DOCSLIB.ORG

Aerobic Microbial Transformations of Sterols and Steroids, a Personal Approach Bernardo Servín-Massieu CONTENTS Overview the Fo

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Aerobic Microbial Transformations of Sterols and Steroids, a Personal Approach Bernardo Servín-Massieu CONTENTS Overview the Fo Aerobic Microbial Transformations of Sterols and Steroids, a personal Approach Bernardo Servín-Massieu CONTENTS Overview The following article has the purpose to publish a malicious bias to give the impression that the development of the steroid industry in Mexico was only the contribution from alumni from the National School of Chemistry Sciences and the Chemistry Institute, both belonging to the National Autonomous University of Mexico in Mexico City promoted by the Mexican Chemistry Society. Not at all, alumni from the National School of Biological Sciences from the National Polytechnic Institute in Mexico City made a substantial contribution to the aerobic microbial transformation of, initially steroid molecules and afterwards in the microbial transformation of sterols. In the 1940’s of the XX century Russell E. Marker designed the transformation of diosgenin to progesterone using wild yams collected in the Metlac ravine near the town of Orizaba in the state of Veracruz about 200 miles east Mexico City. It is known as Marker’s degradation being the kick-off of a new industry in Mexico. These yams were from Dioscorea mexicana known by the local inhabitants as “cabeza de negro” negro’s head, a vine that grows wild in moist subtropical forest in Veracruz, Puebla, Chiapas and Oaxaca states, further along Marker discovered that “Barbasco” Dioscorea compositae and Dioscorea floribunda contained higher contents of diosgenin. Marker consulted the Mexico City yellow pages after checking at the Hotel Geneve, London Street, Pink Zone and found an entry “Laboratorios Hormona, S.A.”, he called Federico Lehmann and agreed to meet. It can be said that the steroid industry boom in Mexico was indirectly due to Adolph Hitler’s Nazism and Francisco Franco’s Fascism that respectively caused the Jewish diaspora in Germany and “refugiados” after the socialist civil war in Spain. Laboratorios Hormona was founded by Federico Lehmann (Germany) and Emeric Somlo (Hungary) and in there team was Jose Erdos (hungary), Francisco Giral, E. Muñoz-Mena, A. Medinaveytia, J. Viró, L. Abramson from Spain, and C. Widmer, a Swiss citizen. During the 1930s-1940s period the only sea port of entry from Europe to Mexico was Veracruz, founded by Hernán Cortés in 1519, via Havana Cuba. Lehmann, Marker and Somlo founded a new company that was called Syntex ( from Synthesis and Mexico), after Marker left, S. Kauffman, G. Rosenkranz and J. Pataki joined Syntex and were able to reproduce Marker’s degradation, that was the beginning of Syntex boom. The operation was set in the outskirts of Mexico City in the Molino de Bezares borough on the road to Toluca. Additionaly the yams were processed in the Ojo de Agua plant in Ixtaczoquitlán, Ver. Near Orizaba, that later was merged by Schering AG Berlin and nowadays is part of Bayer Germany, called PROQUINA (Productos Químicos Naturales). Research: After The Upjohn Company researchers in Kalamazoo, Mich. Discovered that molds could transform the steroid nucleus by microbial hydroxylating carbon 11, among other molds, species of genus Rhizopus could commercially perform in one step this reaction in replacement of the organic chemistry synthesis reactions that could be done in many steps and very small yields, Syntex, began exploring this and other reactions with a wide range of bacteria and mold genera. At Syntex, S.A., Mexico City during the 1950-1960 period a microbial research team formed part of the Syntex Research Division in the outskirts of Mexico City. This group was leaded by Carlos Casas-Campillo, integrated by Fernando Esparza-García, Dora Balandrano, Alfonso Galarza, Ignacio Magaña-Plaza, José Ruiz-Herrera, Miguel Bautista-Susunaga, and several interns from which Bernardo Servín-Massieu and Luis Jiménez-Zamudio formed part. About 50 patents were granted to this group in Mexico, USA, Canada, England, Holland, Japan, Switzerland, France and Germany. Microorganisms of several genera were studied: Panaeolus, Fusarium, Psilocybe, Arthrobacter (Corunebacterium, Mycobacterium, Rhizopus, Curvularia, Streptomyces, Arthrobotrys, Rhizobium, Fusarium, Streptomyces, Mycecoccus. The following substrates were studied: Progesterone (21-hydroxylation); Progesterone as an antimicrobial agent; 19-norprogesterone (11-alpha hydroxylation); 21-21 dimethoxy progesterone antimicrobial properties;19-nortestorenone (1-2 dehydrogenation); Reichstein compound S (11-beta and 6-beta hydroxylation); Reichstein Compound (11-beta hydroxylation); Estrane derivatives (Hydroxylation). The reader should consult Charney & Herzog for details. At Searle de México, S.A. after Marker left Syntex, A group of researchers and engineers formed Productos Esteroides, S.A. (PESA), this company was merged by G.D. Searle of Skokie, Ill. A research group was formed originally led by Luis E. Miramontes-Cárdenas that initially did research on the microbial transformation of dioscin in barbasco yams and the production of glucose oxidase by Aspergillus niger. Luis Miramontes left, and I took the microbiology research team leadership supervised by Robert P. Graber, and a change in scope towards the evaluation of Mycobacteria in the transformation of sterols to AD (4- Androstene-3,17-Dione) and ADD (1,4-Androstadiene-3,17-Dione) as start-up compounds for the synthesis of Spironolactone (7-(Acetylthio)-17-hydroxy-3-oxo-pregn-4-ene-21-carboxylic acid), a major market drug by Searle as Aldactone©®. Among others, this group was formed by Javier Hebrero-Rodríguez, Gilberto García-Gutiérrez, Alejandro Canale-Guerrero, Felipe M. Vera-Solís, Silvia Calva-Salgado. Analytical support was from Alfonso Maldonado’s chemical research group. Several species of Mycobacteria were evaluated using sterols marketed by General Mills as Generols, that are a mixture of Campesterol (24R)-Ergot-5-en-3ß-ol) and ß-Sitosterol (3ß-Stigmast-5-en-3-ol). Also, a by- product of the Upjohn Co. from the separation of Stigmasterol ((3ß,22E)-Stigmsta -5-22-dien-3-ol), that is used by Upjohn in the synthesis of PROVERA ©® , a major market drug by Upjohn. The major source from these sterols is a by-product of the edible oil industry called soapstock that after milling and or solvent extraction of the seeds, the free fatty acids are neutralized with potassium or sodium hydroxide forming a precipitate, down the refining process the high vacuum deodorization of the oil also provides more sterols depending of the oil seed consumed. The pioneering research on this sources was done by Percy Julian that accidentally soya bean oil was mixed with water from which he was able to isolate stigmasterol. Years on, Julian was involved in the Mexican steroid industry boom founding STEROMEX, that he later sold to Smith Kline and French. A thorough literature search was made as to which culture media were used for Mycobacteria and different sterol concentration levels were studied up to 500 grams/liter with several carbon and nitrogen sources combinations using factorial designs as published by Box, Draper, Wilson and others. Promising results obtained in shaked flasks , and 28 and 70 liter fermenters. In particular Mycobacterium phlei NRRL 3805. The obtained results encouraged Searle de Mexico general Manager, Dave Baird to lease a pilot plant from the Laboratori Ricerche of Società Prodotti Antibiotici S.p.A. Milano Italy. All nutrients for two runs were shipped from México to Italy except water and the strain was carried personally by me. This pilot plant consisted of 18 175 liter fermenters and the group supervised by Robert P Graber, included Javier Hebrero- Rodríguez, Gilberto García-Gutiérrez, Alfonso Maldonado and myself. After six weeks in Milan more promising results were obtained, so G.D. Searle leased an old fermentation plant from Hercules Corp. in Harbor Beach, Mich. To scale-up to 9000 liter and 200 000 liter fermenters in early 1975 the company announced the successful start-up of the plant, which reflected favorably on the stock value at Wall Street. The Mexican group to Harbor Beach consisted of Javier Hebrero-Rodríguez, Gilberto García-Gutiérrez, Alejandro Canale-Guerrero, Felipe M. Vera-Solís and myself as group leader. In late 1974 the Harbor Beach was de-mexicanized and the WASPs took over the operation. In the following years Searle de México shut-down its Chemical Division operations based on Dioscorea wild yams in Naucalpan, México and moved the synthesis of AD to Spironolactone to Gosport, England. During the 1971-1974 my group was frequently bullied by the Development group leaded by Humberto Flores and his boss Héctor Flores-Gallardo. Environmental Issues. Last but not least, the presence of steroids in the environment have become an important issue, generally known as Endocrine disruptors, cause disturbances in fauna and to some extent in flora, fish show abnormal sexual features and References: Budavari, Susan (Ed.) (1989) The Merck Index, Eleventh Edition. Merck & Company, Inc. Rahway Casas-Campillo, Carlos, visit www.colegionacional.org.mx Charney, William. & Herzog, Hershel, L. (1967) Microbial Transformations of Steroids. Academic Press, New York Esparza-García, Fernando, (2011) visit www.biotecnologia.cinvestav.mx Fahrbach, Michael (2006) Anaerobic degradation of steroid hormones by novel denitrifying bacteria, a dissertation from the Rheinnisch-Westfälischen Technischen Hochschule Aachen. Jiménez-Zamudio, Luis, (2011) visit www.sepi.encb.ipn.mx Kieslich, Klaus (1976) Microbial Transformations of Non-Steroids Cyclic Compounds. Georg Thieme Stuttgart. Lehmann, P.A. (1992) Early History of Steroid Chemistry in Mexico: the Story of Three Remarkable Men. Steroids 57(8):403-408. Martínez-Cruz, Jovita (1982) Catálogo de Cultivos Microbianos. Departamento de Biotecnología y Bioingeniería, CIEA, IPN, México, D.F. Ruiz-Herrera, José, (2011) visit www.ira.cinvestav.mx Steraloids, Inc. (1976) Steroids Catalog.
Load more

Recommended publications
  • MEDICINAL PLANTS OPIUM POPPY: BOTANY, TEA: CULTIVATION to of NORTH AFRICA Opidjd CHEMISTRY and CONSUMPTION by Loutfy Boulos
    hv'IERIGAN BCXtlNICAL COJNCIL -----New Act(uisition~---------l ETHNOBOTANY FLORA OF LOUISIANA Jllll!llll GUIDE TO FLOWERING FLORA Ed. by Richard E. Schultes and Siri of by Margaret Stones. 1991. Over PLANT FAMILIES von Reis. 1995. Evolution of o LOUISIANA 200 beautiful full color watercolors by Wendy Zomlefer. 1994. 130 discipline. Thirty-six chapters from and b/w illustrations. Each pointing temperate to tropical families contributors who present o tru~ accompanied by description, habitat, common to the U.S. with 158 globol perspective on the theory and and growing conditions. Hardcover, plates depicting intricate practice of todoy's ethnobotony. 220 pp. $45. #8127 of 312 species. Extensive Hardcover, 416 pp. $49.95. #8126 glossary. Hardcover, 430 pp. $55. #8128 FOLK MEDICINE MUSHROOMS: TAXOL 4t SCIENCE Ed. by Richard Steiner. 1986. POISONS AND PANACEAS AND APPLICATIONS Examines medicinal practices of by Denis Benjamin. 1995. Discusses Ed. by Matthew Suffness. 1995. TAXQL® Aztecs and Zunis. Folk medicine Folk Medicine signs, symptoms, and treatment of Covers the discovery and from Indio, Fup, Papua New Guinea, poisoning. Full color photographic development of Toxol, supp~. Science and Australia, and Africa. Active identification. Health and nutritional biology (including biosynthesis and ingredients of garlic and ginseng. aspects of different species. biopharmoceutics), chemistry From American Chemical Society Softcover, 422 pp. $34.95 . #8130 (including structure, detection and Symposium. Softcover, isolation), and clinical studies. 223 pp. $16.95. #8129 Hardcover, 426 pp. $129.95 #8142 MEDICINAL PLANTS OPIUM POPPY: BOTANY, TEA: CULTIVATION TO OF NORTH AFRICA OpiDJD CHEMISTRY AND CONSUMPTION by Loutfy Boulos. 1983. Authoritative, Poppy PHARMACOLOGY TEA Ed.
    [Show full text]
  • Drugs That Changed the World
    Drugs That Changed the World Drugs That Changed the World How Therapeutic Agents Shaped Our Lives Irwin W. Sherman CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2017 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper Version Date: 20160922 International Standard Book Number-13: 978-1-4987-9649-1 (Hardback) This book contains information obtained from authentic and highly regarded sources. While all reasonable efforts have been made to publish reliable data and information, neither the author[s] nor the publisher can accept any legal respon- sibility or liability for any errors or omissions that may be made. The publishers wish to make clear that any views or opinions expressed in this book by individual editors, authors or contributors are personal to them and do not neces- sarily reflect the views/opinions of the publishers. The information or guidance contained in this book is intended for use by medical, scientific or health-care professionals and is provided strictly as a supplement to the medical or other professional’s own judgement, their knowledge of the patient’s medical history, relevant manufacturer’s instructions and the appropriate best practice guidelines. Because of the rapid advances in medical science, any information or advice on dosages, procedures or diagnoses should be independently verified. The reader is strongly urged to consult the relevant national drug formulary and the drug companies’ and device or material manufacturers’ printed instructions, and their websites, before administering or utilizing any of the drugs, devices or materials mentioned in this book.
    [Show full text]
  • Educación Química, Vol. 1, Núm. 0
    PARA QUITARLE EL POLVO Syntex, una historia mexicana La química en la historia, para la enseñanza y su divulgación en el bachillerato Felipe León Olivares1 Resumen de no disponer de hormonas en cantidad y calidad El presente trabajo explica la importancia de las suficiente, generaba un problema ya que la produc- aportaciones de la investigación científica lograda en ción era limitada y los precios muy elevados, en gran México en el campo de la Química por Syntex, medida por los procesos complejos con rendimien- donde se realizó una verdadera revolución mundial tos bajos que usaban las compañías europeas. A en la síntesis orgánica de las hormonas esteroides. pesar de esta situación, mantenían el control tecno- De esta manera, se considera importante su divulga- lógico dominando el mercado internacional de estos ción en el bachillerato, como una experiencia que productos. Por su parte, las sucursales europeas en proyecta interés al estudio de la química a las nuevas Estados Unidos tuvieron un especial éxito comercial generaciones de estudiantes. motivando a éstas a una mayor actividad de investi- gación. Por ejemplo, la Upjohn y la Parke-Davis, Introducción fomentaron una extensa investigación a través de un El presente estudio plantea la alternativa de la divul- programa de becas. Así fue que el químico Russell gación de las aportaciones de la investigación cien- E. Marker, de la Universidad Estatal de Pennsylva- tífica realizada en México en el campo de la Quími- nia, inició sus estudios sobre las hormonas esteroides ca. Ejemplos como el de ‘‘Andrés Manuel del Río’’ (Lehmann, et al., 1973:196). (Carrera, 1956:5), ‘‘Vicente Ortigosa’’ (Chamizo, Marker planteó que el punto clave en la indus- 1999:138), y el de la empresa ‘‘Hojalata y Lámina de tria de las hormonas esteroides estaba en la materia Monterrey’’ (Garritz, 1993:36), entre otros aconteci- prima; con esta hipótesis prestó atención a las plantas mientos dignos de mención, deben ser conocidos como fuente barata y abundante de hormonas.
    [Show full text]
  • Repeated Evolution of Cytochrome P450-Mediated Spiroketal Steroid Biosynthesis in Plants
    Repeated evolution of cytochrome P450- mediated spiroketal steroid biosynthesis in plants The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation Christ, Bastien et al. "Repeated evolution of cytochrome P450- mediated spiroketal steroid biosynthesis in plants." Nature communications 10 (2019): 1038 © 2019 The Author(s) As Published 10.1038/s41467-019-11286-7 Publisher Springer Science and Business Media LLC Version Final published version Citable link https://hdl.handle.net/1721.1/124710 Terms of Use Creative Commons Attribution 4.0 International license Detailed Terms https://creativecommons.org/licenses/by/4.0/ ARTICLE https://doi.org/10.1038/s41467-019-11286-7 OPEN Repeated evolution of cytochrome P450-mediated spiroketal steroid biosynthesis in plants Bastien Christ1,6,7, Chengchao Xu1,7, Menglong Xu1,7, Fu-Shuang Li1, Naoki Wada 2, Andrew J. Mitchell1, Xiu-Lin Han3, Meng-Liang Wen3, Makoto Fujita2,4 & Jing-Ke Weng 1,5 Diosgenin is a spiroketal steroidal natural product extracted from plants and used as the single most important precursor for the world steroid hormone industry. The sporadic 1234567890():,; occurrences of diosgenin in distantly related plants imply possible independent biosynthetic origins. The characteristic 5,6-spiroketal moiety in diosgenin is reminiscent of the spiroketal moiety present in anthelmintic avermectins isolated from actinomycete bacteria. How plants gained the ability to biosynthesize spiroketal natural products is unknown. Here, we report the diosgenin-biosynthetic pathways in himalayan paris (Paris polyphylla), a monocot med- icinal plant with hemostatic and antibacterial properties, and fenugreek (Trigonella foenum–graecum), an eudicot culinary herb plant commonly used as a galactagogue.
    [Show full text]
  • International Historic Chemical Landmark Acclaims Success of Mexican Steroid Industry and a U.S
    Journal of the Mexican Chemical Society ISSN: 1870-249X [email protected] Sociedad Química de México México Raber, Linda Steroid industry honored. International historic chemical landmark acclaims success of mexican steroid industry and a U.S. chemist who made it possible Journal of the Mexican Chemical Society, vol. 43, núm. 6, noviembre-diciembre, 1999, pp. 235-237 Sociedad Química de México Distrito Federal, México Available in: http://www.redalyc.org/articulo.oa?id=47543610 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative Revista de la Sociedad Química de México, Vol. 43, Núm. 6 (1999) 235-237 Noticias Steroid Industry Honored† International Historic Chemical Landmark Acclaims Success of Mexican Steroid Industry and a U.S. Chemist Who Made it Possible Linda Raber American Chemical Society 1155-16th St., N.W, Washington, D.C. 20036. U.S.A. “There are more stories told about Russell Marker than any he founded in Mexico City with Emeric Somlo and Federico other chemist. Although perhaps many of these stories are A. Lehmann. apocryphal, they are so fascinating that most of us cannot bear “This low-cost progesterone eventually became the pre- to stop repeating them. This is the oral history of our profes- ferred precursor in the industrial preparation of the anti- sion that we pass to our colleagues and our students. They are inflammatory drug cortisone. In 1951, Syntex researchers syn- the campfire stories that bind our profession together” – thesized the first useful oral contraceptive from Marker’s start- Steven M.
    [Show full text]
  • Understanding Hormonal Contraception
    Understanding Hormonal Contraception Alexandra Hall MD University of Wisconsin, Stout ACHA 2013 Disclosures • I will discuss off-label use of medications. • I have no financial conflicts of interest. Overview • Mechanisms of Action • Risks & benefits, based on pharmacology & physiologic effects • Safe prescribing, weighing the options Abbreviations • CHC = Combined Hormonal Contraceptive • Estrogen + Progestin • Pills, Patch, & Ring • BC = Birth Control • OC = Oral Contraceptive (COC=Combined Oral Contraceptive) • POP = Progestin-Only Pills, a.k.a. Mini-Pills • LNG-IUS = Levonorgestrel Intrauterine System (Mirena IUD) • DMPA = Depot-medroxyprogesterone acetate (Depo-Provera) • EE = Ethinyl estradiol • SHBG = sex hormone binding globulin • MEC = Medical Eligibility Criteria U.S. MEC www.cdc.gov/reproductivehealth/UnintendedPregnancy/USMEC.htm Resources • Hatcher et al., Contraceptive Technology • Dickey, Managing Contraceptive Pill / Drug Patients • Speroff & Fritz, Clinical Gynecologic Endocrinology and Infertility • Speroff & Darney, A Clinical Guide for Contraception • Association of Reproductive Health Professionals www.arhp.org • Free webinars • Free online resources • Free patient resources • Members get free subscription to journal Contraception LET’S GET STARTED! Case Astara believes strongly in using only natural products and doesn’t want to use anything synthetic. She wonders if there is an all-natural hormonal contraceptive available to her. What do you tell her? a. The hormones in OC’s are identical to the hormones her body normally makes. b. The hormones in a new pill named Natazia are bioidentical to natural hormones. c. The estrogen component of CHC is extracted from horse urine. d. The progestin component of CHC is extracted from yams. e. None of the above. WHAT IS CONTRACEPTION MADE OF? In the beginning… 80,000 sow ovaries = 5 gallons syrup Mexican yams = 12 mg estradiol & 3 kg progesterone 40 mg progesterone via chemical processes called the Marker Degradation Estradiol vs.
    [Show full text]
  • Eric Helms, Mphil, MS, CSCS
    14 Artificial sweeteners are now getting accused of causing diabetes, LOL. By Alan Aragon 17 Evelyn Kocur answers 2 burning questions (pun semi-intended) about the first & second law of thermodynamics. Interviewed by Alan Aragon Copyright © August 1st, 2014 by Alan Aragon Home: www.alanaragon.com/researchreview Correspondence: [email protected] 2 What can be achieved as a natural bodybuilder? By Eric Helms, MPhil, MS, CSCS 8 Comparison of weight loss among named diet programs in overweight and obese adults a meta- analysis. Johnston BC, Kanters S, Bandayrel K, Wu P, Naji F, Siemieniuk RA, Ball GDC, Busse JW, Thorlund K, Guyatt G, Jansen JP, Mills EJ. JAMA. 2014;312(9):923-933. [PubMed] 10 Effects of low-carbohydrate and low-fat diets: a randomized trial. Bazzano LA, Hu T, Reynolds K, Yao L, Bunol C, Liu Y, Chen CS, Klag MJ, Whelton PK, He J. Ann Intern Med. 2014 Sep 2;161(5):309-18. [PubMed] 11 Evaluation of Resettin® on serum hormone levels in sedentary males. Anderson ML. J Int Soc Sports Nutr. 2014 Aug 23;11:43. [PubMed] 12 Effect of Lactobacillus rhamnosus CGMCC1.3724 supplementation on weight loss and maintenance in obese men and women. Sanchez M, Darimont C, Drapeau V, Emady-Azar S, Lepage M, Rezzonico E, Ngom-Bru C, Berger B, Philippe L, Ammon-Zuffrey C, Leone P, Chevrier G, St-Amand E, Marette A, Doré J, Tremblay A. Br J Nutr. 2014 Apr 28;111(8):1507-19. [PubMed] Alan Aragon’s Research Review – August 2014 [Back to Contents] Page 1 case lean mass, expressed numerically.
    [Show full text]
  • The Scientific Impact of Mexican Steroid Research 1935-1965
    The Scientific Impact of Mexican Steroid Research 1935–1965: A Bibliometric and Historiographic Analysis Yoscelina I. Hernandez-Garcia Technology, and Society, Cinvestav-IPN, Apdo postal, Mexico, DF 14–740, Mexico. E-mail: [email protected] José Antonio Chamizo Facultad de Química, Universidad Nacional Autónoma de México, Mexico, DF 04510, Mexico. E-mail: [email protected] Mina Kleiche-Dray Ceped (IRD Université Paris V Descartes), and IFRIS, Paris 75006, France. E-mail: [email protected] Jane M. Russell Instituto de Investigaciones Bibliotecológicas y de la Información, UNAM, Mexico, DF 04510, Mexico. E-mail: [email protected] We studied steroid research from 1935 to 1965 that led to Zubieta Garcia, & Rodriguez-Sala, 2013; Luna-Morales, the discovery of the contraceptive pill and cortisone. Collazo-Reyes, Russell, & Pérez-Angón, 2009). Luna- Bibliometric and patent file searches indicate that the Morales and coauthors identified four different modes of Syntex industrial laboratory located in Mexico and the Universidad Nacional Autónoma de México (UNAM) pro- Mexican scientific production in the first half of the 20th duced about 54% of the relevant papers published in century: amateur, institutional, academic, and industrial. mainstream journals, which in turn generated over 80% The last of these emerged only at the end of this period as a of the citations and in the case of Syntex, all industrial result of the industrial activity associated with steroid patents in the field between 1950 and 1965. This course research (Luna-Morales et al., 2009). of events, which was unprecedented at that time in a developing country, was interrupted when Syntex In the mid-20th century it was inconceivable to imagine moved its research division to the US, leaving Mexico that cutting-edge research like with steroids could be done in with a small but productive research group in the chem- a country such as Mexico (Djerassi, 1992; Redig, 2005), but istry of natural products.
    [Show full text]
  • Thesis Rests with Its Author
    University of Bath PHD The biotransformation of diosgenin and its precursors extracted from Trigonella foenumgraecum L. seed. Saunders, Roger Award date: 1982 Awarding institution: University of Bath Link to publication Alternative formats If you require this document in an alternative format, please contact: [email protected] General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Download date: 08. Oct. 2021 THE BIOTRANSFORMATION OF DIOSGENIN AND ITS PRECURSORS EXTRACTED FROM TRIGONELLA FOENUMGRAECUM L. SEED Submitted by Roger Saunders for the degree of Doctor of Philosophy of the University of Bath 1982 COPYRIGHT "Attention is drawn to the fact that copyright of this thesis rests with its author. This copy of the thesis has been supplied on condition that anyone who consults it is understood to recognise that its copyright rests with its author and that no quotation from the thesis and no information derived from it may be published without the prior written consent of the author." "This thesis may not be consulted, photocopied or lent to other libraries without the permission of the author for 5 years from the date of acceptance of the thesis".
    [Show full text]
  • A Treatise on Topical Corticosteroids in Dermatology
    Koushik Lahiri Editor A Treatise on Topical Corticosteroids in Dermatology Use, Misuse and Abuse Foreword by Jerome Z. Litt 123 A Treatise on Topical Corticosteroids in Dermatology Koushik Lahiri Editor A Treatise on Topical Corticosteroids in Dermatology Use, Misuse and Abuse Editor Koushik Lahiri Department of Dermatology Apollo Gleneagles Hospitals and WIZDERM Kolkata India ISBN 978-981-10-4608-7 ISBN 978-981-10-4609-4 (eBook) DOI 10.1007/978-981-10-4609-4 Library of Congress Control Number: 2017946174 © Springer Nature Singapore Pte Ltd. 2018 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made.
    [Show full text]
  • The History of Natural Progesterone, the Never-Ending Story
    CLIMACTERIC https://doi.org/10.1080/13697137.2018.1462792 REVIEW The history of natural progesterone, the never-ending story P. Piette Consultant at Besins Healthcare Global, Department of R & D, Scientific & Medical Affairs, Brussels, Belgium ABSTRACT ARTICLE HISTORY The term progesterone should only be used for the natural hormone produced by the ovaries or Received 10 January 2018 included in a registered drug. The modern history of progesterone begins with the first book-length Revised 30 March 2018 description of the female reproductive system including the corpus luteum and later with the Nobel Accepted 5 April 2018 Prize winner, Adolf Butenandt who took a crucial step when he succeeded in converting pregnanediol Published online 29 May 2018 into a chemically pure form of progesterone, the corpus luteum hormone. The deficient production of progesterone was shown first to be the cause of the luteal-phase deficiency responsible for infertility KEYWORDS and early pregnancy loss due to inadequate secretory transformation of the endometrium. Later, pro- Progesterone; allopregnano- gesterone was confirmed to be the best and safest method of providing luteal-phase support in lone; pregnancy; assisted reproductive technology. Progesterone provides adequate endometrial protection and is sug- miscarriage; hormone gested to be the optimal progestagen in menopausal hormone therapy in terms of cardiovascular replacement therapy; effects, venous thromboembolism, probably stroke and even breast cancer risk. Neuroprotective effects luteal-phase support; of progesterone have also been demonstrated in several of experimental models including cerebral preterm delivery ischemic stroke and Alzheimer’s disease. Vaginal progesterone was shown to decrease the risk of pre- term birth in women with a mid-trimester sonographic short cervix and to improve perinatal outcomes in singleton and twin gestations.
    [Show full text]
  • Cannot See the Flowers Nor the Tree: Plants and the Pill Bradley C
    Florida International University FIU Digital Commons All Faculty 5-27-2015 Cannot See the Flowers nor the Tree: Plants and the Pill Bradley C. Bennett Department of Biological Sciences, Florida International University, [email protected] Follow this and additional works at: https://digitalcommons.fiu.edu/all_faculty Recommended Citation Bennett, Bradley C., "Cannot See the Flowers nor the Tree: Plants and the Pill" (2015). All Faculty. 118. https://digitalcommons.fiu.edu/all_faculty/118 This work is brought to you for free and open access by FIU Digital Commons. It has been accepted for inclusion in All Faculty by an authorized administrator of FIU Digital Commons. For more information, please contact [email protected]. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Correspondence http://pubs.acs.org/journal/acscii Cannot See the Flowers nor the Tree: Plants and the Pill Bradley C. Bennett* Department of Biological Sciences, Florida International University, Miami, Florida 33157, United States he modern world suffers from a syndrome known as plant natural products] as starting materials for the synthesis of T blindnessthe inability to perceive plants.1 The lack of estrone and estradiolsteroid hormones that had not been awareness occurs in the natural environment, the home part of his synthetic repertoire.”4 landscape, and even the scientific lab. The third article in the Marker had successfully produced progesterone from the inaugural issue of the American Chemical Society’s ACS Central sapogenins diosgenin and sarsasapogenin (Figure 1), but none Science2 recognizes Carl Djerassi’s pioneering work in steroidal of the known plant sources yielded sufficient quantities of syntheses.
    [Show full text]