Wilfordic acid

Natural sesquiterpene pyridine alkaloid formation needs two precursors, one for the pyridinium moiety and another for the sesquiterpene moiety. The a for formation of the pyridinium moiety is nicotinic acid, which reacts with isoleucine and, by oxidative reaction, produces evoninic acid, wilfordic acid or edulinic acids, a for the sesquiterpene moiety is still open to question, but E, E-famesyl cation has been suggested as one possibility and hedycarylol as a second. This moiety is dihydroagarofuran. Therefore, a for the sesquiterpene pyridine alkaloids is nicotinic acid and E, E-famesyl cation and, controversially, hedycaryol. The /3 is amacrocycling ring formation substance (two moieties), from which the alkaloid forms (Figure 62). 

Nonane has been obtained from wilfordic acid and hydroxywilfordic acid by the technique of hydrogenolytic gas chromatography 168). This result, coupled with a study of the NMR-spectra of wilfordic acid and hydroxywilfordic acid, has lead to a revision of the structures of these acids to CVI and CVII respectively. 

The Chinese plant Tripterygium wilfordii (Celastraceae) contains compounds with insecticidal properties. On alkaline hydrolysis, these compounds give rise to wilfordic acid (57) and hydroxywilfordic acid (Strunz and Findlay, 1985). 

In addition to the acids listed in Table V all of the bases on hydrolysis yielded 1 mole of a decahydroxy compound, Ci5H260io, and a dibasic acid whose structure was shown to be LXXXVIII. Wilfordic acid... 

B8. Beroza, M., Alkaloids from tripterygium wilfordii hook. The chemical structure of wilfordic and hydroxywilfordic acids. J. Org. Chem. 28, 3562-3564 (1963). 

Celastraceae also elaborate other, more complex, alkaloids, also polyester sesquiterpenes, incorporating a macrocycle derived from an evonic, wilfordic, cassinic or other type pyridine dicarboxylic acid with an additional alkyl chain of the basic eudesmane cycle at C-3 and C-7 (Table III). Celastraceae alkaloids are well-documented for the European and Asian genera, particularly Catha, Celastrus, Euonymus and Trypterigium but are relatively rare among the Latin... 

This type of polyester sesquiterpenes, is a family of macrolactones that contain a pyridine dicarboxylic acid, such as, evoninic, isoevoninic, wilfordic, isowilfordic, hydrox ilfordic, cassinic, edulinic or cathaic Fig. (11), which bridge the positions C3-C13 of the highly functionalized sesquiterpenoid cores evoninol, euonyminol and isoeounyminol. Fig. (12). 

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