Tuberone

Rifater (Marion Mcrrcll)- Nicazide (IF1) Tuberon (Shionogi)... 

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... 

Several important metabolites of polyunsaturated fatty acids (PUFA) contain a cyclopentane ring. Compounds such as jasmonic acid, cucurbic acid, and tuberonic... 

See olso Scheme I in Otapter 7. FA fatty acid, HU hydn xroxide lyase, IF isomerization faaor(s),JA jasmonic add, MJ methyl josmonate, PDA phytodienoic add,TA-C tuberonic odd glycoside. For other abbreviations see the text... 

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]. 

Simko I, Omer EA, Ewing EE, McMurry S, Koch JL, Davies PJ (1996) Tuberonic (12-OH-jasmonic) acid glucoside and its methyl ester in potato. Phytochemistry 43 727-730 Singh AP, Singh AK, Begum AS, Sahai M (2003) Two acyl sucroses from Petunia nyctaginiflora. Phytochemistry 63 485-489... 

We also achieved the synthesis of methyl tuberonate (MTA, 13) (Scheme 4). Bicyclic alcohol 14 was converted to diol 15. The key of the synthesis was... 

Methyl jasmonate was prq>ared from its commercial racemate in overall 40% yield.We also succeeded to resolve a sterically hindered hydroxy conq)ound 14 using Chirazyme L-9 (Roche), which was the key intermediate of our synthesis of ( )-mediyl tuberonate."... 

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. 

Verley isoiatwl from the oil a body of the formula C H.p,-,0 w hich he considered to be a ketone and which he named tuberone. Hesse is olated from the oil the methyl esters of bsn7.oic and anthranilic acids, the latter being present to the extent of 1 13 per cent. Benzyl bonzoate is also present, as well as free benzyl alcohol. Methyl salicylate wag detected in the oil obtalucd by distilling the enflenrage pomade oil, but not in that obtained from the petroleum ether extract of the flo wenj. 

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