Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybel

~ l t n of ~ ~ d a b ~ m p~ l m o l f o r r m q pdocybn and pliloun d r m o L g l a y n lugb r P ~ b e b epuuuunA s p ~ " r b~ouannformarroo for h,drol,~~alun y ~ m m dm~aoun ~n. or r addd aymthe!#r S . N d ~ 4 I - V ) p U m m e vpr 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 r m bodlbodl pP&,br ~ h x - U)wondmi m s U) m b i m % rr lhc rm oramp.< oia & r e 1 4 bl"ayllhsl,* or s)w""nc rlb ruy, A~ a f lbatraolronnatlon n iv . ~ - ~ l b ~ b xl, k ~~ drmm.-raw wnlhnu(- a N, or aud q w l l i l d P d e m k r a , n H-atm. poablc ~ n m prrcvrnor d &-*lo, l rra
capaelty

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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 st lmprovcment the bmbbomyats to t u ~ h manner us dmon B ovrtrd for anublouc-ordwme acuoornucetcs or vanous aseomvcaer BY m r f o m u o ~a qtlastuauveanal99Lss emd& dkdds pllaaybin and wIwnwnm t h some of P & c y k and I m y k , we found~oagrdcreble m t ~ o wen w h one spec1ar( S m m ~ z l B y ~ ~ n s el 01 1986) as W U as to m l i w ( G u m 1987) Moreova fmtms mvceba ~f P ~ ~ d m b e ~~ nr

GOS

mnhylauon and hydroxylauon r&c OAK= 1988) EnrLer stud~n p u l o q h m h of c -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~LL ol 1966, A ~ U R ~ L L N et and m 1968a,
a

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

d &eds

mNn (2 I) EWPILM dmbk ~m0uot mto l k o r 4 t w ~ u ~ u c b W n P ~ f ~ m t b o m - g a TNbnvIrnnm(Gml987) 01SmN,N~P & f f i y ~ ~ M o (wthess ~ a ; l * o r 1957) wn added m 135g er m mrdnrm Cvmnrton n d wbouladdruon of any hhrl. da(.nflve wa8 d t m d mo mlulob fer orstrnkdtl-n m m dsmM elmwbm ((funl m The G mushrwm umc ~xodurcdb~ thc P d a m u 4- urnurn4 w& 9 m :

N ~ l v a l o n P A r k A d n d mu duc4pe of

-

'1 Rpet

n m ' . Gem (GDR).

Stbs 2nd Intcrnatmal SPWM

M a y 2-7. 1988

on "New B-uw

M t b h Imm Mxrom8a. an o m

mu.)lruum(ti.an 1381) ual kept iu a 5ta'L ~d13m00 % mll a 6 w surfam mlturc or P rrm,,nooio MYWII~ P rrmlmrmr. were p m ro ~ u d dtu (sod) oo a of y z y n t h r ~ d w m vlVl 8% glvmv ((irprr I9861 ConcmPsons w to IOmul of N - m n h > b n m n c m (EICYI) YIR d d d al h,dl~~hl~TlfCto LC I" "L~dl"", btrarfton aod rnbyrts The rxuanron pmccdw fur &xed mwhruont,and m)mlm ns d l M Ihc lPs ormdo.~ l k J ~ 8 b)~r.uls HI'IE uld TLC u~ orxnkd d=whsn (Our7 19al8. b 1987, S s d 7 s ~ ~9861A& . moole pbiur ra. rlrr uud lo the n l ' ( v ~ ~ ~ ~ m r w and vmr- ~ -Pu~r
a~

*,,

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-\"

19W1 I ~ lodotedcrluauri. =r I ~ n~ product. or the~ o ~ 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 r uncme~ruea the b u m MAT CH 6 WWNI m (ronuafloo aorg

I t was fomd that m the fmitmg m & y of P cubcm~p # a t h x h x s l a ~ a n added af 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. r r d y % i a suggested M the molmular furmula T r the mmpound. uh~lc marn rpsdrum rhowed b a g m m l !om o the 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 m h n at 221. 267. 280 and 290 nm usrs vcr) nmllar nad 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 (~T ,mp 105 OC,C O , H) e QN ,, was lmlated ro tugh amounts (1 5 % p r

me

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 d R~wutlrsru1982. WLW el ol 19ffl) 2 1 2M1. 267. 282 and -n 2.

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

P nrbew; mntairu idolemllabids u: both naturally g r o ~ nfrutmg bodzc~ cult>. and ?,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~th and PT wen RC

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 ft the m W y gown mushe rsam (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~ond murhrwm 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 n HPLC was hy + ?do/ Irplatnvc) The deteonon limits for Pl'aod HT w m 20 and M ng. ~SWX~yely

&e &d

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

6v the uv d ~ t ~ c f e r

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b . u d rw 6d r u .

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