CAY-1, a novel antifungal compound from Cayenne pepper. Med Mycol

MycoLogics, Inc., Aurora, Colorado 80010, USA.
Medical Mycology (Impact Factor: 2.34). 03/2003; 41(1):75-81.
Source: PubMed


CAY-1, a novel saponin from Capsicum frutescens (commercially known as cayenne pepper) was investigated to determine its in vitro antifungal activity, mechanism of action and mammalian cell cytotoxicity. CAY-1 was active against 16 different fungal strains, including Candida spp. and Aspergillus fumigatus [minimum inhibitory concentrations (MIC) ranging from 4 to 16 microg ml(-1)], and was especially active against Cryptococcus neoformans (90% inhibition at 1 microg ml(-1)). Synergistic activity was also observed between CAY-1 and amphotericin B against Candida albicans and A. fumigatus. No significant cytotoxicity was demonstrated when CAY-1 was tested against 55 mammalian cell lines at up to 100 microg ml(-1). Importantly, CAY-1 appears to act by disrupting the membrane integrity of fungal cells.

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Available from: John Bland, Oct 04, 2015
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    • "On this hypothesis, the antimicrobial activity of E. platyloba extract and its essential oil was observed against some different microorganisms including S. aureus, P. aeruginosa [6], Alcaligenes faecalis, S. marscescens, P. rettgeri, L. monocytogenes [25], C. albicans [2] [12] and dermatophytes [1]. In recent studies, the antimicrobial activity of E. platyloba was attributed to saponin, alkaloid and flavonoid [17] compounds, other studies exhibited that saponin , alkaloid and flavonoid have the significant antifungal activity [9] [14] [22] [26]. "
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    ABSTRACT: Objectif Candida albicans est l’une des principales causes de vaginite, en particulier dans les formes chroniques et récidivantes. L’apparition des souches résistantes de C. albicans et les effets indésirables des traitements chimiques ont suscité un intérêt pour Echinophora platyloba, l’une des quatre espèces indigènes utilisées en médecine traditionnelle persane-iranienne. Matériel et méthodes Cette étude évalue l’activité antifongique de l’extrait éthanolique de parties aériennes séchées de E. platyloba contre 27 isolats cliniques de C. albicans de femmes souffrant de vaginite chronique récurrente par un test de micro-dilution en milieu liquide. L’effet synergique entre les médicaments azolés et l’extrait éthanolique de E. platyloba a également été étudié par la méthode de diffusion des disques après détermination de la CMI90. Résultats Les résultats de cette étude ont montré un effet synergique puissant entre l’extrait éthanolique de E. platyloba et l’itraconazole (p < 0,01) et le fluconazole (p < 0,001), mais un effet antagoniste avec le clotrimazole et le miconazole contre les isolats cliniques de C. albicans. Conclusion Ces résultats doivent être confirmés par l’utilisation clinique et par des études cliniques complémentaires.
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    ABSTRACT: Invasive fungal infections are prevalent and often deadly in immunocompromised patients. There continues to be a pressing need for the development of novel antifungal compounds since there are currently only 13 compounds licensed for the treatment of invasive fungal infections and antibiotic-resistant strains have been emerging. CAY-1 is an antifungal steroidal saponin which was isolated from the fruit of the cayenne pepper plant in 0.1% yield. In Vitro studies of CAY-1 have shown it to be an effective antifungal agent against sixteen pathogenic fungal strains and it showed no cytotoxicity toward mammalian cells up to 100 ìg/mL. The development of a practical synthesis of CAY-1 will potentially allow for further exploration of its medicinal utility and provide the opportunity to synthesize derivatives of CAY-1 which could be investigated in structure-activity relationship studies. To this end, methods for the preparation of they CAY-1 aglycone and pentasaccharide moieties have been investigated. Through this work, several partially protected stereoisomers of the CAY-1 aglycone have been prepared which can be used for the synthesis of saponin derivatives of CAY-1 for structure-activity relationship studies. Definitive characterization of one of these isomers, 3á-hydroxy-(22S, 25R)-5á-spirostan-2â-yl acetate, was achieved by X-ray crystallography. Furthermore, a quantitative inversion of the C-3 stereochemical configuration of this compound was achieved via an acetate group migration of the corresponding mesylate. The possibility of competition between the acetate migration and substitution mechanisms with various nucleophiles was explored. The results, however, indicate that this inversion only occurs via the acetate migration. Additionally, the CAY-1 pentasaccharide synthesis poses two significant challenges. First, these results demonstrate that the central 2, 3-branched portion can be synthesized efficiently from a partially protected glucopyranosyl acceptor since the C-2 and C-3 alcohols differ in their reactivity in glycosylation reactions. The second challenge is the ƒÀ-(1¨4) linkage to the galactosyl acceptor which significantly increases the complexity of the synthesis as compared to literature reported syntheses of other branched oligosaccharides. Nonetheless, this ƒÀ-(1¨4) linkage was achieved using a disarmed trichloroacetimidate glucosyl donor.
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    ABSTRACT: Biocide effects of alkaloids, saponins and flavonoids extracted from Capsicum frutescens L. (Solanaceae) on Bemisia tabaci (Gennadius) (Homoptera: Aleyrodidae). In an attempt to elaborate a strategy of integrated pest management on vegetable crops in Morocco, insecticidal activities of alkaloids, saponins and flavonoids extracted from Capsicum frutescens L. fruits against eggs and adults of Bemisia tabaci infesting tomato plants, Lycopersicon esculentum Mill. var. Daniella, were carried out under controlled conditions. Alkaloids, saponins and flavonoids, dissolved in ethanol at 1%, were tested at 0, 5, 10 and 20 g.l-1. The three compounds affected egg and adult survival, significantly. The mortality of embryo and adult varied according to the compound considered and for each compound according to concentration and exposure duration. For eggs, the corrected mortality varied from 35 to 59% for alkaloids, 14 to 31% for saponins and 10 to 14% for flavonoids. In adults, the mortalities were spread from 29% to 86%, 14 to 48% and 6 to 29% with alkaloids, saponins and flavonoids, respectively. Significant correlation between egg and adult mortality, due to the compounds tested, were observed. However, eggs required higher concentrations than adults; the LC50 was 13.78 vs. 6.83 g.l-1 for alkaloids, 98.63 vs. 32.28 g.l-1 for saponins and nontoxic vs. 120.65 g.l-1 for the flavonoids. Therefore, alkaloids were shown more effective against B. tabaci than saponins or flavonoids. However, the LT50 estimated for compounds, killing more than 50% of the population studied, was sufficient for viruliferous adults to inoculate TYLCV to plants before they died. The use of these compounds in integrated pest management merit further study.
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