Lignans in flowering aerial parts of Linum species - Chemodiversity in the light of systematics and phylogeny

Phytochemistry

Volumn 71, Issue 14-15, 2010, Pages 1714-1728

  Schmidt, Thomas J ^a   Hemmati, Shiva ^b   Klaes, Michael ^a   Konuklugil, Belma ^c   Mohagheghzadeh, Abdolali ^d   Ionkova, Iliana ^e   Fuss, Elisabeth ^f   Wilhelm Alfermann, A ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

^c ANKARA UNIVERSITY   (Turkey)

^d SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^e MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^f UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Chemosystematics; Evolution; HPLC MS; Lignan; Linaceae; Linum

Indexed keywords

LIGNAN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FLAX; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MOLECULAR EVOLUTION; PHYLOGENY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EVOLUTION, MOLECULAR; FLAX; LIGNANS; MOLECULAR STRUCTURE; PHYLOGENY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

HUGONIA; LINACEAE; LINUM; MAGNOLIOPHYTA; REINWARDTIA;

EID: 77956339965     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.06.015     Document Type: Article

References (45)

1. R.G. Allaby, G.W. Peterson, D.A. Merriwether, and Y.-B. Fu Evidence for the domestication history of flax (Linum usitatissimum L.) from genetic diversity of the sad2 locus Theor. Appl. Genet. 112 2005 58 65
2. S. Apers, A. Vlietinck, and L. Pieters Lignans and neolignans as lead compounds Phytochem. Rev. 2 2003 201 217
3. D.C. Ayres, and J.D. Loike Lignans: Chemical, Biological, and Clinical Properties 1990 Cambridge University Press Cambridge, New York
4. L.B. Davin, and N.G. Lewis An historical perspective on lignan biosynthesis: monolignol, allylphenol and hydrooxycinnamic acid coupling and downstream metaolism Phytochem. Rev. 2 2003 257 288
5. L.B. Davin, H.B. Wang, A.L. Crowell, D.L. Bedgar, D.M. Martin, S. Sarkanen, and N.G. Lewis Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center Science 275 1997 362 366
6. L.B. Davin, M. Jourdes, A.M. Patten, K.-W. Kim, D.G. Vassao, and N.G. Lewis Dissection of lignin macromolecular configuration and assembly: comparison to related biochemical processes in allyl/propenyl phenol and lignan biosynthesis Nat. Prod. Rep. 25 2008 1015 1090
7. P.H. Davis Flora of Turkey and the Aegean Islands vol. 2 1967 University Press Edinburgh pp. 425-450
8. A. Diederichsen, and K. Richards Cultivated flax and the genus Linum L.: taxonomy and germplasm conservation A.D. Muir, N.D. Westcott, Flax - The Genus Linum 2003 Taylor & Francis London 22 54
9. A. Engler, and H. Harms Die Natürlichen Pflanzenfamilien nebst ihren Gattungen und wichtigeren Arten, insbesondere den Nutzpflanzen 1931 Verl. Wilh. Engelmann Leipzig pp. 110-120
10. J.D. Ford, K.-S. Huang, H.-B. Wang, L.B. Davin, and N.G. Lewis Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in Flax (Linum usitatissimum) Seed J. Nat. Prod. 64 2001 1388 1394
11. Y.-B. Fu, and R.G. Allaby Phylogenetic network of Linum species as revealed by non-coding chloroplast DNA sequences Genet. Resour. Crop Evol. 57 2010 667 677
12. J. Gertsch, R. Thöni Toberl, R. Brun, O. Sticher, and J. Heilmann Antifungal, antiprotozoal, cytotoxic and piscicidal properties of justicidin B and a new arylnaphthalide lignan from Phyllanthus piscatorum Planta Med. 69 2003 420 424
13. S. Hemmati, T.J. Schmidt, and E. Fuss (+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B FEBS Lett. 581 2007 603 610
14. S. Hemmati, B. Schneider, T.J. Schmidt, K. Federolf, A.W. Alfermann, and E. Fuss Justicidin B 7-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum perenne Himmelszelt involved in the biosynthesis of diphyllin Phytochemistry 68 2007 2736 2743
15. S. Hemmati, C.B.I. von Heimendahl, M. Klaes, A.W. Alfermann, T.J. Schmidt, and E. Fuss Pinoresinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of Linum usitatissimum L Planta Med. 76 2010 928 934
16. Y.H. Hui, C.J. Chang, J.L. McLaughlin, and R.G. Powell Justicidin B, a bioactive trace lignin from the seed of Sesbania drummondii J. Nat. Prod. 49 1986 1175 1176
17. M. Klaes, T. Ellendorff, and T.J. Schmidt 6-Methoxypodophyllotoxin-7-O-n- hexanoate, a new aryltetralin lignan ester from seeds of Linum flavum Planta Med. 76 2010 719 721
18. B. Konuklugil Lignans from Hugonia tomentosa Int. J. Pharmacogn. 14 1996 390 392
19. B. Konuklugil, I. Ionkova, N. Vasilev, T.J. Schmidt, J. Windhövel, E. Fuss, and A.W. Alfermann Lignans from Linum species of sections Syllinum and Linum Nat. Prod. Res. 21 2007 1 6
20. K. Kranz, and M. Petersen Β-Peltatin 6-O-methyltransferase from suspension cultures of Linum nodiflorum Phytochemistry 64 2003 453 458
21. K.-H. Lee, and Z. Xiao Lignans in treatment of cancer and other diseases Phytochem. Rev. 2 2003 341 362
22. J. McDill, M. Repplinger, B.B. Simpson, and J.W. Kadereit The phylogeny of Linum and Linaceae subfamily Linoideae, with implications for their systematics, biogeography, and evolution of heterostyly Syst. Bot. 34 2009 386 405
23. A. Mohagheghzadeh, T.J. Schmidt, and A.W. Alfermann Arylnaphthalene lignans from in-vitro cultures of Linum austriacum J. Nat. Prod. 65 2002 69 71
24. A. Mohagheghzadeh, T.J. Schmidt, Ü. Bayindir, E. Fuss, I. Mehregan, and A.W. Alfermann Diarylbutyrolactone lignans from Linum corymbulosum in vitro cultures Planta Med. 72 2006 1165 1167
25. A. Mohagheghzadeh, S. Dehshahri, and S. Hemmati Accumulation of lignans by in vitro cultures of three Linum species Z. Naturforsch. 64c 2009 73 76
26. G.A. Molog, U. Empt, S. Kuhlmann, W. van Uden, N. Pras, A.W. Alfermann, and M. Petersen Desoxypododophyllotoxin 6-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum flavum involved in the biosynthesis of cytotoxic lignans Planta 214 2001 288 294
27. D.J. Ockendon, and S.M. Walters LXXXVI Linaceae T.G. Tutin, V.H. Heywoood, N.A. Burges, D.M. Moore, D.H. Valentine, S.M. Walters, D.A. Webb, Flora Europaea. Rosaceae to Umbelliferae vol. 2 1968 Cambridge University Press Cambridge 206 211
28. B. Pickel, M.-A. Constantin, J. Pfanstiel, J. Conrad, U. Beifuss, and A. Schaller An enantiocoplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols Angew. Chem. Int. Ed. 49 2010 202 204
29. K.H. Rechinger Linaceae K.H. Rechinger, Flora Iranica vol. 106 1974 Akademische Druck-u, Verlagsanstalt Graz 1 20
30. C.M. Rogers The systematics of Linum sect. Linopsis (Linaceae) Plant Syst. Evol. 140 1982 225 334
31. M. Saleem, H.J. Kim, M. Shaiq Alic, and Y.S. Lee An update on bioactive plant lignans Nat Prod. Rep. 52 2005 696 716
32. T.J. Schmidt, S. Hemmati, E. Fuss, and A.W. Alfermann A combined HPLC-UV and HPLC-MS method for the identification of lignans and its application to the lignans of Linum usitatissimum L. and L. bienne Mill. Phytochem. Anal. 17 2006 299 311
33. T.J. Schmidt, S. Vößing, M. Klaes, and S. Grimme An aryldihydronaphthalene lignan with a novel type of ring system and further new lignans from Linum perenne L. Planta Med. 73 2007 1574 1580
34. T.J. Schmidt, A.W. Alfermann, and E. Fuss High-performance liquid chromatography/mass spectrometric identification of dibenzylbutyrolactonetype lignans: insights into electrospray ionization tandem mass spectrometric fragmentation of lign-7-eno-9, 90-lactones and application to the lignans of Linum usitatissimum L. (Common Flax) Rapid Commun. Mass Spectrom. 22 2008 3642 3650
35. F. Sharifnia, and M. Assadi Linaceae M. Assadi, M. Khatamsaz, A.A. Maassoumi, Flora of Iran No. 34 2001 Research Institute of Forests and Rangelands Tehran, Iran 1 50
36. Shishkin, B.K., 1949. Flora of the USSR - Geraniales, Sapindales, Rhamnales, vol. XIV. Botanical Institute of the Academy of Sciences of the USSR (English translation: Israel Program for Scientific Translations, Jerusalem 1974).
37. S. Suzuki, and T. Umezawa Biosynthesis of lignans and norlignans J. Wood Sci. 53 2007 273 284
38. T. Umezawa Diversity in lignan biosynthesis Phytochem. Rev. 2 2003 371 390
39. T. Umezawa Phylogenetic distribution of lignan producing plants Wood Res. 90 2003 27 110
40. N. Vasilev, and I. Ionkova Lignan production by cell cultures of Linum setaceum and Linum campanulatum Pharm. Biol. 43 2005 501 511
41. N. Vasilev, P. Nedialkov, I. Ionkova, and S. Ninov HPTLC densitometric determination of justicidin B in Linum cultures in vitro Pharmazie 59 2004 528 529
42. N. Vasilev, R. Ebel, R.A. Edrada, E. Fuss, A.W. Alfermann, I. Ionkova, A. Petrova, M. Repplinger, and T.J. Schmidt Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria Planta Med. 74 2008 273 280
43. S.G. Weiss, M. Tin-Wa, R.E. Perdue, and N.R. Farnsworth Potential anticancer agents II. Antitumor and cytotoxic lignans from Linum album (Linaceae) J. Pharm. Sci. 64 1975 95 98
44. N.D. Westcott, and A.D. Muir Chemical studies on the constituents of Linum spp. A.D. Muir, N.D. Westcott, Flax - The Genus Linum 2003 Taylor & Francis London 55 73
45. B. Youn, S.G.H. Moinuddin, L.B. Davin, N.G. Lewis, and C.H. Kang Crystal structures of apo-form and binary/ternary complexes of Podophyllum secoisolariciresinol dehydrogenase, an enzyme involved in formation of health-protecting and plant defense lignans J. Biol. Chem. 280 2005 12917 12926