caa a22 4500 44586995X CHVBK 20180317145508.0 cr unu---uuuuu 170323e20111201xx s 000 0 eng 10.1007/s11101-010-9176-y doi (NATIONALLICENCE)springer-10.1007/s11101-010-9176-y Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins [Elektronische Daten] [Charles Gauthier, Jean Legault, Marianne Piochon-Gauthier, André Pichette] Lupeol, betulin and betulinic acid are members of the so-called lupane-type triterpenoids. These natural products found worldwide in quite of lot of vegetables, fruits and plant species exhibit promising pharmacological activities including anti-inflammatory, anti-HIV and antitumor activities. Nevertheless, the poor pharmacokinetic properties of these cholesterol-like triterpenoids hampered further pharmaceutical developments. The synthesis of lupane-type saponins, i.e., sugar-derived lupanes, seems to be a good avenue to improve both their water solubility and pharmacological activity. The aims of this review are twofold: first, to describe the biological activity of naturally occurring lupane-type saponins, and second, report the different methodologies employed for the elaboration of glycosidic linkages at the C-3 and/or C-28 positions on the lupane core. The synthesis of both natural and unnatural lupane-type saponins is discussed with an emphasis on molecules exhibiting relevant biological activities. Springer Science+Business Media B.V., 2010 Chemical glycosylation nationallicence Triterpenoid saponins nationallicence Lupeol nationallicence Betulin nationallicence Betulinic acid nationallicence A549 : Human lung carcinoma nationallicence Ara : α-l-Arabinopyranose nationallicence BF3·OEt2 : Boron trifluoride diethyletherate nationallicence CGTase : Cyclodextrin glycosyltransferase nationallicence d -Ara : α-d-Arabinopyranose nationallicence DLD-1 : Human colorectal adenocarcinoma nationallicence Gal : β-d-Galactopyranose nationallicence Glc : β-d-Glucopyranose nationallicence HIV : Human immunodeficiency virus nationallicence IC50 : Half maximal inhibitory concentration nationallicence Man : α-d-Mannopyranose nationallicence PMT : Prodrug monotherapy nationallicence Rha : α-l-Rhamnopyranose nationallicence SAR : Structure-activity relationships nationallicence TCA : Trichloroacetimidate nationallicence TMSOTf : Trimethylsilyl trifluoromethanesulfonate nationallicence Xyl : β-d-Xylopyranose nationallicence Gauthier Charles Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut Legault Jean Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut Piochon-Gauthier Marianne Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut Pichette André Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut Phytochemistry Reviews Springer Netherlands 10/4(2011-12-01), 521-544 1568-7767 10:4<521 2011 10 11101 https://doi.org/10.1007/s11101-010-9176-y text/html Onlinezugriff via DOI 1 review-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11101-010-9176-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Gauthier Charles Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut NATIONALLICENCE 700 1- Legault Jean Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut NATIONALLICENCE 700 1- Piochon-Gauthier Marianne Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut NATIONALLICENCE 700 1- Pichette André Laboratoire LASEVE, Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, G7H 2B1, Chicoutimi, QC, Canada aut NATIONALLICENCE 773 0- Phytochemistry Reviews Springer Netherlands 10/4(2011-12-01), 521-544 1568-7767 10:4<521 2011 10 11101 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer