Advertisement

Journal of Natural Medicines

, Volume 72, Issue 1, pp 246–251 | Cite as

New phenanthrene and 9, 10-dihydrophenanthrene derivatives from the stems of Dendrobium officinale with their cytotoxic activities

  • Gui-Yun Zhao
  • Bo-Wen Deng
  • Chong-Yu Zhang
  • Yi-Da Cui
  • Jia-Yi Bi
  • Guo-Gang ZhangEmail author
Original Paper

Abstract

Two new phenanthrene and 9, 10-dihydrophenanthrene derivatives (1–2) with six known congeners (3–8) were isolated from the extraction of stems of Dendrobium officinale. Compounds 1 and 2 were based on carbon skeleton in which phenanthrene and 9, 10-dihydrophenanthrene moiety were linked with a phenylpropane unit through a dioxane bridge, respectively. Their structures were determined by comprehensive NMR spectroscopic data, the absolute configuration of new compounds were determined by comparing their experimental and calculated ECD for the first time. All the compounds were investigated contains two cancer cell lines (HI-60, THP-1). All the isolates showed cytotoxicity, especially compound 4 showed markedly cytotoxic activities against HI-60 and THP-1 cell lines with IC50 values of 11.96 and 8.92 μM.

Keywords

Dendrobium officinale Phenanthrene derivative 9,10-dihydrophenanthrene Derivative Cytotoxicity 

Notes

Acknowledgements

We are appreciative of the Testing and Analysis Center of Shenyang Pharmaceutical University for the NMR measurements.

Supplementary material

11418_2017_1141_MOESM1_ESM.docx (6.3 mb)
Supplementary material 1 (DOCX 6448 kb)

References

  1. 1.
    Luo Q-L, Tang Z-H, Zhang X-F, Zhong Y-H, Yao S-Z, Wang L-S, Lin C-W, Luo X (2016) Chemical properties and antioxidant activity of a water-soluble polysaccharide from Dendrobium officinale. Int J Biol Macromol 89:219–227CrossRefGoogle Scholar
  2. 2.
    Jiangsu new medical college (1986) Dictionary of Chinese Herb Medicines. Shanghai Scientific and Technologic Press, Shanghai, p 586Google Scholar
  3. 3.
    Liu Q-F, Zhao W-M (2003) A new dendrobine-type alkaloid from Dendrobium nobile. Chin Chem Lett 14:278–279Google Scholar
  4. 4.
    Chen X-J, Mei W-L, Cai C-H, Guo Z-K, Song X-Q, Dai H-F (2014) Four new bibenzyl derivatives from Dendrobium sinense. Phytochem Lett 9:107–112CrossRefGoogle Scholar
  5. 5.
    Zhou X-M, Zheng C-J, Gan L-S, Chen G-Y, Zhang X-P, Song X-P, Li G-N, Sun C-G (2016) Bioactive phenanthrene and bibenzyl derivatives from the Stems of Dendrobium nobile. J Nat Prod 79:1791–1797CrossRefGoogle Scholar
  6. 6.
    Zhang X, Liu H-W, Gao H, Han H-Y, Wang N-L, Wu H-M, Yao X-S, Zhao W (2007) Nine new sesquiterpenes from Dendrobium nobile. HeIv Chim Acta 90:2386–2394CrossRefGoogle Scholar
  7. 7.
    Zhou X-M, Zheng C-J, Wu J-T, Chen G-Y, Chen J, Sun C-G (2016) Five new lactone derivatives from the stems of Dendrobium nobile. Fitoterapia 115:96–100CrossRefGoogle Scholar
  8. 8.
    Xu F-Q, Fan W-W, Zi C-T, Dong F-W, Yang D, Zhou J, Hu J-M (2017) Four new glycosides from the stems of Dendrobium fimbriatum Hook. Nat Prod Res 31:797–801CrossRefGoogle Scholar
  9. 9.
    Yang D, Liu L-Y, Cheng Z-Q, Xu F-Q, Fan W-W, Zi C-T, Dong F-W, Zhou J, Ding Z-T, Hu J-M (2015) Five new phenolic compounds from Dendrobium aphyllum. Fitoterapia 100:11–18CrossRefGoogle Scholar
  10. 10.
    Zhao W-M, Ye Q-H, Tan X-J, Jiang H-L, Li X-Y, Chen K-X, Douglas Kinghorn A (2001) Three new sesquiterpene glycosides from Dendrobium nobile with immunomodulatory activity. J Nat Prod 64:1196–1200CrossRefGoogle Scholar
  11. 11.
    Luo A-X, He X-J, Zhou S-D, Fan Y-J, He T, Chun Z (2009) In vitro antioxidant activities of a water-soluble polysaccharide derived from Dendrobium nobile Lindl. extracts. Int J Biol Macromol 45:359–363CrossRefGoogle Scholar
  12. 12.
    Hu Y, Zhang C-F, Zhao X, Wang Y, Feng D-Q, Zhang M, Xie H-F (2016) (±)-Homocrepidine A, a pair of anti-in flammatory enantiomeric octahydroindolizine alkaloid dimers from Dendrobium crepidatum. J Nat Prod 79:252–256CrossRefGoogle Scholar
  13. 13.
    Kim J-H, Oh S-Y, Han S-B, Uddinn G-M, Kim C-Y (2015) Anti-inflammatory effects of Dendrobium nobile derived phenanthrenes in LPS-stimulated murine macrophages. Arch Pharmacal Res 38:1117–1126CrossRefGoogle Scholar
  14. 14.
    Majumder P-L, Banerjee S, Sen S (1996) Three stilbenoids from the Orchid Agrostophy-llum Callosum. Phytochemistry 42:847–852CrossRefGoogle Scholar
  15. 15.
    Li S-C, He S-C, Zhong S-J, Duan X-M, Ye H-Y, Shi J, Peng A-H, Chen L-J (2011) Elution–extrusion counter-current chromatography separation of five bioactive compounds from Dendrobium chrysototxum Lindl. J Chromatogr A 1218:3124–3128CrossRefGoogle Scholar
  16. 16.
    Huang Y-L, Lai H-L, Shen J-C, Chen F-C, Chen C-C (2000) Stilbenoids from the stems of Dendrobium Sonia. Chin Pharmacol J 52:305–311Google Scholar
  17. 17.
    Juneja R-K, Sharma S-C, Tandon J-S (1985) A substituted 1, 2-diarylethane from Cymbidium giganteum. Phytochemistry 24:321–324CrossRefGoogle Scholar
  18. 18.
    Leong Y-W, Harrison L-J, Powell A-D (1999) Phenanthrene and other aromatic constitue-nts of Bulbophyllum vaginatum. Phytochemistry 50:1237–1241CrossRefGoogle Scholar
  19. 19.
    Shimura H, Matsuura M, Takada N, Koda Y (2007) An antifungal compound involved in symbiotic germination of Cypripedium macranthos var. rebunense (Orchidaceae). Phytochemistr 68:1442–1447CrossRefGoogle Scholar
  20. 20.
    Dongho L, Muriel C, Jose S-V, James G-G, Fernando C, Harry H-SF, John M-P, Kinghorn A-D (2001) A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata. Org Lett 14:2169–2171Google Scholar
  21. 21.
    Sun H, Hu Q, Jin H, Wang Y-Z (2017) Research advances in chemical constituents and pharmacological activities of Dendrobii officinalis caulis. Chin J Exp Tradit Med Form 23:225–234Google Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK 2017

Authors and Affiliations

  • Gui-Yun Zhao
    • 1
  • Bo-Wen Deng
    • 1
  • Chong-Yu Zhang
    • 1
  • Yi-Da Cui
    • 1
  • Jia-Yi Bi
    • 1
  • Guo-Gang Zhang
    • 1
    Email author
  1. 1.School of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyangPeople’s Republic of China

Personalised recommendations