Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides

Abstract

Abstract:In order to develop potential anti-fungal agents, seven glycoconjugates composed of α-L-rhamnose,as the glycone and oleanolic acid as the aglycone were synthesized in an efficient and practical way using glycosyl trichloroacetimidates as donors. The structures of the new compounds were confirmed by MS, 1 H-NMR and 13 C-NMR. Preliminary studies based on means of mycelium growth rate, indicated that all the compounds possess certain fungicidal activity against Sclerotinia sclerotiorum (Lib.)

Synthesis and structure-activity relationship of oleanolic mono- or di-glycosides against Magnaporthe oryzae

“…The [ 13 C] NMR brought out 42 carbons in saponin 3a and 3e, 41 carbons in 3c and 3d, 40 carbon in 3b; C 28 at δ175.20; C 13 =C 12 at δ143.47 and δ121.67; C 3 at δ87.60-87.93 while anomeric carbon C 3 and C 28 at δ105.37 (β-Glc) and δ94.09 (β-Glc), δ106.11 (β-Xyl) and δ93.74 (α-Ara), δ106.00 (β-Gal) and δ93.77 (α-Ara), δ105.77 (α-Ara) and δ94.59 (β-Gal), δ105.94 (β-Gal) and δ94.58 (β-Gal). These NMR data are consistent with those in previous reports (Zhao et al, 2011).…”

“…26-87.95; anomeric carbon at δ105.44 (β-Glc), δ106.12 (β-Gal), δ106.18 (β-Xyl), δ105.85 (α-Ara), δ95.86 (α-Man), δ102.85 (α-Rha). These NMR data are consistent with those in previous reports (Zang, 2004;Sha et al, 2008;Zhao et al, 2011).…”

“…The [ 13 C] NMR indicated 42 carbons in carboxyl C 28 at δ175.2; C 13 =C 12 at δ143.4, δ121.6; C 3 linked hydroxyl at δ76.8 while anomeric carbon at δ94.05 (β-Glc), δ94.58 (β-Gal), δ94.68 (β-Xyl), δ93.76 (α-Ara), δ93.32 (α-Man), δ93.37 (α-Rha), δ102.97 and 95.48 (β-Mal in Pyr-d5). These NMR data are in accordance with previous reports (Li et al, 2009;Zhao et al, 2011).…”

“…1 H]-and [ 13 C]-NMR data from 1c, 1k, 1b, 1j, 1d, 1l, 1n are consistent with those in previous reports (Zang, 2004;Sha et al, 2008;Zhao et al, 2011 20, 144.10, 132.10, 123.00, 118.20, 113.50, 92.50, 81.50, 76.80, 74.10, 71.50, 66.50, 62.20, 55.70, 47.70, 47.10, 46.40, 42.20, 42.10, 39.90, 39.10, 38.80, 37.90, 34.20, 33.10, 32.70, 30.90, 29.00, 26.90, 26.90, 26.00, 25.50, 24.00, 23.80, 23.70, 23.70, 18.60, 17.30, 16.20. 54,143.85,121.44,95.86,80.26,74.46,71.16,71.04,66.89,61.34,54.90,47.03,45.68,45.43,41.33,40.79,38.89,37.89,37.49,36.54,33.30,32.80,32.36,32.07,30.37,28.51,27.17,25.58,23.35,22.91,22.60,21.07,17.84,16.84,16.56, 20, 144.10, 132.10, 123.00, 118.20, 113.70, 92.50, 74.20, 74.10, 73.70, 72.40, 66.50, 55.40, 47.70, 47.10, 46.40, 42.20, 42.10, 39.90, 39.10, 38.80, 37.90, 34.20, 33.10, 32.70, 30.90, 29.00, 26.90, 26.90, 26.00, 25.50, 24.00, 23.80, 23.70, 23.70, 18.60, 17.30, 17.00, 16.20.…”

Advances in Research on Hepatoprotective Activity and Synthesis of Oleanolic Acid Derivatives

“…Oleanolic acid (OA, Figure 1) belongs to pentacyclic triterpenoid compound which exists widely in food or medicinal herbs [1][2]. The chemistry of oleanane-type triterpenoids has been investigated with particular interest and many relevant biological and pharmacological activities of these derivatives have been reported in the literature, among which are antiinflammatory [3][4], antitumoral [5], anticancer [6], hypoglycaemic [7], antiviral [8][9], antibacterial [10][11][12][13] and antifungal [14][15][16] activities. OA is well known for its hepatoprotective effects on acute chemically induced liver injury, chronic liver fibrosis and cirrhosis.…”