DOI QR코드

DOI QR Code

Antitumor Constituents from Anthriscus Sylvestris (L.) Hoffm

  • Chen, Hui (School of Life Science and Engineering, Southwest Jiaotong University) ;
  • Jiang, He-Zhong (School of Life Science and Engineering, Southwest Jiaotong University) ;
  • Li, Yong-Chao (School of Life Science and Engineering, Southwest Jiaotong University) ;
  • Wei, Guo-Qing (School of Life Science and Engineering, Southwest Jiaotong University) ;
  • Geng, Yun (School of Life Science and Engineering, Southwest Jiaotong University) ;
  • Ma, Chao-Ying (School of Life Science and Engineering, Southwest Jiaotong University)
  • Published : 2014.03.30

Abstract

Bioassay-guided chemical investigation of the roots of Anthriscus sylvestris (L.) Hoffm. resulted in the isolation of nine compounds, whose structures were determined by spectroscopic methods. Compound 1 was isolated from this plant for the first time and compounds 3 and 9 were first found from this genus. Different polar fractions of A. sylvestris extract and compounds 1, 6-8 and 9 were evaluated for antitumor activities against HepG2 (human hepatocellular carcinoma), MG-63 (human osteosarcoma cells), B16 (melanoma cells) and HeLa (human cervical carcinoma cells) lines by the MTT method. The petroleum ether fraction of A. sylvestris extract exhibited excellent inhibitory activity with an $IC_{50}$ value of $18.3{\mu}g/ml$. Among the isolates from the petroleum ether fraction, compound 7 showed significant inhibition against the growth of the four tumor cells with $IC_{50}$ values ranging from $12.2-43.3{\mu}g/ml$.

Keywords

References

  1. Alabsi AM, Ali R, Ali AM, et al (2013). Induction of caspase-9, biochemical assessment and morphological changes caused by apoptosis in cancer cells treated with goniothalamin extracted from Goniothalamus macrophyllus. Asian Pac J Cancer Prev, 14, 6273-80. https://doi.org/10.7314/APJCP.2013.14.11.6273
  2. Ayres DC, Loike JD (1990). Lignans-Chemical, Biological and Clinical Properties. Cambridge University Press, 402pp.
  3. Bos R, Koulman A, Woerdenbag HJ, Quax WJ, Pras N (2002). Volatile components from Anthriscus sylvestris (L.) Hoffm. J Chromatogr A, 966, 233-8. https://doi.org/10.1016/S0021-9673(02)00704-5
  4. Dwivedi V, Shrivastava R, Hussain S, et al (2011). Comparative anticancer potential of clove (Syzygium aromaticum) - an indian spice - against cancer cell lines of various anatomical origin. Asian Pac J Cancer Prev, 12, 1989-93.
  5. Elamparuthi E, Fellay C, Neuburger M, et al (2012). Total synthesis of cyrneine A. Angew Chem, 51, 4071-3. https://doi.org/10.1002/anie.201200515
  6. Farshori1 NN, Al-Sheddi1 ES, Al-Oqail1 MM, et al (2013). Anticancer activity of Petroselinum sativum seed extracts on MCF-7 human breast cancer cells. Asian Pac J Cancer Prev, 14, 5719-23. https://doi.org/10.7314/APJCP.2013.14.10.5719
  7. Gayathri R, Priya DKD, Gunassekaran GR, et al (2009). Ursolic acid attenuates oxidative stress - mediated hepatocellular carcinoma induction by diethylnitrosamine in male wistar rats. Asian Pac J Cancer Prev, 10, 933-8.
  8. George VC, Kumar DRN, Suresh PK, et al (2012). Apoptosis - Induced Cell Death due to Oleanolic Acid in HaCaT Keratinocyte Cells a Proof of Principle Approach for Chemopreventive Drug Development. Asian Pac J Cancer Prev, 13, 2015-20. https://doi.org/10.7314/APJCP.2012.13.5.2015
  9. Ikeda R, Nagao T, Okabe H, et al (1998). Antiproliferative constituents in umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chem Pharm Bull, 46, 871-4. https://doi.org/10.1248/cpb.46.871
  10. Jeong G, Kwon O, Park B, et al (2007). Lignans and coumarins from the roots of Anthriscus sylvestris and their increase of caspase-3 activity in HL-60 cells. Chem Pharm Bull, 30, 1340-3. https://doi.org/10.1248/bpb.30.1340
  11. Kiso Y, Konno C, Hikino H, Yagi Y, Hashimoto I (1982). Liverprotective actions of desoxypodophyllotoxin and its analogs. J Pharmacobiodyn, 5, 638-41. https://doi.org/10.1248/bpb1978.5.638
  12. Koulman A, Hendrawati O, Batterman S, et al (2007). The seasonal variations of lignan profiles in Anthriscus sylvestris (L.) Hoffm. Planta Medica, 73, 858.
  13. Kozawa M, Morita N, Hata K (1978a). Structures of anthriscusun, a new phenylpropanoid ester from the roots of Anthriscus sylvestris Hoffm. Chem Pharm Bull, 26, 1337-8. https://doi.org/10.1248/cpb.26.1337
  14. Kozawa M, Morita N, Hata K (1978b). Chemical components of the roots of Anthriscus sylvestris Hoffm. structures of an acyloxycarboxylic acid and a new phenylpropanoidester, anthriscusin. Yakuga Zasshi, 98, 1486-90.
  15. Kumar DRN,George VC, Suresh PK, et al (2012). Cytotoxicity, apoptosis induction and anti-metastatic potential of oroxylum indicum in human breast cancer cells. Asian Pac J Cancer Prev, 13, 2729-34. https://doi.org/10.7314/APJCP.2012.13.6.2729
  16. Kuo YH, Yu MT (1993). A new lignan, formosalactone, from the bark of Juniperus formosana Hay. var. concolor Hay. Heterocycles, 36, 529-35. https://doi.org/10.3987/COM-92-6204
  17. Lee SH, Son MJ, Lin CX, et al (2004). Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells. Biol Pharm Bull, 27, 786-8. https://doi.org/10.1248/bpb.27.786
  18. Liang L, Zhong ZC, Xiao ZY (1990). The study of Anthriscus (Pers) Hoffm. West China J Pharmaceutical Sci, 5, 94-100.
  19. Lim YH, Leem MJ, Shin DH, et al (1999). Cytotoxic constituents from the roots of Anthriscus sylvestris. Arch Pharm Res, 22, 208-12. https://doi.org/10.1007/BF02976548
  20. Lin CX, Son MJ, Moon TC, et al (2004). Deoxypodophyllotoxin, a naturally occurring lignan, inhibits the passive cutaneous anaphylaxis reaction. Planta Med, 70, 474-6. https://doi.org/10.1055/s-2004-818981
  21. Noguchi T, Kawanami M (1940). Studies on the constituents of Anthriscus sylvestris. Hoffm. Yakuga Zasshi, 60, 629-36.
  22. Milovanovic M, Vucelicradovic B, Vrbaski Z, Picuricjovanovic K (1996). Antioxidant effects of flavonoids of Anthriscus sylvestris in lard. J Am Oil Chem Soc, 73, 773-6. https://doi.org/10.1007/BF02517954
  23. Oktavia H, Herman JW, Paul JAM, et al (2011). Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR. Phytochemistry, 72, 2172-9. https://doi.org/10.1016/j.phytochem.2011.08.009
  24. Tozaburo A, Masao I (1979). Studies on the constituents of Anthriscus sylvestris Hoffm.II. Yakuga Zasshi, 99, 602.
  25. Wang FQ, Wu DZ (1982). The miraculous effect proved recipe in Emei. Popular Science Press (pp.42). Beijing.
  26. Wang YF, Geng Y, Zhu LP (2009). Study on the chemical components in the roots of Anthriscus sylvestris. J Anhui Agriculture Science, 37, 11001-2.
  27. Yang C, Tang WJ, Tu XQ, et al (2010). The research of Anthriscus sylvestris (L.) Hoffm. pharmacological actions summary. JAnhui Agricultural Sciences, 17, 9377-8.

Cited by

  1. Gemcitabine for the Treatment of Patients with Osteosarcoma vol.15, pp.17, 2014, https://doi.org/10.7314/APJCP.2014.15.17.7159
  2. Ethnomedicinal, Phytochemical and Pharmacological Profile of Anthriscus sylvestris as an Alternative Source for Anticancer Lignans vol.20, pp.8, 2015, https://doi.org/10.3390/molecules200815003