caa a22 4500 445869968 CHVBK 20180317145508.0 cr unu---uuuuu 170323e20111201xx s 000 0 eng 10.1007/s11101-011-9218-0 doi (NATIONALLICENCE)springer-10.1007/s11101-011-9218-0 A review of acacic acid-type saponins from Leguminosae-Mimosoideae as potent cytotoxic and apoptosis inducing agents [Elektronische Daten] [Marie-Aleth Lacaille-Dubois, Dieudonné Pegnyemb, Olivier Noté, Anne-Claire Mitaine-Offer] The aim of this review is to highlight updated results on the biologically active saponins from Leguminosae-Mimosoideae. Acacic acid-type saponins (AATS), is a class of very complex glycosides possessing a common aglycon unit of the oleanane-type (acacic acid=3β, 16α, 21β trihydroxy-olean-12-en-28 oic acid), having various oligosaccharide moieties at C-3 and C-28 and an acyl group at C-21. About sixty molecules of this type have been actively explored in recent years from Leguminosae family, from a chemical point of view and some fifty were reported to possess cancer related activities. These include cytotoxic/antitumor, immunomodulatory, antimutagenic, and apoptosis inducing properties and appear to depend on the acylation and esterification by different moieties at C-21 and C-28 of the acacic acid-type aglycone. One can observe that the (6S) configuration of the outer monoterpenyl moiety (MT) seems more potent in mediating high cytotoxicity than its (6R) isomer. Furthermore, the trisaccharide moiety {β-d-Xylopyranosyl-(1→2)-β-d-Fucopyranosyl-(1→6)- N-Acetamido 2-β-d-Glucopyranosyl-} at C-3, the tetrasaccharide moiety {β-d-Glucopyranosyl-(1→3)-[α-L-Arabinofuranosyl-(1→4)]-α-l-Rhamnopyranosyl-(1→2)-β-d-Glucopyranosyl} at C-28 of the aglycone, and the inner MT hydroxylated at its C-9, having a (6S) configuration can be important substituent patterns for the induction of apoptosis of AATS. Because of their interesting cytotoxic/apoptosis inducing activity, some AATS can be useful in the search for new potential antitumor agents from Fabaceae. Furthermore, the sequence 28-O-{Glc-(1→3)-[Araf-(1→4)]-Rha-(1→2)-Glc-Acacic acid}, often encountered in the genera Acacia, Albizia, Archidendron, and Pithecellobium may represent a chemotaxonomic marker of the Mimosoideae subfamily. Springer Science+Business Media B.V., 2011 Mimosoideae nationallicence Fabaceae (=Leguminosae) nationallicence Acacic acid-type saponins nationallicence Cytotoxicity nationallicence Apoptosis inducing agents nationallicence AATS : Acacic acid-type saponin nationallicence GlcNAc : Acetamido-β-d-glucopyranosyl nationallicence Glc : β-d-glucopyranosyl nationallicence Xyl : β-d-xylopyranosyl nationallicence Ara : α-l-arabinopyranosyl nationallicence Fuc : β-d-fucopyranosyl nationallicence Qui : β-d-quinovopyranosyl nationallicence Rha : α-l-rhamnopyranosyl nationallicence Araf : α-l-arabinofuranosyl nationallicence Lacaille-Dubois Marie-Aleth Laboratoire de Pharmacognosie, Uunité de Molécules d'Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D'Arc, BP 87900, 21079, Dijon cedex, France aut Pegnyemb Dieudonné Laboratoire de Pharmacochimie, Département de Chimie Organique, Faculté de Sciences, Université de Yaoundé, BP 812, Yaoundé, Cameroon aut Noté Olivier Laboratoire de Pharmacognosie, Uunité de Molécules d'Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D'Arc, BP 87900, 21079, Dijon cedex, France aut Mitaine-Offer Anne-Claire Laboratoire de Pharmacognosie, Uunité de Molécules d'Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D'Arc, BP 87900, 21079, Dijon cedex, France aut Phytochemistry Reviews Springer Netherlands 10/4(2011-12-01), 565-584 1568-7767 10:4<565 2011 10 11101 https://doi.org/10.1007/s11101-011-9218-0 text/html Onlinezugriff via DOI 1 review-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11101-011-9218-0 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Lacaille-Dubois Marie-Aleth Laboratoire de Pharmacognosie, Uunité de Molécules d'Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D'Arc, BP 87900, 21079, Dijon cedex, France aut NATIONALLICENCE 700 1- Pegnyemb Dieudonné Laboratoire de Pharmacochimie, Département de Chimie Organique, Faculté de Sciences, Université de Yaoundé, BP 812, Yaoundé, Cameroon aut NATIONALLICENCE 700 1- Noté Olivier Laboratoire de Pharmacognosie, Uunité de Molécules d'Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D'Arc, BP 87900, 21079, Dijon cedex, France aut NATIONALLICENCE 700 1- Mitaine-Offer Anne-Claire Laboratoire de Pharmacognosie, Uunité de Molécules d'Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D'Arc, BP 87900, 21079, Dijon cedex, France aut NATIONALLICENCE 773 0- Phytochemistry Reviews Springer Netherlands 10/4(2011-12-01), 565-584 1568-7767 10:4<565 2011 10 11101 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer