Cytokinin biochemistry in relation to leaf senescence. III. The senescence-retarding activity and metabolism of 9-substituted 6-benzylaminopurines in soybean leaves

Abstract

A group of 14 9-substituted derivatives of 6-benzylaminopurine (BA), including the alanine conjugate, oxygen heterocyclic and alkyl derivatives, and compounds with a modified 9-ribose moiety, were assessed for their ability to retard soybean leaf senescence. The 9-alanine conjugate was very weakly active, and only two compounds, 9-(2-tetrahydropyranyl)-BA (9THP-BA) and 9-(2-tetrahydrofuranyl)-BA (9THF-BA), proved to be considerably more effective than BA. The metabolism of these three BA derivatives was determined to rationalize their differing activity. The alanine conjugate of BA was largely unmetabolized in leaf discs, but 9THP-BA and 9THF-BA released free BA and were also debenzylated to 9THP-adenine and 9THF-adenine, respectively. The three products of metabolism were identified by mass spectrometry. The enhanced activity of 9THP-BA and 9THF-BA, relative to that of BA, is attributed to their greater stability and their ability to gradually release free BA. This released BA was less susceptible to inactivation by alanine conjugate formation than was exogenous BA. The novel BA analogue 7-benzylaminooxazolo[5,4-d]pyrimidine, in which the 9-NH is replaced by oxygen, was inactive at 100 μM.