Biotransformation of tryptamine derivatives

in mycelial cultures of Psilocybel

u,dnl ~ l t n of P ~ d a b ~ m
r ~ e o lbf o r r m q pdocybn and pliloun d r m o L g l a y n lugb
~ p~b l m
capaelty for h,drol,~~alun or y ~ m m dm~aoun
r ~n.epuuuunA s p ~ " rb~ouannformarroo
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 mi mb % rr lhc rm oramp.<
oia & r e 1 4 bl"ayllhsl,* or s)w""nc rl- b ruy,
A~ anfilv batraolronnatlon
. ~ - ~ l b ~ b xl,- ka ~~Ndrmm.-raw, wnlhnu(- or
P d e m k r a , n H-atm. poablc ~ n m prrcvrnor l 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 ~ 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& GOS
c y k and I m y k , we found~oagrdcreble n s w h one spec1ar( S m m ~ z l B yel~
~ m t ~ o wen
01 1986) as W U as to m l i w (~G~u m 1987) Moreova fmtms mvceba ~f P ~ ~ d m b nre

a 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)pta-
m m s u s paurrorr ufthr W u l d r (AGUR~LLet ol 1966, A ~ U R ~ Land L N m 1968a,
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* d &eds
of P A r k A d n d mu duc4pe
N~lvalon 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&

'1 Rpet Stbs 2nd Intcrnatmal SPWM on "New B-uw Matnbohm Imm Mxrom8a.
n m ' . Gem (GDR). M a y 2-7. 1988
a~ 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, S-
*,,
7 s ~ ~9861A.& - P vmr-
moole pbiur ra. rlrr uud lo the n l ' ( v ~ ~ ~ ~ m r w and u~r~
19W1
I ~=r lodote
I dcrluauri
.
~ no ~ or the~
~ product. 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
-\"

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 CH
(, 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 Pyptarmneden-
wtrn & 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
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
-nd R~wutlrsru1982. WLW el ol 19ffl) 221.2M1. 267. 282 and
mllonn ( C ~ a l m ~ h g la
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 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 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
&&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-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
t.. b6.durdur.w