P-27 神経栄養因子様活性天然物ホーノキオールおよび蛍光プローブ誘導体の合成(ポスター発表の部)

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Honokiol (1), a main biphenyl-type neolignan of the Magnolia Cortex, shows interesting neurotrophic effect in primary cultured rat cortical neurons. We have already proposed a mechanism of honokiol-induced neurite outgrowth promotion in rat cortical neurons. This paper presents the effective synthesis of honokiol (1), and its structure-activity relationship, and furthermore the preparation of its fluorescent derivatives for searching proteins and organs in neurons targeted by honokiol. At first, honokiol was effectively synthesized in 21% yield over 14 steps starting from 5-bromosalichilic acid and p-hydroxybenzoic acid by utilizing Pd-catalyzed Suzuki-Miyaura coupling reaction as a key step. Next, the structure-activity relationship was studied to clarify the mechanism for honokiol-induced neurotrophic effect, suggesting that 5-allyl and 4'-hydroxyl groups in honokiol are essential for affecting the neurotrophic activity. According to these results, the fluorescent derivatives 16-19 attached to luminous groups (7-MCA or NBD) at the 3'-position were synthesized and then the distribution in neurons using them was investigated. Consequently, it was found that 18 penetrated into the neuron and concentrated on the connecting region to the neurite. The competitive experiment between honokiol and 18 suggested that 18 is likely to interact at the same site in the neurons as honokiol. These results indicate that honokiol can penetrate into the neuron and interacts at some specific proteins such as the enzyme.
天然有機化合物討論会の論文
2005-09-15

P-27 神経栄養因子様活性天然物ホーノキオールおよび蛍光プローブ誘導体の合成(ポスター発表の部)

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