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药理学评估类黄酮的结构趋势与化学分类学方面的综述

Review on Structural Trends and Chemotaxonomical Aspects of Pharmacologically Evaluated Flavonoids.

作者信息

Zouaoui Sana, Farman Muhammad, Semmar Nabil

机构信息

Bioinformatics, Biomathematics & Biostatistics Laboratory (BIMS), Pasteur Institute of Tunis, University of Tunis El Manar, Tunis, Tunisia.

Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.

出版信息

Curr Top Med Chem. 2021;21(7):628-648. doi: 10.2174/1568026621666210113165007.

Abstract

INTRODUCTION

This work provides statistical analyses of bibliographic data on pharmacologically evaluated flavonoids from different plant families. By opposition to structural elucidations benefitting from full data aspects, pharmacological evaluations are concerned with partial investigations resulting in sparse information.

METHODS

The limited data availability was overcome by extensive consideration of several small sets of pharmacologically evaluated flavonoids in several plant taxa, alternatively to the traditional intensive analysis of big dataset of a given metabolic family in a given plant taxon. Statistical analyses were carried out using correspondence analysis, cluster analysis, box plots and fisher exact test to highlight structure-structure, structure-plant and structure-activity trends.

RESULTS

Different aglycone types showed opposite trends between hydroxylation (flavonols, anthocyanidins, flavanols), and methoxylation (isoflavones, isoflavanes, neoflavones). Moreover, different carbons showed differential substitution levels in different aglycones: C3 in flavonols, C6, C8 in flavones, flavonols, C2' in flavanones, C6' in isoflavanes. Plant families were well differentiated by different relative occurrences of aglycones: flavones in Lamiaceae, flavanones in Rutaceae, neoflavones in Rubiaceae, flavonols in Asteraceae, isoflavones in Fabaceae. Relatively more hydroxylated flavonoids occurred in Asteraceae, Lamiaceae and Fabaceae vs. more methoxylated ones in Rutaceae and Rubiaceae. Concerning structure-activity trends, flavanols and isoflavones were relatively more concerned with anti-diabetic and anti-inflammatory activities, respectively, vs. balanced distribution of flavones. Anti-inflammatory activity showed significant association with substitution position of same chemical groups (OH, OCH3), whereas anti-diabetic activity was revealed to be mainly influenced by the type of chemical groups (positive effect of OH and glycosyls).

CONCLUSION

These results call for regular updates and further investigations.

摘要

引言

本研究对来自不同植物科的经药理学评估的黄酮类化合物的文献数据进行了统计分析。与受益于完整数据方面的结构解析不同,药理学评估涉及部分研究,导致信息稀疏。

方法

通过广泛考虑几个植物类群中几组经药理学评估的黄酮类化合物的有限数据,替代了对给定植物类群中给定代谢家族的大数据集进行传统的深入分析,从而克服了数据可用性有限的问题。使用对应分析、聚类分析、箱线图和费舍尔精确检验进行统计分析,以突出结构-结构、结构-植物和结构-活性趋势。

结果

不同的苷元类型在羟基化(黄酮醇、花青素、黄烷醇)和甲氧基化(异黄酮、异黄烷、新黄酮)之间呈现相反的趋势。此外,不同的碳原子在不同的苷元中显示出不同的取代水平:黄酮醇中的C3、黄酮和黄酮醇中的C6、C8、黄烷酮中的C2'、异黄烷中的C6'。不同植物科通过苷元的不同相对出现情况得到很好的区分:唇形科中的黄酮、芸香科中的黄烷酮、茜草科中的新黄酮、菊科中的黄酮醇、豆科中的异黄酮。菊科、唇形科和豆科中羟基化黄酮类化合物相对较多,而芸香科和茜草科中甲氧基化黄酮类化合物相对较多。关于结构-活性趋势,黄烷醇和异黄酮分别相对更与抗糖尿病和抗炎活性相关,而黄酮的分布较为均衡。抗炎活性与相同化学基团(OH、OCH3)的取代位置显示出显著关联,而抗糖尿病活性主要受化学基团类型的影响(OH和糖基的积极作用)。

结论

这些结果需要定期更新并进一步研究。

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