Planta Med 2000; 66(7): 618-623
DOI: 10.1055/s-2000-8648
Original Paper
Georg Thieme Verlag Stuttgart · New York

Coumarins and Antiplatelet Constituents from the Root Bark of Zanthoxylum schinifolium

Ian-Lih Tsai1 , Wei-Yu Lin1 , Che-Ming Teng2 , Tsutomu Ishikawa3 , Shin-Lian Doong4 , Mei-Wen Huang1 , Yu-Chang Chen1 , Ih-Sheng Chen1,*
  • 1 School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, R.O.C.
  • 2 Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan, R.O.C.
  • 3 Faculty of Pharmaceutical Sciences, Chiba University, Chiba, Japan
  • 4 Graduate Institute of Microbiology, College of Medicine, National Taiwan University, Taipei, Taiwan, R.O.C.
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Abstract

Further study on the chloroform-soluble portion of the root bark of Zanthoxylum schinifolium led to the isolation of eight new coumarins: methylschinilenol (1), hydroxyepoxycollinin I (2), 8-methoxyanisocoumarin H (3), hydroxyschininallylol (4), hydroxyepoxycollinin II (5), schinitrienin (6), schininallylone (7), and isoschinilenol (8), along with twenty-six known compounds including fourteen coumarins, and nine alkaloids. The structural elucidation was determined by spectroscopic data. Among the isolates, terpenyl-coumarins and furoquinolines were the active constituents with antiplatelet aggregation in vitro and collinin (10) showed significant anti-HBC DNA replication activity.

References

  • 1 Chang  C E,, Hartley  T G.. Rutaceae in Flora of Taiwan,. Editorial Committee of the Flora of Taiwan, Taipei, R.O.C.,; 2nd ed., Vol. III, 1993: p. 541
  • 2 Pharmacopoeia of the People's Republic of China.. Edited by the Pharmacopoeia Commission of P.R.C., Gaungdong Science and Technology Press, Gaungzhou, China,; Vol. 1, 1995: p. 135
  • 3 Chen  I S,, Lin  Y C,, Tsai  I L,, Teng  C M,, Ko  F N,, Ishikawa  T,, Ishii  H.. Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium. .  Phytochemistry. 1995;;  39 1091-7
  • 4 Chang  C T,, Doong  S L,, Tsai  I L,, Chen  I S.. Coumarins and anti-HBV constituents from Zanthoxylum schinifolium. .  Phytochemistry. 1997;;  45 1419-22
  • 5 Tsai  I L,, Lin  W Y,, Chang  C T,, Chen  I S.. Peroxycoumarins from the root bark of Zanthoxylum schinifolium. .  Journal of the Chinese Chemical Society. 1998;;  45 99-101
  • 6 Teng  C M,, Chen  W Y,, Ko  W C,, Ouyang  C.. Antiplatelet effect of butylidenephthalide.  Biochimica et Biophysica Acta. 1987;;  924 375-82
  • 7 O'Brien  J R.,. Platelet aggregation. II. Some results from a new method of study.  Journal of Clinical Pathology. 1962;;  15 452-5
  • 8 Doong  S L,, Tsai  C H,, Schinazi  R F,, Liotta  D C,, Cheng  Y C.. Inhibition of the replication of hepatitis 80 in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues.  Proceedings of the National Academy Science of the U.S.A.. 1991;;  88 8495-9
  • 9 Ngadjui  B T,, Ayafor  J F,, Sondengam  B L,, Connolly  J D.. Prenylated coumarins from the leaves of Clausena anisata. .  Journal of Natural Products. 1989;;  52 243-7
  • 10 Murray  R DH,, Mendez  J,, Brown  S A.. The Natural Coumarins, Occurrence, Chemistry and Biochemistry,. John Wiley & Sons Ltd., New York, U.S.A.; 1982: pp. 27-9
  • 11 Hong  M F,, Pan  J X,, Jiang  T Y,, Li  C L,, Han  G Q.. Isolation and characterization of platelet-activating factor (PAF) inhibitors from Zanthoxylum schinifolium. .  Journal of Chinese Pharmaceutical Sciences. 1992;;  1 13-9
  • 12 Kuznetsova  G A,, Gashimov  N F.. Structure of a new coumarin from Haplophyllum pedicellatum. .  Khimiya Prirodnykh Soedinenii. 1972;;  8 666-7 [Chem. Abstr. 1973; 78: 108171]
  • 13 Chen  I S,, Wu  S J,, Lin  Y C,, Tsai  I L,, Seki  H,, Ko  F N,, Teng  C M.. Dimeric 2-quinolone alkaloid and antiplatelet aggregation constituents from Zanthoxylum simulans. .  Phytochemistry. 1994;;  36 237-9
  • 14 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
  • 15 Chen  I S,, Tsai  I W,, Teng  C M,, Chen  J J,, Chang  Y L,, Ko  F N,, Lu  M C,, Pezzuto  J M.. Pyranoquinoline alkaloids from Zanthoxylum simulans. .  Phytochemistry. 1997;;  46 525-9
  • 16 Ishii  H,, Ishikawa  T,, Lu  S T,, Chen  I S.. Studies on the chemical constituents of Rutaceous plants. XXXI. The chemical constituents of Xanthoxylum cuspidatum Champ. (Fagara cuspidata Engl.).  Yakugaku Zasshi. 1976;;  12 1458-67
  • 17 Addae-Mensah  I,, Achenbach  H,, Thoithi  G N,, Waibel  R,, Mwangi  J W.. Epoxychiromodine and other constituents of Croton megalocarpus. .  Phytochemistry. 1992;;  31 2055-8
  • 18 Jeffs  P W,, Karle  J M,, Martin  N H.. Cinnamic acid intermediates as precursors to mesembrine and some observations on the late stages in the biosynthesis of the mesembrine alkaloids.  Phytochemistry. 1978;;  17 719-28
  • 19 Tsai  I L,, Sheen  W S,, Chen  J J,, Chen  I S.. Isolation of constituents from the leaves of Szygium tripinnatum. .  The Chinese Pharmaceutical Journal. 1994;;  46 401-12
  • 20 Sheen  W S,, Tsai  I L,, Teng  C M,, Chen  I S.. Nor-neolignan and phenyl propanoid from Zanthoxylum ailanthoides. .  Phytochemistry. 1994;;  36 213-5

D. Ph. Ih-Sheng Chen

Professor of Pharmacognosy School of Pharmacy Kaohsiung Medical University

Kaohsiung

Taiwan, R.O.C.

Email: m635013@cc.kmu.edu.tw

Phone: 886-7-321-0683

    >