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KMID : 0370220070510010056
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Yakhak Hoeji
2007 Volume.51 No. 1 p.56 ~ p.62
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Synthetic Derivatives of Diosgenin and Their Antinociceptive and Antihypercholesterolemic Effects
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Kim Hak-soon
Ma Eun-Sook
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Abstract
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Twelve epoxy and hydroxydiosgenin derivatives (DI-1―DI-12) were synthesized from diosgenin (2.5(R-5-spirosten-3β-ol). Diosgenin was epxidized with m-chloroperoxybenzoic acid (mCPBA) to oxidize 2.5(R)-4α,5α-epoxyspirostane (DI-1). Diosgenin was reacted with DDQ to form 2.5(R)-1,4,6-spirostatrien-3-one (DI-2), which was treated with 30%H2O2 to give 2.5(R)-1α,2α-epoxy-4,6-spirostadien-3-one (DI-3) and treated with mCPBA to form 2.5(R)-6α,7α-epoxy-1,4-spirostadien-3-one (DI-7), respectively, DI-3 was reduced with NaBH4 to afford 2.5(R)-1α,2α-epoxy 4,6-spirostadien-3β-ol (DI-4) and reacted with Li metal in absolute ethanol to form 2.5(R)-2-ethoxy-1,4,6-spirostatrien-3one (DI-5). DI-7 was reduced with NaBH4 to produce 2.5(R)-3β,7α-dihydroxy-4-spirostene (DI-8) and treated with Li metal in liquid ammonia to produce 2.5(R)-7α-hydroxy-4-spirosten-3-one (DI-9). DI-2 was reduced with NaBH4 to form 2.5(R))-4,6-spirostadien-3β-ol (DI-10), which was stirred with 30% H2O2 to synthesize 2.5(R)-4,6-spirostadien-3-one (DI-11) and reated with mCPBA to give 2.5(R)-4β,5β-epoxy-6-spirosten-3β-ol (DI-12), respectively. The antinociceptive effects of synthesized compounds were measured by hot plate method and compound DI-7 significantly exhibited antinociceptive effect. DI-2 decreased the serum triglyceride ar.d total cholesterol levels in poloxamer P-407 injected rat.
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KEYWORD
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diosgenin, epoxidation, antinociceptive, antihypercholesterolemic, hot plate mithod, poloxamer P-407
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