Todomatuic acid

Interesting substances possessing juvenile hormone activity against hemipteran bug have been detected in conifers belonging to Abies species (-F)-Juvabione [methyl ester of (-F)-todomatuic acid], isolated from balsam and Japanese fir wood, may have potential use for insecticidal applications. A related compound have been isolated from Douglas fir wood. 

Juvabione, the compound responsible for this activity, was isolated from the balsam fir, Abies balsamea (L.) Miller, and identified as the methyl ester of todomatuic acid, (+)-4(i )-[ 1 R)-S -dimethyl-3 -oxohexyl]-1-cyclohexene-1-carboxylic acid [87]. This compound is a sesquiterpenoid (Fig. (6)) with a cyclohexene group and an a,(3-unsaturated methyl ester group the chemical data for this compound are summarized in Appendix II, Table 1. The IR spectrum suggests that there is a carbonyl ester group present in conjunction with a double bond (1722 and 1645 cm 1) and also an isolated carbonyl group (1712 cm 1) [87]. Mass spectroscopy confirms... 

The dramatic increase in terpene formation, accumulation, and emission in P. abies in response to methyl jasmonate is consistent with the effect of methyl jasmonate or jasmonic acid on many defense compounds in angiosperms. In conifers, jasmonates had been previously shown to promote the formation of heat shock and defense signaling proteins, to enhance resistance to pathogenic fimgi, and to promote colonization with ectomycorrhizae. In relation to terpenes, jasmonates had been shown to promote formation of an oxygenated sesquiterpene, todomatuic acid, and an oxygenated diterpene, paclitaxel (taxol), in cell cultures, but had never before been reported to enhance terpene accumulation in intact plants. 

Wigglesworth [4] confirmed that farnesol and its related compounds showed the juvenoid activity against the bloodsucking bug, Rhodnius prolixus. Slama and Williams [5] found that paper products made from balsam fir, Abies halsamea, showed juvenoid activity against hemipteran bug, Pyrrhocoris apterus, and called the compound the paper factor. The chemical structure of the paper factor was identified as a methyl ester of todomatuic acid, and named juvabione (3) [6]. 

The so-called paper factor responsible for insect juvenile hormone (JH) activity of certain American papers has been identified (1966) as the bisabolane methyl ester, (-h)-juvabione (155), a constituent of balsam fir, Abies balsamea (416). As a matter of fact, the acid corresponding to 155, todomatuic acid (156), had been known earlier as a component of bisulfite-treated pulp oil of Abies sachalinensis (399). Juvabione and related compounds possessing JH activity have been isolated from several species of the family Pinaceae, including (-h)-A -dehydrotodomatuic acid (157) and 7-hydroxytodomatuic acid (158) from wood of Cedrus deodara (33). 

NegishI, E, Sabanski, M, Katz, J.-J. Brown, H, C. "An Efficient Synthesis of Juvabione and Todomatuic Acid via Hydroboration-Oxidation" Tetrahedron 1976, 32,925-926. 

Tirucallol, T46 a-tocopherol, T56 Todomatuic acid, T2 Tolpomycinones, Y26 Tomatidine, T49 Tomatillidine, K34 Torilin, T21 Torreyol, T18 Torulosol, T34 Totarol, T32 Toxol, Y1... 

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