1995
DOI: 10.1016/0005-2736(95)00186-7
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Molecular basis of glycoalkaloid induced membrane disruption

Abstract: In this study the interaction between the glycoalkaloids alpha-chaconine, alpha-solanine and alpha-tomatine and sterols in model membranes was analysed systematically using techniques like membrane leakage, binding experiments, detergent extraction, electron microscopy, NMR and molecular modelling. The most important properties for sterols to interact with glycoalkaloids turned out to be a planer ring structure and a 3 beta-OH group, whereas for alpha-chaconine the 5-6 double bond and the 10-methyl group were … Show more

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Cited by 234 publications
(229 citation statements)
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“…It appears that a certain cholesterol density in the liposomes is required to allow ␣-hederin to induce pores. The importance of this threshold for pore formation by other saponins agrees with observations reported by others (9,10,75,76). On cells, THP-1 macrophages depleted in cholesterol were protected against cytotoxicity induced by ␣-hederin.…”
Section: Discussionsupporting
confidence: 90%
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“…It appears that a certain cholesterol density in the liposomes is required to allow ␣-hederin to induce pores. The importance of this threshold for pore formation by other saponins agrees with observations reported by others (9,10,75,76). On cells, THP-1 macrophages depleted in cholesterol were protected against cytotoxicity induced by ␣-hederin.…”
Section: Discussionsupporting
confidence: 90%
“…buds or small unilamellar vesicles (46 -48, 67), are the most likely. The hexagonal pattern observed at the highest temperature and ␣-hederin concentration could probably be associated with tubular structures as it has been suggested for glycoalkaloids (10).…”
Section: Discussionsupporting
confidence: 53%
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“…This synergism may also be the result of P-gp (permeability glycoprotein) efflux transporter blockade, which was detected previously for tomatidine, the aglycon of ΤΟΜ 31 . The impact on cell membrane structures would be even more important for the overall action of ΤΟΜ because it interacts strongly with cholesterol and may cause cell membrane disruption and intracellular stress [32][33][34] . Whether TOM can also induce apoptosis in solid tumours such as mammary adenocarcinoma in the manner described by Chao et al 16 will need to be clarified by further investigation.…”
Section: Discussionmentioning
confidence: 99%
“…Some flavonoids, 12 diterpenoids, 13,14 sequiterpenoids, 15 monoterpenoids, 16 stilbenes, 17,18 steroidal glycoalkaloid [19][20][21] and triterpenoids 22 have effect against this fungus (inhibition mycelia growth, cytological changes, toxic action and protection cucumber tissue, etc).…”
Section: Introductionmentioning
confidence: 99%