Structure–Activity Relationship of the<i>Warburgia</i>Sesquiterpene Dialdehydes

Taniguchi, Makoto; Adachi, Takeshi; Oi, Susumu; Kimura, Akihiko; Katsumura, Shigeo; Isoe, Sachihiko; Kubo, Isao

doi:10.1080/00021369.1984.10866095

Cited by 14 publications

(16 citation statements)

References 4 publications

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“…Polygodial, a sesquiterpene isolated from Polygonum hydropiper, has been reported to have an affect on the fungal cell membrane and to show synergistic antifungal activity (4, 6). This terpenoid has an a,fl-unsaturated dialdehyde function which is assumed to be responsible for the antifungal activity (23). Antifungal diterpene 1 isolated from A.galanga also has the same functional group.…”

Section: Discussionmentioning

confidence: 99%

Antifungal Activity fromAlpinia galangaand the Competition for Incorporation of Unsaturated Fatty Acids in Cell Growth

et al. 1996

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An antimicrobial diterpene was isolated from Alpinia galanga in the screening for potentiators of phytochemical antibiotic action. The structure was elucidated by spectral data and identified as (E)-8 beta, 17-epoxylabd-12-ene-15, 16-dial (1). Diterpene 1 synergistically enhanced the antifungal activity of quercetin and chalcone against Candida albicans. Antifungal activity of 1 was reversed by unsaturated fatty acids. Protoplasts of C. albicans were lysed by 1. These results suggest that antifungal activity of 1 is due to a change of membrane permeability arising from membrane lipid alternation.

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Section: Discussionmentioning

confidence: 99%

Antifungal Activity fromAlpinia galangaand the Competition for Incorporation of Unsaturated Fatty Acids in Cell Growth

et al. 1996

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“…Sesquiterpenes possessing an unsaturated dialdehyde function are known to exhibit various biological activities such as mutagenic (1)(2)(3) insect antifeedant(4, 5), antimicrobial (6)(7)(8), and antitumour activities (9). Some of these compounds are involved in natural chemical defense systems (10,11).…”

Section: Introductionmentioning

confidence: 99%

Comparison of the Antimicrobial and Cytotoxic Activities of Twenty Unsaturated Sesquiterpene Dialdehydes from Plants and Mushrooms

Anke

Sterner²

1991

Planta Med

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Twenty unsaturated sesquiterpene dialdehydes were tested for antimicrobial, algaecidal, cytotoxic, and mutagenic activity. In addition to the known antifungal activity, polygodial (1) also exhibited antibacterial and cytotoxic activity; epipolygodial (2) was slightly less active. The most active compounds were: isovelleral (7), isoisovelleral (8), velleral (20), and methylmarasmate (6). With the exception of velleral (20), they also exhibited mutagenic activity in the Salmonella/microsome assay. Derivatization to less polar compounds usually increased the antimicrobial and cytotoxic effects and reduced mutagenicity, while the introduction of hydroxyl groups had the reverse effect.

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“…4,5) For this latter activity a structural unit, the enol-aldehyde moiety, was found to be essential. Among the compounds screened, polygodial was structurally the simplest (Fig.…”

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confidence: 99%