By Atherton Seidell
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Extra info for A Handbook of Most Reliable Quantitative Solubility Determinations
When leaf tissue of different plant species was incubated with phenylal anine jff-i4C for 24 hr and the tissue was worked up for the different C e - C i acids we found the highest per cent conversion of this amino acid in the plants shown in Table 1 (Zenk and Müller, 1964). Phenylalanine is well incorporated into the benzoic acids. Syringic acid, which was not labelled in our original T A B L E 1. INCORPORATION R A T E S OF PHENYLALANINE (ß-^'^C) I N T O BENZOIC ACIDS IN D I F F E R E N T P L A N T T I S S U E S ( Z E N K A N D M Ü L L E R .
6). But the question was still open, at which stage did the hydroxylation of the phenylpropane unit occur. -coumaric acid (Table 1). One must not draw any conclusions from these data, because in case of umbel liferone a ring opening was to occur prior to the reaction with the acetate H00C-CH=CHH^^^^0H co-o OH HO ^j^CH=CH OH F I G . 6. Incorporation of /7-coumaric acid-3-**C and umbelliferone-4-^'^C into oxyresveratrol. units. This may slow down the speed of the over-all reaction. Nevertheless the fact that umbelliferone itself is incorporated into oxyresveratrol, although in rather low yields, points to the fact that fully hydroxylated cinnamic acids may act as the immediate precursors of hydroxylated plant stilbenes.
This was not unexpected since heartwood constituents are formed with very low speed. Similar observations have been made during our work with pinosylvin monomethyl ether (Billek and Ziegler, 1962). On the other hand it was necessary to localize the incorporated activity, because such low rates may be due to unwanted side reactions. TABLE 1. PRECURSORS O F OXYRESVERATROL Compound Sodium acetate-l-^'^C /7-Coumaric acid-3-^"^C Umbelliferone-4-^*C Activity (mc) Incorporation (%) 200 0-59 0-23 001 015 002 Degradation followed usual procedures and is shown in Fig.
A Handbook of Most Reliable Quantitative Solubility Determinations by Atherton Seidell