Subscribe to RSS
DOI: 10.1055/s-2008-1074554
© Georg Thieme Verlag KG Stuttgart · New York
Glucosinolate Pattern in Isatis tinctoria and I. indigotica Seeds
Publication History
Received: March 21, 2008
Revised: April 17, 2008
Accepted: April 20, 2008
Publication Date:
06 June 2008 (online)
Abstract
The glucosinolate patterns in seeds of five Isatis tinctoria and two Isatis indigotica accessions were assessed with a recently developed and validated LC-MS assay for direct analysis of glucosinolates without prior desulfatation. Glucosinolate peaks were identified with in-source fragmentation and detection of the sulfate anion (m/z = 97), and by MS/MS experiments. The glucosinolate patterns of the seeds showed characteristic differences compared to leaves. Glucoisatisin and epiglucoisatisin were diagnostic of seed samples. Qualitative and quantitative differences in glucosinolate patterns between both Isatis species were found for seed samples, enabling a differentiation of the two medicinal plants at the level of seed material.
Abbreviations
BPC:base peak chromatogram
COX-2:cyclooxygenase-2
EIC:extracted ion chromatogram
5-LOX:5-lipoxygenase
PLE:pressurized liquid extraction
Key words
Isatis tinctoria - Isatis indigotica - Brassicaceae - pressurized liquid extraction - LC-MS - glucosinolates
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Hamburger M. Isatis tinctoria – from the rediscovery of an ancient medicinal plant towards a novel anti-inflammatory phytopharmaceutical. Phytochem Rev. 2002; 1 333-44
- 2 Danz H, Stoyanova S, Wippich P, Brattström A, Hamburger M. Identification and isolation of the cyclooxygenase-2 inhibitory principle in Isatis tinctoria. . Planta Med. 2001; 67 411-6
- 3 Danz H, Stoyanova S, Thomet O AR, Simon H -U, Dannhardt G, Ulbrich H. et al . Inhibitory activity of tryptanthrin on prostaglandin and leukotriene synthesis. Planta Med. 2002; 68 875-80
- 4 Ishihara T, Kohno K, Ushio S, Iwaki K, Ikeda M, Kurimoto M. Tryptanthrin inhibits nitric oxide and prostaglandin E2 synthesis by murine macrophages. Eur J Pharmacol. 2000; 407 97-204
- 5 Recio M C, Cerda-Nicolas M, Potterat O, Hamburger M, Rios J -L. Anti-inflammatory and antiallergic activity in vivo of lipophilic Isatis tinctoria extracts and tryptanthrin. Planta Med. 2006; 72 539-46
- 6 Recio M C, Cerda-Nicolas M, Hamburger M, Rios J -L. Anti-arthritic activity of a lipophilic woad (Isatis tinctoria) extract. Planta Med. 2006; 72 715-20
- 7 Oberthür C, Schneider B, Graf H, Hamburger M. The elusive indigo precursors in woad (Isatis tinctoria L.) – Identification of the major indigo precursor, isatan A, and a structure revision of isatan B. Chem Biodiv. 2004; 1 174-82
- 8 Heinemann C, Schliemann-Willers S, Oberthür C, Hamburger M, Elsner P. Prevention of experimentally induced irritant contact dermatitis by extracts of Isatis tinctoria compared to pure tryptanthrin and its impact on UVB-induced erythema. Planta Med. 2004; 70 385-90
- 9 Oberthür C, Graf H, Hamburger M. The content of indigo precursors in Isatis tinctoria leaves – a comparative study of selected accessions and post-harvest treatments. Phytochemistry. 2004; 65 3261-8
- 10 Oberthür C, Hamburger M. Tryptanthrin content in Isatis tinctoria leaves – a comparative study of selected strains and post-harvest treatments. Planta Med. 2004; 70 642-5
- 11 Mohn T, Suter K, Hamburger M. Seasonal changes and effect of harvest on glucosinoates in Isatis leaves. Planta Med. 2008; 74 582-7
- 12 Gilbert K G, Garton S, Karam M A, Arnold G M, Karp A, Edwards K J. et al . A high degree of genetic diversity is revealed in Isatis spp. (dyer's woad) by amplified fragment length polymorphism (AFLP). Theor Appl Genet. 2002; 104 1150-6
- 13 Elliott M C, Stowe B B. Distribution and variation of indole glucosinolates in woad (Isatis tinctoria). Plant Physiol. 1971; 48 498-503
- 14 Frechard A, Fabre N, Péan C, Montaut S, Fauvel M -T, Rollin P. et al . Novel indole-type glucosinolates from woad (Isatis tinctoria L.). Tetrahedron Lett. 2001; 42 9015-7
- 15 Lockwood G B, Belkhiri A. Glucosinolate spectrum of some Algerian Cruciferae. Plant Syst Evol. 1991; 176 11-20
- 16 Mohn T, Cutting B, Ernst B, Hamburger M. Extraction and analysis of intact glucosinolates – a validated pressurized liquid extraction/liquid chromatography-mass spectrometry protocol for Isatis tinctoria, and qualitative analysis of other cruciferous plants. J Chromatogr A. 2007; 1166 142-51
- 17 Fabre N, Poinsot V, Debrauwer L, Vigor C, Tulliez J, Fouraste I. et al . Characterisation of glucosinolates using electrospray ion trap and electrospray quadrupole time-of-flight mass spectrometry. Phytochem Anal. 2007; 18 306-19
- 18 Mellon F A, Bennett R N, Holst B, Williamson G. Intact glucosinolate analysis in plant extracts by programmed cone voltage electrospray LC/MS: performance and comparison with LC/MS/MS methods. Anal Biochem. 2002; 306 83-91
- 19 Song L, Morrison J J, Botting N P, Thornalley P J. Analysis of glucosinolates, isothiocyanates, and amine degradation products in vegetable extracts and blood plasma by LC-MS/MS. Anal Biochem. 2005; 347 234-43
- 20 Tian Q, Rosselot R A, Schwartz S J. Quantitative determination of intact glucosinolates in broccoli, broccoli sprouts, Brussels sprouts, and cauliflower by high-performance liquid chromatography-electrspray ionization-tandem mass spectrometry. Anal Biochem. 2005; 343 93-9
Prof. Dr. Matthias Hamburger
Institute of Pharmaceutical Biology
Department of Pharmaceutical Sciences
University of Basel
Klingelbergstrasse 50
4056 Basel
Switzerland
Phone: +41/61/267/1425
Fax: +41/61/267/1474
Email: matthias.hamburger@unibas.ch
- www.thieme-connect.de/ejournals/toc/plantamedica