title: Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR.
abstract: The aryltetralin lignan deoxypodophyllotoxin is much more widespread in the plant kingdom than podophyllotoxin. The latter serves as a starting compound for the production of cytostatic drugs like etoposide. A better insight into the occurrence of deoxypodophyllotoxin combined with detailed knowledge of its biosynthestic pathway(s) may help to develop alternative sources for podophyllotoxin. Using HPLC combined with electrospray tandem mass spectrometry and NMR spectroscopy techniques, we found nine lignans and five related structures in roots of Anthriscus sylvestris (L.) Hoffm. (Apiaceae), a common wild plant in temperate regions of the world. Podophyllotoxone, deoxypodophyllotoxin, yatein, anhydropodorhizol, 1-(3'-methoxy-4',5'-methylenedioxyphenyl)1-ξ-methoxy-2-propene, and 2-butenoic acid, 2-methyl-4-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]-, (2E)-3-(7-methoxy-1,3-benzodioxol-5-yl)-2-propen-1-yl ester, (2Z)- were the major compounds. α-Peltatin, podophyllotoxin, β-peltatin, isopicropodophyllone, β-peltatin-a-methylether, (Z)-2-angeloyloxymethyl-2-butenoic acid, anthriscinol methylether, and anthriscrusin were present in lower concentrations. α-Peltatin, β-peltatin, isopicropodophyllone, podophyllotoxone, and β-peltatin-a-methylether have not been previously reported to be present in A. sylvestris. Based on our findings we propose a hypothetical biosynthetic pathway of aryltetralin lignans in A. sylvestris.
authors: Department of Pharmaceutical Biology, University of Groningen, Groningen, The Netherlands.
authors: Oktavia
authors: O
authors: Hendrawati
authors: Herman J
authors: HJ
authors: Woerdenbag
authors: Paul J A
authors: PJ
authors: Michiels
authors: Herald G
authors: HG
authors: Aantjes
authors: Annie
authors: A
authors: van Dam
authors: Oliver
authors: O
authors: Kayser
mesh_terms: D019661:Apiaceae / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004365:Drugs, Chinese Herbal; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000032:analysis / Q000096:biosynthesis; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D004365:Drugs, Chinese Herbal; D010936:Plant Extracts; C014451:deoxypodophyllotoxin; D011034:Podophyllotoxin