An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process

Tetrahedron

Volumn 62, Issue 29, 2006, Pages 6961-6966

  Wilhelm, Heike ^a   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

8 Prenylnaringenin; Demethylathion; Ether cleavage; Isoxanthohumol; Phytoestrogen; Xanthohumol

Indexed keywords

8 PRENYLNARINGENIN; COLLIDINE; FLAVONOID; PHYTOESTROGEN; POTASSIUM IODIDE; SCANDIUM TRIFLUOROMETHANESULFONATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; XANTHOHUMOL;

ARTICLE; DEMETHYLATION; DRUG ISOLATION; DRUG SYNTHESIS; ESTROGEN SYNTHESIS; HERBAL MEDICINE; PRENYLATION; PRIORITY JOURNAL; PROTECTION; QUANTUM YIELD;

HUMULUS LUPULUS;

EID: 33744905356     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.060     Document Type: Article

References (33)

1. McCormick S., Robson K., and Bohm B. Phytochemistry 25 (1986) 1723-1726
2. Stevens J.F., Ivancic M., Hsu V.L., and Deinzer M.L. Phytochemistry 61 (1997) 1575-1585
3. Stevens J.F., and Page J.E. Phytochemistry 65 (2004) 1317-1330
4. Stevens J.F., Taylor A.W., and Deinzer M.L. J. Chromatogr. A 832 (1999) 97-107
5. Kitaoka M., Kadokawa H., Sugano M., Ichikawa K., Taki M., Takaishi S., Iijima Y., Tsutsumi S., Boriboon M., and Akiyama T. Planta Med. 64 (1998) 511-515
6. Milligan S.R., Kalita J.C., Heyerick A., Rong H., De Cooman L., and De Keukeleire D. J. Clin. Endocrinol. Metab. 84 (1999) 2249-2252
7. Milligan S.R., Kalita J.C., Pocock V., van de Akuter V., Stevens J.F., Deinzer M.L., Rong H., and De Keukeleire D. J. Clin. Endocrinol. Metab. 85 (2000) 4912-4915
8. Zierau O., Gester S., Schwab P., Metz P., Kolba S., Wulf M., and Vollmer G. Planta Med. 68 (2002) 449-451
9. Milligan S.R., Kalita J.C., Heyerick A., De Cooman L., Rong H., and De Keukeleire D. Reproduction 123 (2002) 235-242
10. Jain A.C., Gupta R.C., and Sarpal P.D. Chem. Lett. (1978) 995-998
11. Jain A.C., Gupta R.C., and Sarpal P.D. Tetrahedron 34 (1978) 3563-3567
12. Nagar A., Gurjal V.K., and Gupta S.R. Tetrahedron Lett. 23 (1978) 2031-2034
13. Mizobuchi S., and Sato Y. Agric. Biol. Chem. 48 (1984) 2771-2775
14. Ito C., Mizuno T., Matsuoka M., Kimura Y., Sato K., Kajiura I., Omura M., Ju-Ichi M., and Furukawa H. Chem. Pharm. Bull. 36 (1988) 3292-3295
15. Tahara S., Katagiri Y., Ingham J.L., and Mizutani J. Phytochemistry 36 (1994) 1261-1271
16. Gester S., Metz P., Zierau O., and Vollmer G. Tetrahedron 57 (2001) 1015-1018
17. Sherif E.A., Islam A., and Krishnamurti M. Indian J. Chem., Sect. B 21 (1982) 478-479
18. Verzele M., Stockx J., Fontijn F., and Anteunis M. Bull. Soc. Chim. Belg. 66 (1957) 452-475
19. Biendl, M.; Smith, R. Unpublished/personal communication. Hopsteiner/Hallertauer Hopfenveredelungs GmbH, 2003.
20. Wilhelm, H.; Biendl, M.; Wessjohann, L. A. (Anmelder: Hallertauer Hopfenveredlungsgesellschaft m.b.H.) German Patent Application DE 10 2005 013258.8, 2005.
21. Wang Y., Tan W., Li W.Z., and Li Y. J. Nat. Prod. 64 (2001) 196-199
22. Parker K.A., and Ding Q. Tetrahedron 56 (2000) 10255-10261
23. Gonzalez G.I., and Zhu J. J. Org. Chem. 62 (1997) 7544-7545
24. Hänsel R., and Schulz J. Arch. Pharm. 321 (1988) 37-40
25. Nookandeh A., Frank N., Steiner F., Ellinger R., Schneider B., Gerhäuser C., and Becker H. Phytochemistry 65 (2004) 561-570
26. Chadwick L.R., Nikolic D., Burdette J.E., Overk C.R., Bolton J.L., van Breemen R.B., Fröhlich R., Fong H.H.S., Farnsworth N.R., and Pauli G.F. J. Nat. Prod. 67 (2004) 2024-2032
27. Gellert M., Szendrei K., and Reisch J. Herba Hungarica 21 (1982) 173-178
28. Mizobuchi S. Agric. Biol. Chem. 7 (1985) 2195-2196
29. Fukai T., and Nomura T. Heterocycles 10 (1990) 1861-1872
30. Biller S.A., and Forster C. Tetrahedron 46 (1990) 6645-6658
31. Dodge J.F., Stocksdale M.G., Fahey K.J., and Jones C.D. J. Org. Chem. 60 (1995) 739-741
32. Harrison I.T. J. Chem. Soc., Chem. Commun. (1969) 616
33. Cunico R.F., and Bedell L. J. Org. Chem. 45 (1980) 4797-4798