Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR

Phytochemistry

Volumn 72, Issue 17, 2011, Pages 2172-2179

  Hendrawati, Oktavia ^a   Woerdenbag, Herman J ^a   Michiels, Paul J A ^b   Aantjes, Herald G ^b   Van Dam, Annie ^a   Kayser, Oliver ^a,c  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b Spinnovation Analytical BV   (Netherlands)

^c TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Anthriscus sylvestris L. (Hoffm.); Apiaceae; Aryltetralin lignans; Biosynthetic pathway; Cow parsley; Deoxypodophyllotoxin; LC ESI MS MS; LC SPE NMR; Wild chervil

Indexed keywords

DEOXYPODOPHYLLOTOXIN; DRUG DERIVATIVE; PLANT EXTRACT; PODOPHYLLOTOXIN;

APIACEAE; ARTICLE; BIOSYNTHESIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT ROOT;

APIACEAE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; PLANT EXTRACTS; PLANT ROOTS; PODOPHYLLOTOXIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ANTHRISCUS SYLVESTRIS; APIACEAE; APIALES; PETROSELINUM CRISPUM;

EID: 80053629027     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.08.009     Document Type: Article

References (27)

1. D.C. Ayres, J.A. Harris, P.N. Jenkins, and L. Phillips Lignans and related phenols. Part XII. Application of nuclear magnetic double resonance to the aryltetrahydronaphthalene class J. Chem. Soc. Perkin Trans. 1 1972 1343 1350
2. D.C. Ayres, and J.D. Loike Lignans: Chemical, Biological and Clinical Properties 1990 Cambridge University Press Cambridge, UK
3. A.J. Broomhead, M.M.A. Rahman, P.M. Dewick, D.E. Jackson, and J.A. Lucas Matairesinol as precursor of Podophyllum lignans Phytochemistry 30 1991 1489 1492
4. F.C. Chang, C. Chiang, and V.N. Aiyar Isopicropodophyllone from Podophyllum pleianthum Phytochemistry 14 1975 1440
5. K. Federolf, A.W. Alfermann, and E. Fuss Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin Phytochemistry 68 2007 1397 1406 (Pubitemid 46659730)
6. E. Hulten, and M. Fries Atlas of North European Vascular Plants North of the Tropic of Cancer 1986 Koeltz Scientific Books Konigstein
7. R. Ikeda, T. Nagao, H. Okabe, Y. Nakano, H. Matsunaga, M. Katano, and M. Mori Antiproliferative constituents in umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris HOFFM Chem. Pharm. Bull. 46 1998 871 874 (Pubitemid 28257495)
8. R. Ikeda, T. Nagao, H. Okabe, Y. Nakano, H. Matsunaga, M. Katano, and M. Mori Antiproliferative constituents in umbelliferae plants. IV. Constituents in the fruits of Anthriscus sylvestris HOFFM Chem. Pharm. Bull. 46 1998 875 878 (Pubitemid 28257496)
9. D.E. Jackson, and P.M. Dewick Aryltetralin lignans from Podophyllum hexandrum and Podophyllum peltatum Phytochemistry 23 1984 1147 1152
10. D.E. Jackson, and P.M. Dewick Tumour-inhibitory aryltetralin lignans from Podophyllum pleianthum Phytochemistry 24 1985 2407 2409
11. G. Jeong, O. Kwon, B. Park, S. Oh, K. Ahn, M. Chang, W. Oh, J. Kim, B. Min, Y. Kim, and H. Lee Lignans and coumarins from the roots of Anthriscus sylvestris and their increase of caspase-3 activity in HL-60 cells Biol. Pharm. Bull. 30 2007 1340 1343 (Pubitemid 47037656)
12. W.M. Kamil, and P.M. Dewick Biosynthesis of the lignans α- and β-peltatin Phytochemistry 25 1986 2089 2092
13. W.M. Kamil, and P.M. Dewick Biosynthetic relationship of aryltetralin lactone lignans to dibenzylbutyrolactone lignans Phytochemistry 25 1986 2093 2102
14. A. Koulman, R. Bos, M. Medarde, N. Pras, and W.J. Quax A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related plant species Planta Med. 67 2001 858 862 (Pubitemid 34015552)
15. A. Koulman, M.E. Kubbinga, S. Batterman, H.J. Woerdenbag, N. Pras, J.G. Woolley, and W.J. Quax A phytochemical study of lignans in whole plants and cell suspension cultures of Anthriscus sylvestris Planta Med. 69 2003 733 738 (Pubitemid 37215023)
16. M. Kozawa, K. Baba, Y. Matsuyama, T. Kido, M. Sakai, and T. Takemoto Components of the root of Anthriscus sylvestris HOFFM. II. Insecticidal activity Chem. Pharm. Bull. 30 1982 2885 2888
17. M. Kozawa, N. Morita, and K. Hata Chemical components of the roots of Anthriscus sylvestris HOFFM. I. Structures of an acyloxycarboxylic acid and a new phenylpropanoidester, anthriscusin Yakugaku Zasshi 98 1978 1486 1490 (Pubitemid 9080128)
18. M. Kozawa, N. Morita, and K. Hata Structure of anthriscusin, a new phenylpropanoid ester from the roots of Anthriscus sylvestris HOFFM Chem. Pharm. Bull. 26 1978 1337 1338
19. T. Kurihara, M. Kikuchi, S. Suzuki, and S. Hisamichi Studies on the constituents of Anthriscus sylvestris HOFFM. I. On the components of the radix Yakugaku Zasshi 98 1978 1586 1591 (Pubitemid 9081660)
20. Magnússon, S.H., 2006. NOBANIS - Invasive Alien Species Fact Sheet - Anthriscus sylvestris. - From: Online Database of the North European and Baltic Network on Invasive Alien Species - NOBANIS. Available from: < www.nobanis.org >. (accessed 19.08.2011).
21. J.M. Miguel del Corral, M. Gordaliza, J.L. López, E.D. Olmo, M. Angeles Castro, and M. Luisa López Reassignment of the configuration of several keto-cyclolignans prepared from podophyllotoxin Helv. Chim. Act. 78 1995 1793 1796
22. Nayar, M. P., Sastry, A.P.K., 1990. Botanical survey of India, Calcutta.
23. Nishimura, K., Umehara, K., Nakamura, M., 1997. In: Koho, J. K. T. (Ed.), Cell Differentation-inducing 1,3-Dioxobenzene Derivatives From Anthriscus sylvestris for Cancer or Condyloma. vol. JP 09194369, Japan.
24. 1H NMR assignment of desoxypodophyllotoxin J. Nat. Prod. 52 1989 1290 1295 (Pubitemid 20101780)
25. N. Sakakibara, S. Suzuki, T. Umezawa, and M. Shimada Biosynthesis of yatein in Anthriscus sylvestris Org. Biomol. Chem. 1 2003 2474 2485
26. 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 (Pubitemid 44404613)
27. N.P. Vasilev, M.K. Julsing, A. Koulman, C. Clarkson, H.J. Woerdenbag, I. Ionkova, R. Bos, J.W. Jaroszewski, O. Kayser, and W.J. Quax Bioconversion of deoxypodophyllotoxin into epipodophyllotoxin in E. coli using human cytochrome P450 3A4 J. Biotechnol. 126 2006 383 393 (Pubitemid 44528787)