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1. Importance of the chiral centers of jasmonic acid in the responses of plants. Activities and antagonism between natural and synthetic analogs

Author:
Holbrook, L.; Tung, P.; Ward, K.; Reid, D.M.; Abrams, S.; Lamb, N.; Quail, J.W.; Moloney, M.M.
Source:
Plant physiology 1997 v.114 no.2 pp. 419-428
ISSN:
0032-0889
Subject:
Helianthus annuus; Brassica napus; measurement; chemical degradation; dose response; jasmonic acid; gene expression; Triticum aestivum; Nicotiana tabacum; esters; stereochemistry; enzyme activity; chemical structure; seed germination; transgenic plants; cotyledons; proteinase inhibitors; reporter genes; chemical constituents of plants; chlorophyll; beta-glucuronidase
Abstract:
... The importance of the two chiral centers at C-3 and C-7 in the molecular structure of jasmonic acid in plant responses was investigated. We separated methyl jasmonate (MeJA) into (3R)- and (3S)-isomers with a fixed stereochemistry at C-3, but epimerization at C-7 is possible. The four isomers of the nonepimerizable analog 7-methyl MeJA were synthesized. These six esters and their corresponding aci ...