Aryltetralin lignans from Anthriscus sylvestris L. (Hoffm.)

Anthriscus sylvestris (L.) Hoffm. (Apiaceae) is a common wild plant in Northwest Europe that accumulates considerable amounts of lignans. Deoxypodophyllotoxin as the main attractive constituent can be used as a precursor for the production of podophyllotoxin. Podophyllotoxin is currently receiving great attention as one of the most important aryltetralin-lignan in related to human health. It is used as a semisynthetic precursor for anticancer drugs: Etoposide^®, Teniposide^®, and Etopophos^®to treat various types of neoplasms [1]. To date, podophyllotoxin is obtained by isolation from the plant. In the future, the availability of podophyllotoxin from this source is likely to become a major bottleneck. Podophyllum species have now been listed on the endanger species list, proving that the increasing demand of podophyllotoxin is a serious threat for the plant [2]. An alternative source of podophyllotoxin may be obtained by (biotechnological) hydroxylation of deoxypodophyllotoxin at the C7position. Deoxypodophyllotoxin is much more abundant in the plant kingdom than podophyllotoxin. A better insight in the occurrence of deoxypodophyllotoxin combined with profound knowlegde of its biosynthestic pathway(s) will help to develop alternative sources for the desired lignans. We found several lignans in Anthriscus sylvestris that may be involved in the biosynthetic pathway of deoxypodophyllotoxin using HPLC and Electrospray tandem mass spectra techniques. Podophyllotoxone, α-peltatin, and β-peltatin that have not been previously reported to be present in A. sylvestris could be identified based on the mass spectra, UV spectra and retention times compared with pure reference compounds. Deoxypodophyllotoxin, yatein, and anhydropodorhizol were also present in the extracts. The presence of these compounds in A. sylvestris has been reported earlier. Podophyllotoxone, anhydropodorhizol and deoxypodophyllotoxin were the major compounds, while α-peltatin and β-peltatin, were present in lower concentration. Yatein is an earlier precursor leading to deoxypodophyllotoxin formation, while β-peltatin is the product of the metabolization of dexypodophyllotoxin according to the hypothetical biosynthetic pathway of lignans as reported [3].

References: [1] Ayres, D.C., Loike, J.D., (1990) Chemistry and Pharmacology of Natural Products. Lignans: Chemical, Biological and Clinical Properties. Cambridge University Press, Cambridge.

[2] Nayar, M.P., Sastry, A.P.K., (1990) Red Data Book of Indian Plants. Botanical Survey of India, Calcutta.

[3] Federolf, K. et al. (2007) Phytochemistry 68:1397–1406.