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Some Aspects of Steroid Hormones Biosynthesis by Ovarian Tissue of the Wilson's Phalarope (Steganopus Tricolor)

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Some Aspects of Steroid Hormones Biosynthesis by Ovarian Tissue of the Wilson's Phalarope (Steganopus Tricolor) University of Montana ScholarWorks at University of Montana Graduate Student Theses, Dissertations, & Professional Papers Graduate School 1968 Some aspects of steroid hormones biosynthesis by ovarian tissue of the Wilson's phalarope (Steganopus tricolor) Ho-Jane Yu The University of Montana Follow this and additional works at: https://scholarworks.umt.edu/etd Let us know how access to this document benefits ou.y Recommended Citation Yu, Ho-Jane, "Some aspects of steroid hormones biosynthesis by ovarian tissue of the Wilson's phalarope (Steganopus tricolor)" (1968). Graduate Student Theses, Dissertations, & Professional Papers. 6951. https://scholarworks.umt.edu/etd/6951 This Thesis is brought to you for free and open access by the Graduate School at ScholarWorks at University of Montana. It has been accepted for inclusion in Graduate Student Theses, Dissertations, & Professional Papers by an authorized administrator of ScholarWorks at University of Montana. For more information, please contact [email protected]. SOME ASPECTS OF STEROID HORMONES BIOSYNTHESIS BY OVARIAN TISSUE OF THE WIISON'S PHALAROPE (STEGANOPUS TRICOLOR) by Ho-Jane Yu B*S. National Taiwan University, 196L Presented in partial fulfillment of the requirements for the degree of Master of Science UNIVERSITY OF MCMTANA 1968 Approved by: Ohai Board of Examiners AUG 1 - 1368 Date Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number; EP37752 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. UMT DisMination I^Miahing UMI EP37752 Published by ProQuest LLC (2013). Copyright in the Dissertation held by the Author. Microform Edition © ProQuest LLC. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48 106-1346 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGMENTS I wish to express mjr sincere appreciation to Dr. H. Richard Fevold, Associate Professor of Chemistry, University of Montana, for his advice, guidance, assistance, and checking of my English manuscript throughout the course of this research. Appreciation is also due Dr. M. E. Magar, Assistant Professor of Chemistry, and Dr, E. W. Pfeiffer, Professor of Zoology, for their advice and assistance in writing this thesis, I am also grateful to Mr, J, S, Rice, laboratory assistant, for his help on gas chromatographic tech­ niques. A major portion of this investigation was supported by research grants to Dr. Fevold from National Science Foundation, grant number GB-25^0. H.J.Y. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. PART A CHARACTERIZATION AND IDENTIFICATION OF SOME POLAR PRODUCTS OF W VITRO PRBGN-5-ENE-3417«<*^DI0L-20-0NE(17p<^HÏDR0XYPRBGNEN0L0NE) and PREGN-4-ENE- 1 %(-0L-3,20-DI0NE(1 XjHYDROXYPROGESTERONE) METABOLISM BY WILSON'S PHALAROPE OVARIAN TISSUE TABLE OF CONTENTS PAGE I. INTRODUCTION.................................... • 1 II. HISTORICAL REVIEW ................................................................... 5 A. Biosyn'Uiesis of p reg-4-ene-l20>^3-one and pregn-4-©ne-17e^»2Q^^diol-3-one 5 B. Biosynthesis of estrogen 6 III. EXPERIMENTAL MATERIALS AND PROCEDURES .................................... 17 A. Experimental animals 17 B. Chemicals ................. 17 C. Equipment «....oe................. 20 D. Procedures 21 1. Paper chromatography ................ 21 2. Drying process , , . 21 3. Substrate preparations ............... 21 Tissue preparation ................. 22 5. Preparation of Incubation flasks .......... 22 6. Incubation u. 22 7. Ebctractlon ......... ...o........ 2^ 8 . Product purification, Isolation and Identification . 24 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. iv PAGE IV* RESULTS ooo*eo*ooooo*ooaooooooaaao* 29 Ao Identification of metabolites and X 2 oooo****o 29 Bo Partially characterized metabolites ocoo***.**» 35 V* DISCUSSION 0 0.000000000.0000.0000000. 47 VI. SUMMARY O .............................. O O O O O 0 O 0 O O 0 o o o o . o 53 VII. BIBLIOGRAPHY o.ooooooooaoooooaooooooo. 54 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. LIST OF TABLES TABLE PAGE is Fhalarope ovaries used for incubation 23 2, Chromatographic identification of ooooo«i>o«oo»« 33 3, Chromatographic identification of %2 « » # * * «.............................. 34 4* 3 h/14q ratios of initial substarates and neutral metabolites %2 a*#»»#.#»*»*».»»»»**» 36 5» Percent recovery of estrogens in the isolation processes # * * 36 6 o Retention time of gas chromatographic analysis of methoxy derivatives of #P£ and #P^ *a.a«*«oooo,#* 0 *, 42 7o Rf values of phenolic metabolite #Pj^“A ooooooooaooo 44 8 o Rf values of phenolic metabolite fPj^-B ooaooooocooo 45 9o Rf values of phenolic metabolite #P%—C ,oo»oo**e»oo 46 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. V i LIST OF ILLUSTRATIONS FIGURE PAGE 1» Seasonal changes in androgen secretion by phalarope gonadal tissues (hypothetical curves) eo«ao«o>ooo 3 2. Biosynthesis of androgens «,»«,*** 10 3* Biosynthesis of estrogens from C-19 steroids 13 4. Interrelationship of estrone and ITJi^-estradiol with I 6 and 17 substituted idienolic estrogens oaooeoo«ooa««o I6 5o Tracing of the first chranatographic separation of radio­ active neutral metabolites isolated from incubations of phalarope ovarian tissues cell-free homogenate with 17,^ hydi>cocypregnenolone- 7<^-^ and 17«^hydroxyprogesterone- 4 — Caooeoooeooaeoooesooooooooeoe 30 60 Purification of neutral steroids in the benzene/formamide system by paper chromatography ooeooooooaooeao 31 7« Procedure used for isolation and identification of and X 2 o 32 80 Procedure used for isolation of phenolic metabolites from phalarope ovarian tissue homogenate incubations ooboooo 37 9o Tracing of üie first paper chromatogram of phenolic metabo­ lites isolated from incubation of phalarope ovarian tissues cell-free homogenate with 1 %/^hydroxypregnenolone- and 1 %^hydroxyprogesterone-4-^^C in the benzene/ foz*mamxde system oeeeBcsooooooooooooooo 38 10o Tracing of paper chromatogram of phenolic metabolite #P^ fraction in the chioroform/formamide system o o » o e « » c o 38 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. vil FIGURE PAGE lie Effluent patterns of estrone and 17^©stradiol in silica gel column with different polarity of eluting solvents •••••••••••••••••••••••••. 39 12* Thin-layer chromatogram of methylated estrogen samples in the benzene ; methanol ( 99:1 v/v) system 40 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. PART B m VITRO STUDIES OF 17^-HYDROXYSTEROID DEHYDROGENASE ACTIVITY IN AVIAN OVARIAN AND TESTICULAR TISSUES TABLE OF CONTENTS PAGE I. INTRODUCTICK......................................................................................................... 63 II. HISTORICAL REVIEW..................................................................................................... 65 A. Avian gonadal c y c le s ................................................................................ 65 B. ITf-Hydroxysteroid dehydrogenase ................................................... 71 III. EXPERIMENTAL MATERIALS Aim PROCEDURES................................................... 72 A. Experimental anim als ................................................................................ 72 B. Chemicals ...................................................................................... 73 C. Equipment ..... .................................... .......... 73 D. Procedures . ............................................................. ........ 73 1. Substrate preparation .................................................................... 73 2. Tissue preparation ..................................... ........ 73 3. Preparation of incubation flask ......... 7U L. Incubation ..................................................................................................... 7U 5. Extraction ......................................................... ........ 76 6. Product purification, isolation and identification 76 7. Quantification of metabolites ................................................... 79 IV. RESULTS .......................... 80 A. Effect of substrate concentration on the velocity of the 17'^-hydroxysteroid dehydrogenase reaction in the ovarian and testicular tissues Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ix PAGE B# Rate of formation of testosterone from andro- stenedione in phalarope ovarian and testicular tissue 80 C# Product identification ,## .# . o 88 V. DISCUSSION • • • ..................... 95 VI. SUMMARY ................................... • • • 104 Vn. BIBLIOGRAPHI ...........................................................................105 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. X L IST OF TABLES TABLE PAGE
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