Planta Med 2003; 69(8): 757-764
DOI: 10.1055/s-2003-42796
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Anti-Platelet Aggregation and Chemical Constituents from the Rhizome of Gynura japonica

Wei-Yu Lin1 , Yueh-Hsiung Kuo2 , Ya-Ling Chang3 , Che-Ming Teng3 , Eng-Chi Wang4 , Tsutomu Ishikawa5 , Ih-Sheng Chen1
  • 1Graduate Institute of Pharmaceutical Sciences, Kaohsiung Medical University, Kaohsiung, Taiwan, Republic of China
  • 2Department of Chemistry, National Taiwan University, Taipei, Taiwan, Republic of China
  • 3Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan, Republic of China
  • 4School of Chemistry, College of Life Sciences, Kaohsiung Medical University, Kaohsiung, Taiwan, Republic of China
  • 5Faculty of Pharmaceutical Sciences, Chiba University, Chiba, Japan
This research was supported financially by the National Science Council of R.O.C.
Further Information

Publication History

Received: December 10, 2002

Accepted: May 2, 2003

Publication Date:
06 October 2003 (online)

Abstract

A novel quinonoid terpenoid, (-)-α-tocospirone, a new chromanone, (-)-gynuraone, as well as three new steroids, (22E,24S)-7α-hydroperoxystigmasta-5,22-dien-3β-ol, (22E,24S)-stigmasta-1,4,22-trien-3-one, and (24R)-stigmasta-1,4-dien-3-one, together with 15 known components, were isolated from the rhizome of Formosan Gynura japonica. Structures of the new compounds were determined through spectral analyses and chemical evidence. Several of the isolated compounds, caryophyllene oxide, 6-acetyl-2,2-dimethylchroman-4-one, vanillin, 2,6-dimethoxy-1,4-benzoquinone, and benzoic acid exhibited significant anti-platelet aggregation activity in vitro.

References

  • 1 Chen Y. Gynura in Flora Reipublicae Popularis Sinicae. Tomus 77. Beijing; Science Press 1999: pp. 309-22 Lin W Y Teng C M Tsai I L Chen I S Anti-platelet aggregation constituents from Gynura elliptica Phytochemistry 2000 53 833 6 Teng C M Chen W Y Ko W C Ouyang C Antiplatelet effect of butylidenephthalide Biochim Biophys Acta 1987 924 375 82 Chiang Y M Studies on the constituents of the aerial roots of Ficus microcarpa. Ph. D. Thesis Taipei National Taiwan University 2001 pp. 358 65 Chiang Y M Kuo Y H Two novel α-tocopheroids form the aerial roots of Ficus microcarpa Tetrahedron Lett 2003 44 5125 8 Della Greca M Fiorentino A Molinaro A Monaco P Previtera L Hydroperoxysterols in Arum italicum Nat Prod Lett 1994 5 7 14 Ponce M A Ramirez J A Galagovsky L R Gros E G Erra-Balsells R Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement J Chem Soc, Perkin Trans 2 2000 2351 8 Nagasawa M Bae M Tamura G Arima K Microbial transformation of sterols Part II. Cleavage of sterol side chains by microorganisms Agric Biol Chem 1969 33 1644 50 Murohisa T Iida M Some new intermediates in microbial side chain degradation of β-sitosterol J Ferment Bioeng 1993 76 174 7 Thebtaranonth C Thebtaranonth Y Wanauppathamkul S Yuthavong Y Antimalarial sesquiterpenes from tubers of Cyperus rotundus: structure of 10,12-peroxycalamenene, a sesquiterpene endoperoxide Phytochemistry 1995 40 125 8 Barrero A F Sánchez J F Alvarez-Manzaneda E J Muñoz Dorado M Haidour A Terpenoids and sterols from the wood of Abies pinsapo Phytochemistry 1993 32 1261 6 Chakravarty A K Sarkar T Das B Masuda K Shiojima K A new chiratane triterpenoid from Swertia chirata Indian J Chem Sect B 2001 228 31 Kojima H Sato N Hatano A Ogura H Sterol glucosides from Prunella vulgaris Phytochemistry 1990 29 2351 5 Mehta B K Jain P Kotra S Identification of novel aliphatic compounds from Artabotrys odoratissimus (leaves) Indian J Chem 1999 38B 1304 6 Ishii H Chen I S Akaike M Ishikawa T Lu S T Studies on the chemical constituents of Rutaceous plants. XLIV. The chemical constituents of Xanthoxylum integrifoliolum (Merr.) Merr. (Fagara integrifoliola Merr.) (1) The chemical constituents of the root wood Yakugaku Zasshi 1982 102 182 95 Pouchert C J Behnke J The Aldrich Library of 13C- and 1H-FT NMR Spectra Vol. I Wisconsin Aldrich Chemical Company, Inc 1993 pp. 756B Jong T T Chou-Hwang J Y An optically active chromanone from Gynura formosana Phytochemistry 1997 44 553 4 Webb K S Ruszkay S J Oxidation of aldehydes with Oxone® in aqueous acetone Tetrahedron 1998 54 401 10 Lin C N Lu C M Fang S C Shieh B J Hsu M F Wang J P Ko F N Teng C M Novel antiplatelet constituents from Formosan Moraceous plants J Nat Prod 1996 59 834 8 Yang Y P Cheng M J Teng C M Chang Y L Tsai I L Chen I S Chemical and anti-platelet constituents from Formosan Zanthoxylum simulans Phytochemistry 2002 61 567 72 Jong T T Yang W C Chou-Whang C Y Studies on the chemical compositions of Sauropus androgynus and Gynura formosana Taipei 11th Symposium on Natural products 1996 pp. 66 7

Prof. Dr. I. S. Chen

Graduate Institute of Pharmaceutical Sciences

Kaohsiung Medical University

Kaohsiung

Taiwan 807

Republic of China

Phone: +886-7-3121101 ext 2123

Fax: +886-7-3210683

Email: m635013@kmu.edu.tw

    >