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Planta Med 2003; 69(7): 610-616
DOI: 10.1055/s-2003-41127
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

In vivo Anti-Inflammatory and Antinociceptive Effects of Liriodendrin Isolated from the Stem Bark of Acanthopanax senticosus

Hyun-Ju Jung1 , Hee-Juhn Park1 , Ryung-Gue Kim2 , Kyoung-Min Shin2 , Joohun Ha3 , Jong-Won Choi4 , Hyoung Ja Kim5 , Yong Sup Lee5 , Kyung-Tae Lee2
  • 1Division of Applied Plant Sciences, Sangji University, Woosan-Dong, Wonju, Korea
  • 2College of Pharmacy, Kyung Hee University, Hoegi-Dong, Seoul, Korea
  • 3College of Medicine, Kyung Hee University, Hoegi-Dong, Seoul, Korea
  • 4College of Pharmacy, Kyungsung University, Dayeon-Dong, Pusan, Korea
  • 5Division of Life Sciences, Korea Institute of Science and Technology, Cheongryang, Seoul, Korea
This research was supported by a grant (PF002104-07) from Plant Diversity Research Center of 21st Frontier Research Program funded by Ministry of Science and Technology of Korean government
Further Information

Publication History

Received: September 20, 2002

Accepted: April 26, 2003

Publication Date:
04 August 2003 (online)

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Abstract

In the present study, liriodendrin isolated by activity-guided fractionation from the ethyl acetate (EtOAc) extracts of the stem bark of Acanthopanax senticosus, was evaluated for anti-inflammatory and antinociceptive activities. Liriodendrin (5, 10 mg/kg/day, p. o.) significantly inhibited the increase of vascular permeability induced by acetic acid in mice and reduced an acute paw edema induced by carrageenan in rats. When the analgesic activity was measured by the acetic acid-induced writhing test and hot plate test, liriodendrin showed a dose-dependent inhibition in animal models. In addition, syringaresinol, the hydrolysate of liriodendrin, more potently inhibited the LPS-induced production of NO, PGE2 and TNF-α production of macrophages than liriodendrin. Consistent with these observations, the expression level of iNOS and COX-2 enzyme was decreased by syringaresinol in a concentration-dependent manner. These results suggest that the anti-inflammatory and antinociceptive effects of liriodendrin after oral administration were attributable to the in vivo transformation to syringaresinol, which may function as the active constituent.

Key words

Acanthopanax senticosus - Araliaceae - liriodendrin - syringaresinol - anti-inflammation - antinociceptive

References

  • 1 Shao C J, Kasai R, Xu J , Tanaka O. Saponins from leaves of Acanthopanax senticosus Harms., Ciwujia: Structures of ciwujianosides B, C1, C2, C3, C4, D1, D2 and E.  Chem Pharm Bull. 1988;  36 601-8
    CrossrefPubMedSearch in Google Scholar
  • 2 Shao C J, Kasai R, Xu J D, Tanaka O. Saponins from leaves of Acanthopanax senticosus Harms., Ciwujia: II. Structures of ciwujianosides A1, A2, A3, A4 and D3.  Chem Pharm Bull. 1989;  37 42-5
    PubMedSearch in Google Scholar
  • 3 Nishibe S, Kinoshita H, Takeda H, Okano G. Phenolic compounds from stem bark of Acanthopanax senticosus and their pharmaceutical effect in chronic swimming stressed rats.  Chem Pharm Bull. 1990;  38 1763-5
    PubMedSearch in Google Scholar
  • 4 Fujikawa T, Yamaguchi A, Morita I, Takeda H, Nishibe S. Protective effects of Acanthopanax senticosus Harms from Hokkaido and its components on gastric ulcer in restrained cold water stressed rats.  Biol Pharm Bull. 1996;  19 1227-30
    PubMedSearch in Google Scholar
  • 5 Fang J N, Proksch A, Wagner H. Immunologically active polysaccharides of Acanthopanax senticosus .  Phytochemistry. 1985;  24 2619-22
    CrossrefPubMedSearch in Google Scholar
  • 6 Hibasami H, Fujikawa T, Takeda H, Nishibe S, Satoh T, Fujisawa T, Nakashima K. Induction of apoptosis by Acanthopanax senticosus Harms and its component, sesamin in human stomach cancer KATO III cells.  Oncol Rep. 2000;  7 1213-6
    PubMedSearch in Google Scholar
  • 7 Tsukamoto H, Hisada S, Nishibe S. Coumarins from Fraxunus japonicus and F. mandshurica var.  japonica, Chem Pharm Bull. 1985;  33 4069-73
    PubMedSearch in Google Scholar
  • 8 Deyama T, Ikawa T, Nishibe S. The constituents of Eucommia ulmoides Oliv. II. Isolation and structures of three new lignan glycosides.  Chem Pharm Bull. 1985;  33 3651-7
    PubMedSearch in Google Scholar
  • 9 Park H J, Kwon S H, Lee J H, Lee K H, Miyamoto K, Lee K T. Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides.  Planta Medica. 2001;  67 118-21
    Thieme ConnectPubMedSearch in Google Scholar
  • 10 Higuchi R, Miyahara K, Kawasaki T. Seed saponins of Akebia quinata Decne I. Hederagenin 3-O-glycosides.  Chem Pharm Bull. 1972;  20 1935-9
    PubMedSearch in Google Scholar
  • 11 Whittle B A. The use of change in capillary permeability to distinguish between narcotic and anagesic.  Br J Pharmacol. 1949;  22 246-460
    PubMedSearch in Google Scholar
  • 12 Matsuda H, Samukawa K, Kubo M. Anti-inflammatory activity of ginsenoside Ro.  Planta Medica. 1990;  56 19-23
    PubMedSearch in Google Scholar
  • 13 Bieth J, Metais P, Warter J. Activation, inhibition and protection of tryptic and α-chymotryptic activity by normal human serum.  Clin Chimica Acta. 1969;  20 69-80
    PubMedSearch in Google Scholar
  • 14 Fritz H, Trautschold I, Werle E. Determination of the molecular weight of new trypsin inhibitors with the aid of sephadex gel filtration.  Hoppe Seyler Z Physiol Chem. 1965;  342 253-63
    PubMedSearch in Google Scholar
  • 15 Eddy N B, Leimback D. Synthetic analgesics. II. Dithienbutenyl- and dithienbutenylamines.  J Pharmacol Exp Ther. 1953;  107 385-93
    PubMedSearch in Google Scholar
  • 16 Carvalho J C, Silva M F, Maciel M A, Pinto A C, Nunes D S, Lima R M, Bastos J K, Sarti S J. Investigation of anti-inflammatory and antinociceptive activities of trans-dehydrocrotonin, a 19-nor-clerodane diterpene from Croton cajucara. Part 1.  Planta Medica. 1996;  62 402-4
    PubMedSearch in Google Scholar
  • 17 Green L C, Wagner D A, Glogowsky J, Skipper P L, Wishnok J S, Tannenbaum S R. Analysis of nitrate, nitrite, and (15N)nitrate in biological fluids.  Anal Biochem. 1982;  126 131-8
    CrossrefPubMedSearch in Google Scholar
  • 18 Choi J W, Huh K, Kim S H, Lee K T, Park H J, Han Y N. Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals.  J Ethnopharmacol. 2002;  79 199-204
    CrossrefPubMedSearch in Google Scholar
  • 19 Kim D H, Lee K T, Bae E A, Han M J, Park H J. Metabolism of liriodendrin and syringin by human intestinal bacteria and their relation to in vitro cytotoxicity.  Arch Pharm Res. 1999;  22 30-4
    PubMedSearch in Google Scholar
  • 20 Watkins L R, Maier S F, Goehler L E. Immune activation: the role of proinflammatory cytokines in inflammation, illness response and pathological pain states.  Pain. 1995;  63 289-302
    CrossrefPubMedSearch in Google Scholar

Dr. Kyung-Tae Lee

Department of Biochemistry

College of Pharmacy

Kyung-Hee University

Dongdaemun-Ku

Hoegi-Dong 130-701

Seoul

Korea

Phone: +82-2-9610860

Fax: +82-2-9663885

Email: ktlee@khu.ac.kr