Faculty of Pharmacy , Wroclaw Medical University , Borowska 211a , 50-556 Wroclaw , Poland.
J Nat Prod. 2019 Aug 23;82(8):2106-2115. doi: 10.1021/acs.jnatprod.8b00872. Epub 2019 Jul 26.
The influence of the substituents on the geometry of the central ring system of hypericin has been analyzed. Substitution that causes flattening of the hypericin central rings is connected with introducing the aromatic character of the empty rings. All the hypericin rings have an aromatic character illustrated by the Harmonic Oscillator Measure of Aromaticity (HOMA), Nucleus Independent Chemical Shift (NICS), Fluctuation Index (FLU), and Ellipticity Index (EL) indices. Quantum Theory of Atoms in Molecules (QTAIM) and Natural Bond Orbital (NBO) analyses performed on 7,14-dihydrophenanthro[1,10,9,8-]perylene, its substituted analogues, and hypericin show an influence of this substitution on electron density of the central rings.
已分析取代基对金丝桃素中环系统几何形状的影响。导致金丝桃素中环系统扁平化的取代与空环芳构化的引入有关。所有的金丝桃素环都具有芳香特征，这可以通过芳香性测量的调和振荡器（HOMA）、独立核化学位移（NICS）、波动指数（FLU）和椭圆率指数（EL）来证明。对 7,14-二氢菲并[1,10,9,8-]苝、其取代类似物和金丝桃素进行的分子中的原子量子理论（QTAIM）和自然键轨道（NBO）分析表明，这种取代对中环的电子密度有影响。
