Planta Med 2005; 71(7): 646-653
DOI: 10.1055/s-2005-871271
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Antihepatitis Activity (Anti-HBsAg and Anti-HBeAg) of C19 Homolignans and Six Novel C18 Dibenzocyclooctadiene Lignans from Kadsura japonica

Yao-Haur Kuo1 , Ming-Der Wu1 , 2 , Ray-Ling Huang1 , Li-Ming Yang Kuo1 , Ya-Wen Hsu1 , Chia-Ching Liaw1 , 3 , Chia-Cheng Hung1 , Ya-Ching Shen3 , Chi-Wi Ong2
  • 1National Research Institute of Chinese Medicine, Shih-Pai, Taipei, Taiwan, R.O.C.
  • 2Institute of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan, R.O.C
  • 3Institiute of Marine Resources, National Sun Yat-Sen University, Kaohsiung, Taiwan, R.O.C.
Further Information

Publication History

Received: August 23, 2004

Accepted: January 6, 2005

Publication Date:
18 July 2005 (online)

Abstract

Bioassay-directed fractionation of the EtOAc extract of Kadsura japonica has led to the isolation of six new C18 dibenzocyclooctadiene lignans, schizanrins I, J, K, L, M, N, along with four known C19 homolignans, taiwanschirins A, B, C, and heteroclitin F. The elucidations of the new structures were based on spectral analysis. Bioassay evaluation against human type B hepatitis revealed that taiwanschirins A and B showed strong activity for anti-HBsAg and a medium effect for anti-HBeAg at 25 μg/mL (12.9 and 11.9 μM for taiwanschirins A and B, respectively).

References

  • 1 Bao T T, Xu G F, Liu T G, Sun R H, Song Z Y. A comparison of the pharmacological actions of seven constituents isolated from fruits Schizandrae.  Acta Pharm Sinica. 1979;  14 1-7
  • 2 Lu H, Liu G T. Anti-oxidant activity of dibenzocyclooctene lignans isolated from Schisandraceae.  Planta Med. 1992;  58 311-3
  • 3 Hikino H, Kiso Y, Taguchi H, Ikeya Y. Antihepatotoxic actions of lignoids from Schizandra chinensis Fruits.  Planta Med. 1984;  50 213-8
  • 4 Yang X W, Hattori M, Namba T, Chen D F, Xu G J. Anti-lipid peroxidative effect of an extract of the stems of Kadsura heteroclita and its major constituents, kadsurin, in mice.  Chem Pharm Bull. 1992;  40 406-9
  • 5 Yang X W, Miyashiro H, Hattori M, Namba T, Tezuka Y, Kikuchi T, Chen D F, Xu G J, Hori T, Extine M, Mizuno H. Isolation of novel lignans, heteroclitins F and G, from the stems of Kadsura heteroclita, and anti-lipid peroxidative actions of heteroclitins A - G and related compounds in the in vitro rat liver homogenate system.  Chem Pharm Bull. 1992;  40 1510-6
  • 6 Kuo Y H, Kuo L MY, Chen C F. Four new C19 homolignans, schiarisanrin A, B, D, and cytotoxic schiarisanrin C from Schizandra arisanensis .  J Org Chem. 1997;  62 3242-5
  • 7 Kuo Y H, Huang H C, Kuo L MY, Chen C F. Novel C19 homolignans, taiwanschirin A, B, and cytotoxic taiwanschiric C, and a new C18 lignan, schizanrin A, from Schizandra arisanensis .  J Org Chem. 1999;  64 7023-7
  • 8 Kuo Y H, Li S Y, Huang R L, Wu M D, Huang H C, Lee K H. Schizarin B, C, D, and E, four new lignans from Kadsura matsudai and their antihepatitis activities.  J Nat Prod. 2001;  64 487-90
  • 9 Wu M D, Huang R L, Kuo Y LM, Hung C C, Ong C W, Kuo Y H. The anti-HBsAg and anti-HBeAg C18 dibenzocyclooctadiene lignans from Kadsura matsudai and Schizandra arisanensis .  Chem Pharm Bull. 2003;  51 1233-6
  • 10 Huang R L, Chen C C, Huang Y L, Hsieh D J, Hu C P, Chen C F, Chang C M. Osthole increases glycosylation of hepatitis B surface antigen and suppresses the secretion of hepatitis B virus in vitro .  Hepatology. 1996;  24 508-15
  • 11 Kuo Y H, Li S Y, Shen Y C, Huang H C, Hsu Y W, Tseng R J, Ou J C, Chen C F. Sesquiterpene polyol esters and triterpenes from Celastrus punctatus .  Chin Pharm J. 2001;  53 257-63
  • 12 Chen D F, Zhang S X, Chen K, Zhou B N, Wang P, Cosentino L M, Lee K H. Two new lignans, interiotherins A and B, as anti-HIV principles from Kadsura interior .  J Nat Prod. 1996;  59 1066-8
  • 13 Chen Y G, Wang P, Lin Z W, Sun H D, Qin G W, Xie Y Y. Dibenzocyclooctadiene lignans from Kadsura angustifolia .  Phytochemistry. 1998;  48 1059-62
  • 14 Taguchi H, Ikeya Y. The constituents of Schizandra chinensis Baill. I, The structures of gomisin A, B and C.  Chem Pharm Bull. 1975;  23 3296-8
  • 15 Ikeya Y, Taguchi H, Yosioka I, Kobayashi H. The constituents of Schizandra chinensis Baill. II, Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin. Chem. Pharm.  Bull. 1979;  27 1383-94
  • 16 Ikeya Y, Taguchi H, Yosioka I, Kobayashi H. The constituents of Schizandra chinensis Ball. V. The structures of four new lignans, gomisin N, gomisin O, epigomisin O and gomisin E, and transformation of gomisin N to deangeloylgomisin B.  Chem Pharm Bull. 1979;  27 2695-9
  • 17 Li S Y, Wu M D, Wang C W, Kuo Y H, Huang R L, Lee K H. A novel anti-HBeAg homolignan, taiwanschirin D from Kadsura matsudai .  Chem Pharm Bull. 2000;  48 1992-3

Prof. Yao-Haur Kuo

National Research Institute of Chinese Medicine

Shih-Pai

Taipei 112

Taiwan

Republic of China

Phone: 886-2-28201999 ext. 7061

Fax: +886-2-28236150

Email: kuoyh@nricm.edu.tw

    >