Coumarin Glycosides and Iridoid Glucosides with Neuroprotective Effects from Hydrangea paniculata

Abstract

Five new coumarin glycosides, umbelliferone 7-O-sophoroside (1), umbelliferone 7-O-β-D-glucopyranosyl(1 → 3)-β-D-glucopyranoside (2), umbelliferone 7-O-β-D-glucopyranosyl(1 → 3)-[β-D-apiofuranosyl(1 → 6)]-β-D-glucopyranoside (3), umbelliferone 7-O-β-D-glucopyranosyl(1 → 2)-β-D-apiofuranosyl(1 → 6)-β-D-glucopyranoside (4), and umbelliferone 7-O-β-D-glucopyranosyl(1 → 5)-β-D-apiofuranosyl(1 → 6)-β-D-glucopyranoside (5), and two new iridoid glucosides, 7-O-E-isoferuloyl loganic acid (6) and 7-O-β-D-glucopyranosyl loganin (7), together with eight known compounds (8–15) were isolated from the stems of Hydrangea paniculata. Their structures were established by spectroscopic analysis and chemical methods. At 10 µM, compounds 1, 3, 5, 6, 8, 9, and 13 showed neuroprotective effects against serum deprivation-induced PC12 cell damage.

Key words

Hydrangea paniculata - Saxifragaceae - coumarin glycosides - iridoid glucosides - neuroprotective effects

• References

• 1 Chinese Herbal Medicine Company. Chinese traditional medicine resource records. Beijing: Science Publishing House; 1994: 480
• 2 Zhang DM, Chen XG, Yang JZ, Li Y, Zheng XG. Effective fraction of Hydrangea paniculata and its preparation method, pharmaceutical composition comprising the same, and uses thereof. Chinese patent CN 1690069A 2005
• 3 Zhang DM, Chen XG, Yang JZ, Li Y. Use of skimmin in preparation of medicine for preventing and treating renal insufficiency. Chinese patent CN 1605343A 2005
• 4 Shi J, Yang JZ, Li CJ, Zhang DM. Chemical constituents from Hydrangea paniculata . China J Chin Mater Med 2010; 35: 3007-3009
• 5 Li CJ, Yang JZ, Yu SS, Chen NH, Xue W, Hu JF, Zhang DM. Triterpenoid saponins with neuroprotective effects from the roots of Polygala tenuifolia . Planta Med 2008; 74: 133-141
• 6 Satyanarayana P, Subrahmanyam P, Kasai R, Tanaka O. An apiose-containing coumarin glycoside from Gmelina arborea root. Phytochemistry 1985; 24: 1862-1863
• 7 Kikuchi M, Matsuda N. Flavone glycosides from Lonicera gracilipes var. glandulosa . J Nat Prod 1996; 59: 314-315
• 8 Wang LB, Toshio M, Gao HY, Huang J, Masayuki Y, Wu LJ. Isolation and identification of chemical constituents of flavones from Flos Helichrysi arenarii . J Shenyang Pharm Univ (Shenyang Yaoke Daxue Xuebao) 2009; 26: 792-795
• 9 Kitagawa I, Sakagami M, Hashiuchi F, Zhou JL, Yoshikawa M, Ren J. Apioglycyrrhizin and araboglycyrrhizin, two new sweet oleanene-type triterpene olihoglycosides from the root of Glycyrrhiza inflata . Chem Pharm Bull 1989; 37: 551-553
• 10 Tripetch K, Chayan P, Ryoji K, Kazuo Y. New glucosides from Thai medicinal plant, Balanophora latisepala . Nat Med 2001; 55: 213-216
• 11 Otsuka H, Kashima N, Nakamoto K. A neolignan glycoside and acylated iridoid glucosides from stem bark of Alangium platanifolium . Phytochemistry 1996; 42: 1435-1438
• 12 Takahira M, Kusano A, Shibano M, Kusano G, Miyase T. Piscidic acid and fukiic acid esters from Cimicifuga simplex . Phytochemistry 1998; 49: 2115-2119
• 13 Jensen SR, Lyse-petersen SE, Nielsen BJ. Novel bis-iridoid glucosides from Dipsacus sylvestris . Phytochemistry 1979; 18: 273-277
• 14 Li W, Koike K, Asada Y, Yoshikawa T, Nikaido T. Biotransformation of umbelliferone by Panax ginseng root cultures. Tetrahedron Lett 2002; 43: 5633-5635
• 15 Bergeron C, Marston A, Gauthier R, Hosetettmann K. Iridoids and secoiridoids from Gentiana linearis . Phytochemistry 1997; 44: 633-637
• 16 Calis I, Sticher O. Periclymenosidic acid, a new biosidic ester iridiod glucoside from Lonicera coerulea . J Nat Prod 1985; 48: 108-110
• 17 Itoh A, Tanahashi T, Tabata M, Shikata M, Kakite M, Nagai M, Nagakura N. Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii . Phytochemistry 2001; 56: 623-630