Planta Med 2013; 79(14): 1348-1355
DOI: 10.1055/s-0033-1350674
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Triterpenoid Saponins from the Stem Barks of Schefflera heptaphylla

Chun Wu
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Ying-Hui Duan
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Man-Mei Li
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Wei Tang
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Xia Wu
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Guo-Cai Wang
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Wen-Cai Ye
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Guang-Xiong Zhou
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
,
Yao-Lan Li
1   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
2   Guangzhou Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, P. R. China
› Author Affiliations
Further Information

Publication History

received 08 January 2013
revised 05 June 2013

accepted 29 June 2013

Publication Date:
07 August 2013 (online)

Abstract

Nine new triterpenoid saponins, including four ursane-type triterpenoid saponins named heptursosides A–D (14), four oleanane-type triterpenoid saponins named heptoleosides A–D (58), and one dammarane-type triterpenoid saponin, heptdamoside A (9), along with two known saponins, asiaticoside D (10) and scheffoleoside B (11), were isolated from the stem barks of Schefflera heptaphylla. Their structures were determined on the basis of spectroscopic analysis and chemical methods. It is noteworthy in this study that the aglycone of 16 is reported for the first time, and to the best of our knowledge, this is the first report for the presence of the tetracyclic triterpenoid saponin from Schefflera. All the saponins were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells, and 2, 6, 7, and 10 showed anti-inflammatory activities under their noncytotoxic concentrations.

Supporting Information

 
  • References

  • 1 Sung TV, Peter-Katalinic J, Adam G. A bidesmosidic triterpenoid saponin from Schefflera octophylla . Phytochemistry 1991; 30: 3717-3720
  • 2 Adam G, Lischewski M, Phiet HV, Preiss A, Schmidt J, Sung TV. 3α-Hydroxylup-20(29)-ene-23,28-dioic acid from Schefflera octophylla . Phytochemistry 1982; 21: 1385-1387
  • 3 Li YL, Jiang RW, Ooi LSM, But PPH, Ooi VEC. Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla . Phytother Res 2007; 21: 466-470
  • 4 Kitajima J, Shindo M, Tanaka Y. Two new triterpenoid sulfates from the leaves of Schefflera octophylla . Chem Pharm Bull 1990; 38: 714-716
  • 5 Kong YC. Herbal medicines and teas of Hong Kong. Hong Kong: Commercial Press; 2000: 90-91
  • 6 Chen L, Zhu QH, Lin RC. Chemical constituents and biological activity of Schefflera plant. J Chin Med Mater 2002; 25: 363-366
  • 7 Sung TV, Steglich W, Adam G. Triterpene glycosides from Schefflera octophylla . Phytochemistry 1991; 30: 2349-2356
  • 8 Lischewski M, Ty PD, Schmidt J, Preiss A, Phiet HV, Adam G. 3α,11α-Dihydroxylup-20(29)-ene-23,28-dioic acid from Schefflera octophylla . Phytochemistry 1984; 23: 1695-1697
  • 9 Schmidt J, Nam VV, Lischewski M, Hoang VP, Kuhnt C, Adam G. Long-chain fatty acid esters of 3α-hydroxylup-20(29)-ene-23,28-dioic acid and other triterpenoid constituents from the bark of Schefflera octophylla . Phytochemistry 1984; 23: 2081-2082
  • 10 Kitajima J, Tanaka Y. Two new triterpenoid glycosides from the leaves of Schefflera octophylla . Chem Pharm Bull 1989; 37: 2727-2730
  • 11 Maeda C, Ohtani K, Kasai R, Yamasaki K, Duc NM, Nham NT, Cu GKQ. Oleanane and ursane glycosides from Schefflera octophylla . Phytochemistry 1994; 37: 1131-1137
  • 12 Zhu M, Yang SL, Phillipson JD, Bowery NG, Greengrass PM, Bowen DV. Four new triterpenoid glycosides from Schefflera bodinieri roots. J Nat Prod 1996; 59: 1043-1046
  • 13 Wu C, Wang L, Yang XX, Duan YH, Dai Y, Jiang RW, Ye WC, Li YL. A new ursane-type triterpenoid from Schefflera heptaphylla (L.) Frodin. J Asian Nat Prod Res 2011; 13: 434-439
  • 14 Jiang ZY, Zhang XM, Zhou J, Chen JJ. New triterpenoid glycosides from Centella asiatica . Helv Chim Acta 2005; 88: 297-303
  • 15 Mahato SB, Kundu AP. 13C-NMR Spectra of pentacyclic triterpenoids – a compilation and some salient features. Phytochemistry 1994; 37: 1517-1575
  • 16 Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 2007; 55: 899-901
  • 17 Taniguchi S, Imayoshi Y, Kobayashi E, Takamatsu Y, Ito H, Hatano T, Sakagami H, Tokuda H, Nishino H, Sugita D, Shimura S, Yoshida T. Production of bioactive triterpenes by Eriobotrya japonica calli . Phytochemistry 2002; 59: 315-323
  • 18 Tian Y, Guo HZ, Han J, Guo D. Microbial transformation of 20(S)-protopanaxatriol by Mucor spinosus . J Nat Prod 2005; 68: 678-680
  • 19 Islam MN, Ishita IJ, Jin SE, Choi RJ, Lee CM, Kim YS, Jung HA, Choi JS. Anti-inflammatory activity of edible brown alga Saccharina japonica and its constituents pheophorbide a and pheophytin a in LPS-stimulated RAW 264.7 macrophage cells. Food Chem Toxicol 2013; 55: 541-548