P-4 センダン科植物M. azedarachおよびM. toosendanからのリモノイドの構造と昆虫の摂食阻害活性(ポスター発表の部)

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Limonoid constituents of Meliaceae plants have been well studied, particularly because of their interesting biological activities. At the 35th simposium, we have reported the structures of new limonoid antifeedants from Okinawan and Chinese M. azedarach L., which were meliacarpinins 1 and 2, one of the most active azadirachtin-type compounds, and azedarachins 3-5 and trichilins 7-9, intact apo-euphol skeleton limonoids with a 19/29 bridged acyl acetal, along with a degraded limonoid 14. In the continuous study on limonoids from the Chinese plant, we isolated four new limonoids of three meliacarpinins 18-20 and one azedarachin 21 along with 7 known compounds. On the other hand, from a related plant M. toosendan, 11 new limonoids of two trichilinins 31 and 32, one azedarachin 33, four trichilins 35-38 and four nimbolidins 40-43, were isolated along with 10 known limonoids containing two meliacan skeleton limonoids, azadirone (29) and acetyltrichilenone (30). In the structural study, some novel reactions were observed to be reported. Acylation at 29-hemiacetal of 6 with 2-methylpropanoyl and p-bromobenzoyl chloride in pyridine gave a mixture of the acylated 29-epimers, respectively, but the acetylation and benzoylation gave only their exo-isomers. On the other hand, although acid catalyzed rearrangement of the ring D epoxide into the 15-oxo structure have been known, acetyltrichilenone (30) was converted into neotrichilenone (30-A) with aq Na_2CO_3 in MeOH and treatment of 30-A with Ac_2O and DMAP in pyridine gave 30. Antifeedant properties of the isolated limonoids were tested against the three instar larvae of a Japanese pest insect Spodoptera eridania (Boisduval) by a conventional leaf disk method.
天然有機化合物討論会の論文
1995-09-01

P-4 センダン科植物M. azedarachおよびM. toosendanからのリモノイドの構造と昆虫の摂食阻害活性(ポスター発表の部)

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