Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins

Gauthier, Charles; Legault, Jean; Girard-Lalancette, Karl; Mshvildadze, Vakhtang; Pichette, André

doi:10.1016/j.bmc.2009.01.022

Cited by 174 publications

(130 citation statements)

References 48 publications

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“…This has been detailed in some of the recent publications. 15,19,[23][24][25][26][27][28] Interestingly, most of the studies carried out so far have been on extracts rich in saponins, with only a few illustrated for isolated triterpenes or steroidal saponins.…”

Section: Pharmacological Studiesmentioning

confidence: 99%

“…There have been sporadic reports on the structure-activity relationship, providing a possible correlation between the cytotoxic effects and certain structural features. Readers are referred to some interesting research by Gauthier et al 24,32,33 In a recent study by Liu et al, a synthetic derivative of β-hederin was evaluated for its cytotoxic properties in five human cell lines (ie, HeLa, MCF-7, HL-60, HT1080, and Hep-G2). 34 The authors reported synthesis of 13 novel triterpenoid saponins, designed as amide derivatives of the natural cytotoxic saponin, β-hederin, using a stepwise glycosylation strategy.…”

Section: Saponins As Cytotoxic Agentsmentioning

confidence: 99%

“…Similarly, Gauthier et al have evaluated the lupane-type and oleanane-type saponins from a structureactivity-relationship perspective. 24,33 Numerous human cell lines were tested, including lung carcinoma, and also normal skin fibroblasts. In the case of oleanane-type saponins, the oleanolic acid derivatives were by far the most active, while hederegenin saponins were not so active.…”

Section: Saponins As Cytotoxic Agentsmentioning

confidence: 99%

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Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Thakur¹,

Melzig²,

Fuchs³

et al. 2011

BTAT

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Saponins are bioactive compounds produced mainly by plants but also by some marine organisms and insects. In the recent past, there has been unforeseen interest in the clinical utilization of saponins as chemotherapeutic agents. The research on saponins in various forms as a treatment for cancer has generated a lot of potential. The advent of nanotechnology and the cytotoxicity enhancing properties of saponins are some of the highlights of the current decade. This review gives an updated overview of the clinical potential that saponins hold as cytotoxic agents, and covers the literature for 1957-2011, with the main focus on research conducted in the last decade. It is conceivable that saponins hold a lot of therapeutic potential and could be a lead for identification of synthetic or semisynthetic molecules for the treatment of cancer via membrane-mediated or transport-mediated pathways.

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Section: Pharmacological Studiesmentioning

confidence: 99%

Section: Saponins As Cytotoxic Agentsmentioning

confidence: 99%

Section: Saponins As Cytotoxic Agentsmentioning

confidence: 99%

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Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Thakur¹,

Melzig²,

Fuchs³

et al. 2011

BTAT

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“…[Gauthier et al, 2006a;Gauthier, 2006b]. Les relations de structureactivité ont montré que, entre autres choses, l'ajout d'une section a-Lrhamnopyranose en position C-3 augmentait de manière significative la cytotoxicité de l'acide bétulinique (15) Le chapitre 4, quant à lui, est rédigé sous la forme d'un article scientifique accepté pour publication à Journal of Natural Products [Gauthier et al, 2008c]. Il décrit succintement la synthèse d'une série de saponines bidesmosidiques, c'est-à-dire porteuses de deux sections osidiques, à génines acide bétulinique (15) et bétulinol (16) ainsi que les relations de structure-activité mises en évidence après l'évaluation de la cytotoxicité in vitro des composés cibles sur des cellules cancéreuses humaines en culture.…”

Section: ô » * 21unclassified

Amélioration du comportement biopharmaceutique de triterpènes naturels anticancéreux par synthèse de saponines mono- et bidesmosidiques /

Gauthier¹

2008

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UIUQAC Mise en garde/AdviceAfin de rendre accessible au plus grand nombre le résultat des travaux de recherche menés par ses étudiants gradués et dans l'esprit des règles qui régissent le dépôt et la diffusion des mémoires et thèses produits dans cette Institution, l'Université du Québec à Chicoutimi (UQAC) est fière de rendre accessible une version complète et gratuite de cette oeuvre.Motivated by a desire to make the results of its graduate students' research accessible to all, and in accordance with the rules governing the acceptation and diffusion of dissertations and theses in this Institution, the Université du Québec à Chicoutimi (UQAC) is proud to make a complete version of this work available at no cost to the reader.L'auteur conserve néanmoins la propriété du droit d'auteur qui protège ce mémoire ou cette thèse. Ni le mémoire ou la thèse ni des extraits substantiels de ceux-ci ne peuvent être imprimés ou autrement reproduits sans son autorisation.The author retains ownership of the copyright of this dissertation or thesis. Neither the dissertation or thesis, nor substantial extracts from it, may be printed or otherwise reproduced without the author's permission. "L'imprévisible est dans la nature même de l'entreprise scientifique. Si ce qu 'on va trouver est vraiment nouveau, alors c'est par définition quelque chose d'inconnu à l'avance. "-François Jacob, médecin et biologiste français, prix Nobel de médecine (1965) Ill RESUME Cette thèse décrit les travaux réalisés concernant la synthèse et l'évaluation des activités anticancéreuse et hémolytique de saponines triterpéniques naturelles et nonnatureËes à génine de type lupane. D'une part, deux saponines naturelles à section a-L-rhamnopyranosyl-(l-»2)-a-L-arabinopyranose provenant de plantes de la médecine traditionnelle orientale, une librairie de huit saponines bidesmosidiques à génine bétulinol et acide bétulinique ainsi que plusieurs dérivés chacotriosidiques de type lupane et germanicane ont été préparés par l'utilisation judicieuse de différents groupements protecteurs et procédures de glycosylation. D'autre part, l'étude des relations structure-activité démontre que les sections osidiques hautement polaires à la position C-3 du squelette lupane ont, dans la plupart des cas, un impact négatif sur l'activité anticancéreuse tandis que l'activité est augmentée pour les triterpènes de type germanicane. En revanche, la présence d'une section L-rhamnose à cette position accroît la cytotoxicité des saponines de type lupane. Notablement, le bétulinol 3,28-O-bis-cc-L-rhamnopyranoside s'est révélé un puissant agent anticancéreux inhibant sélectivement la croissance des cellules provenant des cancers les plus prévalents chez l'homme (IC50 = 1,7-1,9 fimol # L"'). À l'inverse des saponines naturelles de type oléanane telles que Pa-hédérine et l'hédéracolchiside Ai, la majorité des saponines de type lupane, tout comme leurs homologues triterpéniques (bétulinol et acide bétulinique), n'induisent pas l'hémolyse des globules rouges (HD50 >100 jurnol'L" 1 ), et c...

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“…There are many types of triterpenoidal saponins found in GFA or GSF: about 19 saponins have been isolated and identified, which were also reported to possess numerous bioactivities (8)(9)(10)(11)(12)(13). The aglycones of these saponins were identified as echinocystic acid and oleanolic acid and were proposed to be active ingredients in numerous medicinal herbs (14)(15)(16)(17). At present, the aglycons of saponin compounds are considered to be appropriate chemical compounds for the quality control of herbal medicines, since they are convenient in terms of method development and marker availability (18)(19)(20).…”

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confidence: 99%

Chemical fingerprinting and quantitative analysis of two common Gleditsia sinensis fruits using HPLC-DAD

Chen¹,

Zhong-gui²,

Guo³

et al. 2013

Acta Pharmaceutica

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Gleditsiae Fructus Abnormalis and Gleditsiae Sinensis Fructus are obtained from different developmental stages of fruits from Gleditsia sinensis Lam. (Leguminosae). The possible interchangeable usage of the two fruits, however, has long been very controversial. Here, high performance liquid chromatography coupled with diode array detection was developed to explore their chemical fingerprinting profiles. Besides, the amounts of aglycones of saponin compounds, echinocystic acid and oleanolic acid in both fruits were quantified. The results indicated that there was no significant difference in the content of aglycones from the two types of fruits. However, their chromatographic fingerprints showed distinct characteristics. Therefore, the interchangeable application of these fruits has to be taken with a specific precaution.

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Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins

Cited by 174 publications

References 48 publications

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Amélioration du comportement biopharmaceutique de triterpènes naturels anticancéreux par synthèse de saponines mono- et bidesmosidiques /

Chemical fingerprinting and quantitative analysis of two common Gleditsia sinensis fruits using HPLC-DAD

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