frequently used in Asia. In the past several decades, bioactive components from A lappa have attracted the attention of researchers due to their promising therapeutic effects. In the current article, we aimed to provide an overview of the pharmacology of AR and arctiin, focusing on their anti-inflammatory effects, pharmacokinetics properties and clinical efficacies. Compared to acrtiin, AR was reported as the most potent bioactive component of A lappa in the majority of studies. AR exhibits potent anti-inflammatory activities by inhibiting inducible nitric oxide synthase (iNOS) via modulation of several cytokines. Due to its potent anti-inflammatory effects, AR may serve as a potential therapeutic compound against both acute inflammation and various chronic diseases. However, pharmacokinetic studies demonstrated the extensive glucuronidation and hydrolysis of AR in liver, intestine and plasma, which might hinder its in vivo and clinical efficacy after oral administration. Based on the reviewed pharmacological and pharmacokinetic characteristics of AR, further pharmacokinetic and pharmacodynamic studies of AR via alternative administration routes are suggested to promote its ability to serve as a therapeutic agent as well as an ideal bioactive marker for A lappa. -
Deuterium Labelling and Rearrangement Studies of Lignans
Laboratory of Organic Chemistry Department of Chemistry Faculty of Science University of Helsinki Finland Deuterium labelling and rearrangement studies of lignans Monika Pohjoispää ACADEMIC DISSERTATION To be presented, with the permission of the Faculty of Science of the University of Helsinki, for public examination in Auditorium A110, Department of Chemistry, on 12th September 2014, at 12 noon. Helsinki 2014 Supervisor Professor Kristiina Wähälä Laboratory of Organic Chemistry Department of Chemistry University of Helsinki Finland Reviewers Professor William J. S. Lockley Department of Chemistry University of Surrey United Kingdom Professor Scott A. Snyder Department of Chemistry The Scripps Research Institute Jupiter, FL, USA Opponent Professor Øyvind M. Andersen Department of Chemistry University of Bergen Norway ISBN 978-951-51-0048-1 (paperback) ISBN 978-951-51-0049-8 (PDF) Unigrafia Oy Helsinki 2014 Abstract Lignans are naturally occurring compounds, polyphenolic secondary plant and mammalian metabolites. Due to their ubiquitous presence and biological activity, lignans have attracted the interest of scientists from different areas, like nutrition scientists, pharmaceutical researchers and synthetic chemists. The research is very active, and the number of lignan related publications has proliferated. Lignans vary widely in the structure, and the present work focuses mainly on the (hydroxy)lignano-9,9’-lactones, their rearranged products, and 9,9’- epoxylignanes. The literature review introduces the stereochemistry and assignment of the absolute configuration of these lignans. In addition, stable isotope labelling of lignans is reviewed. The experimental part is focused on deuteration of lignans and rearrangement and stereochemistry studies. The deuteration reaction utilising acidic H/D exchange within the lignan skeleton was investigated. -
Variation in Fasting and Non-Fasting Serum Enterolactone Concentrations in Women of the Malmo¨ Diet and Cancer Cohort
European Journal of Clinical Nutrition (2008) 62, 1005–1009 & 2008 Macmillan Publishers Limited All rights reserved 0954-3007/08 $30.00 www.nature.com/ejcn ORIGINAL ARTICLE Variation in fasting and non-fasting serum enterolactone concentrations in women of the Malmo¨ Diet and Cancer cohort E Sonestedt1, U Ericson1, B Gullberg1, JL Pen˜alvo2, H Adlercreutz2 and E Wirfa¨lt1 1Department of Clinical Sciences, Lund University, Malmo¨, Sweden and 2Institute for Preventive Medicine, Nutrition and Cancer, Folkha¨lsan Research Center and Division of Clinical Chemistry, University of Helsinki, Helsinki, Finland Objectives: The aim of this study was to examine the variation of enterolactone from fasting and non-fasting blood of middle- aged healthy women eating a normal diet to determine the usefulness of a single sample in epidemiological studies. Subjects and methods: Twenty-six women born between 1940 and 1950 were recruited within the Malmo¨ Diet and Cancer cohort. Three non-fasting and two overnight fasting samples were collected from each individual during a 5-week period. Twenty-one participated in all measurements. Enterolactone concentrations were analyzed by time-resolved fluoroimmunoassay. Results: The within-subject and between-subject variations (coefficient of variations, CV) were estimated to 59 and 89% respectively for fasting samples and 71 and 67% for non-fasting samples. The intraclass correlation coefficients (ICC) were estimated to 0.66 (95% confidence interval (CI) 0.35–0.84) for fasting and 0.48 (95% CI, 0.22–0.72) for non-fasting samples. Conclusions: Although the estimated ICC for blood samples was moderate, it indicates that enterolactone levels of both fasting and non-fasting blood samples should be useful in future projects within the Malmo¨ Diet and Cancer cohort. -
WO 2018/002916 Al O
(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/002916 Al 04 January 2018 (04.01.2018) W !P O PCT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C08F2/32 (2006.01) C08J 9/00 (2006.01) kind of national protection available): AE, AG, AL, AM, C08G 18/08 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, (21) International Application Number: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, PCT/IL20 17/050706 HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, (22) International Filing Date: KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 26 June 2017 (26.06.2017) MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (25) Filing Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 246468 26 June 2016 (26.06.2016) IL kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, (71) Applicant: TECHNION RESEARCH & DEVEL¬ UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, OPMENT FOUNDATION LIMITED [IL/IL]; Senate TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, House, Technion City, 3200004 Haifa (IL). -
Planta Medica
www.thieme.de/fz/plantamedica | www.thieme-connect.de/ejournals Planta Medica July 2009 · Page 877 – 1094 · Volume 75 9 · 2009 Editorial Poster 877 Editorial 903 Topic A: Lead finding from Nature 928 Topic B: Conservation and biodiversity issues 878 Lectures 939 Topic C: Plants and aging of the population 944 Topic D: Natural products and neglected diseases Workshops 882 WS1 Workshops for Young Researchers: 966 Topic E: Anti-cancer agents Validation of Analytical Methods 988 Topic F: HIV and viral diseases 882 WS2 Workshops for Young Researchers: Cell Culture 991 Topic G: Quality control and safety assessments of phytomedicines 882 WS3 Permanent Committees on Manufacturing and Quality Control of Herbal Remedies and 1007 Topic H: Prevention of metabolic diseases Regulatory Affairs of Herbal Medicinal Products by medicinal plants and nutraceuticals 883 WS4 Permanent Committee on Biological and 1019 Topic I: Cosmetics, flavours and aromas Pharmacological Activity of Natural Products: Phytoestrogens: risks and benefits for human 1029 Topic J: Free Topic health 883 WS5 Permanent Committee on Breeding and 1083 Authors’ Index Cultivation of Medicinal Plants: Genetic Resources, Conservation and Breeding 1094 Masthead 884 Short lectures Editorial 877 57th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research Date/Place: Geneva, Switzerland, August 16 – 20, 2009 Chairman: Kurt Hostettmann Dear Colleagues, The 57th Congress of the Society of Medicinal Plant and Natural Product research will be held this year in Geneva, Switzerland. The congress venue is going to be at the CICG (Centre International des Confrences Genve) which is very well equipped to host such an important scientific event.