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Sunlight-Driven Environmental Benign Production of Bioactive Natural Products with Focus on Diterpenoids and the Pathways Involved in Their Formation
Natural Products: source of INNovatIoN CHIMIA 2017, 71, No. 12 851 doi:10.2533/chimia.2017.851 Chimia 71 (2017) 851–858 © Swiss Chemical Society Sunlight-driven Environmental Benign Production of Bioactive Natural Products with Focus on Diterpenoids and the Pathways Involved in their Formation Dan Luo, Birger Lindberg Møller, and Irini Pateraki* Abstract: Diterpenoids are high value compounds characterized by high structural complexity. They constitute the largest class of specialized metabolites produced by plants. Diterpenoids are flexible molecules able to engage in specific binding to drug targets like receptors and transporters. In this review we provide an account on how the complex pathways for diterpenoids may be elucidated. Following plant pathway discovery, the com- pounds may be produced in heterologous hosts like yeasts and E. coli. Environmentally contained production in photosynthetic cells like cyanobacteria, green algae or mosses are envisioned as the ultimate future production system. Keywords: Alcohol dehydrogenases · Cytochrome P450s · Ingenol mebutate · Light-driven production · Terpene synthases 1. Introduction anticancer agent widely used today as a Coleus forskohlii, is used in the treatment therapeutic in combinatorial treatments of glaucoma and heart failure based on 1.1 Plant Diterpenoids and their of ovarian cancer, breast cancer, lung can- its activity as a cyclic AMP booster.[8,9] Application as Pharmaceuticals cer, Kaposi sarcoma, cervical cancer, and Ginkgolides from the leaves of Ginkgo bi- Plants produce a wide variety of natural pancreatic cancer.[6,7] Forskolin, a labdane- loba L. are a series of diterpene lactones products that play important roles in both type diterpene produced from the roots of with anti-platelet-activating antagonist ac- general and specialized metabolism.[1,2] Terpenoids constitute the largest and most diverse class of bio-active natural prod- Fig 1. -
Thesis-1966D-R342b.Pdf
I I THE BIOSYNTHESIS OF NEPETALACTONE By FREDERICK EUGENE REGNIER 01 Bachelor of Science Peru State College Peru, Nebraska 1960 Submitted to the Faculty of the Graduate School of the Oklahoma State University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY May, 1966 THE BIOSYNTHESIS OF NEPETALACTONE Thesis Approved: l/ ~;==chool ii ACKNOWLEDGEMENTS The author wishes to express his gratitude and appreciation to: Dr. G. R. Waller and Dr. E. J. Eisenbraun for their guidance, counsel and assistance during the course of this study. Dr. E. C. Horning for placing the combined mass spectrometer-gas chromatograph at my disposal. Mr. Sten Wikstrom for his technical assistance in operating the mass spectrometer. Dr. M. H. Brooks for her assistance in the histological studies. Dr. W. R. Kays for providing plant material. Dr. V. T. Waterfall for making botanical classification. Dr. H. Auda and Mr. G. V. Odell for their suggestions and technical assistance. Mrs. Linda M. Regnier for her assistance and encouragement during this study. iii TABLE OF CONTENTS Chapter Page I. INTRODUCTION 1 II. LITERATURE REVIEW 3 III. COMPOSITION OF THE ESSENTIAL OIL OF NEPETA cataria L.. 13 IV. THE DISTRIBUTION AND ANALYSIS OF NEPETALACTONE ISOMERS FROM DIFFERENT NEPETA SPECIES 54 V. THE BIOSYNTHESIS OF NEPETALACTONE 70 VI. SUMMARY 103 BIBLIOGRAPHY 105 iv LIST OF TABLES Table Page CHAPTER III I. Tabulation of the Intense Ions in the Spectra of the Compounds in Fraction A 21+ II. Tabulation of the Intense Ions in the Spectra of the Compounds in Fraction B 27 III. Tabulation of the Intense Ions in the Spectrum of Sample c4 . -
A Splodesheetablished Online in 2010
USOO8685381 B2 (12) United States Patent (10) Patent No.: US 8,685,381 B2 Schlessinger et al. (45) Date of Patent: Apr. 1, 2014 (54) TOPICAL BASE AND ACTIVE 4,346,086 A 8, 1982 Sattler et al. .................. 514f179 AGENTCONTAINING COMPOSITIONS, AND 25.6; A . 3. signe et al. :g - ww. Oil ......... E. RMPROVING AND 4,393,044 A 7/1983 Takada et all ... 424/64 4.478,853. A 10, 1984 Chaussee ... 514,772 4496,554 A 1/1985 Wong......... 514, 179 (76) Inventors: Joel Schlessinger, Omaha, NE (US); 4,504,465. A 3/1985 Sampson et al. ... 424/65 Daniel Isaac Schlessinger, Omaha, NE 4,610,978 A 9, 1986 Dikstein et al. 51446 (US) 263 A 38; unniSNi et A" 33 c 4,702,916 A 10, 1987 Geria ......... ... 424/400 (*) Notice: Subject to any disclaimer, the term of this 4,847,069 A 7, 1989 Bissett et al. ... 424/47 patent is extended or adjusted under 35 4,847,071 A 7, 1989 Bissett et al. 424,59 U.S.C. 154(b) by 0 days. 4,847,072 A 7, 1989 Bissett .......... ... 424,59 4,879,274 A 11, 1989 Kamiya et al. ... 424/780 (21) Appl. No.: 13/233,012 is: A 1982 alm 5:8: 4,902,682 A 2f1990 Sattler ........ 514, 179 (22) Filed: Sep. 14, 2011 4,996,044 A * 2/1991 Mercado et al. ... 424/64 5,061,700 A 10, 1991 Dow et al. ..... 514,169 (65) Prior Publication Data 5,185,150 A 2f1993 DeLuca et al. ... 424/401 5,254,109 A 10, 1993 Smith et al. -
Drug Metabolism Chemical and Enzymatic Aspects Textbook Edition
DRUG METABOLISM Chemical and Enzymatic Aspects TEXTBOOK EDITION Jack P. Uetrecht University of Toronto Ontario, Canada William Trager University of Washington Seattle, Washington, USA Uetrecht_978-1420061031_TP.indd 2 5/11/07 2:28:26 PM OTE/SPH OTE/SPH uetrecht IHUS001-Uetrecht May 10, 2007 3:29 Char Count= Informa Healthcare USA, Inc. 52 Vanderbilt Avenue New York, NY 10017 C 2007 by Informa Healthcare USA, Inc. Informa Healthcare is an Informa business No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10987654321 International Standard Book Number-10: 1-4200-6103-8 International Standard Book Number-13: 978-1-4200-6103-1 This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequence of their use. No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechan- ical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC) 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registra- tion for a variety of users. -
Acyclic Monoterpene Primary Alcohol :NADP+ Oxidoreductase of Rauwolfia Serpentina Cells: the Key Enzyme in Biosynthesis of Monoterpene Alcohols
J. Biochem. 109, 341-347 (1991) Acyclic Monoterpene Primary Alcohol :NADP+ Oxidoreductase of Rauwolfia serpentina Cells: The Key Enzyme in Biosynthesis of Monoterpene Alcohols Hiromitsu Ikeda, * Nobuyoshi Esaki, ** Shunji Nakai, * Keij i Hashimoto, Shinichi Uesato,*•' Kenji Soda,** and Tetsuro Fujita*2 *Department of Natural Product Chemistry , Faculty of Pharmaceutical Sciences,Kyoto University,Sakyo-ku, Kyoto, Kyoto 606; **Laboratory of Microbial Biochemistry,Institute for ChemicalResearch, Kyoto University, Uji, Kyoto 611; and *`'Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Kyoto 607 Received for publication, August 1, 1990 Acyclic monoterpene primary alcohol: NADP+ oxidoreductase, a key enzyme in the biosynthesis of monoterpene alcohols in plants, is unstable and has been only poorly characterized. However we have established conditions which stabilize the enzyme from Rauwolfza serpentina cells, and then purified it to homogeneity. It is a monomer with a molecular weight of about 44,000 and contains zinc ions. Various branched-chain allylic primary alcohols such as nerol, geraniol, and 10-hydroxygeraniol were substrates, but ethanol was inert. The enzyme exclusively requires NADP+ or NADPH as the cofactor. Steady-state kinetic studies showed that the nerol dehydrogenation proceeds by an ordered Bi-Bi mechanism. NADP+ binds the enzyme first and then NADPH is the second product released from it. Gas chromatography-mass spectrometric analysis of the reaction products showed that 10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 10-oxogeraniol or 10-hydroxygeranial, which are oxidized further to give 10-oxogeranial, the direct precursor of iridodial. The enzyme has been found to exclusively transfer the pro-R hydrogen of NADPH to neral. The N-terminal sequence of the first 21 amino acids revealed no significant homology with those of various other proteins including the NAD(P)+-dependent alcohol dehydrogenases registered in a protein data bank. -
The Wonderful Activities of the Genus Mentha: Not Only Antioxidant Properties
molecules Review The Wonderful Activities of the Genus Mentha: Not Only Antioxidant Properties Majid Tafrihi 1, Muhammad Imran 2, Tabussam Tufail 2, Tanweer Aslam Gondal 3, Gianluca Caruso 4,*, Somesh Sharma 5, Ruchi Sharma 5 , Maria Atanassova 6,*, Lyubomir Atanassov 7, Patrick Valere Tsouh Fokou 8,9,* and Raffaele Pezzani 10,11,* 1 Department of Molecular and Cell Biology, Faculty of Basic Sciences, University of Mazandaran, Babolsar 4741695447, Iran; [email protected] 2 University Institute of Diet and Nutritional Sciences, Faculty of Allied Health Sciences, The University of Lahore, Lahore 54600, Pakistan; [email protected] (M.I.); [email protected] (T.T.) 3 School of Exercise and Nutrition, Deakin University, Victoria 3125, Australia; [email protected] 4 Department of Agricultural Sciences, University of Naples Federico II, 80055 Portici (Naples), Italy 5 School of Bioengineering & Food Technology, Shoolini University of Biotechnology and Management Sciences, Solan 173229, India; [email protected] (S.S.); [email protected] (R.S.) 6 Scientific Consulting, Chemical Engineering, University of Chemical Technology and Metallurgy, 1734 Sofia, Bulgaria 7 Saint Petersburg University, 7/9 Universitetskaya Emb., 199034 St. Petersburg, Russia; [email protected] 8 Department of Biochemistry, Faculty of Science, University of Bamenda, Bamenda BP 39, Cameroon 9 Department of Biochemistry, Faculty of Science, University of Yaoundé, NgoaEkelle, Annex Fac. Sci., Citation: Tafrihi, M.; Imran, M.; Yaounde 812, Cameroon 10 Phytotherapy LAB (PhT-LAB), Endocrinology Unit, Department of Medicine (DIMED), University of Padova, Tufail, T.; Gondal, T.A.; Caruso, G.; Via Ospedale 105, 35128 Padova, Italy Sharma, S.; Sharma, R.; Atanassova, 11 AIROB, Associazione Italiana per la Ricerca Oncologica di Base, 35128 Padova, Italy M.; Atanassov, L.; Valere Tsouh * Correspondence: [email protected] (G.C.); [email protected] (M.A.); [email protected] (P.V.T.F.); Fokou, P.; et al. -
High Throughput Search of Drought Tolerant Genes in Agave Sisalana L
High Throughput Search of Drought Tolerant Genes in Agave sisalana L. SANIA RIAZ CENTRE OF EXCELLENCE IN MOLECULAR BIOLOGY UNIVERSITY OF THE PUNJAB LAHORE PAKISTAN (2015) High Throughput Search of Drought Tolerant Genes in Agave sisalana L. A THESIS SUBMITTED TO UNIVERSITY OF THE PUNJAB IN FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN MOLECULAR BIOLOGY By SANIA RIAZ Supervisor: Dr. Tayyab Husnain (Prof & Acting Director) Centre of Excellence in Molecular Biology. University of the Punjab, Lahore CERTIFICATE It is certified that the research work described in this thesis is the original work of the author Ms. Sania Riaz and has been carried out under my direct supervision. I have personally gone through all the data reported in the manuscript and certify their correctness and authenticity. It is further certified that the material included in this thesis have not been used in part or full manuscript already submitted or in the process of submission in partial/complete fulfillment of the award of any other degree from any other institution. It is also certified that the thesis has been prepared under my supervision according to the prescribed format and we endorse its evaluation for the award of Ph.D degree through the official procedures of the university. In accordance with the rules of the centre, data book #852 is declared as unexpendable document that will be kept in the registry of the Centre for a minimum of three years from the date of the Thesis defense examination. Signature of the supervisor________________________________ Name: Dr. Tayyab Husnain Designation: Prof & Acting Director (Allah) Most Gracious! It is He Who has taught the Qur'an. -
Downloaded from Uniprotkb/Swiss-Prot ( and Concatenated with the Reverse One
International Journal of Molecular Sciences Article Root Proteomic Analysis of Two Grapevine Rootstock Genotypes Showing Different Susceptibility to Salt Stress Bhakti Prinsi , Osvaldo Failla , Attilio Scienza and Luca Espen * Department of Agricultural and Environmental Sciences—Production, Landscape, Agroenergy (DiSAA), Università degli Studi di Milano, Via Celoria 2, 20133 Milano, Italy; [email protected] (B.P.); [email protected] (O.F.); [email protected] (A.S.) * Correspondence: [email protected]; Tel.: +39-02-503-16610 Received: 21 December 2019; Accepted: 4 February 2020; Published: 6 February 2020 Abstract: Salinity represents a very limiting factor that affects the fertility of agricultural soils. Although grapevine is moderately susceptible to salinity, both natural causes and agricultural practices could worsen the impact of this abiotic stress. A promising possibility to reduce this problem in vineyards is the use of appropriate graft combinations. The responses of grapevine rootstocks to this abiotic stress at the root level still remain poorly investigated. In order to obtain further information on the multifaceted responses induced by salt stress at the biochemical level, in the present work we analyzed the changes that occurred under control and salt conditions in the root proteomes of two grapevine rootstock genotypes, M4 and 101.14. Moreover, we compared the results considering that M4 and 101.14 were previously described to have lower and higher susceptibility to salt stress, respectively. This study highlighted the greater capability of M4 to maintain and adapt energy metabolism (i.e., synthesis of ATP and NAD(P)H) and to sustain the activation of salt-protective mechanisms (i.e., Na sequestration into the vacuole and synthesis of osmoprotectant compounds). -
Deciphering the Genome Repertoire of Pseudomonas Sp. M1 Toward B-Myrcene Biotransformation
GBE Deciphering the Genome Repertoire of Pseudomonas sp. M1 toward b-Myrcene Biotransformation Pedro Soares-Castro and Pedro M. Santos* CBMA—Centre of Molecular and Environmental Biology, Department of Biology, University of Minho, Campus de Gualtar, Braga, Portugal *Corresponding author: E-mail: [email protected]. Accepted: November 21, 2014 Data deposition: The Whole Genome Shotgun project of Pseudomonas sp. M1 has been deposited at DNA Data Bank of Japan/EMBL/GenBank under the accession ANIR00000000. The version described in this paper is ANIR00000000.2. Abstract Pseudomonas sp. M1 is able to mineralize several unusual substrates of natural and xenobiotic origin, contributing to its competence to thrive in different ecological niches. In this work, the genome of M1 strain was resequenced by Illumina MiSeq to refine the quality of a published draft by resolving the majority of repeat-rich regions. In silico genome analysis led to the prediction of metabolic pathways involved in biotransformation of several unusual substrates (e.g., plant-derived volatiles), providing clues on the genomic complement required for such biodegrading/biotransformation functionalities. Pseudomonas sp. M1 exhibits a particular sensory and biotransformation/biocatalysis potential toward b-myrcene, a terpene vastly used in industries worldwide. Therefore, the genomic responsiveness of M1 strain toward b-myrcene was investigated, using an RNA sequencing approach. M1 cells challenged with b-myrcene(compared with cells grown in lactate) undergo an extensive alteration of the transcriptome expression profile, including 1,873 genes evidencing at least 1.5-fold of altered expression (627 upregulated and 1,246 downregulated), toward b-myrcene- imposed molecular adaptation and cellular specialization. -
Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Migraine
Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Migraine Chemical Activity Count (+)-ALLOMATRINE 1 (+)-ALPHA-VINIFERIN 1 (+)-BORNYL-ISOVALERATE 1 (+)-CATECHIN 3 (+)-EUDESMA-4(14),7(11)-DIENE-3-ONE 1 (+)-GALLOCATECHIN 1 (+)-HERNANDEZINE 1 (+)-ISOCORYDINE 3 (+)-PSEUDOEPHEDRINE 1 (+)-T-CADINOL 1 (-)-16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 (-)-ALPHA-BISABOLOL 3 (-)-ANABASINE 1 (-)-APOGLAZIOVINE 1 (-)-ARGEMONINE 1 (-)-BETONICINE 1 (-)-BORNYL-CAFFEATE 1 (-)-BORNYL-FERULATE 1 (-)-BORNYL-P-COUMARATE 1 (-)-DICENTRINE 2 (-)-EPIAFZELECHIN 1 (-)-EPICATECHIN 2 (-)-EPIGALLOCATECHIN-GALLATE 1 (1'S)-1'-ACETOXYCHAVICOL-ACETATE 1 (15:1)-CARDANOL 1 (E)-4-(3',4'-DIMETHOXYPHENYL)-BUT-3-EN-OL 1 0-METHYLCORYPALLINE 2 Chemical Activity Count 1,7-BIS-(4-HYDROXYPHENYL)-1,4,6-HEPTATRIEN-3-ONE 1 1,8-CINEOLE 7 10-ACETOXY-8-HYDROXY-9-ISOBUTYLOXY-6-METHOXYTHYMOL 1 10-DEHYDROGINGERDIONE 1 10-GINGERDIONE 1 11-HYDROXY-DELTA-8-THC 1 11-HYDROXY-DELTA-9-THC 1 12,118-BINARINGIN 1 12-ACETYLDEHYDROLUCICULINE 1 12-METHOXYDIHYDROCOSTULONIDE 1 13',II8-BIAPIGENIN 1 13-OXYINGENOL-ESTER 1 14-ACETOXYCEDROL 1 16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 16-EPIMETHUENINE 1 16-HYDROXYINGENOL-ESTER 1 2'-HYDROXY-FLAVONE 1 2'-O-GLYCOSYLVITEXIN 1 2-BETA,3BETA-27-TRIHYDROXYOLEAN-12-ENE-23,28-DICARBOXYLIC-ACID 1 2-METHYLBUT-3-ENE-2-OL 2 2-NAPTHOL 1 20-DEOXYINGENOL-ESTER 1 22BETA-ESCIN 1 24-METHYLENE-CYCLOARTANOL 2 3,4-DIMETHOXYTOLUENE 1 3,4-METHYLENE-DIOXYCINNAMIC-ACID-BORNYL-ESTER 2 3,4-SECOTRITERPENE-ACID-20-EPI-KOETJAPIC-ACID 1 2 Chemical Activity Count 3-ACETYLACONITINE -
Alternative Treatments for Cancer Prevention and Cure [Part 1]
Advances in Pharmacology and Clinical Trials ISSN: 2474-9214 Alternative Treatments for Cancer Prevention and Cure [Part 1] Abdul Kader Mohiuddin* Review Article Secretary & Treasurer Dr M. Nasirullah Memorial Trust, Tejgaon, Dhaka, Bangladesh Volume 4 Issue 4 Received Date: September 02, 2019 *Corresponding author: Abdul Kader Mohiuddin, Secretary & Treasurer Dr M Published Date: October 17, 2019 Nasirullah Memorial Trust, Tejgaon, Dhaka, Bangladesh, Tel: +8802-9110553; Email: DOI: 10.23880/apct-16000168 [email protected] Abstract Many lay people along with some so called “key opinion leaders” have a common slogan “There's no answer for cancer”. Again, mistake delays proper treatment and make situation worse, more often. Compliance is crucial to obtain optimal health outcomes, such as cure or improvement in QoL. Patients may delay treatment or fail to seek care because of high out-of- pocket expenditures. Despite phenomenal development, conventional therapy falls short in cancer management. There are two major hurdles in anticancer drug development: dose-limiting toxic side effects that reduce either drug effectiveness or the QoL of patients and complicated drug development processes that are costly and time consuming. Cancer patients are increasingly seeking out alternative medicine and might be reluctant to disclose its use to their oncology treatment physicians. But there is limited available information on patterns of utilization and efficacy of alternative medicine for patients with cancer. As adjuvant therapy, many traditional medicines shown efficacy against brain, head and neck, skin, breast, liver, pancreas, kidney, bladder, prostate, colon and blood cancers. The literature reviews non-pharmacological interventions used against cancer, published trials, systematic reviews and meta-analyses. -
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cover next page > Cover title: The Psychopharmacology of Herbal Medicine : Plant Drugs That Alter Mind, Brain, and Behavior author: Spinella, Marcello. publisher: MIT Press isbn10 | asin: 0262692651 print isbn13: 9780262692656 ebook isbn13: 9780585386645 language: English subject Psychotropic drugs, Herbs--Therapeutic use, Psychopharmacology, Medicinal plants--Psychological aspects. publication date: 2001 lcc: RC483.S65 2001eb ddc: 615/.788 subject: Psychotropic drugs, Herbs--Therapeutic use, Psychopharmacology, Medicinal plants--Psychological aspects. cover next page > < previous page page_i next page > Page i The Psychopharmacology of Herbal Medicine < previous page page_i next page > cover next page > Cover title: The Psychopharmacology of Herbal Medicine : Plant Drugs That Alter Mind, Brain, and Behavior author: Spinella, Marcello. publisher: MIT Press isbn10 | asin: 0262692651 print isbn13: 9780262692656 ebook isbn13: 9780585386645 language: English subject Psychotropic drugs, Herbs--Therapeutic use, Psychopharmacology, Medicinal plants--Psychological aspects. publication date: 2001 lcc: RC483.S65 2001eb ddc: 615/.788 subject: Psychotropic drugs, Herbs--Therapeutic use, Psychopharmacology, Medicinal plants--Psychological aspects. cover next page > < previous page page_ii next page > Page ii This page intentionally left blank. < previous page page_ii next page > < previous page page_iii next page > Page iii The Psychopharmacology of Herbal Medicine Plant Drugs That Alter Mind, Brain, and Behavior Marcello Spinella < previous page page_iii next page > < previous page page_iv next page > Page iv © 2001 Massachusetts Institute of Technology All rights reserved. No part of this book may be reproduced in any form by any electronic or mechanical means (including photocopying, recording, or information storage and retrieval) without permission in writing from the publisher. This book was set in Adobe Sabon in QuarkXPress by Asco Typesetters, Hong Kong and was printed and bound in the United States of America.