Minor glycosides of Hedera colchica

Mshvildadze, Vakhtang; Dekanosidze, G. E.; Kemertelidze, É. P.

doi:10.1007/bf00630674

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“…In the course of our phytochemical investigation of Hedera genus growing in Georgia, 1) we have previously reported the isolation of triterpene saponins from leaves and berries of Hedera colchica 2,3) and their biological activities in vitro. a-Hederin and hederacolchiside A were the more active against Candida glabra (LD 100 ϭ6.25 mg/ml) and dermatophytes sp.…”

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confidence: 99%

Triterpenoid Saponins from Leaves of Hedera pastuchowii

Mshvildadze

Élias

Faure

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Five new triterpenoid saponins, pastuchoside A (1), B (3), C (5), D (7) and E (9), were isolated from the leaves of Hedera pastuchowii. They have oleanolic acid or hederagenin as aglycone. The structures were established by NMR spectroscopy including gs (gradient selected)-COSY, gs-HSQC, gs-HSQC-TOCSY and gs-HMBC experiments, and mass spectrometry ( ESI-HR-MS). Heptaoside saponins, compounds 1 and 3, are described for the first time in the genus Hedera.

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confidence: 99%

Triterpenoid Saponins from Leaves of Hedera pastuchowii

Mshvildadze

Élias

Faure

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Hederacolchiside A (26) and hederacolchiside Ai (27) were isolated from the leaves of Hedera colchica and purified according to literature [Mshvildadze et al, 1992;Mshvildadze et al, 1993]. The chemical structures (Tables 1 and 2) of all triterpenes and saponins used in this study were confirmed by spectral data (MS, ' *H and 13 C NMR) and their purity was determined by HPLC ( ^5%).…”

Section: Triterpenes and Saponinsmentioning

confidence: 86%

“…To our knowledge, this is the first report on the haemolytic activity and SAR of saponins having betulinic acid (1) or betulin (2) as aglycones. As shown in Tables 1 and 2, natural oleanane-type saponins such as hederagenin 3p-O-p-D-giucopyranoside (7), ô-hederin (23), ot-hederin (24), P-hederin (25), hederacolchiside A (26) and hederacolchiside Ai (27) isolated from species of the Hedera genus [Elias et al, 1991;Mshvildadze et al, 1992; Mshvildadze et al, 1993;Mshvildadze et al, 2001] were also investigated and their activities were compared to lupane-type saponins (5, 6,(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(28)(29)(30)(31)(32)(33)(34)(35) and triterpenoid aglycones (1-4). a-Hederin (24) and hederacolchiside Ai (27) were already shown to possess strong haemolytic [Chwalek et al, 2006] and anticancer activities [Lee et al, 2000; Muthu Kurnara et al, 2001; Park et al, 2001; Bang et al, 2005b; both in vitro and in vivo which are related to their capacity to interact with biological membranes .…”

Section: -Q-(x-l-rhamnopymno$yl Betulinic Acid 3p-o-a-l-rhamnopyranmentioning

confidence: 99%

“…Mshvildadze et al, 2001Elias et al, 1991Mshvildadze et al, 1992 Mshvildadze et al, 1993 * Natural compounds. …”

Section: Cells Culturementioning

confidence: 99%

“…Hederagenin 3P-0-P-D-glucopyranoside (7), ô-hederin (23) and a-hederin (24) were isolated from the berries of Hedera colchica and purified as described previously [Mshvildadze et al, 2001]. Hederagenin (3) and P-hederin (25) were obtained by acid and alkaline hydrolysis from hederasaponins C and B, respectively, isolated from the leaves of Hedera helix [Elias et al, 1991].Hederacolchiside A (26) and hederacolchiside Ai (27) were isolated from the leaves of Hedera colchica and purified according to literature [Mshvildadze et al, 1992; Mshvildadze et al, 1993]. The chemical structures (Tables 1 and 2) of all triterpenes and saponins used in this study were confirmed by spectral data (MS, ' *H and 13 C NMR) and their purity was determined by HPLC ( ^5%).…”

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confidence: 99%

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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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Arjunolic acid derivative glycoside from the stems of Hedera colchica

Mshvildadze¹,

Kunert

Dekanosidze³

et al. 2004

Chem Nat Compd

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Five triterpenoid saponins were isolated from the stems of Hedera colchica K. Koch, Araliaceae. Two of them are new natural substances. derivative of arjunolic acid is described for the first time in Araliaceae family. The chemical structures of isolated compounds were established on the base of chemical and 1D and 2D NMR experiments.Hedera colchica K. Koch, Araliaceae, is an endemic plant growing mainly in West Georgia. Wide application of different parts of this plant in traditional medicine as a bronchospasmolitic, secrotolitic, and antiinflammatory remedy [1,2] was the main reason for the begining of its deep phytochemical investigation. The chemical constitutents of triterpene saponins from the leaves and berries of H. colchica was described previously [3][4][5][6].The isolated triterpene glycosides have shown a wide spectrum of biological activities [7][8][9][10][11]. The aim of the present work was the investigation of triterpene saponins from the stems of H. colchica for the purpose of determining the chemical structure-biological activity relationship of glycosides isolated from the different parts of this plant. In this paper we describe the isolation and structure determination of five saponins from the stems of H. colchica (Fig. 1). Saponins HCS-A (1) and HCS-B (2) were new compounds, and the derivative of arjunolic acid (1) was described for the first time in the Araliaceae family. The n-butanolic extract of the stems containing crude saponins was subjected to repeated chromatography affording saponins 1-5 (see experimental part). The glycosides 3, 4, and 5 were identified as hederasaponin C [12], and hederacolchisides E and F [3, 4] respectively.

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Minor glycosides of Hedera colchica

Cited by 5 publications

References 0 publications

Triterpenoid Saponins from Leaves of Hedera pastuchowii

Triterpenoid Saponins from Leaves of Hedera pastuchowii

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

Arjunolic acid derivative glycoside from the stems of Hedera colchica

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