Download PDF
Planta Med 2005; 71(12): 1128-1133
DOI: 10.1055/s-2005-873169
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

Evaluation of Antiviral Activity of Compounds Isolated from Ranunculus sieboldii and Ranunculus sceleratus

Haibo Li1 , ChangXin Zhou1 , Yunxue Pan1 , Xiaozhong Gao1 , Xiumei Wu2 , Hua Bai2 , Linfu Zhou3 , Zhi Chen3 , Shuili Zhang1 , Shuyun Shi1 , Jiali Luo2 , Juanhua Xu1 , Liurong Chen1 , Xiaoxiang Zheng4 , Yu Zhao1
  • 1Department of Traditional Chinese Medicine and Natural Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, P. R. China
  • 2Zhejiang Hisun Naturelite Pharmaceutical R&D Co., Ltd., Hangzhou, P. R. China
  • 3Institute of Infectious Diseases, First Affiliated Hospital, School of Medicine, Zhejiang University, Hangzhou, P. R. China
  • 4Department of Biomedical Engineering, College of Biomedical Engineering and Instrument Sciences, Zhejiang University, Hangzhou, P. R. China
Further Information

Publication History

Received: November 25, 2004

Accepted: July 13, 2005

Publication Date:
10 November 2005 (online)

Also available at
    Permissions and Reprints

Abstract

Nineteen compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus were tested for inhibitory effects on hepatitis B virus (HBV) and Herpes simplex virus type-1 (HSV-1). The results showed that apigenin 4′-O-α-rhamnopyranoside (1), apigenin 7-O-β-glucopyranosyl-4′-O-α-rhamnopyranoside (4), tricin 7-O-β-glucopyranoside (5), tricin (12), and isoscopoletin (18) possessed inhibitory activity against HBV replication. Protocatechuyl aldehyde (19) exhibited an inhibiting activity on HSV-1 replication. It is therefore suggested that further investigations on these bioactive compounds might be needed to discover and develop new antiviral agents.

Key words

Anti-virus - Ranunculus sieboldii - Ranunculus sceleratus - Ranunculaceae - hepatitis B virus - Herpes simplex virus type-1 - flavone glycosides

References

  • 1 Prieto J M, Recio M C, Giner R M, Manez S, Rios J L. Pharmacological approach to the pro-and anti-inflammatory effects of Ranunculus sceleratus L.  J Ethnopharmacol. 2003;  89 131-7
    CrossrefPubMedSearch in Google Scholar
  • 2 Xie Z W. Compilation of Chinese Herb Medicine. 2nd edition Beijing; People’s Health Press 1996: pp 201-2
    Search in Google Scholar
  • 3 Nakagawa K, Nakajima M, Okazaki H. Microbial preparation of rhamnosyl derivatives of pharmaceutical phenolic compounds. Japanese Patent 02 211 892, 1990 : 08 - 23
  • 4 Liu W J, Hu X B, Yang P Q. Studies on the chemical constituents of Drosera peltata Smith Var. Lunata collected in Tibet.  West China J Pharm Sci. 1992;  7 201-2
    PubMedSearch in Google Scholar
  • 5 Jean C, Dellamonica G, Besson E. C-Galactosylflavones from Polygonatum multiflorum .  Phytochemistry. 1977;  16 1999-2001
    CrossrefPubMedSearch in Google Scholar
  • 6 Yong J, John N S, Cecil C S. Bioactive flavonoids from endophyte-infected blue grass.  Agric Food Chem. 1988;  46 3785-8
    PubMedSearch in Google Scholar
  • 7 Zhao X H, Chen D H, Si J Y, Pan R L, Shen L G. Studies on the phenolic acid constituents from Chinese medicine ”sheng-ma”, rhizome of Cimicifuga foetida L.  Acta Pharm Sin. 2002;  37 535-8
    PubMedSearch in Google Scholar
  • 8 Nathan P J, Deminguez M, Ortega D A. Shift reagent 1H HMR study of methoxycoumarins.  J Heterocycl Chem. 1984;  21 1141-4
    PubMedSearch in Google Scholar
  • 9 Guo X M, Zhou Z L, Hong Y F. Chemical constituents of Ranunculus ternatus Thunb.  Acta Pharm Sin. 1995;  30 931-4
    PubMedSearch in Google Scholar
  • 10 Lin W H, Wang T X, Cai M S, Sheng E. Studies on the structures of new cinnamol glucoside from the roots of Veronicastrum sibiricus .  Acta Pharm Sin. 1995;  30 752-6
    PubMedSearch in Google Scholar
  • 11 Ma J Y, Wang Z T, Xu L S, Xu G J, Wang Y X. Chemical constituents of Ixens sonchifolia Hance.  J China Pharm Univ. 1998;  29 94-6
    PubMedSearch in Google Scholar
  • 12 Hiroki T, Sueo H, Sansei N. Coumarins from Olea africana and Olea capensis .  Phytochemistry. 1984;  23 699-700
    CrossrefPubMedSearch in Google Scholar
  • 13 Wu T S, Li C Y, Leu Y L, Hu C Q. Limonoids and alkaloids of the root bark of Dictamnus angustifolius .  Phytochemistry. 1999;  50 509-12
    CrossrefPubMedSearch in Google Scholar
  • 14 Greca M D, Monaco P, Previtera L. Stigmasterols from Typha latifolia .  J Nat Prod. 1990;  53 1430-5
    CrossrefPubMedSearch in Google Scholar
  • 15 Kong L Y, Li Y, Min Z D, Li X, Zhu T R. Coumarins from Peucedanum praeruptorum .  Phytochemistry. 1996;  41 1423-6
    CrossrefPubMedSearch in Google Scholar
  • 16 Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
    CrossrefPubMedSearch in Google Scholar
  • 17 Kim T G, Kang S Y, Jung K K, Knag J H, Lee E, Han M H. et al . Antiviral activities of extracts isolated from Terminalis chebula Retz., Sanguisorba officinalis L., Rubus coreanus Miq. and Rheum palmatum L. against hepatitis B virus.  Phytother Res. 2001;  15 718-20
    CrossrefPubMedSearch in Google Scholar
  • 18 Brechtbuehl K, Whalley S A, Dusheiko G M, Saunders N A. A rapid real-time quantitative polymerase chain reaction for hepatitis B virus.  J Virol Methods. 2001;  93 105-13
    CrossrefPubMedSearch in Google Scholar
  • 19 Ying C X, Clercq E D, Neyts J. Selective inhibition of hepatitis B virus replication by RNA interference.  Biochem Biophys Res Commun. 2003;  309 482-4
    CrossrefPubMedSearch in Google Scholar
  • 20 Ying C, Pelt J V, Yap S H, Clercq E D, Neyts J. Use of digoxigenin-labelled probes for the quantitation of HBV-DNA in antiviral drug evaluation.  J Virol Methods. 1999;  81 155-8
    CrossrefPubMedSearch in Google Scholar
  • 21 Han C B, Li F, Yang X F, Mao X Y, Wu D Y, Xin Y. Alterations of mtDNA copy number in gastric carcinoma.  World Chin J Digestol. 2004;  12 258-61
    PubMedSearch in Google Scholar
  • 22 Biesecker G, Karimi S, Desjardins J, Meyer D, Abbott B, Bendele R. et al . Evaluation of mitochondrial DNA content and enzyme levels in tenofovir DF-treated rats, rhesus monkeys and woodchucks.  Antivir Res. 2003;  58 217-25
    PubMedSearch in Google Scholar
  • 23 Binns S E, Hudson J, Merali S, Arnason J T. Antiviral activity of characterized extracts from Echinacea spp. (Heliantheae: Asteraceae) against Herpes simplex virus (HSV-1).  Planta Med. 2002;  68 780-3
    Thieme ConnectPubMedSearch in Google Scholar
  • 24 Kim H K, Jeon W K, Ko B S. Flavanone glycosides from Citrus junos and their anti-influenza virus activity.  Planta Med. 2001;  67 548-9
    Thieme ConnectPubMedSearch in Google Scholar
  • 25 Lake B G, Beamand J A, Tredger J M, Barton P T, Renwick A B, Price R J. Inhibition of xenobiotic-induced genotoxicity in cultured precision-cut human and rat liver slices.  Mutat Res. 1999;  440 91-100
    CrossrefPubMedSearch in Google Scholar
  • 26 Zielinska M, Gulden M, Seibert H. Effects of quercetin and quercetin-3-O-glycosides on oxidative damage in rat C6 glioma cells.  Environ Toxicol Pharmacol. 2000;  13 47-53
    PubMedSearch in Google Scholar

Prof. Dr. Yu Zhao

Department of Traditional Chinese Medicine and Natural Drug Research

College of Pharmaceutical Sciences

Zhejiang University

Hangzhou 310031

People’s Republic of China

Fax: +86-571-8527-0026

Email: dryuzhao@zju.edu.cn