Two New Phenolic Glycosides from the Barks of Hydnocarpus annamensis and their Anti-Inflammatory and Anti-Oxidation Activities

Abstract

Two new phenolic glycosides 1 and 2 were isolated from the barks of Hydnocarpus annamensis, along with eighteen known compounds. The structures of all compounds were deduced using spectroscopic methods. Anti-inflammatory and anti-oxidation activities were evaluated. Among the isolates, compounds 1, 5, 15 and 17 exhibited COX-2 inhibitory activities, with an inhibitory rate of 60.3 - 63.4 % at 10 μM. Compounds 7, 12, 13 and 20 showed anti-oxidation capacities in the DPPH free-radical assay, with a scavenging effect of 60.9 - 69.4 % at 50 μM, and 18.5 - 34.6 % at 10 μM.

Supporting information available online at http://www.thieme-connect.de/ejournals/toc/plantamedica

References

• 1 Zhonghuabencao Editorial Board. Zhonghuabencao, Vol. 5. Shanghai; Shanghai Scientific and Technological Press 1999: p 4479-81
• 2 Shaari K, Waterman P G. Scoloposides A - E, a series of 2-glucopyranosyloxy-5-hydroxybenzyl alcohol derivatives from Scolopia spinosa .  Phytochemistry. 1994;  36 1021-6
• 3 Regla I, Reyes A, Körber C, Demare P, Estrada O, Juaristi E. Novel applications of Raney nickel/isopropanol: efficient system for the reduction of organic compounds.  Synth Commun. 1997;  27 817-23
• 4 Inoshiri S, Sasaki M, Hirai Y, Kohda H, Otsuka H, Yamasaki K. Inhibition of mast cell histamine release by 2,6-dimethoxy-p-benzoquinone isolated from Berchemia racemosa .  Chem Pharm Bull. 1986;  34 1333-6
• 5 Sy L K, Brown G D. Coniferaldehyde derivatives from tissue culture of Artemisia annua and Tanacetum parthenium .  Phytochemistry. 1999;  50 781-5
• 6 Crombie L, Jamieson S V. Dihydrostilbenes of cannabis. synthesis of canniprene.  J Chem Soc Perkin Trans. 1982;  1 1467-75
• 7 Kikuzaki H, Hara S, Kawai Y, Nakatani N. Antioxidative phenylpropanoids from berries of Pimenta dioica .  Phytochemistry. 1999;  52 1307-12
• 8 Achenbach H, Waibel R, Addae-Mensah I. Lignans and other constituents from Carissa edulis .  Phytochemistry. 1983;  22 749-54
• 9 Wang M A, Wang M K, Peng S L, Ding L S. Chemical constituents from the barks of Pteroceltis tatarinowii .  Nat Prod Res Dev. 2002;  13 5-8
• 10 Ishikawa T, Fujimatu E, Kitajima J. Water-soluble constituents of anise: new glucosides of anethole glycol and its related compounds.  Chem Pharm Bull. 2002;  50 1460-6
• 11 Comte G, Vercauteren J, Chulia A J, Allais D P, Delage C. Phenylpropanoids from leaves of Juniperus phoenicea .  Phytochemistry. 1997;  45 1679-82
• 12 Wang A X, Zhang Q, Jia Z J. Phenylpropanoids, lignans and other constituents from Cremanthodiium ellisii .  Pharmazie. 2004;  59 889-92
• 13 Ekabo O A, Farnsworth N R, Santisuk T, Reutrakul V. Phenolic, iridoid and ionyl glycosides from Homalium ceylanicum .  Phytochemistry. 1993;  32 747-54
• 14 Fan G J, He Z S. Studies on the chemical constituents of thinleaf adina (Adina rubella) (III).  Chin Tradit Herb Drugs. 1997;  28 195-8
• 15 Kijima H, Ide T, Otsuka H, Ogimi C, Hirata E, Takushi A. et al . Water-soluble phenolic glycosides from leaves of Alangium premnifolium .  Phytochemistry. 1997;  44 1551-7
• 16 Tang L, Jiang Y, Chang H T, Zhao M B, Tu P F, Cui J R. et al . Triterpene saponins from the leaves of Ilex kudingcha .  J Nat Prod. 2005;  68 1169-74
• 17 Hu W H, Guo Z R, Chu F M, Bai A P, Yi X, Cheng G F. et al . Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: a new series of selective COX-2 inhibitors.  Bioorg Med Chem. 2003;  11 1153-60
• 18 Li X M, Lin M, Wang Y H, Liu X. Four new stilbenoids from the lianas of Gnetum montanum f. megalocarpum .  Planta Med. 2004;  70 160-5
• 19 Lee Y Y, Jang D S, Jin J L, Yun-Choi H S. Anti-platelet aggregating and anti-oxidative activities of 11-O-(4′-O-methylgalloyl)-bergenin, a new compound isolated from Crassula cv. ‘Himaturi’.  Planta Med. 2005;  71 776-7