Planta Med 2010; 76(4): 358-361
DOI: 10.1055/s-0029-1186157
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Three New Phenolic Glycosides and a New Triterpenoid from the Stems of Scolopia chinensis

Ya-Nan Lu1 , Xing-Yun Chai1 , 2 , Zheng-Ren Xu1 , Dan Bi1 , Hong-Yan Ren1 , Min Zhao1 , Peng-Fei Tu1
  • 1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, P. R. China
  • 2Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, P. R. China
Further Information

Publication History

received June 24, 2009 revised August 18, 2009

accepted August 25, 2009

Publication Date:
29 September 2009 (online)

Abstract

Three new phenolic glycosides, scolochinenosides C–E (13), and a new triterpenoid, scolopianate A (4), were isolated from the stems of Scolopia chinensis, along with 15 known compounds. The structures of the new compounds were elucidated by means of extensive spectroscopic and chemical methods. Compound 3 contains a novel highly oxygenated lactone bridge ring attached at the aglycone. Six lanostane triterpenoids (1015) were discovered for the first time in a species other than Ganoderma lucidum (Polyporaceae). In addition, the phenolic glycosides were evaluated for their inhibitory activity against snake venom phosphodiesterase I.

References

  • 1 Shi H M, Wen J, Jia C Q, Jin W, Zhang X F, Yao Z R, Tu P F. Two new phenolic glycosides from the barks of Hydnocarpus annamensis and their anti-inflammatory and anti-oxidation activities.  Planta Med. 2006;  72 948-950
  • 2 Chai X Y, Xu Z R, Ren H Y, Shi H M, Lu Y N, Li F F, Tu P F. Itosides A–I, new phenolic glycosides from Itoa orientalis.  Helv Chim Acta. 2007;  90 2176-2185
  • 3 Shi H M, Yao Z R, Chai X Y, Xu Z R, Zhou Y H, Wen J, Tu P F. A new phenolic glycoside from the stems of Hydnocarpus hainanensis.  Nat Prod Res. 2008;  22 633-637
  • 4 Xu Z R, Chai X Y, Bai C C, Ren H Y, Lu Y N, Shi H M, Tu P F. Xylocosides A–G, phenolic glycosides from the stems of Xylosma controversum Clos.  Helv Chim Acta. 2008;  91 1346-1354
  • 5 Lu Y N, Xie G B, Bi D, Shi H M, Tu P F. Constituents form leavs of Scolopia chinensis.  Helv Chim Acta. 2008;  91 825-831
  • 6 Chai X Y, Bai C C, Shi H M, Xu Z R, Ren H Y, Li F F, Lu Y N, Song Y L, Tu P F. Six insecticidal isoryanodane diterpenoids from the bark and twigs of Itoa orientalis.  Tetrahedron. 2008;  64 5743-5747
  • 7 Chai X Y, Song Y L, Xu Z R, Shi H M, Bai C C, Bi D, Wen J, Li F F, Tu P F. Itosides J–N from Itoa orientalis and the structure-anti-COX-2 activity relationship of phenolic glycosides.  J Nat Prod. 2008;  71 814-819
  • 8 Lu Y N, Xu Z R, Chai X Y, Ren H Y, Tu P F. Studies on the chemical constituents from the stems of Scolopia chinensis (Lour.) Clos.  Chin Tradit Herb Drugs. 2008;  39 1624-1626
  • 9 Chai X Y, Ren H Y, Xu Z R, Bai C C, Zhou F R, Ling S K, Pu X P, Li F F, Tu P F. Investigation of two Flacourtiaceae plants: Bennettiodendron leprosipes and Flacourtia ramonchi.  Planta Med. 2009;  75 1246-1252
  • 10 Gibbons S, Gray A I, Waterman P G, Hockless D C R, Skelton B W, White A H. Benzoylated derivatives of 2-β-glucopyranosyloxy-2,5-dihydroxybenzyl alcohol from Xylosma flexuosum: structure and relative configuration of xylosmin.  J Nat Prod. 1995;  58 554-559
  • 11 Shaari K, Waterman P G. Scoloposides A–E, a series of 2-glucopyranosyloxy-5-hydroxybenzyl alcohol derivatives from Scolopia spinosa.  Phytochemistry. 1994;  36 1021-1026
  • 12 Ishikawa T, Nishigaya K, Takami K, Uchikoshi H, Chen I S, Tsai I L. Isolation of salicin dervatives from Homalium cochinchinensis and their antiviral activities.  J Nat Prod. 2004;  67 659-663
  • 13 Nishitoba T, Sato H, Sakamura S. Triterpenoids from the fungus Ganoderma lucidum.  Phytochemistry. 1987;  26 1777-1784
  • 14 Shaari K, Waterman P G. Glucosides of 2, 5-dihydroxybenzyl alcohol from Homalium longifolium.  Phytochemistry. 1995;  39 1415-1421
  • 15 Arisawa M, Fujita A, Hayashi T, Shimizu M, Morita N, Kikuchi T, Kadota S, Tezuka Y. Revision of proton and carbon-13 NMR assignments of lanostanoids from Ganoderma lucidum by 2D-NMR studies.  J Nat Prod. 1988;  51 54-59
  • 16 Min B S, Nakamura N, Miyashiro H, Bae K W, Hattori M. Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease.  Chem Pharm Bull. 1998;  46 1607-1612
  • 17 Sato H, Nishitoba T, Shirasu S, Oda K, Sakamura S. Ganoderiols A and B, new triterpenoids from the fungus Ganoderma lucidum (Reishi).  Agric Biol Chem. 1986;  50 2887-2890
  • 18 Ha T B T, Gerhauser C, Zhang W D, Nadine H C L, Fouraste I. New lanostanoids from Ganoderma lucidum that induce NAD(P)H: quinone oxidoreductase in cultured hepalclc7 murine hepatoma cells.  Planta Med. 2000;  66 681-684
  • 19 Nishitoba T, Oda K, Sato H, Sakamura S. Novel triterpenoids from the fungus Ganoderma lucidum.  Agric Biol Chem. 1988;  52 367-372
  • 20 Foo L Y, Newman R, Waghorn G, McNabb W C, Ulyatt M J. Proanthocyanidins from Lotus corniculatus.  Phytochemistry. 1996;  41 617-624
  • 21 Cui C B. Studies on the constituents of a fern, Davallia mariesii Moore [dissertation]. Toyama, Japan; Toyama Medical and Pharmaceutical University 1992: 92
  • 22 Baderschneider B, Winterhalter P. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and liganans from riesling wine and screening for antioxidant activity.  J Agric Food Chem. 2001;  49 2788-2798
  • 23 The Angiosperm Phylogeny Group . An update of the angiosperm phylogeny group classification for the orders and families of flowering plants: APG II.  Bot J Linn Soc. 2003;  141 399-436
  • 24 Mosaddik M A, Forster P I, Booth R, Waterman P G. Phenolic glycosides from some Australian species of Flacourtiaceae (Salicaceae sensu lato).  Biochem Syst Ecol. 2007;  35 166-168
  • 25 Chai X Y, Lu Y N, Ren H Y, Tu P F. Advances in studies on chemical constituents and bioactivities of plants from Flacourtaceae.  Chin J Chin Mater Med. 2006;  31 271-279

Prof. Peng-Fei Tu

State Key Laboratory of Natural and Biomimetic Drugs
School of Pharmaceutical Sciences
Peking University Health Science Center

38 Xueyuan Road

Haidian District

100191 Beijing

People's Republic of China

Phone: + 86 10 82 80 27 50

Fax: + 86 10 82 80 27 50

Email: pengfeitu@vip.163.com

>