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Planta Med 2018; 84(17): 1292-1299
DOI: 10.1055/a-0638-8255
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Six New neo-Clerodane Diterpenoids from Aerial Parts of Scutellaria barbata and Their Cytotoxic Activities

Guo-Chun Yang
1   School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China
,
Jia-Hui Hu
1   School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China
,
Bing-Long Li
1   School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China
2   School of Pharmacy, Taishan Medical University, Taiʼan, P. R. China
,
Huan Liu
1   School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China
,
Jia-Yue Wang
1   School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China
,
Li-Xin Sun
1   School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China
› Author Affiliations
Further Information

Publication History

received 14 March 2018
revised 17 May 2018

accepted 30 May 2018

Publication Date:
20 June 2018 (online)

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Abstract

Six new neo-clerodane diterpenoids (1–6), scutebatas X – Z, A1-C1, along with twelve known ones (7–18) were obtained via the phytochemical investigation of the aerial parts of Scutellaria barbata. Their structures were established by detailed spectroscopic analysis. The absolute configurations of 1 and 2, as the representative members of this type, were identified based on a circular dichroic exciton chirality method. Moreover, in vitro cytotoxicity of compounds 1–6 were evaluated against three human cancer cell lines (SGC-7901, MCF-7, and A-549) using the MTT method. Compound 6 showed cytotoxic activities against all the three cell lines with IC50 values of 17.9, 29.9, and 35.7 µM, respectively.

Key words

neo-clerodane diterpenoid - Scutellaria barbata - Lamiaceae - absolute configuration - cytotoxicity

Supporting Information

    1D and 2D NMR and HRMS spectra of compounds 1–6 as well as the dose-response curves leading to the IC50 determination of compounds 1, 4, and 6 are available as Supporting Information.

  • Supporting Information
 

  • References

  • 1 Editorial Committee of Flora of China, Chinese Academy of Sciences. Flora of China, Vol. 65 (2). Beijing: Science Press; 1977: 229-232
    Google Scholar
  • 2 Editorial Committee of Chinese Pharmacopoeia. Pharmacopoeia of China, Part 1. Beijing: China Medical Science Press; 2015: 118-119
    Google Scholar
  • 3 Li YY, Tang XL, Jiang T, Li PF, Li PL, Li GQ. Bioassay-guided isolation of neo-clerodane diterpenoids from Scutellaria barbata . J Asian Nat Prod Res 2013; 15: 941-949
    CrossrefPubMedGoogle Scholar
  • 4 Nie XP, Qu GW, Yue XD, Li GS, Dai SJ. Scutelinquanines A–C, three new cytotoxic neo-clerodane diterpenoid from Scutellaria barbata . Phytochem Lett 2010; 3: 190-193
    CrossrefPubMedGoogle Scholar
  • 5 Dai SJ, Peng WB, Shen L, Zhang DW, Ren Y. New norditerpenoid alkaloids from Scutellaria barbata with cytotoxic activities. Nat Prod Res 2011; 25: 1019-1024
    CrossrefPubMedGoogle Scholar
  • 6 Zhu F, Di YT, Liu LL, Zhang Q, Fang X, Yang TQ, Hao XJ, He HP. Cytotoxic neoclerodane diterpenoids from Scutellaria barbata . J Nat Prod 2010; 73: 233-236
    CrossrefPubMedGoogle Scholar
  • 7 Dai SJ, Sun JY, Ren Y, Liu K, Shen L. Bioactive ent-clerodane diterpenoids from Scutellaria barbata . Planta Med 2007; 73: 1217-1220
    Article in Thieme ConnectPubMedGoogle Scholar
  • 8 Wang F, Ren FC, Li YJ, Liu JK. Scutebarbatines W–Z, new neo-clerodane diterpenoids from Scutellaria barbata and structure revision of a series of 13-spiro neo-clerodanes. Chem Pharm Bull 2010; 58: 1267-1270
    CrossrefPubMedGoogle Scholar
  • 9 Nguyen VH, Pham VC, Nguyen TTH, Tran VH, Doan TMH. Novel antioxidant neo-clerodane diterpenoids from Scutellaria barbata . Eur J Org Chem 2009; 2009: 5810-5815
    CrossrefPubMedGoogle Scholar
  • 10 Dai SJ, Wang GF, Chen M, Liu K, Shen L. Five new neo-clerodane diterpenoid alkaloids from Scutellaria barbata with cytotoxic activities. Chem Pharm Bull 2007; 55: 1218-1221
    CrossrefPubMedGoogle Scholar
  • 11 Yeon ET, Lee JW, Lee C, Jin QH, Jang HR, Hong JT, Kim YS, Lee MKY, Hwang BY, Lee DH, Ahn JS. neo-Clerodane diterpenoids from Scutellaria barbata and their inhibitory effects on LPS-induced nitric oxide production. J Nat Prod 2015; 78: 2292-2296
    CrossrefPubMedGoogle Scholar
  • 12 Zhu F, Di YT, Li XY, Liu LL, Zhang Q, Li Y, Hao XJ, He HP. Neoclerodane diterpenoids from Scutellaria barbata . Planta Med 2011; 77: 1536-1541
    Article in Thieme ConnectPubMedGoogle Scholar
  • 13 Dai SJ, Liang DD, Ren Y, Liu K, Shen L. New neo-clerodane diterpenoid alkaloids from Scutellaria barbata with cytotoxic activities. Chem Pharm Bull 2008; 56: 207-209
    CrossrefPubMedGoogle Scholar
  • 14 Dai SJ, Shen L, Ren Y. Two new neo-clerodane diterpenoids from Scutellaria barbata . J Integr Plant Biol 2008; 50: 699-702
    CrossrefPubMedGoogle Scholar
  • 15 Yuan QQ, Song WB, Wang WQ, Xuan LJ. Scubatines A–F, new cytotoxic neo-clerodane diterpenoids from Scutellaria barbata D. Don. Fitoterapia 2017; 119: 40-44
    CrossrefPubMedGoogle Scholar
  • 16 de la Torre MC, Rodriguez B, Bruno M, Piozzi F, Savona G, Vassallo N, Servettaz O. Neo-clerodane diterpenoids from Scutellaria alpina . Phytochemistry 1995; 38: 181-187
    CrossrefPubMedGoogle Scholar
  • 17 Hussein AA, de la Torre MC, Jimeno ML, Rondriguez B, Bruno M, Piozzi F, Servettaz O. A neoclerodane diterpenoid from Scutellaria baicalensis . Phytochemistry 1996; 43: 835-837
    CrossrefPubMedGoogle Scholar
  • 18 Ogawa KK, Nakamura SK, Asada YK, Yamashita M, Matsuda H. Oxazonigelladine and dolabellane-type diterpene constituents from Nigella damascena seeds. Tetrahedron 2017; 73: 7054-7060
    CrossrefPubMedGoogle Scholar
  • 19 Hua J, Liu Y, Xiao CJ, Jing SX, Luo SH, Li SH. Chemical profile and defensive function of the latex of Euphorbia peplus . Phytochemistry 2017; 136: 56-64
    CrossrefPubMedGoogle Scholar
  • 20 Jiao W, Lu L, Deng MC, Shao HW, Lu RH. Chemical constituents in seeds of Euphorbia lathyris . China Tradit Herb Drugs 2010; 41: 181-187
    PubMedGoogle Scholar
  • 21 Seip EH, Hecker E. Lathyrane type diterpenoid esters from Euphorbia characias . Phytochemistry 1983; 22: 1791-1795
    CrossrefPubMedGoogle Scholar
  • 22 Xiao K, Zhang L, Han QT, Dai SJ. neo-Clerodane diterpenoids from Scutellaria galericulata . Chin J Chin Mater Med 2016; 41: 3366-3370
    PubMedGoogle Scholar
  • 23 Dai SJ, Zhang L, Xiao K, Han QT. New cytotoxic neo-clerodane diterpenoids from Scutellaria strigillosa . Bioorg Med Chem Lett 2016; 26: 1750-1753
    CrossrefPubMedGoogle Scholar
  • 24 Ashihara H, Yin YL, Katahira RK, Watanabe S, Mimura T, Sasamoto H. Comparison of the formation of nicotinic acid conjugates in leaves of different plant species. Plant Physiol Biochem 2012; 60: 190-195
    CrossrefPubMedGoogle Scholar