PLANT PHYSIOLOGY , Vol 110, Issue 4 1177-1186, Copyright © 1996 by American Society of Plant Biologists
|
DEVELOPMENT AND GROWTH REGULATION |
N4-Hexanoylspermidine, a New Polyamine-Related Compound That Accumulates during Ovary and Petal Senescence in Pea
M. A. Perez-Amador, J. Carbonell, J. L. Navarro, T. Moritz, M. H. Beale, M. J. Lewis and P. Hedden
Departamento de Biologia del Desarrollo, Instituto de Biologia Molecular y Celular de Plantas, Universidad Politecnica de Valencia-Consejo Superior de Investigaciones Cientificas, Camino de Vera 14, E-46022 Valencia, Spain (M.A.P.-A., J.C.)
A previously unknown polyamine conjugate that accumulates in senescing
ovaries of pea (Pisum sativum L.) was shown by mass spectrometry, nuclear
magnetic resonance, and chemical synthesis to be N4-hexanoylspermidine
(hexanoyl-spd) This structure was indicated by analysis of the dansylated
polyamine using fast atom bombardment mass spectrometry, following
purification by high-performance liquid chromatography. Furthermore, acid
hydrolysis of the compound yielded spermidine and hexanoic acid. 1H-nuclear
magnetic resonance suggested that spermidine was substituted at N4 in the
conjugate. Hexanoyl-spd was synthesized, and its didansyl derivative was
shown to have an identical mass spectrum and high-performance liquid
chromatography retention time as the derivatized natural compound. Further
confirmation of its structure was obtained by comparison of the synthetic
and natural polyamines as trifluoroacetyl derivatives using gas
chromatography-mass spectrometry. This new polyamine conjugate is present
in pea ovaries at low levels at anthesis and its concentration remains low
in developing seeded fruit or in parthenocarpic fruit that have been
induced by application of growth regulators to emasculated flowers or by
topping the plant. Conjugate levels are also low in parthenocarpic fruit
induced naturally in the slender (la crys) mutant. However, levels of
hexanoyl-spd increase progressively in senescing petals and ovaries,
beginning at anthesis or 2 d later, respectively.