Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana.,The Journal of Organic Chemistry

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Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-17 , DOI: 10.1021/acs.joc.0c00783
Bin Zhou ₁ , Yvette Alania ₂ , Mariana Reis ₂ , Rasika S Phansalkar ₁ , Joo-Won Nam _{1,

3} , James B McAlpine _{1,

4} , Shao-Nong Chen _{1,

4} , Ana K Bedran-Russo ₂ , Guido F Pauli _{1,

4}

Affiliation

Guided by dentin biomechanical bioactivity, this phytochemical study led to the elucidation of an extended set of structurally demanding proanthocyanidins (PACs). Unambiguous structure determination involved detailed spectroscopic and chemical characterization of four A-type dimers (2 and 4–6), seven trimers (10–16), and six tetramers (17–22). New outcomes confirm the feasibility of determining the absolute configuration of the catechol monomers in oligomeric PACs by one-dimensional (1D) and two-dimensional (2D) NMR. Electronic circular dichroism as well as phloroglucinolysis followed by mass spectrometry and chiral phase high-performance liquid chromatography (HPLC) analysis generated the necessary chiral reference data. In the context of previously reported dentin-bioactive PACs, accurately and precisely assigned ¹³C NMR resonances enabled absolute stereochemical assignments of PAC monomers via (i) inclusion of the ¹³C NMR γ-gauche effect and (ii) determination of differential ¹³C chemical shift values (Δδ_C) in comparison with those of the terminal monomer (unit II) in the dimers 2 and 4–6. Among the 13 fully elucidated PACs, eight were identified as new, and one structure (11) was revised based on new knowledge gained regarding the subtle, stereospecific spectroscopic properties of PACs.

中文翻译：

来自马尾松的具有牙本质生物活性的三聚体和四聚体原花青素。

在牙本质生物力学生物活性的指导下，这项植物化学研究阐明了一组扩展的结构要求高的原花青素 (PAC)。明确的结构确定涉及四种 A 型二聚体（2和4-6）、七种三聚体（10-16）和六种四聚体（17-22 ）的详细光谱和化学表征). 新结果证实了通过一维 (1D) 和二维 (2D) NMR 确定低聚 PAC 中儿茶酚单体绝对构型的可行性。电子圆二色性以及间苯三酚分解随后进行质谱分析和手性相高效液相色谱 (HPLC) 分析产生了必要的手性参考数据。在先前报道的牙本质生物活性 PAC 的背景下，准确且精确分配的¹³ C NMR 共振通过 (i) 包含¹³ C NMR γ-gauche 效应和 (ii) 差异¹³ C 化学物质的测定实现了 PAC 单体的绝对立体化学分配移位值（Δδ _C) 与二聚体2和4-6中的末端单体（单元 II）相比。在 13 种完全阐明的 PAC 中，有 8 种被确定为新的，一种结构 ( 11 ) 根据获得的有关 PAC 微妙的立体特异性光谱特性的新知识进行了修改。

更新日期：2020-07-02

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