40 F. C. STEWARD AND J. K. POLLARD 
Sith gl 42s «1100 73 
CH orphan 
oe | HO-CH,| | HOCH: a |. 
| ; 3 
OOOH a coon A. ‘COEt 
NH NH we! 
(A) (B) (C) 
the structure of this compound (BIEMANN, DEFFNER AND STEWARD®, 1961). There- 
fore, although the compound corresponding to structure A has not yet been found 
in plants, it may occur. 
A compound present in Phlox (Fig. 16), which also occurs in Hemerocallis (Fig. 17), 
yields upon hydrolysis hydroxyglutamic acid, ammonia and a still unidentified 
carbon residue. The hydroxyglutamic acid also occurs free in Phlox (Fig. 16; ef. 
VIRTANEN AND HreTAra**), A recent isolation by one of us (J.K.P.) has permitted 
the unequivocal proof of the identity of this acid as y-hydroxyglutamic acid. 
Since WINITz has recently resolved the hydroxyglutamic acids into its four stereo- 
isomers, it is now, therefore, possible to identify the natural product with its syn- 
thetic counterpart (cf. the contribution of WiniITz to this Symposium, and also 
BENOITON eé¢ al.°). 
The list of new nitrogenous compounds, with unexpected structure, continues to 
mount. A new histidine isomer which contains the pyrazole ring, isolated and proven 

Fig. 16. The ninhydrin-reactive, alcohol-soluble compounds of the seeds of Phlox paniculata. Com- 
pounds designated by Nos. 2—23 follow the convention of Fig. 1. U-103H is now known to be y- 
hydroxyglutamic acid. U-103 is now known to yield y-hydroxyglutamic acid, ammonia and an un- 
identified residue on hydrolysis. 
References p. 42 
