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Planta Med 2000; 66(3): 251-256
DOI: 10.1055/s-2000-8562
Original Paper
Georg Thieme Verlag Stuttgart · New York

Anti-Platelet Aggregation Alkaloids and Lignans from Hernandia nymphaeifolia

Jih-Jung Chen1 , Ya-Ling Chang2 , Che-Ming Teng2 , Ih-Sheng Chen3,*
  • 1 Department of Pharmacy, Tajen Institute of Technology, Pingtung, Taiwan, Republic of China
  • 2 Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan, Republic of China
  • 3 Graduate Institute of Pharmaceutical Sciences, Kaohsiung Medical College, Kaohsiung, Taiwan, Republic of China
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Publication History

Publication Date:
31 December 2000 (online)

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Abstract

A new aporphine, N-(N-methylcarbamoyl)-O-methylbulbocapnine (1), together with seven known compounds, (-)-5′-methoxypodorhizol (2), a mixture of β-sitosterone (3) and stigmasta-4,22-dien-3-one (4), a mixture of 3β-hydroxystigmast-5-en-7-one (5) and 3β-hydroxystigmasta-5,22-dien-7-one (6), and a mixture of 6α-hydroxystigmast-4-en-3-one (7) and 6α-hydroxystigmasta-4,22-dien-3-one (8), were isolated in continuing studies on the trunk bark of Formosan Hernandia nymphaeifolia. The structures of these compounds were determined through spectral analyses. In addition, the previously reported six alkaloids, laurotetanine, oxohernagine, thalicarpine, reticuline, (+)-vateamine-2′-β-N-oxide, (+)-hernandaline and six lignans, (+)-epiaschantin, (+)-epimagnolin, (+)-epiyangambin, (-)-hernone, (-)-yatein, (-)-deoxypodophyllotoxin were demonstrated to have anti-platelet aggregation activity.

Key words

Hernandia nymphaeifolia - Hernandiaceae - bark - aporphine alkaloids - lignans - N-(N-methylcarbamoyl)-O-methylbulbocapnine - anti-platelet aggregation activity

References

  • 1 Yang  Y P,, Lu  S Y.. Flora of Taiwan, 28. Hernandiaceae. Editorial Committee of the Flora of Taiwan, Second Edition, Taipei, Taiwan; 1996; Vol. 2: 500-1
    Search in Google Scholar
  • 2 Kan  W S.. Manual of Medicinal Plants in Taiwan. National Research Institute of Chinese Medicine, Taiwan; 1970; Vol. 1: 178-9
    Search in Google Scholar
  • 3 Richomme  P,, Bruneton  J,, Cabalion  P,, Debray  M M.. Étude des Hernandiacées, IX. Lignanes de Deux Hernandia Mélanésiens.  Journal of Natural Products. 1984;;  47 879-81
    CrossrefPubMedSearch in Google Scholar
  • 4 Cava  M P,, Venkateswarlu  A.. Dehydroocopodine, dicentrinone, and other alkaloids from Ocotea macropoda and Hernandia jamaicensis. .  Tetrahedron. 1971;;  27 2639-43
    CrossrefPubMedSearch in Google Scholar
  • 5 Chalandre  M C,, Bruneton  J,, Cabalion  P,, Guinaudeau  H.. Étude des Hernandiacées. XII. Dimères Aporphine-benzylisoquinoléine Originaux Isolés de Hernandia peltata.  Can. J. Chem.. 1986;;  64 123-6
    PubMedSearch in Google Scholar
  • 6 Ito  C,, Matsui  T,, Wu  T S,, Furukawa  H.. Isolation of 6,7-demethylenedeoxypodophyllotoxin from Hernandia ovigera.  Chem. Pharm. Bull.. 1992;;  40 1318-21
    PubMedSearch in Google Scholar
  • 7 Chen  I S,, Chen  J J,, Tsai  I L,, Chang  Y L,, Teng  C M.. New p-quinonoid aporphine alkaloids and antiplatelet aggregation constituents of Hernandia sonora.  Planta Medica. 1995;;  61 537-9
    PubMedSearch in Google Scholar
  • 8 Chen  J J,, Ishikawa  T,, Duh  C Y,, Tsai  I L,, Chen  I S.. New dimeric aporphine alkaloids and cytotoxic constituents of Hernandia nymphaeifolia.  Planta Medica. 1996;;  62 528-33
    PubMedSearch in Google Scholar
  • 9 Chen  I S,, Chen  J J,, Duh  C Y,, Tsai  I L.. New cytotoxic lignans from Formosan Hernandia nymphaeifolia.  Phytochemistry. 1997;;  45 991-96
    CrossrefPubMedSearch in Google Scholar
  • 10 Teng  C M,, Chen  W Y,, Ko  W C,, Ouyang  C.. Antiplatelet effect of butylidenephthalide.  Biochem. Biophys. Acta. 1987;;  924 375-82
    PubMedSearch in Google Scholar
  • 11 O'Brien  J R.. Platelet aggregation II. Some results from a new method of study.  J. Clin. Path.. 1962;;  15 452-5
    PubMedSearch in Google Scholar
  • 12 Lu  S T,, Wang  S J,, Lai  P H,, Lin  C M,, Lin  L C.. Studies on the alkaloids of Formosan Lauraceous plants. XV. Alkaloids of Lindera oldhamii Hemsl. (1).  Yakugaku Zasshi. 1972;;  92 910-7
    PubMedSearch in Google Scholar
  • 13 Achenbach  H,, Renner  C,, Addae-Mensah  I.. Inhaltsstoffe Westafrikanischer Arzneipflanzen. X. Untersuchung der Inhaltsstoffe von Hexalobus crispiflorus.  Liebigs Ann. Chem.. 1982;  1623-33
    PubMedSearch in Google Scholar
  • 14 Richomme  P,, Bruneton  J, Cavé  A.. 5′-Methoxyyatein and 5′-methoxypodorhizol: new lignans isolated from Hernandia cordigera Viell.  Heterocycles. 1985;;  23 309-12
    PubMedSearch in Google Scholar
  • 15 Wu  T S,, Jong  T T,, Tien  H J,, Kuoh  C S,, Furukawa  H,, Lee  K H.. Annoquinone-A, an antimicrobial and cytotoxic principle from Annona montana.  Phytochemistry. 1987;;  26 1623-5
    CrossrefPubMedSearch in Google Scholar
  • 16 Notaro  G,, Piccialli  V,, Sica  D.. New steroidal hydroxyketones and closely related diols from the marine sponge Cliona copiosa.  Journal of Natural Products. 1992;;  55 1588-94
    CrossrefPubMedSearch in Google Scholar
  • 17 Achenbach  H,, Schwinn  A.. Aporphinoid alkaloids and terpenoids from Piptostigma fugax. .  Phytochemistry. 1995;;  38 1037-48
    CrossrefPubMedSearch in Google Scholar
  • 18 Della Greca  M,, Monaco  P,, Previtera  L.. Stigmasterols from Typha latifolia. .  Journal of Natural Products. 1990;;  53 1430-5
    CrossrefPubMedSearch in Google Scholar
  • 19 Khan  A Q,, Malik  A.. A steroid from Calotropis procera. .  Phytochemistry. 1989;;  28 2859-61
    CrossrefPubMedSearch in Google Scholar
  • 20 Vane  J R.. Inhibition of prostaglandin biosynthesis as a mechanism of action for aspirin-like drugs.  Nature (New Biology). 1971;;  231 232-5
    PubMedSearch in Google Scholar

Prof. Dr. I. S. Chen

Graduate Institute of Pharmaceutical Sciences Kaohsiung Medical College

Kaohsiung

Taiwan

Republic of China

Email: m635013@cc.kmc.edu.tw

Phone: +886-7-3210683