Membrane Permeability and Aqueous Stability Study of Linear and Cyclic Diarylheptanoids from <i>Corylus maxima</i>
Seven diarylheptanoids were isolated from <i>Corylus maxima</i> by flash chromatography and semipreparative high-performance liquid chromatography (HPLC) and identified by Orbitrap<sup>®</sup> mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy as linear...
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| Main Authors: | , , , , , , , , |
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| Format: | Book |
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MDPI AG,
2022-06-01T00:00:00Z.
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| Summary: | Seven diarylheptanoids were isolated from <i>Corylus maxima</i> by flash chromatography and semipreparative high-performance liquid chromatography (HPLC) and identified by Orbitrap<sup>®</sup> mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy as linear diarylheptanoids: hirsutanonol-5-<i>O</i>-β-D-glucopyranoside (<b>1</b>), platyphyllonol-5-<i>O</i>-β-D-xylopyranoside (<b>4</b>), platyphyllenone (<b>5</b>); and cyclic derivatives: alnusonol-11-<i>O</i>-β-D-glucopyranoside (<b>6</b>), alnusone (<b>7</b>), giffonin F (<b>8</b>), carpinontriol B (<b>9</b>). Cyclic diarylheptanoids are reported in <i>C. maxima</i> for the first time. The aqueous stability of the isolated compounds and other characteristic constituents of <i>C. maxima</i>, oregonin (<b>2</b>), hirsutenone (<b>3</b>), quercitrin (<b>10</b>) and myricitrin (<b>11</b>) was evaluated at pH 1.2, 6.8 and 7.4. The passive diffusion of the constituents across biological membranes was investigated by parallel artificial membrane permeability assay for the gastrointestinal tract (PAMPA-GI) and the blood-brain barrier (PAMPA-BBB) methods. The cyclic diarylheptanoid aglycones and quercitrin were stable at all investigated pH values, while a pH-dependent degradation of the other compounds was observed. A validated ultrahigh-performance liquid chromatography-diode-array detection (UHPLC-DAD) method was utilized for the determination of compound concentrations. The structures of the degradation products were characterized by UHPLC-Orbitrap<sup>®</sup> MS. Platyphyllenone and alnusone possessed log <i>P<sub>e</sub></i> values greater than −5.0 and −6.0 in the PAMPA-GI and PAMPA-BBB studies, respectively, indicating their ability to cross the membranes via passive diffusion. However, only alnusone can be considered to have both good aqueous stability and satisfactory membrane penetration ability. |
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| Item Description: | 10.3390/pharmaceutics14061250 1999-4923 |