Of -polygodial

The only current therapeutic use of an unsaturated 1,4-dialdehyde in the Western hemisphere is the use of polygodial (Kolorex Capsules and Cream) to control localized candidiasis. According to the producer polygodial damages the cell wall of Candida albicans and other fungi (Sterner and Szallasi, 1999). 

Figure 1. a. Section of untreated control cell of S. cerevisiae. b. Section of S. cerevisiae cell treated with 50 /xg/ml of polygodial for 10 min. CW, cell wall PM, plasma membrane (cell membrane) N, nucleus M, mitochondrion V, vacuole. 

Figure 2. Leakage of a, folin-reagent and b, phenol-HjS04 positive substances from S. cerevisiae cells during incubation with polygodial. o-o. None c-c, 1 /xg/ml of polygodial 10...

Table 2. Antifungal activity of polygodial (3) in combination with MMIC of phenylpropanoids (15-10).

K. Mori and H. Watanabe, Synthesis of both the enantiomers of polygodial, an insect antifeedant sesquiterpene. Tetrahedron, 42 (1986) 273-281. 

M. Taniguchi, Y. Yano, E. Tada, K. Dcenishi, S. Oi, H. Haraguchi, K. Hashimoto and I. Kubo, Mode of action of polygodial, an antifungal sesquiterpene dialdehyde, Agric. Biol. Chem., 52 (1988) 1409-1414. 

I. Kubo, Synergistic effect of polygodial on antifungal activity. Drug News Persp., 2 (1989) 292-295. 

I. Kubo and M. Himejima, Anethole, a synergist of polygodial against filamentous microorganisms, J. Agric. Food Chem., 39, (1991) 2290-2292. 

M. Himejima and I. Kubo, Fungicidal activity of polygodial in combination with anethole and indole against Candida albicans, J. Agric. Food Chem., in press. 

When Mr. Watanabe (now Prof. Watanabe at the University of Tokyo) and I tasted the synthetic samples, both (—)-64 and (+)-64 were extremely hot-tasting. Examination of piscicidal activity by Prof. Asakawa and that of antifeedant activity by Prof. Pickett showed no difference between the enantiomers of polygodial. In this particular case, both the enantiomers 64 and 64 showed the same bioactivity.44... 

Further results from this screening programme were the isolation and determination of polygodial (9), warburganal (10) and ugandensidial (11) from the bark of the plants Warburgia stuhlmannii and W. ugandensis (Kubo and Nakanishi, 1977 Nakanishi and Kubo, 1977 Meinwald et al., 1978). 

The amount of polygodial (107) needed to inhibit the yeast C. utilis and S, cerevisiae is reduced to one quarter of the uncombined MIC at the same time that the concentration of perillaldehyde (103) is reduced fourfold from its uncombined MIC. A similar but more dramatic combination effect occurs against C. albicans and M. mucedo where a fourfold decrease from the uncombined MIC of polygodial (107) at 1.95 ig/mL reduces the amount of perillaldehyde (103) required for inhibition by as much as 32-fold and 16-fold, respectively. Further limited reduction in polygodial (107) concentration will maintain the synergistic effect, provided there is a corresponding increase in perillaldehyde (103) concentration, as seen with C. utilis, C. albicans, M. mucedo, and P. chrysogenum. 

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