Felegyi-Tóth Csenge Anna, Tóth Zsófia, Garádi Zsófia, Boldizsár Imre, Nedves Andrea Nagyné, Simon Alexandra, Felegyi Kristóf, Alberti Ágnes, Riethmüller Eszter
Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary.
Department of Plant Anatomy, Eötvös Loránd University, 1117 Budapest, Hungary.
Pharmaceutics. 2022 Jun 12;14(6):1250. doi: 10.3390/pharmaceutics14061250.
Seven diarylheptanoids were isolated from by flash chromatography and semipreparative high-performance liquid chromatography (HPLC) and identified by Orbitrap mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy as linear diarylheptanoids: hirsutanonol-5--β-D-glucopyranoside (), platyphyllonol-5--β-D-xylopyranoside (), platyphyllenone (); and cyclic derivatives: alnusonol-11--β-D-glucopyranoside (), alnusone (), giffonin F (), carpinontriol B (). Cyclic diarylheptanoids are reported in for the first time. The aqueous stability of the isolated compounds and other characteristic constituents of , oregonin (), hirsutenone (), quercitrin () and myricitrin () 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 MS. Platyphyllenone and alnusone possessed log 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.
通过快速柱色谱和半制备高效液相色谱（HPLC）从[具体来源未提及]中分离出七种二芳基庚烷类化合物，并通过轨道阱质谱（MS）和核磁共振（NMR）光谱鉴定为线性二芳基庚烷类化合物：hirsutanonol - 5 - -β-D-吡喃葡萄糖苷（[具体编号未给出]）、platyphyllonol - 5 - -β-D-吡喃木糖苷（[具体编号未给出]）、platyphyllenone（[具体编号未给出]）；以及环状衍生物：alnusonol - 11 - -β-D-吡喃葡萄糖苷（[具体编号未给出]）、alnusone（[具体编号未给出]）、giffonin F（[具体编号未给出]）、carpinontriol B（[具体编号未给出]）。环状二芳基庚烷类化合物首次在[具体来源未提及]中被报道。在pH 1.2、6.8和7.4条件下评估了分离出的化合物以及[具体来源未提及]的其他特征成分oregonin（[具体编号未给出]）、hirsutenone（[具体编号未给出]）、quercitrin（[具体编号未给出]）和myricitrin（[具体编号未给出]）的水稳定性。通过胃肠道平行人工膜通透性测定法（PAMPA - GI）和血脑屏障平行人工膜通透性测定法（PAMPA - BBB）研究了这些成分跨生物膜的被动扩散。环状二芳基庚烷类苷元以及quercitrin在所有研究的pH值下均稳定，而观察到其他化合物存在pH依赖性降解。采用经过验证的超高效液相色谱 - 二极管阵列检测（UHPLC - DAD）方法测定化合物浓度。通过UHPLC - 轨道阱MS对降解产物的结构进行了表征。在PAMPA - GI和PAMPA - BBB研究中，platyphyllenone和alnusone的log P值分别大于 - 5.0和 - 6.0，表明它们能够通过被动扩散穿过膜。然而，只有alnusone可以被认为同时具有良好的水稳定性和令人满意的膜渗透能力。
