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Studies on Reaction of Mimosine with Various Amines and Effects of Mimosine on Tyrosine Decarboxylation

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Studies on Reaction of Mimosine with Various Amines and Effects of Mimosine on Tyrosine Decarboxylation South Dakota State University Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange Electronic Theses and Dissertations 1972 Studies on Reaction of Mimosine with Various Amines and Effects of Mimosine on Tyrosine Decarboxylation Paul D. Ballata Follow this and additional works at: https://openprairie.sdstate.edu/etd Recommended Citation Ballata, Paul D., "Studies on Reaction of Mimosine with Various Amines and Effects of Mimosine on Tyrosine Decarboxylation" (1972). Electronic Theses and Dissertations. 4625. https://openprairie.sdstate.edu/etd/4625 This Thesis - Open Access is brought to you for free and open access by Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange. For more information, please contact [email protected]. STUDIES ON REACTION OF MIMOSINE WITH VARIOUS AMINES AND EFFECTS OF MIMOSINE ON TYROSINE DECARBOXYLATION BY D. BALLATA PAUL A thesis submitted in partial fullfillment of the requirements for the degree Master of Science, Majo:r in _ __ Chemistry, South Dakota State University 1972 SOUTH D OTA STATE UN_l ERSITY LIB ARY STIJDIES ON REACJION OF MIMJSINE WITH VARIOUS AMINES AND EFFECTS OF MIMOSINE ON TYROSINE DECARBOXYLATION This thesis is approved as a creditable and independent investigation by a cand idate for the degree, Master of Science, and is acceptable for meeting the thesis requirements for this degree. Acceptance of thi s thesis does not imply that the conclusions reached by the candidate are necessarily the conclusions of the major department . Thesis Adviser Date Head , Chemistry Department Date ..,. ; DEDICATION To she who walks in beauty "Phyllis" Acknowledgment s The author wishes to express his appreciat ion to Dr . John Grove for his assistance with the conception, development , and culmination of this research and part icularly "for his patience during the writing of this thesis. The author al so wi shes to thank other members of the faculty for their helpful advice given throughout this research and Mrs. Maris Knutson who typed this thesis. TABLE OF CONTENTS I NTR.ODUCTI ON ••••••••••••••••••••••• • •••••••••••••••••••••••••••••••••1 L::�RATURE REVIEW Mirnosine ••••••••••••••••••••••••••••••••••••••••••••••••••••••••3 Pyridoxal-5-phosphate ••••••••••••••••••••••• ••••••••••••••••••••7 EXPERIMENTAL Apparatus and Materials ••••••••••••••••••••••••••••••••••••••••12 Isolation and Purification of Mimosine •••••••••••••••••••••••••12 Tyro sine Decarboxylase Studies •••••••••••••••••••••••••••••••••14 Effect of L-Canaline on Mimo sine-induced Decarboxylation •••••••15 Ultraviolet Studies ••••••••••••••••••• ••••••.••••••••••••••••••1 6 a ••••••••••••••• •••••••••• n-Butyl mine and Mimo sine Interaction � 17 Sephadex G-10 Chromatography ••••••••••••••••••••••••• ••••••••••17 Paper Chromatography ••••••••••••••••••••• ••••••••••••••••••••••18 RESULTS Characterization of I solated Mimosine ••••••••••••••••••••••••••20 Tyrosine Decarboxylase Results •••••••••••••••••••• •••••••••••••20 Effect of L-Canaline on Mimosine Catalyzed Reaction••••• •••••••29 Ultraviolet Studies ••••••• ••••••••••••••••••• • •••29 Sephadex G-10 Chromatography ••••••••••••••••••••••••••••••••••• _ 34 Paper Chromatography ••••••••••••••••••••••••••••••••••••••••••• 40 DISCUSSION •••••••••••••••••••••••••••••••••••• •••••••••••••••••• ••••4 7 •••••••••••••••••• . .. ....... ... ... •••• 6 SUMM.ARY . ...� ........... 5 •••••••••••••••••.•••••••• . .. .. ... • •• APPENDIX .. ... .. ... .. ... 58 REI=ERENCES •••••••••••• ••••••••••••••••••••••••••••••••••••••••••••••6 0 LIST OF FIGURES Figure Page . 1. 21-22 Infrared Spectrum of Purified Mimosine ••••••••••••••••••• 2. Reciprocal Plot of Tyrosine Decarboxylat ion Reaction Rates with Variable Mimosine Concentrat ion and Constant Tyrosine Concentrat ion............. .. .......... 27 3. Reciprocal Plot of Tyrosine Decarboxylat ion Reaction Rates with Variable Tyrosine Concentration and Constant Mimosine Concentration. ..... ............. ..... .. 28 4. J0-31 Ultraviolet Spectrum of Iso lated Mimosine •• •••••••••••••• 5. Ultraviolet Spectra of the Reaction of Mimosine and 32-33 L -Valine at Varying L -Val ine Concentrat ion •••••••••••••• • 6. Ultraviolet Spectra for the Reaction Between n-Butylamine 35-36 and Mimosine•• ••••••••••••••••• •• •••••• •••••••••••• •••••• 7. Infrared Spectrum of Residue from Mixture of Mimo sine and n-Butylamine in Benzene............ .................. 37 8. 38-39 Ultraviolet Spectrum of Mimosine�Mimosine Reaction ••••••• 9. Sephadex G-10 Column Fractions... ..... ........... ........ 41 10. Radiochromatogram of Timed Reaction Mixture of 14C-Tyrosine Mimosine, and Enzyme..................................... 44 11. Paper C0romatogram of Reaction Mixture and Fraction 49 from Sephadex G-10 Column......... ... .... ...... ......... 46 .r -... LIST OF TABLES Table Page I. Conditions and Representat ion Reaction Rates for Tyrosine Decarboxylase Manometric Assays ••••••• •••••••••••2 3 II. Tyros ine Decarboxylation Reaction Rates with Varvinq Mimosine Concentrat ions + Constant Tyros ine Concentration •••••••••••••••••••••••••••••••••••••••••••••25 III. Tyrosine Decarboxylat ion Reaction Rates with Varying Tyrosine Concentrations + Constant Mimo sine Concentrat ion ••••••••••••••••••••••••••••••• ••••••••••••••26 IV. Paper Chromatogram Rf Values fo� Known Compound s Detected with Diazotized sulfanilic acid - NH40H Spray •••••••••••••4 2 V. Paper Chromatogram Rf 'Values for Known and Unknown Components of Tyrosine Decarboxylase Reaction Mixture •••••43 1 IN1RODUCTION As early as 1897 the toxic effects of mimosine were observed and animals ingesting mimo sine showed symptoms of hair loss, infertility, and retardation of growth. 1 Mimosine occurs naturally in leguminous plants ind igenous throughout the tropics of the world. Since the forage of these plants ha s a protein content as high as al falfa and is reli shed by all kinds of livestock, 2 the mechani sm of the toxicity of mimo sine should be explained . Although the effects of mimosine have been known for a long time, the reason or mechanism fo� these effects ha s not been explained. Mu ch work ha s been done on the po ssible interference of mimosine with the incorporation of certain amino acids into proteins. How mimosine may cause its toxic effects by the inhibition of metal- Gontaining enzymes or by complexing with pyridoxal-5-phosphate has also been studied. However, this work has not yielded any conclusive mechanism for mimosine's toxicity. Because of varied result s, the observation that mimosine-induced growth inhibition could be reduced or completely eliminated by supplying animals with additional amino acids has not clarified the mechanism for the toxic. effects of mimosine. Therefore , this research wa s undertaken to help clarify the mechanism for the adverse effects of mimo sine. It wa s noted that mimo sine structurally ha s many of the same functional groups as pyridoxal , including an ortho hydroxyl group and an oxygen of a carbonyl group being in conjugation with the ring nitrogen. Because of thi s similarity to pyridoxal, experiments were ""' --- 2 done to attempt to show that this resemblance is functionally important and may be the main cause for the toxic effects of mimosine. 0 I I H ()° 0 I . -{;H-C-OHJI CH 2 NHr 2 Mimosine Pyridoxal 3 LITERATURE REVIEW Mimosine or 3-hydro xy-4-ox�-1(4H)-pyridine alanine Loss of hair in animals following ingestion of seeds and foliage of Leucaena glauca was first reported in. 1897. 1 Inge stion of mimosine by sheep not only causes the loss of wool but may eventual ly cause the animal to die. 3 Mirnosine ha s been reported to completely inhibit the 4 growth of coli. The cessation of the estrous cycle and eventual E. complete infertility of female rats has also been attributed to mimosine ingestion.5 Sudden loss of ha ir in native women has been 6 ascribed to consumption of Leucaena qlauca seeds. Two papers have 7 described the inhibition of growth of hair by mimosine and other effects caused by mimo sine in several animals.8 In 1950 Malmquist showed that Leucaena glauca did in fact contain mimosine as an unbound amino acid. 9 The structure of mimosine was 10 first proposed by Wibaut and proved by Adams and Johnson. 11 Organi c synthesis of mimosine was reported by Spenser and Notation in 1962 from J-benzyloxy-4-pyrone and -amino-�-tosylaminopropionic acid. 12 .B Much work on the bio synthesis of mimosine has been done during . the past ten years. Hylin in 1963 showed that the .administration of 14 2- c) -DL-lysine to Leucaena glauca results in the incorporation of � radioactivity into the pyridone ring of mimosine. 13 Notation and 14 Spenser in 1964 also showed that C-labelled aspart ic acid was incorporated into the pyridone nuc leus of mimosine . 14 In 1965 Tiwari and Spenser reported that succinic acid was incorporated into the nucleus; while glycerol and glyceric acid contributed label to the 4 side chain of mimosine. In it wa s determined that ser ine 15 1967 serves as a precursor of the alanyl side-chain of mimosine and that o<.-aminoadipi c acid is incorporated into the pyridine nucleus. 16 Just recently it has been .shown that an extract of Leucaena glaucaseedlings can_ catalyze an enzymatic synthesis of mimo sine from 3,4-dihydroxypyridine and o(-acetylserine.
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