y-GLUTAMYL PEPTIDES IN PLANTS 57 
B-N-(y-L-Glutamyl)-4-hydroxymethylphenylhydrazine (Agaritine). From the press 
juice of commercial mushrooms (Agaricus bisporus), a ninhydrin-reactive material 
was isolated in crystalline form. Acid hydrolysis liberated L-glutamic acid and a com- 
pound which oxidized to an aryldiazonium salt. The latter could be hydrolyzed to 
p-hydroxybenzylalcohol. This evidence plus elemental analyses, and liberation of 
CO, with ninhydrin indicated the structure”. 
N-(y-L-Glutamyl)-4-hydroxyaniline. An acid-labile substance was isolated from the 
non-protein fraction of a mushroom (Agaricus hortensis), by chromatography on 
activated charcoal and Dowex-1 (ref. 14). The crystalline material hydrolyzed to 
L-glutamic acid and p-hydroxyaniline as shown by comparison of infrared spectra. 
Final proof was obtained by comparison of synthetic N-(y-L-glutamyl)-4-hydroxy- 
aniline with the isolated compound by infrared. 
y-Glutamylcysteine. y-Glutamylcysteine has been known to be an intermediate in 
glutathione synthesis in plants and animals”? 21. This peptide must have widespread 
occurrence although it may never accumulate to a sufficient extent to be isolated in 
quantity. 
TABLE I 
OCCURRENCE OF Y-GLUTAMYL COMPOUNDS IN PLANTS 

Motety attached to y-carboxyl 

of glutamic acid Source Evidence Reference 
Lt-Phenylalanine Onion bulb Isolation and degradation 5 
Soy bean seed Isolation, degradation and 8 
synthesis 
L-Tyrosine Soy bean seed Isolation, degradation and 8 
synthesis 
L-Valine Onion bulbs Isolation and degradation 5 
L-Isoleucine Onion bulbs Isolation and degradation 5 
Leucine Lima bean seeds Isolation and chromatography 3 
Kidney beanseed Chromatography and synthesis 8 
Alanine Pea seedlings Chromatography 9 
Methionine Kidney beanseed Chromatography 8 
S-Methyl-L-cysteine Kidney beanseed Isolation, degradation and 2 
synthesis 
Lima bean seed Isolation and degradation 3 
p-Alanine Iris bulb Isolation, degradation and 7 
synthesis 
fp-Aminoisobutyric acid Iris bulbs Isolation and degradation 4 
a-Amino-f- (2-methylene- Ackee fruit Isolation and degradation 6 
cyclopropyl) propionic 
acid (hypoglycin A) 
L-Cysteinylglycine Most plants Complete = 
S-($-Carboxy-n-propyl)-L- Onion bulb Isolation, degradation and 5 
cysteinylglycine synthesis 
Ethylamine Tea leaves Isolation, degradation and 12, 18 
synthesis 
Mushrooms Isolation, degradation and 13 
synthesis 
f-Aminopropionitrile Sweet pea seed Isolation, degradation and Ir, 19 
synthesis 
p-Hydroxyphenylhydrazine Mushrooms Isolation and degradation 10 
p-Hydroxyaniline Mushrooms Isolation, degradation and 14 
Ammonia 
Most plants 
synthesis 
Complete 

References p. 64 
