Planta Med 2015; 81(03): 241-246
DOI: 10.1055/s-0034-1396151
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Icetexane Diterpenoids from Perovskia atriplicifolia

Zhi-Yong Jiang
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
,
Yi-Jiang Yu
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
,
Chao-Guan Huang
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
,
Xiang-Zhong Huang
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
2   Key Laboratory of Yi Medicine Resources & Pharmacodynamics Research, Yunnan Minzu University, Kunming, Yunnan, China
,
Qiu-Fen Hu
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
,
Guang-Yu Yang
3   Key Laboratory of Tobacco Chemistry of Yunnan Province, Yunnan Academy of Tobacco Science, Kunming, Yunnan, China
,
Hong-Bin Wang
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
,
Xiang-Yu Zhang
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
,
Gan-Peng Li
1   School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming, Yunnan, China
› Author Affiliations
Further Information

Publication History

received 17 August 2014
revised 26 November 2014

accepted 28 November 2014

Publication Date:
22 January 2015 (online)

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Abstract

Five new icetexane diterpenoids, namely, perovskatones B–D (1, 3, 4), 1α-hydroxybrussonol (2), and 1α-hydroxypisiferanol (5), were isolated from Perovskia atriplicifolia, together with a new natural product (6) and two known compounds, przewalskin E (7) and brussonol (8). The structures of the new compounds were elucidated by detailed analyses of their MS, IR, 1D, and 2D NMR data. Compounds 1–8 were assayed for their inhibitory hepatitis B virus activities in the HepG 2.2.15 cell line. The results suggested that compounds 1 and 2 possessed noticeable anti-hepatitis B virus activity in vitro, suppressing the replication of hepatitis B virus DNA with selectivity index values of 154.3 and 137.7, respectively.

Key words

Perovskia atriplicifolia - Lamiaceae - icetexane diterpenoids - anti-HBV activity

Supporting Information

 

  • References

  • 1 Editorial Committee of Flora of China, Chinese Academy of Sciences. Flora of China, Vol. 17. Beijing: Science Press; 1994: 222-223
    Google Scholar
  • 2 Alia MS, Saleema M, Erianb AW. A new acylated steroid glucoside from Perovskia atriplicifolia . Fitoterapia 2001; 72: 712-714
    CrossrefPubMedGoogle Scholar
  • 3 Sefidkon F, Ahmadi L, Mirza M. Volatile components of Perovskia atriplicifolia Benth. J Essent Oil Res 1997; 9: 101-103
    CrossrefPubMedGoogle Scholar
  • 4 Jiang ZY, Huang CG, Xiong HB, Tian K, Liu WX, Hu QF, Wang HB, Yang GY, Huang XZ. Perovskatone A: a novel C23 terpenoid from Perovskia atriplicifolia . Tetrahedron Lett 2013; 54: 3886-3888
    CrossrefPubMedGoogle Scholar
  • 5 Moujir L, Gutiérrez-Navarro AM. Bioactive diterpenoids isolated from Salvia mellifera . Phytother Res 1996; 10: 172-174
    CrossrefPubMedGoogle Scholar
  • 6 Majetich G, Zou G. Total synthesis of (−)-barbatusol, (+)-demethylsalvicanol, (−)-brussonol, and (+)-grandione. Org Lett 2008; 10: 81-83
    CrossrefPubMedGoogle Scholar
  • 7 Xu G, Peng LY, Tu L, Li XL, Zhao Y, Zhang PT, Zhao QS. Three new diterpenoids from Salvia przewalskii Maxim. Helv Chem Acta 2009; 92: 409-413
    CrossrefPubMedGoogle Scholar
  • 8 Fraga BM, Díaz CE, Guadaňo A, González-Coloma A. Diterpenes from Salvia broussonetii transformed roots and their insecticidal activity. J Agric Food Chem 2005; 53: 5200-5206
    CrossrefPubMedGoogle Scholar
  • 9 Fraga BM, González AG, Herrera JR, Luis JG, Ravelo AG. Diterpenes from the roots of Salvia canariensis . Phytochemistry 1985; 25: 269-271
    CrossrefPubMedGoogle Scholar
  • 10 Gonzales AG, Andres LS, Luis JG, Brito I, Rodrfguez ML. Diterpenes from Salvia mellifera . Phytochemistry 1991; 30: 4067-4070
    CrossrefPubMedGoogle Scholar
  • 11 Wu SH, Zhang HJ, Lin ZW, Sun HD. Terpenoids from Isodon grandifolia var. atuntzensis . Phytochemistry 1993; 34: 1176-1178
    CrossrefPubMedGoogle Scholar
  • 12 Simmons EM, Sarpong R. Structure, biosynthetic relationships and chemical synthesis of the icetexane diterpenoids. Nat Prod Rep 2009; 26: 1195-1217
    CrossrefPubMedGoogle Scholar
  • 13 Aoyagi Y, Takahashi Y, Satake Y, Fukaya H, Takeya K, Aiyama R, Matsuzaki T, Hashimoto S, Shiina T, Kurihara T. Biomimetic synthesis of grandione from demethylsalvicanol via hetero-Diels-Alder type dimerization and structure revision of grandione. Tetrahedron Lett 2005; 46: 7885-7887
    CrossrefPubMedGoogle Scholar
  • 14 Simmons EM, Yen JR, Sarpong R. Reconciling icetexane biosynthetic connections with their chemical synthesis: total synthesis of (±) − 5, 6- dihydro − 6α-hydroxysalviasperanol, (±)- brussonol, and (±) – abrotanone. Org Lett 2007; 9: 2705-2708
    CrossrefPubMedGoogle Scholar
  • 15 Khaliq S, Volk FJ, Frahm AW. Phytochemical investigation of Perovskia abrotanoides . Planta Med 2007; 73: 77-83
    Article in Thieme ConnectPubMedGoogle Scholar
  • 16 Lin TC, Fang JM, Cheng YS. Terpenes and lignans from leaves of Chamaecyparis formosensis . Phytochemistry 1999; 51: 793-801
    CrossrefPubMedGoogle Scholar
  • 17 Jiang ZY, Zhang XM, Zhang FX, Liu N, Zhao F, Zhou J, Chen JJ. A new triterpene and anti-hepatitis B virus active compound from Alisma orientalis . Planta Med 2006; 72: 951-954
    Article in Thieme ConnectPubMedGoogle Scholar
  • 18 Zhang GL, Li YX, Zheng SQ, Liu M, Li X, Tang H. Suppression of hepatitis B virus replication by microRNA-199a-3p and microRNA-210. Antiviral Res 2010; 88: 169-175
    CrossrefPubMedGoogle Scholar
  • 19 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
    CrossrefPubMedGoogle Scholar