Tuberonic acid

Tuberonic acid (cis isomer), R = H tuberonic acid glucoside,... 

Recently, the protected tuberonic acid was synthesized by using the method shown in Scheme 10 and deprotection was studied with success to afford tuberonic acid for the first time (Scheme 13)846 Through the synthesis it was revealed that tuberonic acid and its derivative are liable to epimerization more easily than epi-jasmonic acid. In addition, exposure of tuberonic acid to NaOH in aqueous MeOH produced 12-hydroxyjas-monic acid. 

Tuber formation is also known to be induced by a JA derivative called tuberonic acid.8 7 Tuberonic acid has been primarily found in potato as a tuber-inducing substance, and named as tuberonic acid. This compound is also shown as a substrate of a sulfotransferase in Arabidopsis910... 

Tuberonic acid (5) was isolated as a lactone from J. grandiflorum L. [19], An acetyl tuberonic acid amide with phenylalanine was isolated from Praxelis dematidea [20] and the glucoside was isolated from Solanum tuberosum L. as a potato tuber-inducing substance [21,22], The methylester of the glucoside was isolated from Helianthus... 

Metabolism and transport of jasmonic acid in potato plants were studied [47]. The C-labelled compound applied to the leaves was metabolised to a tuberonic acid... 

Tuberization in potato plants is considered to be controlled by a specific active compound. The structure of an active tuber-inducing compound from potato leaves was determined to be 3-oxo-2-(5 -3-D-glucopyranbsyloxy-2 -(E)-pentenyl)-cyclopentane-l-acetic acid. The aglycone of this glucoside is 12-OH-jasmonic acid, termed tuberonic acid [53]. Jasmonic acid, methyl jasmonate and cucurbic acid were also shown to be capable of inducing tuberization in potato in vitro [53]. In addition, jasmonic acid seems to be involved in tuberization in yam [54], Jerusalem artichoke [55] and in bulb formation of garlic [56]. 

Formation of (+)-7-/60-jasmonic acid which is sequentially enzymatically converted to (-)-jasmonic acid JA and its methyl ester methyl jasmonate (MJ) [4], and also to other jasmonate compounds such as tuberonic acid, etc. 

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