Planta Med 2012; 78(15): 1661-1666
DOI: 10.1055/s-0032-1315260
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Five New 3,4-Seco-Lanostane-type Triterpenoids with Antiproliferative Activity in Human Leukemia Cells Isolated from the Roots of Kadsura coccinea

Nan Wang
1   Key Laboratory of Structure-Based Drug Design & Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang, PR China
2   School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China
,
Zhan-lin Li
1   Key Laboratory of Structure-Based Drug Design & Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang, PR China
2   School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China
,
Dan-dan Song
1   Key Laboratory of Structure-Based Drug Design & Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang, PR China
,
Wei Li
3   Department of Pharmacognosy, Toho University, Funabashi, Chiba, Japan
,
Yue-hu Pei
1   Key Laboratory of Structure-Based Drug Design & Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang, PR China
2   School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China
,
Yong-kui Jing
4   Department of Medicine, Mount Sinai School of Medicine, New York, NY, USA
,
Hui-ming Hua
1   Key Laboratory of Structure-Based Drug Design & Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang, PR China
2   School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China
› Author Affiliations
Further Information

Publication History

received 31 March 2012
revised 08 July 2012

accepted 23 July 2012

Publication Date:
04 September 2012 (online)

Abstract

Five new 3,4-seco-lanostane-type triterpenoids, seco-coccinic acids G–K (15), and a known compound, seco-coccinic F, were isolated from the roots of Kadsura coccinea (Lem.) A. C. Sm. Their structures were elucidated by spectroscopic methods, including 2D-NMR and HR-MS techniques. The cell growth inhibitory effects of these compounds were assayed in human leukemia HL-60 cells, and it was found that 1, 5, and 6 showed antiproliferative effects with GI50 values of 28.4, 15.2, and 16.6 µM, respectively.

Supporting Information

 
  • References

  • 1 Song LR, Hong X, Ding XL, Zang ZY. Dictionary of modern science of Chinese materia medica, Volume 2. Beijing: Peopleʼs Health Publishing House; 2001: 2172-2173
  • 2 Jiangsu New Medical College. Dictionary of traditional Chinese medicine. Shanghai: Shanghai Science and Technology Publishing House; 1999: 3330-3331
  • 3 Li LN, Xue H, Tan R. Dibenzocyclooctadiene lignans from roots and stems of Kadsura coccinea . Planta Med 1985; 51: 297-300
  • 4 Liu JS, Li L. Schisantherins L–O and acetylschisantherin L from Kadsura coccinea . Phytochemistry 1993; 32: 1293-1296
  • 5 Liu JS, Li L. Kadsulignans L–N, three dibenzocyclooctadiene lignans from Kadsura coccinea . Phytochemistry 1995; 38: 241-245
  • 6 Li HR, Feng YL, Yang ZG, Wang J, Daikonya A, Kitanaka S, Xu LZ, Yang SL. New lignans from Kadsura coccinea and their nitric oxide inhibitory activities. Chem Pharm Bull 2006; 54: 1022-1025
  • 7 Li HR, Wang LY, Yang ZG, Kitanaka S. Kadsuralignans H–K from Kadsura coccinea and their nitric oxide production inhibitory effects. J Nat Prod 2007; 70: 1999-2002
  • 8 Li LN, Xue H. Triterpenoids from roots and stems of Kadsura coccinea . Planta Med 1986; 52: 492-493
  • 9 Gao XM, Pu JX, Huang SX, Lu Y, Luo LG, Li RT, Xiao WL, Chang Y, Sun HD. Kadcoccilactones A–J, triterpenoids from Kadsura coccinea . J Nat Prod 2008; 71: 1182-1188
  • 10 Gao XM, Pu JX, Xiao WL, Huang SX, Lou LG, Sun HD. Kadcoccilactones K–R, triterpenoids from Kadsura coccinea . Tetrahedron 2008; 64: 11673-11679
  • 11 Li HR, Wang LY, Miyata S, Kitanaka S. Kasuracoccinic acids A–C, ring-A seco-lanostane triterpenes from Kadsura coccinea and their effects on embryonic cell division of Xenopus laevis . J Nat Prod 2008; 71: 739-741
  • 12 Sy LK, Brown GD. Novel seco-cycloartanes from Kadsura coccinea and the assisted autoxidation of a tri-substituted alkene. Tetrahedron 1999; 55: 119-132
  • 13 Wang N, Li ZL, Song DD, Li W, Fu HW, Koike K, Pei YH, Jing YK. Lanostane-type triterpenoids from the roots of Kadsura coccinea . J Nat Prod 2008; 71: 990-994
  • 14 Wang N, Li ZL, Li DY, Pei YH, Hua HM. Five new triterpenoids from the roots of Kadsura coccinea . Helv Chim Acta 2009; 92: 1413-1418
  • 15 Ban NK, Thanh BV, Kiem PV, Minh CV, Cuong NX, Nhiem NX, Huong HT, Anh HT, Park EJ, Sohn DH, Kim YH. Dibenzocyclooctadiene lignans and lanostane derivatives from the roots of Kadsura coccinea and their protective effects on primary rat hepatocyte injury induced by t-butyl hydroperoxide. Planta Med 2009; 75: 1253-1257
  • 16 Wang F, Hua HM, Pei YH, Chen D, Jing YK. Triterpenoids from the resin of Styrax tonkinensis and their antiproliferative and differentiation effects in human leukemia HL-60 cells. J Nat Prod 2006; 69: 807-810
  • 17 Liu JS, Huang MF, Tao Y. Anwuweizonic acid and manwuweizic acid, the putative anticancer active principle of Schisandra propinqua . Can J Chem 1988; 66: 414-415
  • 18 Arjun HB, Yasuhiro T, Kim QT, Ken T, Ikuo S, Shigetoshi K. Thirteen novel cycloartane-type triterpenes from Combretum guadrangulare . J Nat Prod 2000; 63: 57-64