53 メボウキ(シソ科)精油に含まれる幼若ホルモン活性物質,ジュボシメン-IおよびIIの化学構造

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Two compounds with highly potent juvenile hormone activity were isolated from oil of sweet basil, Ocimum basilicum L., Labiatae. Each substance exhibited the activity in the milkweed bug juvenile hormone test in the picogram range. Structures of these compounds were determined to be I and II from their spectrometric analyses, and preparation of the skeletal compounds to III and IV, respectively. Since these compounds possess exceedingly high juvenile hormone activity and contain ocimene as a portion of their structure, we have named them juvocimene-I and II. In order to confirm the geometry of 2-methyl-1,3-butadienyl moiety, several analogs were studied, including trans and cis-dihydrojuvocimene (XV, XVI) which were prepared photochemically from a derivative of α-pinene (XIV). Synthesis of I was successfully achieved by a coupling reaction between a lithium salt of β-ocimene and p-methoxycinnamyl chloride. Epoxidation of I with m-chloroperbenzoic acid yielded II as a mixture of the diastereomers. These racemic I and II showed the same physical constants, and the same level of the biological activity as those of juvocimene-I and II isolated from oil of sweet basil. The unique structures and activity of the juvocimenes suggest that sweet basil may have developed such a chemical difense against insect predation through hormonal derangement of insect morphogenic development.
天然有機化合物討論会の論文
1980-09-10