Barringtogenol C-type Triterpenoid Saponins from the Stem Bark of Norway Maple (Acer Platanoides)

Abstract

Four new barringtogenol C-type triterpenoid saponins, namely acerplatanosides A – D (1–4), along with 22 known compounds (5–26), were isolated from the stem bark of Norway maple (Acer platanoides). Their structures were elucidated on the basis of comprehensive spectroscopic analyses and chemical hydrolysis. This is the first report of triterpenoid saponins isolated from Norway maple. Compounds 1, 3, and 4 showed cytotoxicity against 4 human cancer cell lines with IC₅₀ values ranging from 9.4 to 39.5 µM.

Key words

Acer platanoides - Sapindaceae - Norway maple - Barringtogenol C-type - triterpenoid saponins - cytotoxicity

• References

• 1 Bi W, Gao Y, Shen J, He C, Liu H, Peng Y, Zhang C, Xiao P. Traditional uses, phytochemistry, and pharmacology of the genus Acer (maple): a review. J Ethnopharmacol 2016; 189: 31-60
• 2 Zhang Y, Yuan T, Li L, Nahar P, Slitt A, Seeram NP. Chemical compositional, biological, and safety studies of a novel maple syrup derived extract for nutraceutical applications. J Agric Food Chem 2014; 62: 6687-6698
• 3 Liu W, Wei Z, Ma H, Cai A, Liu Y, Sun J, DaSilva NA, Johnson SL, Kirschenbaum LJ, Cho BP, Dain JA, Rowley DC, Shaikh ZA, Seeram NP. Anti-glycation and anti-oxidative effects of a phenolic-enriched maple syrup extract and its protective effects on normal human colon cells. Food Funct 2017; 8: 757-766
• 4 Yu T, Lee J, Lee YG, Byeon SE, Kim MH, Sohn EH, Lee YJ, Lee SG, Cho JY. In vitro and in vivo anti-inflammatory effects of ethanol extract from Acer tegmentosum . J Ethnopharmacol 2010; 128: 139-147
• 5 González-Sarrías A, Li L, Seeram NP. Anticancer effects of maple syrup phenolics and extracts on proliferation, apoptosis, and cell cycle arrest of human colon cells. J Func Foods 2012; 4: 185-196
• 6 Gonzalez-Sarrias A, Ma H, Edmonds ME, Seeram NP. Maple polyphenols, ginnalins A–C, induce S- and G2/M-cell cycle arrest in colon and breast cancer cells mediated by decreasing cyclins A and D1 levels. Food Chem 2013; 136: 636-642
• 7 Apostolidis E, Li L, Lee C, Seeram NP. In vitro evaluation of phenolic-enriched maple syrup extracts for inhibition of carbohydrate hydrolyzing enzymes relevant to type 2 diabetes management. J Funct Foods 2011; 3: 100-106
• 8 Wu D, Wu XD, You XF, Ma XF, Tian WX. Inhibitory effects on bacterial growth and beta-ketoacyl-ACP reductase by different species of maple leaf extracts and tannic acid. Phytother Res 2010; 24 (Suppl. 01) S35-S41
• 9 Zhao WH, Gao LF, Gao W, Yuan YS, Gao CC, Cao LG, Hu ZZ, Guo JQ, Zhang YX. Weight-reducing effect of Acer truncatum Bunge may be related to the inhibition of fatty acid synthase. Nat Prod Res 2011; 25: 422-431
• 10 Wan C, Yuan T, Li L, Kandhi V, Cech NB, Xie M, Seeram NP. Maplexins, new alpha-glucosidase inhibitors from red maple (Acer rubrum) stems. Bioorg Med Chem Lett 2012; 22: 597-600
• 11 Yuan T, Wan C, Gonzalez-Sarrias A, Kandhi V, Cech NB, Seeram NP. Phenolic glycosides from sugar maple (Acer saccharum) bark. J Nat Prod 2011; 74: 2472-2476
• 12 Muhsinah AB, Ma H, Dasilva NA, Yuan T, Seeram NP. Bioactive glucitol-core containing gallotannins and other phytochemicals from silver maple (Acer saccharinum) leaves. Nat Prod Commun 2017; 12: 83-84
• 13 Zhang L, Tu ZC, Yuan T, Ma H, Niesen DB, Wang H, Seeram NP. New gallotannin and other phytochemicals from sycamore maple (Acer pseudoplatanus) leaves. Nat Prod Commun 2015; 10: 1977-1980
• 14 Wei F, Ma LY, Jin WT, Ma SC, Han GZ, Khan IA, Lin RC. Anti-inflammatory triterpenoid saponins from the seeds of Aesculus chinensis . Chem Pharm Bull 2004; 52: 1246-1248
• 15 Mills C, Carroll AR, Quinn RJ. Acutangulosides A–F, monodesmosidic saponins from the bark of Barringtonia acutangula . J Nat Prod 2005; 68: 311-318
• 16 Zhang Z, Koike K, Jia Z, Nikaido T, Guo D, Zheng J. New saponins from the seeds of Aesculus chinensis . Chem Pharm Bull 1999; 47: 1515-1520
• 17 Cheng JT, Chen ST, Guo C, Jiao MJ, Cui WJ, Wang SH, Deng Z, Chen C, Chen S, Zhang J, Liu A. Triterpenoid saponins from the seeds of Aesculus chinensis and their cytotoxicities. Nat Prod Bioprospect 2018; 8: 47-56
• 18 Zhang X, Zhang S, Yang Y, Wang D, Gao H. Natural barrigenol-like triterpenoids: A comprehensive review of their contributions to medicinal chemistry. Phytochemistry 2019; 161: 41-74
• 19 Yoshikawa M, Murakami T, Matsuda H, Yamahara J, Murakami N, Kitagawa I. Bioactive saponins and glycosides. III. Horse chestnut. (1): The structures, inhibitory effects on ethanol absorption, and hypoglycemic activity of escins Ia, Ib, IIa, IIb, and IIIa from the seeds of Aesculus hippocastanum L. Chem Pharm Bull 1996; 44: 1454-1464
• 20 Zhang Z, Li S, Zhang S, Gorenstein D. Triterpenoid saponins from the fruits of Aesculus pavia . Phytochemistry 2006; 67: 784-794
• 21 Kurimoto S, Sasaki YF, Suyama Y, Tanaka N, Kashiwada Y, Nakamura T. Acylated triterpene saponins from the stem bark of Acer nikoense (Aceraceae). Chem Pharm Bull 2016; 64: 924-929
• 22 Glensk M, Wlodarczyk M, Bassarello C, Pizza C, Stefanowicz P, Switalska M. A major saponin from leaves extract of Acer velutinum . Z Naturforsch B 2009; 64: 1081-1086
• 23 Kupchan SM, Takasugi M, Smith RM, Steyn PS. Tumor inhibitors. LXII. The structures of acerotin and acerocin, novel triterpene ester aglycones from the tumor inhibitory saponins of Acer negundo . J Org Chem 1971; 36: 1972-1976