Advertisement

Cytotoxicity against cholangiocarcinoma and HepG2 cell lines of lignan derivatives from Hernandia nymphaeifolia

  • Jittra Suthiwong
  • Jaroon Wandee
  • Siripit Pitchuanchom
  • Punchapat Sojikul
  • Veerapol Kukongviriyapan
  • Chavi Yenjai
Original Research
  • 14 Downloads

Abstract

Twelve lignan derivatives were synthesized from deoxypodophyllotoxin isolated from Hernandia nymphaeifolia. Cytotoxicity evaluation against cholangiocarcinoma, KKU-100, and HepG2 cell lines showed that compounds 3, 9, 10, and 13 exhibited stronger cytotoxicity than the starting material, 1, with IC50 ranging from 0.42 to 2.01 μM. Compound 10 displayed interesting activity by showing IC50 values of 0.75 and 0.46 μM against KKU-100 and HepG2 cell lines, respectively. From these observation, 10 seems to be useful as a lead compound for the development of anticancer agents.

Keywords

Hernandia nymphaeifolia Deoxypodophyllotoxin KKU-100 HepG2 

Notes

Acknowledgements

The Post-Doctoral Training Program from Research Affairs and Graduate School, Khon Kaen University for Jittra Suthiwong is acknowledged (Grant no. 590012). This work was supported by the Thailand Research Fund (RSA5980022), Khon Kaen University and The Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2018_2214_MOESM1_ESM.docx (3.3 mb)
Supplementary Information

References

  1. Bogucki DE, Charlton JL (1995) An asymmetric synthesis of (-)-deoxypodophyllotoxin. J Org Chem 60:588–593CrossRefGoogle Scholar
  2. Chang LC, Song LL, Park EJ, Luyengi L, Lee KJ, Farnsworth NR, Pezzuto JM, Kinghorn AD (2000) Bioactive constituents of Thuja occidentalis. J Nat Prod 63:1235–1238CrossRefPubMedGoogle Scholar
  3. Chao YY, Su W, Jan CR, Ko YC, Chen JJ, Cheng JS, Liu CP, Lo YK, Chou KJ, Lee KC, Chen WC, Chen IS (2002) Novel action of lignans isolated from Hernandia nymphaeifolia on Ca2+ signaling in human neutrophils. Arch Toxicol 75:695–702CrossRefPubMedGoogle Scholar
  4. Chen IS, Chen JJ, Duh CY, Tsai IL (1997) Cytotoxic lignans from Formosan Hernandia nymphaeifolia. Phytochemistry 45:991–996CrossRefPubMedGoogle Scholar
  5. Chen JJ, Chang YL, Teng CM, Chen IS (2000) Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med 66:251–256CrossRefPubMedGoogle Scholar
  6. Chen JJ, Tsai IL, Chen IS (1996) New oxoaporphine alkaloids from Hernandia nymphaeifolia. J Nat Prod 59:156–158CrossRefGoogle Scholar
  7. Feliciano AS, Medarde M, Lamamie de Clairaca RP, López JL, Puebla P, Gravalos DG, Lázaro PR, Garcia de Quesada T (1993) Synthesis and biological activity of bromolignans and cyclolignans. Arch Pharm 326:421–426CrossRefGoogle Scholar
  8. Gordaliza M, Castro A, Miguel del Corral J, López-Vázquez L, Garcia PA, Feliciano AS, Garcia-Grávalos D, Broughton H (1997) Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring. Tetrahedron 53:15743–15760CrossRefGoogle Scholar
  9. Jiang RW, Zhou JR, Hon PM, Li SL, Zhou Y, Li LL, Ye WC, Xu HX, Shaw PC, But PPH (2007) Lignans from Dysosma wersipellis with inhibitory effects on prostate cancer cell lines. J Nat Prod 70:283–286CrossRefPubMedGoogle Scholar
  10. Kan WS (1970) Manual of Medicinal Plants in Taiwan. Vol. 1. National Research Insititute of Chinese Medicine, Taiwan, p 178–179Google Scholar
  11. Lim YH, Leem MJ, Shin DH, Chang HB, Hong SW, Moon EY, Lee DK, Yoon SJ, Woo WS (1999) Cytotoxic constituents from the roots of Anthriscus sylvestris. Arch Pharm Res 22:208–212CrossRefPubMedGoogle Scholar
  12. McGlynn KA, Tarone RE, El-Serag HB (2006) A comparison of trends in the incidence of hepatocellular carcinoma and intrahepatic cholangiocarcinoma in the United States. Cancer Epidemiol Biomark Prev 15:1198–1203CrossRefGoogle Scholar
  13. Pettit GR, Meng Y, Gearing RP, Herald DL, Pettit RK, Doubek DL, Chapuis JC, Tackett LP (2004) Antineoplastic Agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives). J Nat Prod 67:214–220CrossRefPubMedGoogle Scholar
  14. Sampson LK, Vickers SM, Ying W, Phillips JO (1997) Tamoxifen-mediated growth inhibition of human cholangiocarcinoma. Cancer Res 57:1743–1749PubMedGoogle Scholar
  15. Songsiang U, Pitchuanchom S, Boonyarat C, Hahnvajanawong C, Yenjai C (2010) Cytotoxicity against cholangiocarcinoma cell lines of zerumbone derivatives. Eur J Med Chem45:3794–3802CrossRefPubMedGoogle Scholar
  16. Sripa B, Pairojkul C (2008) Cholangiocarcinoma: lessons from Thailand. Curr Opin Gastroenterol 24:349–356CrossRefPubMedPubMedCentralGoogle Scholar
  17. Suthiwong J, Boonloh K, Kukongviriyapan V, Yenjai C (2018) Cytotoxicity against cholangiocarcinoma and HepG2 cell lines of lignans from Hernandia nymphaeifolia. Nat Prod Commun 13:61–63Google Scholar
  18. Tusskorn O, Prawan A, Senggunprai L, Kukongviriyapan U, Kukongviriyapan V (2013) Phenethyl isothiocyanate induces apoptosis of cholangiocarcinoma cells through interruption of glutathione and mitochondrial pathway. Naunyn Schmiede Arch Pharmacol 386:1009–1016CrossRefGoogle Scholar
  19. Wickramaratne DB, Mar W, Chai H, Castlllo J, Farnsworth NR, Soejarto DD, Cordell GA, Pezzuto IM, Kinghorn AD (1995) Cytotoxic constituents of Bursera permollis. Planta Med 61:80–81CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Jittra Suthiwong
    • 1
  • Jaroon Wandee
    • 2
  • Siripit Pitchuanchom
    • 3
  • Punchapat Sojikul
    • 4
  • Veerapol Kukongviriyapan
    • 2
  • Chavi Yenjai
    • 1
  1. 1.Department of Chemistry, Faculty of Science, Natural Products Research Unit, The Center of Excellence for Innovation in ChemistryKhon Kaen UniversityKhon KaenThailand
  2. 2.Department of Pharmacology, Faculty of MedicineKhon Kaen UniversityKhon KaenThailand
  3. 3.Department of Chemistry, Faculty of Science, Natural Products Research Unit, The Center of Excellence for Innovation in ChemistryMahasarakham UniversityMahasarakhamThailand
  4. 4.Department of Biotechnology, Faculty of ScienceMahidol UniversityBangkokThailand

Personalised recommendations