Naturally Occurring Simple Oxygenated Benzophenones: Structural Diversity, Distribution, and Biological Properties

Abstract

Naturally occurring benzophenones represent a relatively small group of plant metabolites with narrow distribution, mainly in members of Clusiaceae, Gentianaceae, Hypericaceae, Polygalaceae, Myrtaceae, etc.; however, there were reports of several compounds derived from microorganisms belonging to the Aspergillaceae and Valsaceae families and propolis. Benzophenones exhibit many biological activities, such as antioxidant, anti-inflammatory, cytotoxic, antimicrobial, etc. Few reviews on benzophenones that have appeared in the literature were focused on their prenylated derivatives. Summarized information on structural diversity, distribution, and biological activities of simple oxygenated naturally occurring benzophenones and their glycosides has not been found in the literature. Until 2000, only benzophenone C-glycosides were known to occur in nature. Since then, many O-glycosides have been isolated, structurally, and biologically characterized. This review covers the years from 1850 to 2023 and was compiled using databases such as Chemical Abstracts, Scopus, Google Scholar, PubMed, and ResearchGate. Based on their degree of oxidation, 210 chemical structures of benzophenone derivatives and glycosides were grouped into six categories. In addition, in one group of 40 miscellaneous benzophenones, where one or several protons are replaced by a methyl, alcohol, carboxyl, or acyl group, glycosidic forms with such an aglycone and dimeric compounds with xanthone was included. Simple oxygenated benzophenones and their glycosides were found in 77 plant genera belonging to 44 families. The allergy-associated bezophenone-1, benzophenone-2 and benzophenone-3 have limited distribution across natural sources. A wide range of biological activities (antioxidant, anti-inflammatory, cytotoxic, antitumor, cytoprotective, antimicrobial, MAO-A, antiarthritic, anticholinesterase, anti-atherosclerotic, laxative, etc.) of simple oxygenated benzophenones and their glycosides that appeared in the literature were discussed.