Planta Med 2000; 66(4): 333-336
DOI: 10.1055/s-2000-8540
Original Paper
Georg Thieme Verlag Stuttgart · New York

Anti-Herpes Simplex Virus Type-1 Flavonoids and a New Flavanone from the Root of Limonium sinense

Lie-Chwen Lin, Yuh-Chi Kuo, Cheng-Jen Chou
  • National Research Institute of Chinese Medicine, Pettou, Taipei, Taiwan, Republic of China
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Abstract

From the root of Limonium sinense (Girard) Ktze a new (2R,3S)-3,5,7,4′-tetrahydroxy-3′,5′-dimethoxyflavanone was isolated and named isodihydrosyringetin (3), together with nine other known compounds, (-)-epigallocatechin 3-O-gallate (1), samarangenin B (2), myricetin (4), myricetin 3-O-α-rhamnopyranoside (5), quercetin 3-O-α-rhamnopyranoside (6), (-)-epigallocatechin (7), gallic acid (8), N-trans-caffeoyltyramine (9), and N-trans-feruloyltyramine (10). All of them were examined for their inhibitory effects on herpes simplex virus type-1 (HSV-1) replication in Vero cells. Both compounds 1 and 2 exhibited potent inhibitory activities in HSV-1 replication. Comparison of the IC50 values indicated that compounds 1 and 2 had higher inhibitory activities than the positive control acyclovir (38.6 ± 2.6 vs. 55.4 ± 5.3 μM, P < 0.001; 11.4 ± 0.9 vs. 55.4 ± 5.3 μM, P < 0.0005). Cytotoxicity was unlikely involved because no cell deaths were observable in the Vero cells following 5 day treatments with compound 1 or 2.

References

  • 1 Li  H L.. Plumbaginaceae, Flora of Taiwan. Editorial Committee of the Flora of Taiwan. Vol. IV, Edited. & Published, Taipei; 1978: 90-3
  • 2 Compiled by Jiangsu New Medicine College.. Chinese Meteria Medica Dictionary,. Vol. 2, Shanghai Science and Technology Press, Shanghai; 1977: 2762
  • 3 Rawls  W E,, Campione-Diccardo  G.. The epidemiology and clinical manifestations of Herpes simplex virus infection, the human herpesviruses. In: Nahmias AJ, Dawdle WD, Schinazi RF, editors Elsevier, New York; 1981: 137-52
  • 4 Bracha  R Z,, Quan  P C,, Rosner  M,, Moller  J R,, Bloom  B R.. Role of NK cells in protection of mice against Herpes simplex virus-1 infection.  J. Immunol.. 1987;;  138 884-8
  • 5 Kuo  Y C,, Lin  C Y.. Recurrent Herpes simplex virus type-1 infection precipitated by the impaired production of interleukin-2, alpha-Interferon, and cell-mediated cytotoxicty.  J. Med. Virol.. 1990;;  31 183-9
  • 6 Levy  J A,, Fraenkel-Conrat  H,, Owens  R A.. Virology. Prentice Hall, New Jersey; 1994: 360-2
  • 7 Pottage  J C,, Jr Kessler  H A.. Herpes simplex virus resistance to acyclovir: clinical relevance.  Infectious Agents and Diseases. 1995;;  4 115-24
  • 8 Kuo  Y C,, Ou  J C,, Tsai  W J,, Wu  C L,, Sun  C M.. Evaluation of Chinese herbs that affect the cell-mediated immunity (I).  J. Chin. Med.. 1995;;  6 211-22
  • 9 Davis  A L,, Cai  Y,, Davies  A P,, Lewis  J R.. 1H and 13C NMR assignments of some green tea polyphenols.  Magn. Reson. Chem.. 1996;;  34 887-90
  • 10 Markham  K R,, Ternai  B,, Stanley  R,, Geiger  H,, Mabry  T J.. Carbon-13 NMR studies of flavonoids - III. Naturally occurring flavonoid glycosides and their acylated derivatives.  Tetrahedron. 1978;;  34 1389-97
  • 11 Shen  C C,, Chang  Y S,, Ho  L K.. Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids.  Phytochemistry. 1993;;  34 843-5
  • 12 Nonaka  G I,, Aiko  Y,, Aritake  K,, Nishioka  I.. Tannins and related compounds. CXIX. Samarangenins A and B, novel and proanthocyanidins with doubly bonded structures, from Syzygium samarangens and S. aqueum.  Chem. Pharm. Bull.. 1992;;  40 2671-3
  • 13 Wu  Y C,, Chang  G Y,, Ko  F N,, Teng  C M.. Bioactive constituents from the stems of Annona montana. .  Planta Medica. 1995;;  61 146-9
  • 14 Munoz  O,, Piovano  M,, Garbarino  J,, Hellwing  V,, Breitmaier  E.. Tropane alkaloids from Schizanthus litoralis. .  Phytochemistry. 1990;;  43 709-13
  • 15 Kuo  Y C,, Liu  W T,, Lin  C Y.. Herpes simplex virus type-1 genes in human mononuclear cells and affecting cell-mediated immunity.  J. Med. Virol.. 1993;;  41 138-45
  • 16 Gao  F,, Wang  H,, Mabry  T J,, Kinghorn  A D.. Dihydroflavonol sweeteners and other constituents from Hymenoxys turneri.  Phytochemistry. 1990;;  29 2865-9
  • 17 Sakakibara  M,, Dan Difeo  J R,, Nakatani  N,, Timmermann  B,, Mabry  T J.. Flavonoid methyl ethers on the external leaf surface of Larrea tridentata and L. divaricata. .  Phytochemistry. 1976;;  15 727-31
  • 18 Pardhasaradhi  M,, Sidhu  G S.. Syringetin and dihydrosyringetin from Soymida febrifuga. .  Phytochemistry. 1971;;  11 1520-2
  • 19 Gaffield  W.. Absolute configurations of the cis-dihydroquercetin-3-O-β-L-rhamnosides isoastilbin and neoisoastilbin.  Chem. Pharm. Bull.. 1996;;  44 1102-3

Dr. Lie-Chwen Lin

National Research Institute of Chinese Medicine

No. 155-1, Sec. 2, Li-Nung St., Pettou

Taipei (112)

Taiwan

Republic of China

Email: lclin@cma23.nricm.edu.tw

Phone: +886-2-28264276

    >