Anti-Allergic Prenylated Flavonoids from the Roots of Sophora flavescens

Abstract

The bioassay-guided fractionation of the MeOH extract from the root of Sophora flavescens led to the isolation of eight known prenylated flavonoids (1 - 8) responsible for the in vitro anti-allergic activity. Among them, kushenol N (3), sophoraflavanone G (6), and leachianone A (7) demonstrated significant inhibition of the release of β-hexosaminidase from cultured RBL-2H3 cells with IC₅₀ values ranging from 15 to 30 μM.

Key words

Sophora flavescens - Leguminosae - anti-allergic activity - prenylated flavonoids

References

• 1 Blank U, Ra C, Miller L, White K, Metzger H, Kinet J P. Complete structure and expression in transfected cells of high affinity IgE receptor.  Nature. 1989;  337 187-9
• 2 Kinet J P. The high-affinity receptor for IgE.  Curr Opin Immunol. 1989;  2 499-505
• 3 Reth M. Antigen receptor tail clue.  Nature. 1989;  338 383-4
• 4 Cambier J C. Antigen and Fc receptor signaling. The awesome power of the immunoreceptor tyrosine-based activation motif (ITAM).  J Immunol. 1995;  155 3281-5
• 5 Rivera J. Molecular adapters in Fc(epsilon)RI signaling and the allergic response.  Curr Opin Immunol. 2002;  14 688-93
• 6 Ryu S Y, Oak M H, Kim K M. Inhibition of mast cell degranulation by tanshinones from the roots of Salvia miltiorrhiza. .  Planta Med. 1999;  65 654-5
• 7 Ryu S Y, Kou N Y, Choi H S, Ryu H, Kim T S, Kim K M. Cnidicin, a coumarin, from the root of Angelica koreana, inhibits the degranulation of mast cell and the NO generation in RAW 264.7 cells.  Planta Med. 2001;  67 172-4
• 8 Schwartz L B, Austen K F, Wasserman S I. Immunologic release of beta-hexosaminidase and beta-glucuronidase from purified rat serosal mast cells.  J Immunol. 1979;  123 1445-50
• 9 Choi O H, Kim J H, Kinet J P. Calcium mobilization via sphingosine kinase in signalling by the Fc epsilon RI antigen receptor.  Nature. 1996;  380 634-6
• 10 Oak M H, Cheong H, Kim K M. Activation of Fc epsilon RI inhibits the pyruvate kinase through direct interaction with the gamma-chain.  Int Arch Allergy Immunol. 1999;  119 95-100
• 11 Jakupovic J, Paredes L, Bohlmann F, Watson L. Prenyly flavanes from Marshallia species.  Phytochemistry. 1988;  27 3273-5
• 12 Kang S S, Kim J S, Son K H, Chang H W, Kim H P. A new prenylated flavanone from the roots of Sophora flavescens. .  Fitoterapia. 2000;  71 511-5
• 13 Ryu S Y, Lee H S, Kim Y K, Kim S H. Determination of isoprenyl and lavandulyl positions of flavonoids from Sophora flavescens by NMR experiment.  Arch Pharm Res. 1997;  20 491-5
• 14 Kang T H, Jeong S J, Ko W G, Kim N Y, Lee B H, Inagaki M. et al . Cytotoxic lavandulyl flavanones from Sophora flavescens. .  J Nat Prod. 2000;  63 680-1
• 15 Iinuma M, Tanaka T, Mizuno M, Shirataki Y, Yokoe I, Komatsu M. et al . Two flavanones in Sophora leachiano and some related structures.  Phytochemistry. 1990;  29 2667-9

1 Both authors contributed equally