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I. an Investigation of the Organic Compounds in the Media and Mycelium of Naucoria Confragosa

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I. an Investigation of the Organic Compounds in the Media and Mycelium of Naucoria Confragosa Scholars' Mine Masters Theses Student Theses and Dissertations 1965 I. An investigation of the organic compounds in the media and mycelium of Naucoria confragosa. II. Study of the extra-cellular pigments of an unknown fungus Yueh-Tsun Chen Follow this and additional works at: https://scholarsmine.mst.edu/masters_theses Part of the Chemistry Commons Department: Recommended Citation Chen, Yueh-Tsun, "I. An investigation of the organic compounds in the media and mycelium of Naucoria confragosa. II. Study of the extra-cellular pigments of an unknown fungus" (1965). Masters Theses. 5238. https://scholarsmine.mst.edu/masters_theses/5238 This thesis is brought to you by Scholars' Mine, a service of the Missouri S&T Library and Learning Resources. This work is protected by U. S. Copyright Law. Unauthorized use including reproduction for redistribution requires the permission of the copyright holder. For more information, please contact [email protected]. 7 ( . I. A!J Il!VESTIGATIOU OF THE OaGAHIC CO:·~OUHDS Irr THZ ECDIA JJ!D ::YCELIUH OF IrAUCORIA . CON'FRAG00A II. STUDY OF THE EXTRA-CELLULAR PIG!!ENTS OF A...'l UI-Jt:NQ;;N ::!'tU!GUS BY YUEH TSUU CHEN1ttt31 A THESIS submitted to the faculty of the illv"IVERSITY OF HISSOUill: AT ROLLA in partial fulfillment of the requirement for the ' ·; Degree of !'..ASTER OF SCIENCE IN · CHE1-1ISTRY ROLLA, IliSSOURI 1965 T!1e funeal r:etabol1:~es excreted. into the cuture fluid by ba::;i- diom.ycetes zro,rl.ng on synthetic zlucose media as \'lOll as fol'·med in the ~.. cella of t::e orgaJl.is.~G uere investi~ated in this thesis. E'lrller unpublished 1:rork had sho1·m that Eaucoria confr~:::-os~ e.x.crcted into the mediu."'n compounds vrhich 1-rere thought to be phc:1ols. Inm1fficient material -vms recovered from an ethy~ acet~te extract of the mediu.-:-.. in the present study for further investigat1.on. Colorimetric methods 1·rere er:.ployed both for the quantitntive estirr~tion of reducing sugar not consu.~ed by the microorsanisms as uell as for a measure of the total orea.r...ic solids present in the spent beer. A survey of the z;lucose utilization by cultures of Lcucopa.:·::.:i.llus 12-ar:-;tc_o.:::.us, and Crepidotus agror:horus on a synthetic glucose medium were also made. The mycelium of l'i. confragosa 1·rcts e:;ct,racted vtith ether and then 1·r:th ethanol. A ycllm-rish solid material separated from the ~oncen- trated ether e:dract, but vras not identified. Three different kinds of crystals separated from the. conccr.trated ethanol e~~ract of the rnycellum. T1ro o:f theoe 1-rere identified; one 1-ro.s mannitol and the other as ergosterol. The presence o:f a second polyol and an amino acid, neither of 1·rhich l.Tas idonti:fied, -was sho-;·m. The identification of the polyol compounds by paper chromato- craphy 1-ro.s attempted. Colum."l and thin layer chromatography vrere ~~loyed for the separation and identification of ergosterol fo~ed by tl• confragosa. -iii- An unl-..no~·m .fun.sus (A-l-C) 'tihich l'ro.s isoJ.a.te1 in this labo:--atory, c;rm., Hell in ~our percent !:'.alt med:l.ur:~.. After seven days the :nedi1..1r.1 turned red. The spent medium \.. -n.s e..'Ctra.cted 't·rith ether and fro~ the eth~r extract yellow red crystals separated. Thin layer chronnto­ graphy indicated that the e.:-:tract contained at least t1ro yello1-1 pigments. Ho further work t-.ra.s done on the purification and identification of the pi~ent. The rate of formation of the pigments by the unknov.n fun~s -vms studied. The U. V. and visible absorption spectra of the isolated pigments 't-lere deferm:Lned. -iv- TA:SLE OF COIITENTS TITIZ PA(}F: ••••••••••••••••••••••••••••••••••••••••••••••••••••••• ADSTR/1CT •• ••••••••••••••••••••••••••••••••••••••••••••••••••••••• ii T/i.DIZ OF CO:·.JTZ:ITS ••••••••••••• ••••••••••••••••••••••••••••••••••• LICT OF FIGtJIES •••••••••••••••••••••••••••••••••••••••••••••••••• vii: LIST OF . .. .. .. .. .. .. .. .. .. .. vii:L I. INTRCDUCTIO:I. .. .. .. .. .. .. .. .. .. .. l II. L.LTE:t.l\.Tt!::?J: p~TTh1I ••••••••••••••••••••••••••••••••••••••• 2 l\.. Studies on Glucose IIetabolism :Ln Fungi. .. .. .. 2 B. Polyols Produced by Fungi ••••• .. .. .. .. ~ . 5 c. !2.nnitol :<'orr.1ation in Fungi •••• .. .. .. .. ll D. Ergosterol Fo::t"T"...s.tion in Fungi. .. .. .. .. .. .. E. Pigm.ents Produced by Funei •• .. .. .. .. .. .. .. .. l5 F. The Separation~ Qualitative~ and Quantitative Analysis o~ Isolated Compounds.............................. l6 Chror.latographic Uethods ••••••••••••••••••••••• Paper ChromatoGrnphy ••• .. .. .. .. .. 16 Coluiun Chro:nlt."'l.tography ••••••••••• .. .. l6 Thin Layer Chrooatography ••••••••••• .. /. .. l7 ..., ..:... and Colorimetric l:ethods. .. .. lC Somog-Ji Hi.cro Copper ;:ethod. .. .. .. lS Nelson Cc:tor.imetr:Lc :':cthod ••••••••••••••••••• lC III. }!ATETI.I.~-LS A!ID APP .."-.r'1/ .. TUS • •••••••••••••••••••••••••••••••• l9 A. Haterials •••• .. .. .. .. .. .. .. .. .. ].9 B. Apparntus •••••••••••••••••••••••••••••••••••••••••• 20 -v- "T"':T ~~. l~Tl:OD3 ••••••••••••••••••••••••••••••••••••••••••••••••• Cultivation of' l:icroorganisms in Shake Fl~sks •••••• ., .... l·!icroor.3a.nisr:ls . •••••••••••••••••••••••••...••• 22 ~- Cultt1.re ~·:edia and Conditions •••••••••••••••••• 22 :-:ethods o:r f.nalysis of Spent Uedium. •••••••••••••••• l. Carbohydrate f~alysis ••••••••••••••••••••••••• Somog:.'"i I·1ethod for Reducing Sugar •••••••••••• ~· .. Nelson's Co~orim.etric I·!ethod :for Rcducinc Sugar •••••• ...••• .-... • . • • • • • • • • • . • . • • . • . • 23 2. Total Oreanic Solids fuia~rsis ••••••••••••••••• c. Paper Chromatography •••••...••••••••.••.••.••••••.. JO l. .30 2. ~'lo Di:m.ansiona.l Paper Chromatography •••••••••• JO D. Thin Layer Chromatoerarhy· 11cthod ••••••••••••••••••• Jl l. Preparation of.Thin Le.yer Plates •••••••••••••• 2. Application of Sample~ and Developruent of Thin Layer Chromatograms.................. Jl E. Colur.m Chror...atosraph~r liethod ••••••••••••••••••••••• .32 v. ~.Y..PI:R.I.ll!:!:l-JTS .J\!ID IBSULTS ••••••••••••••••••••••••••••••••• 33 A. Attempt to Isolate and. Identi.fy HateriaJ.s from the the Spent !·~cdi.a • .••••..••...•••.•••...•....•... l. Analysis of the Spent 1-Iedium of L. paradoxus, C. a,-srophorus, a."'ld H. confragosa. • • • • • • • • • • • • 33 2 •. EthyJ..acetate e.."'Ctraction o:f Spent. Ledia of IJ. confra~osa •••••• ~····•••••••••••••••••••• 33 -·li- B. Isolation and Identification of Compounds from the !-Iycclia o.f N. confrar;osa ••••••••••••• .... JS Ether =::ct.raction ••••••• • • • • • • • • • • • • • • • • • • • • • • • 38 2. Ethane~ I.::-:tract:i.on ••••••••••• ................. 33 Iso~ation via Colu.-rn •• ·•••••••••••••••••••••••• 4. tr:,rdrol:,~sis in. a Carit1S Tube • •.••....•.•••••... 41 c. Iso~ation and Characterization of Pigments ••••••••• 41 1. Cultivation of Fungus A-~-C ••••••••••••••••• .. 4~ 2. Extraction of the Pigments \'lith ether and n-butano~................................... 41 3. Preparation of acetone-dried cells •••••••••••• 42 Preparative Thin Layer Chrom.s.tocraphy ••••••••• 42 VI. DISCUSSIOI'J • ••••••••••••••••.••••••••••••••••••.•••••.•••• 45 VII. COI~CLUSION • •••••••••••••••.••••••••••••••••••••••••••••• VIII. :!3IBLIOG:1APIIY •••• .. .. .. .. .. .. .. .. .. .. 52 IX. .. .. .. .. 55 X. VITJ.'i. • •••••••••••••••• ·• •••••••••••••••••••••••••••••••••• 56 -vii- IJ:ST OF FIGURES ,..,.. ;..'lGUl"e l. Alternate Hetabolic Fates o:f Glucose 6-rhosphate •••••• ?iguro ...., The .J.oact1.ons in GJ.:rcolysis ••••••••••••••••••••••••••• 7 Figure _,.'? The Citric Acid Cycle................................. 8 Figure 4. Enzyme-Catalyzed Reactions o:f the Pentose Phosphate Pa.th1..;ay. • . • • • • • • • • • • • • • • . • • • • • • • • • • • • • • • • • • • • • • • • • • • • 9 .clcure...... 5 • Proposed ::etabolic Path-vro.y :for Formation o.r D-Xj.. lose and I-Arabinose in Penicillitun Chryso;:;~........... lO Figure 6. Somo~~ I£thod Standard Curve ••••••••••••••••••••••••• 29 Fieu.re 7. .l1.n Zxa.":lple o:f a Thin Layer Chromatogram o£ lT. con.frap;osa. 1-Iyccl.ial E.."rlracJ'c,.. • . • • • • • • . • • • • • • • . • • • • • • • • • . • 39 Fi.c.;ure S. .An J:Y..ample of A Thi..J. Layer Chrooatogram of H. confrarosa ~--~celia~ E..'..-tract .•. ..••..•.•••• •. • . • • • • • • • • • • • • • • • • . 40 Fiv.u-e 9. Pigments Produced by A-l-C vs. Time •••••• ~ •••••••••••• .. ·. -v:U.i- LIST OF '.i'ABLES Table I. Cor:q;:osition o:f the Synthetic Glucose !reditll:'.•••••••••• Table ........TT 2onozyi :r.retho<.l Standard Cu!""ves. • • • • • • • • • • • • • • • • • • • • • • 26 Tabl.e III. J.eagents for Somogyi Hethod.......................... 27 Table IV. ~eacents for Hclson I:ethod........................... 28 Table v. Carbohydrate and Total Organic Solids P~alysis Data........................................ 34 Table VI. Developing Solvent Syst e.-:1.s •••••••.•.••..••.•••.•••.•• 35 Table VII. 7isualization Reagents for Paper and Thin Layer Chromatography ••••••••••••••••••••••••••••••••• 36 Table VIII. Pigments Produced vs. Time by A-1-C •••••••••••••••••• 43 -l- ·..~.~~..! e r.1~~~~.a.rYJ.J ......... .. J.Jr.roduct.s o~..1. ...~ w~£u...J.. ~~ r::o...~ab o 1·:Lsw a::-e T1o-:fcver, .fu.r:,:i are knm·:n to exc:-otc many cccondary products into the ':'he deter- r;;.ir:.ati.o:J. of ·..rhct:·wr there are seconc!ary y:,rodacts for:n.ed 2:;- fur:~;i is co~1pounds. The best 1m:-· to detoct sccor..dary product forr..ation is to run a "carbon balance 11 bet'\·reen substrate conswned and proi..iucts fo:::~:r.cd. A detailed c:nd cor.1prehensive car~on Lala.-·1ce v.."tls described
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