Lignans from Schisandra propinqua with Inhibitory Effects on Lymphocyte Proliferation

Abstract

Seven new dibenzocyclooctadiene lignans, named propinquain E–K, together with 11 known lignans were isolated from the ethanol extract of the roots of Schisandra propinqua subsp. sinensis. The structures of the new compounds were elucidated by spectroscopic methods, including ¹H- and ¹³C-NMR, 2D-NMR, HR ESI-MS, and CD spectra. Two dibenzocyclooctadienes revealed inhibitory effects on lymphocyte proliferation.

Key words

Schisandraceae - Schisandra propinqua subsp. sinensis - dibenzocyclooctadiene lignin - diaryldimethylbutane lignin - lymphocyte proliferation

• References

• 1 Hausott B, Greger H, Marian B. Naturally occurring lignans efficiently induce apoptosis in colorectal tumor cells. J Cancer Res Clin Oncol 2003; 129: 569-576
• 2 Xu LJ, Huang F, Chen SB, Li LN, Chen SL, Xiao PG. A cytotoxic neolignan from Schisandra propinqua (Wall.) Baill. J Integr Plant Biol 2006; 48: 1493-1497
• 3 Pu JX, Li RT, Xiao WL, Gong NB, Huang SX, Lu Y, Zheng QT, Lou LG, Sun HD. Longipedlactones A–I, nine novel triterpene dilactones possessing a unique skeleton from Kadsura longipedunculata . Tetrahedron 2006; 62: 6073-6081
• 4 Xiao WL, Pu JX, Chang Y, Li XL, Huang SX, Yang LM, Li LM, Lu Y, Zheng YT, Li RT, Zheng QT, Sun HD. Sphenadilactones A and B, two novel nortriterpenoids from Schisandra sphenanthera . Org Lett 2006; 8: 1475-1478
• 5 Choi YW, Takanatsu S, Khan SI, Srinivas PV, Ferreira D, Zhao JP, Khan IA. Schisandrene, a dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans. J Nat Prod 2006; 69: 356-359
• 6 Xiao WL, Tian RR, Pu JX, Li X, Wu L, Lu Y, Li SH, Li RT, Zheng YT, Zheng QT, Sun HD. Triterpenoids from Schisandra lancifolia with anti-HIV-1 activity. J Nat Prod 2006; 69: 277-279
• 7 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
• 8 Xiao WL, Yang LM, Gong NB, Wu L, Wang RR, Pu JX, Li XL, Huang SX, Zheng YT, Li RT, Lu Y, Zheng QT, Sun HD. Rubriflordilactones A and B, two novel bisnortriterpenoids from Schisandra rubriflora and their biological activities. Org Lett 2006; 8: 991-994
• 9 Li RT, Han QB, Zheng YT, Wang RR, Yang LM, Lu Y, Sang SQ, Zheng QT, Zhao QS, Sun HD. Structure and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton from Schisandra micrantha . Chem Commun 2005; 23: 2936-2938
• 10 Kuo YH, Li SY, Huang RL, Wu MD, Huang HC, Lee KH. Schizarin B, C, D, and E, four new lignans from Kadsura matsudai and their antihepatitis activities. J Nat Prod 2001; 64: 487-490
• 11 Tang MH, Chiu PY, Ko KM. Hepatoprotective action of schisandrin B against carbon tetrachloride toxicity was mediated by both enhancement of mitochondrial glutathione status and induction of heat shock proteins in mice. Biofactors 2003; 19: 33-42
• 12 Xu LJ, Huang F, Chen SB, Chen SL, Xiao PG. A new triterpene and dibenzocyclooctadiene lignans from Schisandra propinqua (Wall.) Baill. Chem Pharm Bull 2006; 54: 542-545
• 13 Li XN, Pu JX, Du X, Yang LM, An HM, Lei C, He F, Luo X, Zheng YT, Lu Y, Xiao WL, Sun HD. Lignans with anti-HIV activity from Schisandra propinqua var. sinensis . J Nat Prod 2009; 72: 1133-1141
• 14 Xu LJ, Huang F, Chen SB, Zhang QX, Li LN, Chen SL, Xiao PG. New lignans and cytotoxic constituents from Schisandra propinqua . Planta Med 2006; 72: 169-174
• 15 Liu JS, Ma YT, Huang MF. Studies on the constituents of Schisandraceae plants in Shennongjia district. Acta Chim Sin 1988; 46: 345-348
• 16 Zhou Y, Yang JS, Wang LW, Xiao PG. Study on chemical constituents of Schisandra propinqua I. Chin Pharm J 2002; 37: 260-261
• 17 Xu LJ, Liu HT, Peng Y, Xiao W, Chen SL, Chen SB, Xiao PG. Chemical constituents from stems of Schisandra propinqua . Chin J Chin Mater Med 2008; 33: 521-523
• 18 Lei C, Huang SX, Chen JJ, Pu JX, Yang LB, Zhao Y, Liu JP, Gao XM, Xiao WL, Sun HD. Lignans from Schisandra propinqua var. propinqua . Chem Pharm Bull 2007; 55: 1281-1283
• 19 Shen GX. Experimental techniques of modern immunology. Hubei: Hubei Scientific and Technical Press; 1998: 309-310
• 20 Ikeya Y, Taguchi H, Yosioka I, Kobayashi H. The constituents of Schizandra chinensis Bill. I. 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: 1383-1394
• 21 Gao XM, Pu JX, Huang SX, Yang LM, Huang H, Xiao WL, Zhang YT, Sun HD. Lignans from Kadsura angustifolia . J Nat Prod 2008; 71: 558-563
• 22 Liu JS, Li L. Kadsulignans L–N, three dibenzocyclooctadiene lignans from Kadsura coccinea . Phytochemistry 1995; 38: 241-245
• 23 Liu JS, Huang MF. Kadsulignans E–G from Kadsura longipedunculata . Phytochemistry 1992; 31: 957-960
• 24 Liu HT, Xu LJ, Peng Y, Yang XW, Xiao PG. Two new lignans from Schisandra henryi . Chem Pharm Bull 2009; 57: 405-407
• 25 Liu JS, Ma TY. Studies on the constituents of Schisandraceae plants in shennongjia district III. Isolation and structures of schisantherin G, H and I. Acta Chim Sin 1988; 46: 465-471
• 26 Kuo YH, Wu MD, Huang RL. Antihepatitis activity (Anti-HBsAg and Anti-HBeAg) of C₁₉ homolignans and six novel C₁₈ dibenzocyclooctadiene lignans from Kadsura japonica . Planta Med 2005; 71: 646-653
• 27 Liu HT, Xu LJ, Peng Y. Complete assignments of ¹H and ¹³C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia . Magn Reson Chem 2009; 47: 609-612
• 28 Shen YC, Liaw CC, Cheng YB. C₁₈ dibenzocyclooctadiene lignans from Kadsura philippinensis . J Nat Prod 2006; 69: 963-966
• 29 Liu JS, Ma YT. Studies on the constituents of Schisandraceae plants in Shennongjia district II. The isolation and structure of schisantherin F. Acta Chim Sin 1988; 46: 460-464
• 30 Kuo YH, Yang Kuo LM, Chen CF. Four new C19 homolignans, schiarisanrins A, B, and D and cytotoxic schiarisanrin C, from Schizandra arisanensis . J Org Chem 1997; 62: 3242-3245
• 31 Kuo YH, Huang HC, Yang Kuo LM, Chen CF. Novel C19 homolignans, taiwanschirin A, B, and cytotoxic taiwanschirin C, and a new C18 lignan, schizanrin A, from Schizandra arisanensis . J Org Chem 1999; 64: 7023-7027