Planta Med 2013; 79(12): 1051-1055
DOI: 10.1055/s-0032-1328747
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Dibenzocyclooctane Lignans from the Stems of Schisandra wilsoniana

Wen-Hui Ma
Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, P. R. China
,
Yan Lu
Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, P. R. China
,
Dao-Feng Chen
Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, P. R. China
› Author Affiliations
Further Information

Publication History

received 05 February 2013
revised 20 April 2013

accepted 06 June 2013

Publication Date:
09 July 2013 (online)

Abstract

Five new dibenzocyclooctane lignans, schisanwilsonins K–O (15), together with eighteen known lignans (623) were isolated from the stems of Schisandra wilsoniana. The structures of these new compounds were elucidated by spectroscopic methods, including 2D-NMR techniques. Several compounds were found to show anti-HIV and anti-HBV activity.

Supporting Information

 
  • References

  • 1 Yang GY, Xiao WL, Chang Y, Wang RR, Pu JX, Gao XM, Lei C, Lu Y, Zheng YT, Sun HD. Nortriterpenoids from Schisandra wilsoniana . Helv Chim Acta 2008; 91: 1871-1878
  • 2 Yang GY, Li YK, Wang RR, Li XN, Xiao WL, Yang LM, Pu JX, Zheng YT, Sun HD. Dibenzocyclooctadiene lignans from Schisandra wilsoniana and their anti-HIV-1 activities. J Nat Prod 2010; 73: 915-919
  • 3 Yang GY, Li YK, Wang RR, Xiao WL, Yang LM, Pu JX, Zheng YT, Sun HD. Dibenzocyclooctadiene lignans from the fruits of Schisandra wilsoniana and their anti-HIV-1 activities. J Asian Nat Prod Res 2010; 12: 470-476
  • 4 Yang GY, Wang RR, Mu HX, Li YK, Xiao WL, Yang LM, Pu JX, Zheng YT, Sun HD. Neolignans from Schisandra wilsoniana and their anti-human immunodeficiency virus-1 activities. Chem Pharm Bull 2011; 59: 1344-1347
  • 5 Zhang XJ, Yang GY, Wang RR, Pu JX, Sun HD, Xiao WL, Zheng YT. 7,8-Secolignans from Schisandra wilsoniana and their anti-HIV-1 activities. Chem Biodivers 2010; 7: 2692-2701
  • 6 Ma WH, Huang H, Zhou P, Chen DF. Schisanwilsonenes A–C, anti-HBV carotane sesquiterpenoids from the fruits of Schisandra wilsoniana . J Nat Prod 2009; 72: 676-678
  • 7 Ma WH, Lu Y, Huang H, Zhou P, Chen DF. Schisanwilsonins A–G and related anti-HBV lignans from the fruits of Schisandra wilsoniana . Bioorg Med Chem Lett 2009; 19: 4958-4962
  • 8 Wang HJ, Chen YY. Studies of lignans from Schisandra rubriflora Rhed et Wils. Acta Chim Sin 1985; 20: 832-841
  • 9 Ikeya Y, Taguchi H, Yosioka I, Kobayashi H. The structures of four new lignans, gomisin H and its derivatives, angeloyl-, tigloyl- and benzoyl-gomisin H. Chem Pharm Bull 1979; 27: 1576-1582
  • 10 Chen M, Liao ZX, Chen DF. Four new dibenzocyclooctene lignans from Kadsura renchangiana . Helv Chim Acta 2004; 87: 1368-1376
  • 11 Liu JS, Li L. Schisantherins L–O and acetylschisantherin L from Kadsura coccinea . Phytochemistry 1993; 32: 1293-1296
  • 12 Ikeya Y, Taguchi H, Sasaki H, Nakajima K, Yosioka I. The constituents of Schizandra chinensis Baill VI 13C nuclear magnetic resonance spectroscopy of dibenzocyclooctadiene lignans. Chem Pharm Bull 1980; 28: 2414-2421
  • 13 Ikeya Y, Miji E, Okada M, Mitsuhashi H, Chai JG. Benzoylgomisin Q and benzoylgomisin P, two new lignans from Schisandra sphenanthera REHD et WILS. Chem Pharm Bull 1990; 38: 1408-1411
  • 14 Ikeya Y, Sugama K, Okada M, Mitsuhashi H. Two lignans from Schisandra sphenanthera . Phytochemistry 1991; 30: 975-980
  • 15 Chen DF, Zhang SX, Chen K, Zhou BN, Wang P, Cosentino LM, Lee KH. Two new lignans, interiotherins A and B, as anti-HIV principles from Kadsura interior . J Nat Prod 1996; 59: 1066-1068
  • 16 Ikeya Y, Taguchi H, Yosioka I, Kobayashi H. The constituents of Schizandra chinensis BAILL 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: 2695-2709
  • 17 Ikeya Y, Taguchi H, Yosioka I. The constituents of Schizandra chinensis BAILL. XII. Isolation and structure of a new lignan, gomisin R, the absolute structure of wuweizisu C and isolation of schisantherin D. Chem Pharm Bull 1982; 30: 3207-3211
  • 18 Ikeya Y, Taguchi H. The constituents of Schizandra chinensis Baill. The structures of two new lignans, pre-gomisin and gomisin J. Chem Pharm Bull 1978; 26: 682-684
  • 19 Tan R, Li LN, Fang QC. Studies on the chemical constituents of Kadsura longipedunculata: isolation and structure elucidation of five new lignans. Planta Med 1984; 50: 414-416
  • 20 Chen YG, Qin GW, Xie YY. Dibenzocyclooctadiene lignans from Schisandra propinqua . Chem J Chin Univ 2001; 22: 1518-1521
  • 21 Li LN, Hung X, Tan R. Dibenzocyclooctadiene lignans from roots and stems of Kadsura coccinea . Planta Med 1985; 4: 297-299
  • 22 Ikeya Y, Taguchi H, Mitsuhashi H, Takeda S, Kase Y, Aburada M. A lignan from Schizandra chinensis . Phytochemistry 1988; 27: 569-573
  • 23 Ikeya Y, Ookawa N, Taguchi H, Yosioka I. The constituents of Schizandra chinensis BAILL. XI. The structures of three new lignans, angeloylgomisin O, and angeloyl- and benzoylisogomisin O. Chem Pharm Bull 1982; 30: 3202-3206
  • 24 Chen M, Kilgore N, Lee KH, Chen DF. Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora . J Nat Prod 2006; 69: 1697-1701
  • 25 Wu T, Huang H, Zhou P. The inhibitory effects of enduracidin on hepatitis B virus in vitro . Zhongguo Bing Du Xue 1998; 13: 46-50