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

 

 Buy Article Permissions and Reprints

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
  CrossrefPubMedGoogle Scholar
• 2 Adlercreutz H. Phytoestrogens. State of the Art.  Environmental Toxicology and Pharmacology. 1999;  7 201-7
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 8 Kamil W M, Dewick P M. Biosynthetic relationship of aryltetralin lactone lignans to dibenzylbutyrolactone lignans.  Phytochemistry. 1986;  25 2093-102
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 10 Van der Meijden R, Weeda E J, Adema F ACB, Joncheere G J. Heukels’ Flora van Nederland. Groningen; Wolters-Noordhoff 1983: 256-77
  Google Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  Google Scholar
• 17 Rahman M A, Dewick P M, Jackson D E, Lucas J A. Lignans of Forsythia intermedia .  Phytochemistry. 1990;  29 1971-80
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar

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