Aromaticity and Electron Density of Hypericin

被引：8

作者：

Szymanski, Sebastian ^{[1
]}

Majerz, Irena ^{[1
]}

机构：

[1] Wroclaw Med Univ, Fac Pharm, Borowska 211a, PL-50556 Wroclaw, Poland

来源：

JOURNAL OF NATURAL PRODUCTS | 2019年 / 82卷 / 08期

关键词：

ST-JOHNS-WORT; INDEPENDENT CHEMICAL-SHIFTS; PHOTODYNAMIC THERAPY; PERFORATUM; DELOCALIZATION; EXTRACTION; SIGMA; BIODISTRIBUTION; ANTIDEPRESSANT; DEPRESSION;

D O I：

10.1021/acs.jnatprod.8b00872

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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-opqra]perylene, its substituted analogues, and hypericin show an influence of this substitution on electron density of the central rings.

引用

页码：2106 / 2115

页数：10

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