Die Saponine ausThinouia coriacea

Abstract

The investigation of the stems of Thinouia coriacea Britton (Sapindaceae), an ichthyotoxic plant from South Brazil, afforded eight glycosides of oleanolic acid. Structures were assigned based on data from partial hydrolysis. 13C-NMR and mass spectral procedures as 3-O-alpha-L-arabinopyranoside (1), 3-O-alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranoside+ ++ (2), 3-O-beta-D-glucopyranosyl-(1----4)-alpha-L-arabinopyranoside (3), 3-O-beta-D-glucopyranosyl-(1----3)-alpha-L-rhamnopyranosyl-(1----2 )-alpha-L-arabinopyranoside (4), 3-O-alpha-L-rhamnopyranosyl-(1----2)[beta-D-glucopyranosyl-(1----4 )]-alpha-L-arabinopyranoside (5), 3-O-beta-D-xylopyranosyl-(1----3)-alpha-L-rhamnopyranosyl-(1----2) [beta-D-glucopyranosyl-(1----4)[alpha-L-arabinopyranoside (6), 3-O-beta-D-glucopyranosyl-(1----3)-alpha-L-rhamnopyranosyl-(1----2 )[beta-D-glucopyranosyl-(1----4)]-alpha-L-arabinopyranoside (8). Saponin 7 showed the same sugars as 8, but the attachment between the sugars could not be elucidated. The same saponins were present in the roots, but not in the leaves.

Identification of Defense Compounds inBarbarea vulgarisagainst the HerbivorePhyllotreta nemorumby an Ecometabolomic Approach

“…Bidesmosidic saponins (with two sugar chains, often with one attached through a linkage at C-3 and the second attached through an ester linkage at C-28) are known to either lack or exhibit attenuated properties of the corresponding monodesmosides (with a single sugar, normally attached at C-3; Hostettmann and Marston, 1995). Saponin glycosides in monodesmoside form exhibit a broad spectrum of activity against yeast, fungi, mollusks, frogs, and fish, while those in bidesmoside form are generally inactive (Parkhurst et al, 1974;Schenkel et al, 1991;Favel et al, 1994;Lee et al, 2001;Sparg et al, 2004). In addition, the number, kind, and sequence of the sugar residues significantly modify antifungal effects of saponins (Mshvildadze et al, 2000;Zhang et al, 2005).…”

Isolation of Nematicidal Triterpenoid Saponins from Pulsatilla koreana Root and Their Activities against Meloidogyne incognita

“…Their structures were elucidated as cernuoside A ( 1 ) [13], hederacholchiside E ( 2 ) [14], beesioside Q ( 3 ) [15], 3- O - β - d -glucopyranosyl (1→4)- β - d -glucopyranosyl (1→3)- α - l -rhamnopyranosyl (1→2)[ β - d -glucopyranosyl(1→4)]- α - l -arabinopyranosyl oleanolic acid 28- O - α - l -rhamnopyranosyl (1→4)- β - d -glucopyranosyl (1→6)- β - d -glucopyranoside ( 4 ) [16], hederacoside B ( 5 ) [17], raddeanoside R17 ( 6 ) [18], 3- O - β - d -glucopyranosyl (1→3)- α - l -rhamno-pyranosyl (1→2) [ β - d -glucopyranosyl (1→4)]- α - l -arabinopyranosyl oleanolic acid ( 7 ) [19], 3- O - β - d -glucopyranosyl (1→3)- α - l -rhamnopyranosyl (1→2)- α - l -arabinopyranosyl oleanolic acid ( 8 ) [20], raddeanoside R13 ( 9 ) [20], 3- O - β - d -glucopyranosyl (1→4)- β - d -glucopyranosyl (1→3)- α - l -rhamno-pyranosyl (1→2)[ β - d -glucopyranosyl(1→4)]- α - l -arabinopyranosyl oleanolic acid ( 10 ) [21], 3- O - β - d -glucopyranosyl(1→4)- β - d -glucopyranosyl (1→3)- α - l -rhamnopyranosyl (1→2) [ β - d -glucopyranosyl-(1→4)]- α - l -arabinopyranosyl oleanolic acid ( 11 ) [21], hederacholchiside F ( 12 ) [14], fatsiaside G ( 13 ) [22], pulsatilla saponin F ( 14 ) [23], pulsatilloside F ( 15 ) [24], patrinia saponin H3 ( 16 ) [25], hederasaponin D ( 17 ) [23], cernuoside B ( 18 ) [26], scabioside C ( 19 ) [20], hederoside C ( 20 ) [23], pulsatilla saponin D ( 21 ) [27], kalopanaxsaponin H ( 22 ) [28], scabioside A ( 23 ) [29], 23-hydroxy-3 β -[( O -α- l -rhamnopyranosyl-(1→2)- O -[ β - d -glucopyranosyl-(1→4) -β - d -glucopyranosyl-(1→4)]- α - l -arabino-pyranosyl)oxy]lup-20(29)-en-28-oic acid 28- O - α - l -rhamnopyranosyl-(1→4)- O - β - d -glucopyranosyl-(1→6)- β - d -glucopyranosyl ester ( 24 ) [30], pulsatilloside E ( 25 ) [20], anemoside B4 ( 26 ) [20], 23-hydroxy-3 β -[( O -α- l -rhamnopyranosyl-(1→2)- O -[ β - d -glucopyranosyl-(1→4)]- α - l -arabinopyranosyl)-oxy] lup-20(29)-en-28-oic acid ( 27 ) [12], 3 β -[ O - β - d -glucopyranosyl-(1→3)- O -α- l -rhamnopyranosyl-(1→2)- O - α - l -arabinopyranosyl)oxy] lup-20(29)-en-28-oic acid ( 28 ) [20], 3 β -[( O - α - l -rhamno-pyranosyl-(1→2)- α - l -arabinopyranosyl)oxy] lup-20(29)-en-28-oic acid 28- O - β - d -glucopyranosyl-(1→6)- β - d -glucopyranosyl ester ( 29 ) [14], cussosaponin C ( 30 ) [30], betulinic acid 3 β - O - α - l -rhamnopyranosyl-(1→2)- O - α - l -arabinopyranoside ( 31 ) […”

Anti-Inflammatory and PPAR Transactivational Effects of Oleanane-Type Triterpenoid Saponins from the Roots of Pulsatilla koreana

“…Their structures were elucidated as cernuoside A (1) (Zhang et al ., 2000), hederacholchiside E (2) (Yang et al ., 2010), beesioside Q (3) (Tommasi et al ., 2000), 3- O -β-D-glucopyranosyl (1→4)-β-D-glucopyranosyl (1→3)-α-L-rha m no pyra nosyl (1→2) [β-D-glucopyranosyl(1→4)]-α-L-arabinopyranosyl ole a nolic acid 28- O -α-L-rhamnopyranosyl (1→4)-β-D-gluco py ranosyl (1→6)-β-D-glucopyranoside (4) (Liu et al ., 2012), hederacoside B (5) (Majester-Savornin et al ., 1991), raddeanoside R17 (6) (Sun et al ., 2008), 3- O -β-D-glucopyranosyl (1→3)-α-L-rhamnopyranosyl (1→2) [β-D-glucopy ranosyl (1→4)]-α-L-arabinopyranosyl oleanolic acid (7) (Schenkel et al ., 1991), 3- O -β-D-glucopyranosyl (1→3)-α-L-rhamno py ranosyl (1→ 2)-α-L-arabinopyranosyl oleanolic acid (8) (Bang et al ., 2005), raddeanoside R13 (9) (Bang et al ., 2005), 3- O -β-D-glucopyranosyl (1→4)-β-D-glucopyranosyl (1→3)-α- L-rhamnopyranosyl (1→2) [β-D-glucopyranosyl(1→4)]-α-L-ara binopyranosyl oleanolic acid (10) (Mimaki et al ., 1999), 3- O -β-D-glucopyranosyl(1→4)-β-D-glucopyranosyl (1→3)-α-L-rhamnopyranosyl (1→2) [β-D-glucopyranosyl(1→4)]-α-L-arabinopyranosyl oleanolic acid (11) (Mimaki et al ., 1999), hederacholchiside F (12) (Yang et al ., 2010), fatsiaside G (13) (Li et al ., 1990), Pulsatilla saponin F (14) (Tran et al ., 2011), pulsatilloside F (15) (Li et al ., 2013a), patrinia saponin H3 (16) (Kang et al ., 1997), hederasaponin D (17) (Tran et al ., 2011), cernuoside B (18) (Zhang et al ., 2000), scabioside C (19) (Bang et al ., 2005), hederoside C (20) (Li et al ., 1990), Pulsatilla saponin D (21) (Shimizu et al ., 1978), kalopanaxsaponin H (22) (Ye et al ., 1996), and scabioside A (23) (Baykal et al ., 1997) (Fig. 1).…”