Planta Med 2011; 77(13): 1536-1541
DOI: 10.1055/s-0030-1270797
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Neoclerodane Diterpenoids from Scutellaria barbata

Feng Zhu1 , 2 , Ying-Tong Di1 , Xing-Yao Li1 , Ling-Li Liu1 , Qiang Zhang1 , Yan Li1 , Xiao-Jiang Hao1 , Hong-Ping He1
  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China
  • 2Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
Further Information

Publication History

received Sept. 14, 2010 revised Nov. 10, 2010

accepted January 24, 2011

Publication Date:
25 February 2011 (online)

Abstract

Eight new neoclerodane diterpenoids (18), scutebatas H–O, together with eight known compounds, have been isolated from the whole plant of Scutellaria barbata D. Don. Their structures were elucidated on the basis of spectroscopic studies. In vitro cytotoxicity of selected compounds against cancer cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480 was evaluated. Compounds 5, 6, 7 showed moderate cytotoxicities against several human cancer cell lines, with IC50 values ranging from 12.6–31.4 µM. In addition, compound 1 showed selective cytotoxicity against MCF-7.

Supporting information available online at http://www.thieme-connect.de/ejournals/toc/plantamedica

References

  • 1 Paton A. The adaptive significance of calyx and nutmeg morphology in Scutellaria. Harley RM, Reynolds T Advances in Labiatae science. Kew; Royal Botanic Gardens 1992: 203-210
  • 2 Jiansu New Medical College .The big dictionary of traditional Chinese medicine. Shanghai; Shanghai People's Press 1977: 783-784
  • 3 Rugo H, Shtivelman E, Perez A, Vogel C, Franco S, Tan C E, Melisko M, Tagliaferri M, Cohen I, Shoemaker M, Tran Z, Tripathy D. Phase 1 trial of antitumor effects of BZL101 for patients with advanced breast cancer.  Cancer Res Treat. 2007;  105 17-28
  • 4 Fong S, Shoemaker M, Cadaocas J, Lo A, Liao W, Tagliaferri M, Cohen I, Shtivelman E. Molecular mechanisms underlying selective cytotoxic activity of BZL101, an extract of Scutellaria barbata, towards breast cancer cells.  Cancer Biol Ther. 2008;  32 1-10
  • 5 Goh D, Lee Y H, Ong E S. Inhibitory effects of a chemically standardized extract from Scutellaria barbata in human colon cancer cell lines, LoVo.  J Agric Food Chem. 2005;  53 8197-8204
  • 6 Yin X, Zhou J, Jie C, Xing D, Zhang Y. Anticancer activity and mechanism of Scutellaria barbata extract on human lung cancer cell line A549.  Life Sci. 2004;  75 2233-2244
  • 7 Cha Y Y, Lee E O, Lee H J, Park Y D, Ko S G, Kim D H, Kim H M, Kang I C, Kim S H. Methylene chloride fraction of Scutellaria barbata induces apoptosis in human U937 leukemia cells via the mitochondrial signaling pathway.  Clin Chim Acta. 2004;  348 41-48
  • 8 Suh S J, Yoon J W, Lee T K, Jin U H, Kim S L, Kim M S, Kwon D Y, Lee Y C, Kim C H. Chemoprevention of Scutellaria bardata on human cancer cells and tumorigenesis in skin cancer.  Phytother Res. 2007;  21 135-141
  • 9 Dai Z J, Liu X X, Xue Q, Ji Z Z, Wang X J, Kang H F, Guan H T, Ma X B, Ren H T. Anti-proliferative and apoptosis-inducing activity of Scutellaria barbata containing serum on mouse's hepatoma H22 cells.  Zhongyaocai. 2008;  31 550-553
  • 10 Lee T K, Cho H L, Kim D I, Lee Y C, Kim C H. Scutellaria barbata D. Don induces c-fos gene expression in human uterine leiomyomal cells by activating beta2-adrenergic receptors.  Int J Gynecol Cancer. 2004;  14 526-531
  • 11 Dai S J, Tao J Y, Liu K, Jiang Y T, Li S. neo-Clerodane diterpenoids from Scutellaria barbata with cytotoxic activities.  Phytochemistry. 2006;  13 1326-1330
  • 12 Dai S J, Peng W B, Zhang D W, Li S, Wang W Y, Ren Y. Cytotoxic neoclerodane diterpenoid alkaloids from Scutellaria barbata.  J Nat Prod. 2009;  10 1793-1797
  • 13 Dai S J, Liang D D, Ren Y, Liu K, Shen L. New neo-clerodane diterpenoid alkaloids from Scutellaria barbata with cytotoxic activities.  Chem Pharm Bull. 2008;  56 207-209
  • 14 Zhu F, Di Y T, Liu L L, Zhang Q, Fang X, Yang T Q, Hao X J, He H P. Cytotoxic neoclerodane diterpenoids from Scutellaria barbata.  J Nat Prod. 2010;  73 233-236
  • 15 Lee H, Kim Y, Choi I, Min B S, Shim S H. Two novel neoclerodane diterpenoids from Scutellaria barbata.  Bioorg Med Chem Lett. 2010;  20 288-290
  • 16 Mosmann T. Rapid colorimetric assay for cellular growth and survival application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
  • 17 Peter Y M, Georgi Y P. Neoclerodane diterpenoids from Scuterllaria orientalis subsp. pinnatifida.  Phytochemistry. 1996;  43 173-178
  • 18 Esquivel B, Dominguez R M, Toscano R A. Neoclerodane diterpenoids from Scutellaria caerulea.  J Nat Prod. 2001;  64 778-782
  • 19 Bozov P I, Malakov P Y, Papanov G Y, Torre M C, Rodriguez B, Perales A. Scutalpin A, a neoclerodane diterpenoid from Scutellaria alpine.  Phytochemistry. 1993;  34 453-456
  • 20 Ohno A, Kizu H, Tomimori T. Studies on Nepalese crude drugs XXI. On the diterpenoid constituents of the aerial part of Scutellaria discolor colebr.  Chem Pharm Bull. 1996;  44 1540-1545
  • 21 Torre M C, Rodriguez B, Bruno M, Vassallo N, Bondi M L, Piozzi F, Servettaz O. Neoclerodane diterpenoids from Scutellaria polyodon.  J Nat Prod. 1997;  60 1229-1235
  • 22 Dai S J, Sun J Y, Ren Y, Liu K, Shen L. Bioactive ent-clerodane diterpenoids from Scutellaria barbata.  Planta Med. 2007;  73 1217-1220
  • 23 Wang Z Q, Xu F M, Yan X Z, Zhu Y. Scutebarbatine A, a new neoclerodane-type diterpenoid alkaloid from Scutellaria barbata.  Chin Chem Lett. 1996;  7 333-334
  • 24 Dai S J, Shen L, Ren Y. Two new neoclerodane diterpenoids from Scutellaria barbata.  J Integr Plant Biol. 2008;  50 699-702

Prof. Dr. Xiao-Jiang Hao

State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
Chinese Academy of Sciences

132 Lanhei Road

Heilongtan

Kunming 650204, Yunnan

P. R. China

Phone: +86 87 15 22 32 63

Fax: +86 87 15 22 30 70

Email: haoxj@mail.kib.ac.cn

Dr. Hong-Ping He

State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
Chinese Academy of Sciences

132 Lanhei Road

Heilongtan

Kunming 650204, Yunnan

P. R. China

Phone: +86 87 15 22 32 63

Fax: +86 87 15 22 30 70

Email: hehongping@mail.kib.ac.cn

>