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Preparative isolation and purification of deoxypodophyllotoxin from the rhizomes of Anthriscus sylvestris by high-speed counter-current chromatography

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Abstract

A simple and rapid purification method of deoxypodophyllotoxin from the crude methanol extract of rhizomes of Anthriscus sylvestris was established using high-speed counter-current chromatography. From the crude extract (288.9 mg), deoxypodophyllotoxin (8.8 mg) was separated using a two-phase solvent system composed of n-hexane/ethyl acetate/methanol/water (7:3:5:5, v/v). The final purity of the deoxypodophyllotoxin was determined to be over 98% by ultra-performance liquid chromatography-UV analysis.

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References

  • Chen JJ, Chang YL, Teng CM, and Chen IS (2000) Antiplatelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med 66, 251–256.

    Article  CAS  Google Scholar 

  • Chen LJ and Sutherland I (2006) How to achieve rapid separations in counter-current chromatography. J Chromatogr A 1114, 29–34.

    Article  CAS  Google Scholar 

  • Conway WD and Ito Y (1984) Development of countercurrent chromatography. Anal Chem 56, 534–554.

    Article  Google Scholar 

  • Dall’Acqua S, Giorgetti M, Cervellati R, and Innocenti G (2006) Deoxypodophyllotoxin content and antioxidant activity of aerial parts of Anthriscus sylvestris Hoffm. Z Naturforsch C 61, 658–62.

    Google Scholar 

  • Fonseca SF, Ruveda EA, and McChesney JD (1980) 13C NMR analysis of podophyllotoxin and some of its derivatives. Phytochemistry 19, 1527–1530.

    CAS  Google Scholar 

  • Gao R, Gao CF, Tian X, Yu XY., Di XD, Xiao H, and Zhang X (2004) Insecticidal activity of deoxypodophyllotoxin, isolated from Juniperus Sabina L, and related lignans against larvae of Pieris rapae L. Pest Manage Sci 60, 1131–1136.

    Article  CAS  Google Scholar 

  • Ikeda R, Nagao T, Okabe H, Nagao Y, Matsunaga H, Katano M, and Mori M (1998) Antiproliferative constituents in umbelliferae plants. IV. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chem Pharm Bull 46, 875–878.

    Article  CAS  Google Scholar 

  • Ito J and Bowman RL (1970) Countercurrent chromatography: liquid-liquid chromatography without solid support. Science 167, 281–283.

    Article  CAS  Google Scholar 

  • Inamori Y, Kato Y, Kubo M, Baba K, Ishida T, Nomoto K, and Kozawa M (1985) The biological actions of deoxypodophyllotoxin (anthricin). I. Physiological activities and conformational analysis of deoxypodophyllotoxin. Chem Pharm Bull 33, 704–709.

    Article  CAS  Google Scholar 

  • Jeong GS, Kwon OK, Park BY, Oh SR, Chang MJ, Oh WK, Kim JC, Min BS, Kim YC, and Lee HK (2007) Ligans and coumarins from the roots of Anthiscus syvestris and their increase of caspase-3 activity in HL-60 cells. Biol Pharm Bull 30, 1340–1343.

    Article  CAS  Google Scholar 

  • Kim Y, Kim SB, You YJ, and Ahn BZ (2002) Deoxypodophyllotoxin; the cytotoxic and antiangiogenic component from Pulsatilla koreana. Planta Med 68, 271–274.

    Article  CAS  Google Scholar 

  • Kozawa M, Morita N, and Hata K (1978a) Sturctures of anthriscusin, a new phenylpropanoid ester from the roots of Anthriscus sylvestris Hoff. Chem Pharm Bull 26, 1337–1338.

    Article  CAS  Google Scholar 

  • Kozawa M, Morita N, and Hata K (1978b) Chemical components of the roots of Anthriscus sylvestris Hoff. I. Structures of an acyloxycarboxylic acid and a new phenylpropanoid ester, Anthriscusin. Yakugaku Zassh 98, 1486–1490.

    CAS  Google Scholar 

  • Lee SH, Son MJ, Ju HK, Lin CX, Moon TC, Choi HG, Son JK, and Chang HW (2004) Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells. Biol Pharm Bull 27, 786–788.

    Article  CAS  Google Scholar 

  • Lin CX, Lee E, Jin MH, Yook J, Quan Z, Ha K, Moon TC, Kim MJ, Kim KJ, Lee SH, and Chang HW (2006) Deoxypodophyllotoxin (DPT) inhibits eosinophil recruitment into the airway and Th2 cytokine expression in an ovalbum-induced lung inflammation. Planta Med 72, 786–791.

    Article  CAS  Google Scholar 

  • Masuda T, Oyama Y, Yonemori S, Takeda Y, Yamazaki Y, Mizuguchi S, Nakata M, Tanaka T, Chikahisa L, Inaba Y, and Okada Y (2002) Flow cytometric estimation on cytotoxic activity of leaf extracts from seashore plants in subtropical Japan: Isolation, quantification and cytotoxic action of (-)-deoxypodophyllotoxin. Phytother Res 16, 353–358.

    Article  CAS  Google Scholar 

  • Noguchi T and Kawanami M. (1940) Studies on the constituents of Anthriscus sylvestris Hoffm. Yakugaku Zasshi 60, 629–636.

    CAS  Google Scholar 

  • Slacanin I, Marston A, and Hostettmann K (1989) Modifications to a high-speed counter-current chromatography for improved separation capability. J Chromatogr A 482, 234–239.

    Article  CAS  Google Scholar 

  • Sudo K, Konno K, Shigeta S, and Yokota T (1998) Inhibitory effects of podophyllotoxin derivatives on Herpes simplex virus replication. Antivir Chem Chemother 9, 263–267.

    CAS  Google Scholar 

  • Sutherland IA and Fisher D (2009) Role of counter-current chromatography in the modernization of Chinese herbal medicines. J Chromatogr A 1216, 740–753.

    Article  CAS  Google Scholar 

  • Van Uden W, Bos JA, Boeke GM, Woerdenbag HJ, and Pras N (1997) The large-scale isolation of deoxypodophyllotoxin from rhizomes of Anthriscus sylvestris followed by its bioconversion into 5-methoxypodophyllotoxin β-D-glucoside by cell cultures of Linum flavum. J Nat Prod 60, 401–403.

    Article  Google Scholar 

  • Yong YY, Shin SY, Lee YH, and Lim Y (2009) Antitumor activity of deoxypodophyllotoxin isolated from Anthriscus sylvestris: Induction of G2/M cell cycle arrest and caspase-dependent apoptosis. Bioorg Med Chem Lett 19, 4367–4371.

    Article  CAS  Google Scholar 

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Correspondence to Sei-Ryang Oh.

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Quan, GH., Chin, YW., Lee, HK. et al. Preparative isolation and purification of deoxypodophyllotoxin from the rhizomes of Anthriscus sylvestris by high-speed counter-current chromatography. J. Korean Soc. Appl. Biol. Chem. 53, 110–113 (2010). https://doi.org/10.3839/jksabc.2010.019

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  • DOI: https://doi.org/10.3839/jksabc.2010.019

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