Jochen Gartz - Biotransformation Of Tryptamine Derivatives In Mycelial Cultures Of Psilocybe

Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybel

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~ l t n of r ~ P ~ d a b ~ m ~ p~b l m e o lbf o r r m q pdocybn and pliloun d r m o L g l a y n lugb ~n.epuuuunA s p ~ " rb~ouannformarroo for h,drol,~~alun or y ~ m m dm~aoun r addd aymthe!#r S . N d ~ 4 I - V ) p U m m evpr foulld lllvr lush amovnll of & b y d r o ~ ~ - N . N d l c l b y l ~ txm~oc[up tu J 3%) and a m#omq u l i l y or p-4. (0.01 0 8.J ra. mlaw rmn rmms bodlbodl pP&,br ~ h x -U) U)wondmi m i mb % rr lhc rm oramp.< oia & r e 1 4 bl"ayllhsl,* or s)w""nc rlb ruy, A~ anfilv batraolronnatlon . ~ - ~ l b ~ b xl,- ka ~~Ndrmm.-raw , wnlhnu(or aud q w l l i l d P d e m k r a , n H-atm. poablc ~ n m prrcvrnor l d &-*lo, rra capaelty

featurff for msdlcll and blslogxal puB;L therc n a gat lack of bass k n o v l d i h c h uould enable stlmprovcment the bmbbomyats to t u ~ hB manner us dmon ovrtrd for anublouc-ordwme acuoornucetcs or vanous aseomvcaer BY m r f o m u o ~a qtlastuauveanal99Lssthemd& dkdds pllaaybin and wIwnwnm some of P & c y k and I m y k , we found~oagrdcreble ~ m t ~ o wen n s w h one spec1ar( S m m ~ z l B yel~ 01 1986) as W U as to m l i w (~G~u m 1987) Moreova fmtms mvceba ~f P ~ ~ d m b nre

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mnhylauon and hydroxylauon r&c OAK= 1988) EnrLer stud~nof p u l o q h m hc-yotheus lo subrncrgcd m l t u r c of Psrlucy& Ntenru reveakd that u,ptophan and tr)ptam m s u s paurrorr ufthr W u l d r (AGUR~LLet ol 1966, A ~ U R ~ Land L N m 1968a, a

In the pnrnt p r , the hotranafo-tlon o f fed synthetlo kyplmm denvah~esby myxllal cuthnes of Psilocybc c u k m ~ dand P s e ~ : r h c a @(FR) Kmm M (-I 1977) m dcrabed Mat*

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N~lvalon of P A r k A d n d mu duc4pe

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mNn (2 I) EWPILM mto lk dmbk ~m0uot o r 4 t w ~ u ~ u c b W n P ~ f ~ m t b o m - g a TNbnvIrnnm(Gml987) ~P 01SmN,N& f f i y ~ ~ M o (wthess n d ~ a ; l * o r 1957) wn added m 135g er m mrdnrm Cvmnrton wbouladdruon of any hhrl. da(.nflve wa8 dm t m d mo mlulob fer orstrnkdtl-n m dsmM elmwbm ((funl9m The Gm mushrwm umc ~xodurcdb~ thc P d a m u 4:- urnurn4 w&

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Stbs 2nd Intcrnatmal SPWM

n m ' . Gem (GDR).

M a y 2-7. 1988

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Matnbohm Imm Mxrom8a.

mu.)lruum(ti.an 1381) ual kept iu a 5ta'L ~d13m006 % mll aw surfam mlturc or P rrm,,nooio MYWII~of P rrmlmrmr. were p m ro ~ u d dtu y (sod) oo a z y n t h r ~m d w m vlVl 8% glvmv ((irprr I9861 ConcmPsons w to IOmul of N - m n h > b n m n c (EICYI) YIR d d d al h,dl~~hl~TlfC I" to LC "L~dl"", btrarfton aod rnbyrts The rxuanron pmccdw fur &xed mwhruont,and m)mlm ns d l M Ihc lPs ormdo.~s l k J ~ 8 b) d ~r.uls HI'IE uld TLC u~ orxnkd d=whsn (Our7 19al8. b 1987, S7 s ~ ~9861A.& moole pbiur ra. rlrr uud lo the n l ' ( v ~ ~ ~ ~ m r w and - P vmru~r~ a~

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19W1 I ~=r lodote I dcrluauri ~ . no ~ product. ~ or the~ hlovanrrmrtlon uuc vokrcd hmn m h a n o b cxaans of Ihr mwhmona by alluloa. m l m chromntosaphy as a-kd for laolllw or p a d a y k (K#n&sn a I 19811 MW spacromnry ~ a s r e p c l r runcme~rueam the b u m MAT CH 6 WWNI (ronuafloo aorg

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I t was fomd that m the fmitmg my& of P cubcm~pa # t h x h x s l a ~ a naf added svnfMtc DT m the Cmt>o.of tbc mdole nildew awured 1Fre 1). 4-Phos~horrlor~-

rooms ( O . e & r dry we@!) by &llulae column c&oida~&&~hy.M r r d y % i a suggested the molmular furmula Tor the mmpound. uh~lcthe marn rpsdrum rhowed b a g m m l !om atm;cI32(f,, M'-HPO,), 188(f,-N C H (, 187(f,-NH (C,H,J,), 174(f,CH,N(C2HJ2) -surd U V manlma m mnhand at 221. 267. 280 and 290 nm usrs vcr) nmllar to roported data of pslloeybm and could be athiuted to a Csobntltnted Pyptarmnedenwtrn & o m era/ 1981, Rep= and LESLIE 1D77, Wuasr a d 1984) 4-H~my-N,N ~ y l u y p (H ~T), e mp 105 OC,CQ ,O , N, was lmlated ro tugh amounts (1 5 % p r

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dry wn&ht) from fntml!n~tmdhu, of P mhmux 11 &spla]ed the same mar$ rpeOrum as phuaphor8c ertrr (II] Thc L'V rpaua nf the compcund shovrd *cry r~m~lar maima as mllonn ( C ~ a l m ~ h g la -nd R~wutlrsru1982. WLW el ol 19ffl) 221.2M1. 267. 282 and

293 om Bv mne rllialrne ohamhataw a camolete olea~weof P?' and a subsequent formatlen

P. nrbew; mntairu idolemllabids u: both naturally g r o ~ nfrutmg bodzc~and cult>?,aced mushrooms ((inwn 1987) n e mushrooms eatalnlng the ethylsompotmd3 PI and 111 (Fir ?I had omalla cads than the fruit hodros from the culUvauon wthoul lryp &M d z t k e (Flg. 33 )fo<ever, the sporrs of the m e s h r m w~thRC and PT wen

normi mslzennd germmxed wen onmalt agar.Thcsemusluooms developed a blue-green wloqr h a n d k g but not the deep blhe cokmr c h w m fet the m W y gown mushrsam (Om= 1987) Tbs obwahon a >n pod amemnt mth model reactms woocrr tbe rraydanoo dplne pslla d W reported In the lltcnrture gUB88P aod FkXuTh

1963) Tahie Ishews tbat LhF WeJs 9f HT and PT from* sc~ondmurhrwm CoIbva.tl0~W e d W m one Qush t o the nexl The standard demauon of the d e t m a t ~ o nhy HPLC was + ?do/ Irplatnvc) The deteonon limits for Pl'aod HT w m 20 and M ng. ~SWX~yely

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The TLC analGs of PT show. the rsmo Rd-\loln culnur ansrng rRm the rrman of plucybio wiIh EIIIILICH',reagent ( ( ~ A R I Z 198Sb). On ullca gd, rppnol-water-acette andl10 3 3 1 a l I d ~ c l c a r r ~ o l u t m o f ~ ~ R f 0 . 1 7 1 . r r ~ dIKf0.23).M'(RfO301. w~bin

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