Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybel

u,dnl ~ l t n r ~ of P ~ d a b ~ ~ ~ m b mpble o l fo r rmq pdocybn and pliloun d r m o L g l a y n lugb capaelty for h,drol,~~alun or y ~ m m r dm~aoun ~n. epuuuun A s p ~ " r b~ouannformarroo addd aymthe!#r S.Nd~4I-V)pUmme vpr foulld lllvr lush amovnll of & b y d r o ~ ~ - N . N d l c l b y l ~ p txm~oc [up tu J 3%) and a m#om q u l i l y or 4.p- (0.01 0 8.J ra. mlaw rmn rmms bodlbodl pP&,br ~ h x - U) U)wondmi immb % rr lhc rm oramp.< oia & r e 1 4 bl"ayllhsl,* or s)w""nc rl- b r u y ,

A~ anfilv. batraolronnatlon ~ - ~ l b ~ b - k ~ xl, a ~ N , drmm.-raw wnlh nu(- or P d e m k r a , n H-atm. poablc ~ n m l prrcvrnor d &-*lo, rra aud q w l l i l d

featurff for msdlcll and blslogxal pu- B;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 B manner us dmon ovrtrd for anublouc-ordwme acuoornucetcs or vanous aseomvcaer BY m r f o m u o ~ a qtlastuauve anal99Ls sthe md& dkdds pllaaybin and wIwnwnm some GOS of P& c y k and I m y k , we found ~oagrdcreble ~ m t ~ o n s wen w h one spec1ar ( S m m ~ z l B y ~ el 01 1986) as W U as to m l i w ~ ~ (Gum 1987) Moreova fmtms mvceba ~f P ~ ~ d m b e nr

a mnhylauon and hydroxylauon r&c OAK= 1988) EnrLer stud~n of 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)pta- mms u s paurrorr ufthr W u l d r (AGUR~LL et ol 1966, A ~ U R ~ L L and N m 1968a,

In the pnrnt p r , the hotranafo-tlon of fed synthetlo kyplmm denvah~es by myxllal cuthnes of Psilocybc cukm~d and P s e ~ : r h c a @ (FR ) Kmm (MI- 1977) m dcrabed

Mat* d &eds

N ~ l v a l o n of P A r k A d n d mu duc4pe - 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 T ~ P NbnvIrnnm(Gml987) 01SmN,N- & f f i y ~ ~ M o n d (wthess ~ a ; l * o r 1957) wn added m 13 5g er m mrdnrm Cvmnrton wbouladdruon of any hhrl. da(.nflve wa8 dm t m d mo mlulob fer orstrnkdtl-n m dsmM elmwbm ((fun l9m The Gm mushrwm umc ~xodurcd b~ thc P damu 4:- urnurn4 w&

'1 Rpet Stbs 2nd Intcrnatmal SPWM on "New B-uw Matnbohm Imm Mxrom8a. n m ' . Gem (GDR). May 2-7. 1988

a~ mu.)lruum(ti.an 1381) ual kept iu a 5ta'L ~d13m00 6 % mll aw surfam mlturc or P rrm,,nooio MYWII~ of P rrmlmrmr. were p m ro ~ u d y dtu (sod) oo a

z y n t h r ~ m d w m vlVl 8% glvmv ((irprr I9861 ConcmPsons w to IOmul of N -mnh>bnmnc (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 kJ~8d~ b) r.uls HI'IE uld TLC u~ orxnkd d=whsn (Our7 19al8. b 1987, S- 7 s ~ *,,, ~9861 A.& moole pbiur ra. rlrr uud lo the n l ' ( v ~ ~ ~ ~ m r w - P u ~ r ~ and vmr- 19W1 I ~ I ~ ~ ~ ~ =r lodote dcrluauri. no product. or the hlovanrrmrtlon uuc

vokrcd hmn mhanob cxaans of Ihr mwhmona by alluloa. m l m chromntosaphy as a-kd for laolllw or p a d a y k (K#n&s n a I 19811

MW spacromnry ~asrepc l r r uncme~ruea m the b u m MAT CH 6 WWNI (ronuafloo aorg ." -\"

It was fomd that m the fmitmg my& of P cubcm~p a #t h x h x s l a ~ a n af 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~lc the marn rpsdrum rhowed bagmml !om atm;cI32(f,, M'-HPO,), 188(f,-N (C,H 187(f,-NH (C,H,J,), 174(f,CH,N(C2HJ2) me -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 Pyptarmne den- wtrn & o m era/ 1981, Rep= and LESLIE 1D77, Wuasr ad 1984) 4-H~my-N,N- ~ y l u y p ~ e (HT), mp 105 OC, C,,Q,ON,, was lmlated ro tugh amounts (1 5 % pr

dry wn&ht) from fntml!n~ tmdhu, of P mhmux 11 &spla]ed the same mar$ rpeOrum as phuaphor8c ertrr ( I I ] Thc L'V rpaua nf the compcund shovrd *cry r~m~lar maima as mllonn (C~alm~hgl- and R~wutlrsru 1982. WLW el ol 19ffl) 221. 2M1. 267. 282 and 293 om Bv mne rllialrne ohamhataw a camolete olea~we of P?' and a subsequent formatlen

P. nrbew; mntairu idolemllabids u: both naturally g r o ~ n frutmg 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~th RC and PT wen normi mslzennd germmxed wen onmalt agar.Thcse musluooms 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 mush- rsam (Om= 1987) Tbs obwahon a >n pod amemnt mth model reactms woocrr

tbe rraydanoo dplne psll- a d W reported In the lltcnrture gUB88P aod FkXuTh 1963) Tahie I shews 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 hy HPLC was + ?do/ Irplatnvc) The deteonon limits for Pl' aod HT w m 20 and M ng. ~SWX~yely. &&ed 6v the uv d ~ t ~ c f e r

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-acet te 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 ~ d w ~ b i n IKf0.23).M'(RfO301.

t.. b6.durdur.w