Gedunin型リモノイド7―deacetoxy―7α―hydroxygeduninの7位に修飾したアナログの構造活性相関について

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  • The structure-activity relationship in a Gedunin-type Limonoid (7―Deacetoxy―7α―hydroxygedunin) with a modified functional group at the 7―position
  • Geduninガタリモノイド7―deacetoxy―7α―hydroxygeduninノ7イニシュウショクシタアナログノコウゾウカッセイソウカンニツイテ

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Chinese toon, or Cedrela sinensis Juss. (Meliaceae), is a broad-leafed tree found in China and South Korea. Gedunin (1)1 is a limonoid that is abundant in plants in the Meliaceae family. Gedunin (1) is reported to have antimalarial activity comparable to that of quinine2. However, gedunin-type limonoid molecules have numerous functional groups and the reactivity of those groups is not known, so few studies have chemically modified gedunin-type limonoids. Studies have examined the structure-activity relationship of ring B of gedunin-type limonoids by comparing similar natural limonoids. Those studies found that the functional group at the 7―position affects whether gedunin-type limonoids have antimalarial activity2―4 or whether they have biological activity, e.g. inhibiting insect growth5 or intake6. Gedunin (1) has an acetyl group at the 7―position and it has potent antimalarial activity. When gedunin is acetylated (2), however, that activity is attenuated2. In comparison to gedunin (1), its deacetylated form (2) has somewhat greater inhibition of growth and intake5. Very few previous studies have compared the anti-tumor activity of limonoid analogues with a chemically modified ring B. Thus, the current study used 7―deacetoxy―7α―hydroxygedunin (2) to obtain new findings regarding structure and activity relationships with anti-tumor activity. This study synthesized 6 new analogues (3-8) by substituting an acyl group for the acetyl group at the 7―position on ring B, and this study examined their cytotoxic activity against murine P―388 leukemia cells. Compounds with an acyl group in place of an acetyl group at the 7―position on ring B had more potent activity if they had more chlorine atoms.

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