Subscribe to RSS
DOI: 10.1055/s-2000-8540
Anti-Herpes Simplex Virus Type-1 Flavonoids and a New Flavanone from the Root of Limonium sinense
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.
Key words
Limonium sinense - Plumbaginaceae - isodihydrosyringetin - herpes simplex virus type-1 - inhibition
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