Planta Med 2001; 67(9): 858-862
DOI: 10.1055/s-2001-18849
Original Paper
Analysis
© Georg Thieme Verlag Stuttgart · New York

A Fast and Simple GC MS Method for Lignan Profiling in Anthriscus sylvestris and Biosynthetically Related Plant Species

Albert Koulman1 , Rein Bos1 , Manuel Medarde2 , Niesko Pras1 , Wim J. Quax1
  • 1 Department of Pharmaceutical Biology, GUIDE (Groningen University Institute for Drug Exploration), Groningen, The Netherlands
  • 2 Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain
Further Information

Publication History

December 8, 2000

March 23, 2001

Publication Date:
06 December 2001 (online)

Abstract

A new GC-MS method for monitoring lignans was developed to study the variation in plants and elucidate the biosynthetic steps. A simple and fast extraction procedure for lyophilised plant material was developed, giving a lignan-rich extract. A GC-MS method was set up using an apolar WCOT fused silica column using a high temperature programme (150 °C to 320 °C at 15 °C min-1). This new GC-MS method gave a clear lignan profile of plant material. It was possible to show the large variation in the concentrations of deoxypodophyllotoxin (DOP), yatein and anhydropodorhizol (AHP) in Anthriscus sylvestris (L.) Hoffm. plants growing on different locations using cinchonidin as an internal standard. In contrast with existing GC methods for lignan analysis no derivatisation is needed. It is also possible to use this method for the detection of different classes of lignans in biosynthetically related plant species.

References

  • 1 Cho J Y, Kim A E, Yoo E S, Baik K U, Park M H. Immunomodulatory effect of arctigenin, a lignan compound, on tumour necrosis factor-alpha and nitric oxide production, and lymphocyte proliferation.  Journal of Pharmacy and Pharmacology. 1999;  51 1267-73
  • 2 Adlercreutz H. Phytoestrogens. State of the Art.  Environmental Toxicology and Pharmacology. 1999;  7 201-7
  • 3 Meagher L P, Beecher G R, Flanagan V P, Li B W. Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal.  Journal of Biological Chemistry. 1999;  47 3173-80
  • 4 Choudhary D K, Kaul B L, Khan S. Cultivation and conservation of Podophyllum hexandrum - An overview.  Journal of Medicinal and Aromatic Plant Sciences. 1998;  20 1071-3
  • 5 Broomhead A J, Rahman M A, Dewick P M, Jackson D E, Lucas J A. Matairesinol as precursor of Podophyllum lignans.  Phytochemistry. 1991;  30 1489-92
  • 6 Van Uden W, Bos J A, Boeke G M, Woerdenbag H J, Pras N. The large scale isolation of deoxypodophyllotoxin from rhizomes of Anthriscus sylvestris followes by its bioconversion into 5-methoxypodophyllotoxin β-D-glucoside by cell cultures of Linum flavum .  Journal of Natural Products. 1997;  60 401-3
  • 7 Kondo K, Ogura M, Midorikawa Y, Kozawa M, Tsuijbo H. et al . The conversion of deoxypodophyllotoxin to epipodophyllotoxin by Penicillium F-0543.  Agricultural and Biological Chemistry. 2000;  52 2673-4
  • 8 Kamil W M, Dewick P M. Biosynthetic relationship of aryltetralin lactone lignans to dibenzylbutyrolactone lignans.  Phytochemistry. 1986;  25 2093-102
  • 9 Medarde M, Pelaez-Lamamie de Clairac R, Tome F, Lopez J L, San Feliciano A. Heterolignanolides: Antitumor activity of furyl, thienyl, and pyridyl analogs of lignanolides.  Archiv der Pharmazie. 1995;  328 403-7
  • 10 Van der Meijden R, Weeda E J, Adema F ACB, Joncheere G J. Heukels’ Flora van Nederland. Groningen; Wolters-Noordhoff 1983: 256-77
  • 11 Shah V P, Midha K K, Dighe S, McGilveray I J, Skelly J P. et al . Analytical methods validation: biovailablity, bioequivalence and pharmacokinetic studies.  Pharmaceutical Research. 1992;  9 588-92
  • 12 Ikeda R, Nagao T, Okabe H, Nakano Y, Matsunaga H. et al . Antiproliferative constituents in Umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm.  Chemical Pharmaceutical Bulletin. 1998;  46 871-4
  • 13 Lim C K. Analysis of aryltetrahydronaphthalene lignans and their glucoside conjugates in podophyllin resin by high-peformance liquid chromatography.  Journal of Chromatography A. 1996;  722 267-71
  • 14 Morton M, Arisaka O, Miyake A, Evans B. Analysis of phyto-oestrogens by gas chromatography-mass spectrometry.  Environmental Toxicology and Pharmacology. 1999;  7 221-5
  • 15 Ganzera M, Moraes-Cerdeira R M, Khan I A. Separation of Podophyllum lignans by micellar electrokinetic capillary chromatography (MECC).  Chromatographia. 1999;  49 552-5
  • 16 Arimoto M, Yamaguchi H, Nishibe S. Structure elucidation and synthesis of the lignans from the seeds of Hernandia ovigera . In: Attu-ur-Rahman, editor Studies in Natural Product Chemistry. Vol. 18 Amsterdam; Elsevier 1996: 551-606
  • 17 Rahman M A, Dewick P M, Jackson D E, Lucas J A. Lignans of Forsythia intermedia .  Phytochemistry. 1990;  29 1971-80
  • 18 Van Uden W, Bouma A S, Bracht Waker J F, Middel O, Wichers H J. et al . The production of podophyllotoxin and its 5-methoxy derivative through bioconversion of cyclodextrin-complexed desoxypodophyllotoxin by plant cell cultures.  Plant Cell Tissue and Organ Culture. 1995;  42 73-9
  • 19 Umezawa T, Davin L B, Lewis N G. Formation of lignan, (-)-secoisolariciresinol, by cell free extracts of Forsythia intermedia .  Biochemical and biophysical research communications. 1990;  171 1008-14

Dr. Niesko Pras

Department of Pharmaceutical Biology

University of Groningen

A. Deusinglaan 1

9713 AV Groningen

The Netherlands

Email: N.Pras@farm.rug.nl

Fax: +31-50-3633000

Phone: Tel.: +31-50-3633299