Selective induction of secondary metabolism in Phaseolus lunatus by 6-substituted indanoyl isoleucine conjugates.
A novel and highly efficient route to new indanoyl isoleucine conjugates is described, which allows a wide range of substituents to be attached to the 6-position of the indanoyl moiety. We report the synthesis of conjugates with methyl, methoxy, propoxy, allyloxy, pentoxy, and 2-(2-methoxy-ethoxy)-ethoxy 6-position substituents. Preliminary biological activities of the novel compounds with significantly enhanced water solubility were determined using the Lima bean (Phaseolus lunatus) volatile bioassay. The compounds induce variable volatile patterns, and structure-activity relationships show an ability to differentially induce separate pathways leading to secondary metabolites.
Lauchli
Ryan
R
Max-Planck-Institut für Chemische Okologie, Winzerlaer Str. 10, Jena, Germany.
Schüler
Göde
G
Boland
Wilhelm
W
D000215:Acylation; D000478:Alkylation; D008401:Gas Chromatography-Mass Spectrometry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007532:Isoleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D027805:Phaseolus / Q000187:drug effects / Q000378:metabolism*; D015398:Signal Transduction / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014835:Volatilization
D007189:Indans; D007532:Isoleucine