title: Arylnaphthalene and aryltetralin-type lignans in hairy root cultures of Linum perenne, and the stereochemistry of 6-methoxypodophyllotoxin and one diastereoisomer by HPLC-MS and NMR spectroscopy.
abstract: BACKGROUND
  Hairy root cultures of Linum sp. are an alternative for the high production of lignans. Linum perenne is known to produce arylnaphthalene-type lignans such as justicidin B, isojusticidin and diphyllin.
  
  
  OBJECTIVE
  To elucidate the presence of aryltetralin-type lignan diastereoisomers, besides the known arylnaphthalene-type lignans, in hairy roots of Linum perenne, and to determine the configurations of one diastereoisomer of 6-methoxypodophyllotoxin (6-MPTOX).
  
  
  METHODS
  Lignans from hairy root cultures of Linum perenne were extracted and separated by HPLC. Arylnaphthalene-type lignans were identified by LC-MS, according to the literature. Two diastereoisomers of aryltetralin-type lignans were analysed by mass spectrometry and NMR spectroscopy.
  
  
  RESULTS
  Numerous arylnaphthalene-type lignans (diphyllin-2-hexose-pentose, diphyllin-3-pentose and diphyllin-hexose) were identified in hairy root cultures. Methoxypodophyllotoxin, an aryltetralin-type lignan, was also identified, as well as one diastereoisomer. This aryltetralin-type lignan could be derived via 7-hydroxymatairesinol as a hypothetical biosynthetic pathway. The stereochemical configurations of aryltetralin isomers were determined.
  
  
  CONCLUSIONS
  Arylnaphthalene and two diastereoisomers of aryltetralin-type lignans are produced in Linum perenne hairy root cultures. Matairesinol, the precursor of justicidin B, also seems to be converted into 6-MPTOX via 7-hydroxymatairesinol. This is the first report of the stereochemical configurations of an aryltetralin-type lignan other than podophyllotoxin (PTOX).
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: Nathalie
authors.initials: N
authors.lastname: Jullian-Pawlicki
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: Michelle
authors.initials: M
authors.lastname: Lequart-Pillon
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.|Biotechnology Laboratory, An Giang University, Van Khiêm Street, 18, Long Xuyên City, An Giang Province, Viet Nam.
authors.forename: Luyen
authors.initials: L
authors.lastname: Huynh-Cong
authors.affiliation: Laboratoire de Glycochimie Antimicrobiens et Agroressources (LG2A), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: David
authors.initials: D
authors.lastname: Lesur
authors.affiliation: Plate-forme analytique, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: Dominique
authors.initials: D
authors.lastname: Cailleu
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: François
authors.initials: F
authors.lastname: Mesnard
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: Jean Claude
authors.initials: JC
authors.lastname: Laberche
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Gontier
authors.affiliation: Unité de Recherche Biologie des Plantes et Innovation (BIOPI- EA 3900), Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: Michèle
authors.initials: M
authors.lastname: Boitel-Conti
mesh_terms: D053898:Biosynthetic Pathways; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D019597:Flax / Q000737:chemistry*; D017705:Lignans / Q000032:analysis* / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008956:Models, Chemical; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry* / Q000254:growth & development; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry / Q000379:methods*; D046509:Tissue Culture Techniques / Q000379:methods
chemical_list: C502514:6-methoxypodophyllotoxin; D017705:Lignans; C419306:hydroxymatairesinol; D011034:Podophyllotoxin
keywords: Cytotoxic lignans; LC-MS/MS; Linum perenne; NMR; transformed roots