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SECOND INTERNATIONAL SYMPOSIUM
ON THE ROLE OF SOY
IN PREVENTING AND TREATING CHRONIC DISEASESeptember 15-18, 1996
Brussells, Belgium
POSTER ABSTRACTSThe Phase Transfer Catalysed Synthesis of the Isoflavone - O - Glucosides Ononin and Sissotrin
Kristiina Wähälä and Philip Lewis
Laboratory of Organic Chemistry, University of Helsinki, P.O. Box 55,00014, Helsinki, Finland
The two isoflavone 7-O- glucosides ononin and sissotrin have been isolated from numerous sources along with their corresponding aglycones formononetin and biochanin A 1. Reports upon their biological activities, although scarce, show potential for a wide range of applications including the control of cancer 2 and viral infections, 2,3 antibacterial activity,4 plant growth inhibition, 5 their use in cosmetics to inhibit melanin formation 6 and in the treatment of alcohol dependance and abuse by inhibition of aldehyde dehydrogenase.7
A limiting factor in the further study of the biological activities of isoflavone glucosides in general has been the expense of extrated compounds and the unreliable low yielding syntheses so far published.
These have included the cyclization of glucosyl chalcones ( 9.1%)8 with TI (NO3)3.3H2O producing ononin in 25% yield,9 and the selective methylation of another glucoside giving sissotrin (13%).10
Our method provides a simple reproducable direct glucosilation of both formononetin and biochanin A that offers greatly improved yields over previous syntheses.
The method is also thought to be easily adaptable to enable reaction of isoflavones with numerous other carbohydrates.
References
1. The Flavonoids, Advances in Research Since 1986, edited by J.B. Harbone, Chapman and Hall; London 1994
2. Kijima Takao; Tokuda Harukuni; Kozuka Mutsuo; Tananbe Masahiro; Jpn. Kokai Tokkyo Koho JB 02 67,218; 31 Aug 1990 Chem. Abs 113: P224564b
3. Konoshima Takao; okamoto Emiko; Kozuka Mutsuo; Nishino Hoyoku; Tokuda Harukuni; J. Nat Prod; 51(6), 1270- 4,1988
4. Banduykova, V.A.; Cherevatyi, V.S. Ozimina, I.I. Andreeva, O.A. Lebedeva, A.I Davydov, V.S. Vashchenko, T.N. Postinikova, N.V. Rastit. Resur; 1987, 23(4),607-12;Chem. Abs. 108;71937V
5. Inderijt; Dakshini, K.M.M. J. chem. Ecol. 1992, 18(5), 713-18 Chem. Abs. 117: 4351X
6. Ichimaru Farukosu K.K. Jpn Kokai Tokkyo Koho J.P. 58,225,004, 27 Dec 1983; Chem Abs 100: P126730q
7. Vallee Bert L. ; Keung Wing Ming; PCT Int. Appl: WO 93 00,896 21 Jan 1993; Chem Abs 118:P1857706f
8. L. Reichel and R. Schikle; cmhem Ber. 76 , 1134, 1943
9. S. Antus and M. Nogradi; Chem. Ber. 112, 480-483,1979
10. L. Farkas, M. Nogradi, G. Mezey - Vandor and A. Gottsegen; Acta. Chemica Academiae Scientiarium Tomus, 60(3) 293-299,1969
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