Biphenyl-neolignans, such as honokiol, magnolol, obovatol and 4-O-methylhonokiol, was isolated from Magnolia species and exhibits various biological activities, involved in anti-inflammatory, anti-allergic, anti-bacterial, and anti-depressant activities. Among these biphenyl-neolignans, 4-O-methylhonokiol has the higher anti-inflammatory activity (e.g., IC50 of 0.06 �M for COX-2) than honokiol and a variety of honokiol analogs. Moreover, 4-O-methylhonokiol was recently found to exhibit neurotropic and memory improving activity. However, it was shown to be metabolized rapidly by rat and human liver microsomes in the presence of NADPH and UDPGA, indicating cytochrome P450- and UDP-glucuronosyltransferase-mediated metabolism.Therefore, 4-O-methylhonokiol analogs were designed and prepared to modify the potential metabolic soft spot of 4-O-methylhonokiol and to increase the polar surface area for the future assessment of structure-property relationship. In addition, their anti-inflammatory activities were evaluated through inhibition assay of NO production, cyclooxygenase-2 (COX-2) enzyme and PGF1 production.

Synthesis and biological evaluation of 4-<i>O</i>-methylhonokiol analogs

243rd National Meeting (2012)

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Synthesis and biological evaluation of 4-O-methylhonokiol analogs