The Antifungal Activity of Naphthoquinones: An Integrative Review

Abstract

Naphthoquinones are the most commonly occurring type of quinones in nature. They are a diverse family of secondary metabolites that occur naturally in plants, lichens and various microorganisms. This subgroup is constantly being expanded through the discovery of new natural products and by the synthesis of new compounds via innovative techniques. Interest in quinones and the search for new biological activities within the members of this class have intensified in recent years, as evidenced by the evaluation of the potential antimicrobial activities of quinones. Among fungi of medical interest, yeasts of the genus Candida are of extreme importance due to their high frequency of colonization and infection in humans. The objective of this review is to describe the development of naphthoquinones as antifungals for the treatment of Candida species and to note the most promising compounds. By using certain criteria for selection of publications, 68 reports involving both synthetic and natural naphthoquinones are discussed. The activities of a large number of substances were evaluated against Candida albicans as well as against 7 other species of the genus Candida. The results discussed in this review allowed the identification of 30 naphthoquinones with higher antifungal activities than those of the currently used drugs.

Anti-tubercular profile of new selenium-menadione conjugates against Mycobacterium tuberculosis H37Rv (ATCC 27294) strain and multidrug-resistant clinical isolates

“…In this context, naphthoquinones are a characteristic group of quinones that exist as secondary metabolites largely present in plants, lichens and microorganisms. Some of them can be extracted and used in traditional medical practices and folk medicine [ 8 ]. Naphthoquinones present a chemical structure of naphthalene with two ketone groups at position C-1 and C-2 (1,2-naphthoquinones) or C-1 and C-4 (1,4-naphthoquinones) [ 9 ].…”

“…Naphthoquinones present a chemical structure of naphthalene with two ketone groups at position C-1 and C-2 (1,2-naphthoquinones) or C-1 and C-4 (1,4-naphthoquinones) [ 9 ]. The considerable interest in these compounds is based on their pharmacological activities, especially as antimicrobial [ [8] , [9] , [10] , [11] ] and antitumor agents [ [12] , [13] , [14] , [15] ]. Most recently, 1,4-naphthoquinones, such as menadione (vitamin K3), have aroused a lot of interest due to relevant anticancer activity [ 16 ].…”

Enhancing the Production of the Fungal Pigment Aurofusarin in Fusarium graminearum

“…Naphthoquinones, including dimeric naphthoquinones, have previously been described as having antibiotic activity against both Gram-positive and Gram-negative bacteria, as well as yeast of the genus Candida [ 18 , 19 ]. In fact, 22 naphthoquinones from F. solani and F. oxysporum were examined by Baker and colleagues, of which 12 were antimicrobial against Streptococcus pyogenes and 15 were active against Staphylococcus aureus [ 20 ].…”

Antifungal Activity of Euclea divinorum Root and Study of its Ethnobotany and Phytopharmacology

“…Shikonin and deoxyshikonin were isolated from roots of Lithospermum erythrorhizon showed strong antifungal activities, against Candida krusei (MIC: 4 mg/mL) [43]. The antifungal activities of 30 different naphthoquinones against some Candida species such as C. albicans were demonstrated [44]. Thirteen synthetic naphthoquinones containing sulphur atoms showed higher antifungal activity than amphotericin B against Candida tropicalis, Aspergillus niger, Trychophyton tonsurans and Fusarum oxysporum [45].…”