Assessment Report on Humulus Lupulus L., Flos
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Key Enzymes Involved in the Synthesis of Hops Phytochemical Compounds: from Structure, Functions to Applications
International Journal of Molecular Sciences Review Key Enzymes Involved in the Synthesis of Hops Phytochemical Compounds: From Structure, Functions to Applications Kai Hong , Limin Wang, Agbaka Johnpaul , Chenyan Lv * and Changwei Ma * College of Food Science and Nutritional Engineering, China Agricultural University, 17 Qinghua Donglu Road, Haidian District, Beijing 100083, China; [email protected] (K.H.); [email protected] (L.W.); [email protected] (A.J.) * Correspondence: [email protected] (C.L.); [email protected] (C.M.); Tel./Fax: +86-10-62737643 (C.M.) Abstract: Humulus lupulus L. is an essential source of aroma compounds, hop bitter acids, and xanthohumol derivatives mainly exploited as flavourings in beer brewing and with demonstrated potential for the treatment of certain diseases. To acquire a comprehensive understanding of the biosynthesis of these compounds, the primary enzymes involved in the three major pathways of hops’ phytochemical composition are herein critically summarized. Hops’ phytochemical components impart bitterness, aroma, and antioxidant activity to beers. The biosynthesis pathways have been extensively studied and enzymes play essential roles in the processes. Here, we introduced the enzymes involved in the biosynthesis of hop bitter acids, monoterpenes and xanthohumol deriva- tives, including the branched-chain aminotransferase (BCAT), branched-chain keto-acid dehydroge- nase (BCKDH), carboxyl CoA ligase (CCL), valerophenone synthase (VPS), prenyltransferase (PT), 1-deoxyxylulose-5-phosphate synthase (DXS), 4-hydroxy-3-methylbut-2-enyl diphosphate reductase (HDR), Geranyl diphosphate synthase (GPPS), monoterpene synthase enzymes (MTS), cinnamate Citation: Hong, K.; Wang, L.; 4-hydroxylase (C4H), chalcone synthase (CHS_H1), chalcone isomerase (CHI)-like proteins (CHIL), Johnpaul, A.; Lv, C.; Ma, C. -
Beer As a Source of Hop Prenylated Flavonoids, Compounds with Antioxidant, Chemoprotective and Phytoestrogen Activity
BEER AS A SOURCE OF HOP PRENYLATED FLAVONOIDS, COMPOUNDS WITH ANTIOXIDANT, CHEMOPROTECTIVE AND PHYTOESTROGEN ACTIVITY Dana Urminská*1 and Nora Jedináková2 Address(es): Doc. RNDr. Dana Urminská, CSc., 1Slovak University of Agriculture, Faculty of Biotechnology and Food Sciences, Department of Biochemistry and Biotechnology, Trieda Andreja Hlinku 2, 949 76 Nitra-Chrenová, Slovakia, phone number: +421 37 641 4696. *Corresponding author: [email protected] https://doi.org/10.15414/jmbfs.4426 ARTICLE INFO ABSTRACT Received 4. 3. 2021 Beer is an alcoholic beverage consumed worldwide, which is given its typical taste by the presence of hops. Hops contain an array Revised 1. 6. 2021 technologically important substances, which are primarily represented by hop resins (humulones, lupulones, humulinones, hulupones, Accepted 1. 6. 2021 etc.), essential oils (humulene, myrcene, etc.) and tannins (phenolic compounds quercetin, catechin, etc.). In addition to their sensory Published 1. 8. 2021 properties, these molecules contribute to the biological and colloidal stability of beer with their antiseptic and antioxidant properties. Recently, an increased attention has been given to prenylated hop flavonoids, particularly xanthohumol, isoxanthohumol and 8- prenylnaringenin. Xanthohumol is a prenylated chalcone that exhibit antioxidant, anticancer and chemoprotective effects. Its only source Regular article in human nutrition is beer, nevertheless a large part of xanthohumol from hops is isomerized by heat to isoxanthohumol and desmethylxanthohumol, from which a racemic mixture of 6- and 8-prenylnaringenins is formed during the beer production. Xanthohumol is also converted to isoxanthohumol by digestion, leading to the formation of 8-prenylnaringenin that is being catalyzed by the enzymes of the intestinal microorganisms as well as liver enzymes. -
The Variability of Hop Latent Viroid As Induced Upon Heat Treatment
Virology 287, 349–358 (2001) doi:10.1006/viro.2001.1044, available online at http://www.idealibrary.com on View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Elsevier - Publisher Connector The Variability of Hop Latent Viroid as Induced upon Heat Treatment Jaroslav Matousˇek,* Josef Patzak,† Lidmila Orctova´,* Jo¨rg Schubert,‡ Luka´sˇ Vrba,* Gerhard Steger,§ and Detlev Riesner§,1 *Department of Molecular Genetics, Institute of Plant Molecular Biology Czech Academy of Sciences, Branisˇovska´31, 37005 Cˇ eske´Bude˘jovice, Czech Republic; †Department of Virology, Institute of Hop Research and Breeding, Kadanˇska´2525, 438 46 Zˇatec, Czech Republic; ‡Federal Centre for Breeding Research, Institute for Resistance Research and Pathogen Diagnostics, Theodor-Roemer-Weg 4, 06449 Aschersleben, Germany; and §Institute of Physical Biology, Heinrich-Heine Universita¨t Du¨sseldorf, Universita¨tsstraße 1, D-40225 Du¨sseldorf, Germany Received March 28, 2001; returned to author for revision March 30, 2001; accepted June 11, 2001; published online August 2, 2001 We have previously shown that heat treatment of hop plants infected by hop latent viroid (HLVd) reduces viroid levels. Here we investigate whether such heat treatment leads to the accumulation of sequence variability in HLVd. We observed a negligible level of mutated variants in HLVd under standard cultivation conditions. In contrast, the heat treatment of hop led to HLVd degradation and, simultaneously, to a significant increase in sequence variations, as judged from temperature gradient–gel electrophoresis analysis and cDNA library screening by DNA heteroduplex analysis. Thirty-one cDNA clones (9.8%) were identified as deviating forms. -
Plant Genera Cannabis and Humulus Share the Same Pair of Well- Differentiated Sex Chromosomes
Research Plant genera Cannabis and Humulus share the same pair of well- differentiated sex chromosomes Djivan Prentout1 , Natasa Stajner2, Andreja Cerenak3, Theo Tricou1 , Celine Brochier-Armanet1, Jernej * * Jakse2 , Jos Kafer¨ 1 and Gabriel A. B. Marais1,4 1Laboratoire de Biometrie´ et Biologie Evolutive, UMR 5558, Universite´ de Lyon, Universite´ Lyon 1, CNRS, Villeurbanne F-69622, France; 2Department of Agronomy, Biotechnical Faculty, University of Ljubljana, Jamnikarjeva 101, Ljubljana SI-1000, Slovenia; 3Slovenian Institute of Hop Research and Brewing, Cesta Zalskega Tabora 2, Zalec SI-3310, Slovenia; 4LEAF- Linking Landscape, Environment, Agriculture and Food, Instituto Superior de Agronomia, Universidade de Lisboa, Lisboa 1349-017, Portugal Summary Author for correspondence: We recently described, in Cannabis sativa, the oldest sex chromosome system documented Djivan Prentout so far in plants (12–28 Myr old). Based on the estimated age, we predicted that it should be Email: [email protected] shared by its sister genus Humulus, which is known also to possess XY chromosomes. Here, we used transcriptome sequencing of an F1 family of H. lupulus to identify and study Received: 19 February 2021 the sex chromosomes in this species using the probabilistic method SEX-DETECTOR. Accepted: 29 April 2021 We identified 265 sex-linked genes in H. lupulus, which preferentially mapped to the C. sativa X chromosome. Using phylogenies of sex-linked genes, we showed that a region of the New Phytologist (2021) sex chromosomes had already stopped recombining in an ancestor of both species. Further- doi: 10.1111/nph.17456 more, as in C. sativa, Y-linked gene expression reduction is correlated to the position on the X chromosome, and highly Y degenerated genes showed dosage compensation. -
Influence of Growing Area, Plant Age, and Virus Infection on the Contents of Hop Secondary Metabolites
Czech J. Food Sci. Vol. 30, 2012, No. 6: 541–547 Influence of Growing Area, Plant Age, and Virus Infection on the Contents of Hop Secondary Metabolites Lukáš JELÍNEK, Monika DOLEČKOVÁ, Marcel KARABÍN, Tereza HUDCOVÁ, Blanka KOTLÍKOVÁ and Pavel DOSTÁLEK Department of Biotechnology, Faculty of Food and Biochemical Technology, Institute of Chemical Technology Prague, Prague, Czech Republic Abstract Jelínek L., Dolečková M., Karabin M., Hudcová T., Kotlíková B., Dostálek P. (2012): Influence of growing area, plant age, and virus infection on the contents of hop secondary metabolites. Czech J. Food Sci., 30: 541–547. Hops and hop products (pellets and extracts) belong to the major raw materials employed in brewing industry. Many effects such as the growing area, hop plant age, and virus infection influence the contents of the brewing-important hop secondary metabolites (α- and β-bitter acids, essential oils, and polyphenols). The clones of the Czech cultivars Saaz and German cv. Taurus were used in this work and compared with the aim to investigate the influence of the effects mentioned on the contents of hop secondary metabolites. Keywords: Humulus lupulus; hop plant age; polyphenols; essential oils; α- bitter acids; β-bitter acids The external conditions such as the growing In recent years, the effort of many scientists area, virus infection, and cultivar age have very has been to investigate the influence of the virus strong impacts on the yield of hop cone second- infection on the contents of hop secondary me- ary metabolites commonly employed in brewing tabolites, mainly BA. They found out that many (bitter acids, essential oils, and polyphenols). -
Differential Anticancer Activity of Pterostilbene Against Three
ANTICANCER RESEARCH 37 : 6153-6159 (2017) doi:10.21873/anticanres.12064 Differential Anticancer Activity of Pterostilbene Against Three Subtypes of Human Breast Cancer Cells REI WAKIMOTO, MISAKI ONO, MIKAKO TAKESHIMA, TAKAKO HIGUCHI and SHUJI NAKANO Graduate School of Health and Nutritional Sciences, Nakamura Gakuen University, Fukuoka, Japan Abstract. Although pterostilbene, a natural analog of factor receptor 2 (HER2) expression. Therapeutic options for resveratrol, has potent antitumor activity against several patients with advanced breast cancer are limited and depend human cancer types, the possible inhibitory mechanisms on the breast cancer subtype. Although survival of patients against subtypes of human breast cancer with different with breast cancer has been improved by hormonal and hormone receptor and human epidermal growth factor receptor targeted therapy in recent years, triple-negative breast cancer, 2 (HER2) status remain unknown. We investigated the which is clinically negative for expression of ER, PR and anticancer activity of pterostilbene using three subtypes of HER2, is associated with a poor prognosis (2). Because there breast cancer cell lines. Pterostilbene treatment exhibited a are a limited number of treatments for triple-negative breast dose-dependent antiproliferative activity, with the greatest cancer, development of novel treatment options and prevention growth inhibition observed in triple-negative MDA-MB-468 for this type of breast cancer is extremely important. In this cells. Although pterostilbene arrested cell-cycle progression at context, fruit and vegetables have attracted attention because the G 0/G 1 phase regardless of breast cancer subtype, its their intake has been shown to reduce the risk of breast cancer apoptosis-inducing activity was highly apparent in MDA-MB- (3), and differentially affect ER-negative and -positive breast 468 cells. -
(12) Patent Application Publication (10) Pub. No.: US 2004/0121040 A1 Forster Et Al
US 20040121040A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0121040 A1 Forster et al. (43) Pub. Date: Jun. 24, 2004 (54) METHOD OF PRODUCING A (21) Appl. No.: 10/724,237 XANTHOHUMOL-CONCENTRATED HOP EXTRACTED AND USE THEREOF (22) Filed: Dec. 1, 2003 (75) Inventors: Adrian Forster, Wolnzach (DE); Josef (30) Foreign Application Priority Data Schulmeyr, Wolnzach (DE); Roland Schmidt, Wolnzach (DE); Karin Nov. 30, 2002 (DE)..................................... 102 56 O31.5 Simon, Pfaffenhofen (DE); Martin O O Ketterer, Wolnzach (DE); Birgit Publication Classification Forchhammer, Neustadt (DE); Stefan 7 Geyer, Wolnzach (DE); Manfred s - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - close Gehrig, Woln Zach (DE) ( ) O O - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - f Correspondence Address: (57) ABSTRACT BROWDY AND NEIMARK, P.L.L.C. 624 NINTH STREET, NW SUTE 300 In a method of producing a Xanthohumol-concentrated hop WASHINGTON, DC 20001-5303 (US) extract, the Xanthohumol-containing hop extract is extracted from a Xanthohumol-containing hop raw material by highly (73) Assignee: NATECO2 GMBH & CO. KG, Woln compressed CO as a solvent at pressures above 500 bar and Zach (DE) temperatures above 60° C. US 2004/O121040 A1 Jun. 24, 2004 METHOD OF PRODUCING A the finished beer or other kinds of food or used by itself as XANTHOHUMOL-CONCENTRATED HOP a chemo-preventive preparation. EXTRACTED AND USE THEREOF 0010 Presently, there are two prior art solutions. DE 199 39350 A1 describes a method of producing a xanthohumol BACKGROUND OF THE INVENTION enriched hop extract, with combinations of water and etha nol being used preferably in two steps of extraction. 5 to 15 0001) 1. Field of the Invention percent by weight of Xanthohumol are specified as being 0002 The invention relates to a method of producing a typical. -
Hops – a Guide for New Growers 2017
Hops – a guide for new growers 2017 growers new – a guide for Hops Hops a guide for new growers FIRST EDITION 2017 first edition 2017 Author: Kevin Dodds www.dpi.nsw.gov.au Hops a guide for new growers Kevin Dodds Development Officer – Temperate Fruits NSW Department of Primary industries ©NSW Department of Primary Industries 2017 Published by NSW Department of Primary Industries, a part of NSW Department of Industry, Skills and Regional Development You may copy, distribute, display, download and otherwise freely deal with this publication for any purpose, provided that you attribute NSW Department of Industry, Skills and Regional Development as the owner. However, you must obtain permission if you wish to charge others for access to the publication (other than at cost); include the publication advertising or a product for sale; modify the publication; or republish the publication on a website. You may freely link to the publication on a departmental website. First published March 2017 ISBN print: 978‑1‑76058‑007‑0 web: 978‑1‑76058‑008‑7 Always read the label Users of agricultural chemical products must always read the Job number 14293 label and any permit before using the product and strictly comply with the directions on the label and the conditions of Author any permit. Users are not absolved from any compliance with Kevin Dodds, Development Officer Temperate Fruits the directions on the label or the conditions of the permit NSW Department of Primary Industries by reason of any statement made or omitted to be made in 64 Fitzroy Street TUMUT NSW 2720 this publication. -
L-Citrulline
L‐Citrulline Pharmacy Compounding Advisory Committee Meeting November 20, 2017 Susan Johnson, PharmD, PhD Associate Director Office of Drug Evaluation IV Office of New Drugs L‐Citrulline Review Team Ben Zhang, PhD, ORISE Fellow, OPQ Ruby Mehta, MD, Medical Officer, DGIEP, OND Kathleen Donohue, MD, Medical Officer, DGIEP, OND Tamal Chakraborti, PhD, Pharmacologist, DGIEP, OND Sushanta Chakder, PhD, Supervisory Pharmacologist, DGIEP, OND Jonathan Jarow, MD, Advisor, Office of the Center Director, CDER Susan Johnson, PharmD, PhD, Associate Director, ODE IV, OND Elizabeth Hankla, PharmD, Consumer Safety Officer, OUDLC, OC www.fda.gov 2 Nomination • L‐citrulline has been nominated for inclusion on the list of bulk drug substances for use in compounding under section 503A of the Federal Food, Drug and Cosmetic Act (FD&C Act) • It is proposed for oral use in the treatment of urea cycle disorders (UCDs) www.fda.gov 3 Physical and Chemical Characterization • Non‐essential amino acid, used in the human body in the L‐form • Well characterized substance • Soluble in water • Likely to be stable under ordinary storage conditions as solid or liquid oral dosage forms www.fda.gov 4 Physical and Chemical Characterization (2) • Possible synthetic routes – L‐citrulline is mainly produced by fermentation of L‐arginine as the substrate with special microorganisms such as the L‐arginine auxotrophs arthrobacterpa rafneus and Bacillus subtilis. – L‐citrulline can also be obtained through chemical synthesis. The synthetic route is shown in the scheme below. This -
10/12/2019 Herbal Preparations with Phytoestrogens- Overview of The
Herbal preparations with phytoestrogens- overview of the adverse drug reactions Introduction For women suffering from menopausal symptoms, treatment is available if the symptoms are particularly troublesome. The main treatment for menopausal symptoms is hormone replacement therapy (HRT), although other treatments are also available for some of the symptoms (1). In recent years, the percentage of women taking hormone replacement therapy has dropped (2, 3). Many women with menopausal symptoms choose to use dietary supplements on a plant-based basis, probably because they consider these preparations to be "safe" (4). In addition to product for relief of menopausal symptoms, there are also preparations on the market that claim to firm and grow the breasts by stimulating the glandular tissue in the breasts (5). All these products contain substances with an estrogenic activity, also called phytoestrogens. These substances are found in a variety of plants (4). In addition, also various multivitamin preparations are on the market that, beside the vitamins and minerals, also contain isoflavonoids. Because those are mostly not specified and present in small quantities and no estrogenic effect is to be expected, they are not included in this overview. In 2015 and 2017 the Netherlands Pharmacovigilance Centre Lareb informed the Netherlands Food and Consumer Product Safety Authority (NVWA) about the received reports of Post-Menopausal Vaginal Hemorrhage Related to the Use of a Hop-Containing Phytotherapeutic Products MenoCool® and Menohop® (6, 7). Reports From September 1999 until November 2019 the Netherlands Pharmacovigilance Centre Lareb received 51 reports of the use of phytoestrogen containing preparations (see Appendix 1). The reports concern products with various herbs to which an estrogenic effect is attributed. -
On the Origin of Hops: Genetic Variability, Phylogenetic Relationships, and Ecological Plasticity of Humulus (Cannabaceae)
ON THE ORIGIN OF HOPS: GENETIC VARIABILITY, PHYLOGENETIC RELATIONSHIPS, AND ECOLOGICAL PLASTICITY OF HUMULUS (CANNABACEAE) A DISSERTATION SUBMITTED TO THE GRADUATE DIVISION OF THE UNIVERSITY OF HAWAI‘I AT MĀNOA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN BOTANY MAY 2014 By Jeffrey R. Boutain DISSERTATION COMMITTEE: Will C. McClatchey, Chairperson Mark D. Merlin Sterling C. Keeley Clifford W. Morden Stacy Jørgensen Copyright © 2014 by Jeffrey R. Boutain ii This dissertation is dedicated to my family tree. iii ACKNOWLEDGEMENTS There are a number of individuals to whom I am indebted in many customs. First and foremost, I thank my committee members for their contribution, patience, persistence, and motivation that helped me complete this dissertation. Specifically, thank you Dr. Will McClatchey for the opportunity to study in a botany program with you as my advisor and especially the encouragement to surf plant genomes. Also with great gratitude, thank you Dr. Sterling Keeley for the opportunity to work on much of this dissertation in your molecular phylogenetics and systematics lab. In addition, thank you Dr. Mark Merlin for numerous brainstorming sessions as well as your guidance and expert perspective on the Cannabaceae. Also, thank you Dr. Cliff Morden for the opportunity to work in your lab where the beginnings of this molecular research took place. Thank you Dr. Jianchu Xu for welcoming me into your lab group at the Kunming Institute of Botany, Chinese Academy of Sciences (CAS) and the opportunity to study the Yunnan hop. In many ways, major contributions towards the completion of this dissertation have come from my family, and I thank you for your unconditional encouragement, love, and support. -
Hop Compounds: Extraction Techniques, Chemical Analyses, Antioxidative, Antimicrobial, and Anticarcinogenic Effects
nutrients Review Hop Compounds: Extraction Techniques, Chemical Analyses, Antioxidative, Antimicrobial, and Anticarcinogenic Effects Maša Knez Hrnˇciˇc 1,†, Eva Španinger 2,†, Iztok Jože Košir 3, Željko Knez 1 and Urban Bren 2,* 1 Laboratory of Separation Processes and Product Design, Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova ulica 17, SI-2000 Maribor, Slovenia; [email protected] (M.K.H.); [email protected] (Ž.K.) 2 Laboratory of Physical Chemistry and Chemical Thermodynamics, Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova ulica 17, SI-2000 Maribor, Slovenia; [email protected] 3 Slovenian Institute of Hop Research and Brewing, Cesta Žalskega Tabora 2, SI-3310 Žalec, Slovenia; [email protected] * Correspondence: [email protected]; Tel.: +386-2-2294-421 † These authors contributed equally to this work. Received: 7 December 2018; Accepted: 18 January 2019; Published: 24 January 2019 Abstract: Hop plants comprise a variety of natural compounds greatly differing in their structure and properties. A wide range of methods have been developed for their isolation and chemical analysis, as well as for determining their antioxidative, antimicrobial, and antigenotoxic potentials. This contribution provides an overview of extraction and fractionation techniques of the most important hop compounds known for their health-promoting features. Although hops remain the principal ingredient for providing the taste, stability, and antimicrobial protection of beer, they have found applications in the pharmaceutical and other food industries as well. This review focuses on numerous health-promoting effects of hops raging from antioxidative, sedative, and anti-inflammatory potentials, over anticarcinogenic features to estrogenic activity.