In the current era, an ever-emerging threat of multidrug-resistant (MDR) pathogens pose serious health challenges to mankind. Researchers are uninterruptedly putting their efforts to design and develop alternative, innovative strategies to tackle the antibiotic resistance displayed by varied pathogens. Among several naturally derived and chemically synthesized compounds, quinones have achieved a distinct position to defeat microbial pathogens.
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Name and Structure of the Naphthoquinone Derivative | Source of Plant Material | Reference |
---|---|---|
(A) Juglone: 5-Hydroxy-1,4-naphthalenedione![]() |
Caesalpinia sappan | [30] |
(B) Plumbagin: 5-Hydroxy-2-methyl-naphthalene-1,4-dione![]() |
Plumbago zeylanica | [31] |
Plumbago auriculata | [32] | |
Plumbago indica | [33] | |
(C) Lawsone: 2-Hydroxy-1,4-naphthoquinone![]() |
Plumbago zeylanica | [34] |
Lawsonia inermis | [35] | |
(D) Shikonin: 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone![]() |
Arnebia euchroma | [36] |
Lithospermum erythrorhizon | [37] | |
(E) Lapachol: 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-Naphthalenedione![]() |
Tabebuia ochracea | [38,39] |
Type of Naphthoquinone | Active against Bacterial Strains | MIC (µg/mL) | Reference |
---|---|---|---|
Shikonin from Arnebia euchroma root extract | Staphylococcus aureus | 128 | [36] |
Streptococcus agalactiae | 128 | ||
Escherichia coli | 256 | ||
Salmonella isolates | 256 | ||
Pseudomonas aeruginosa | 512 | ||
Plumbagin from Plumbago zeylanica | Staphylococcus aureus | 0.5 | [43] |
Escherichia coli | 8 | ||
Klebsiella pneumoniae | 2 | ||
Pseudomonas aeruginosa | 8 | ||
Plumbagin from Plumbago zeylanica | S. aureus (MRSA) | 4–8 | [31] |
Lawsone from Plumbago zeylanica root extract | Staphylococcus aureus | 400 | [34] |
Salmonella typhi | 200 | ||
Bacillus cereus | 200 | ||
Bacillus subtilis | 200 | ||
Pseudomonas aeruginosa | 800 | ||
Escherichia coli | 800 | ||
Shigella dysenteriae | 400 | ||
Serratia marcescens | >1600 | ||
Proteus mirabilis | >1600 | ||
Klebsiellapneumoniae | 800 | ||
Enterobacter | 800 | ||
Acinetobacter baumannii | 800 | ||
Naphthoquinone pigments from Onosma visianii | Bacillus megaterium | 9.54–54.28 | [44] |
Montrichardia arborescens | 6.82–54.28 | ||
Micrococcus luteus | 9.54–76.20 | ||
Staphylococcus epidermidis | 9.54–54.28 | ||
Enterococcus faecalis | 6.82–38.10 | ||
Citrobacter koseri | 6.82–76.20 | ||
Hafnia alvei | 6.82–54.28 | ||
Pseudomonas proteolytica | 4.77–76.20 | ||
Stenotrophomonas maltophilia | 4.77–76.20 | ||
Yersinia intermedia | 6.82–76.20 | ||
- | (values depict MIC90) | ||
Shikonin from Lithospermum erythrorhizon | Staphylococcus aureus (MRSA) | 7.8–31.2 | [37] |
Staphylococcus aureus (MSSA) | 7.8 | ||
Plumbago auriculata root extracts | Proteus vulgaris | Strong activity | [32] |
Klebsiella. pneumoniae | Strong activity | ||
Escherichia coli | Moderate activity | ||
Pseudomonas aeruginosa | Less activity | ||
Naphthoquinone from Alkanna orientalis extracts | Bacillus megaterium | 125 | [45] |
Bacillus mesentericus | 125 | ||
Bacillus mycoides | 125 | ||
Bacillus subtilis | 125 | ||
Brevibacterium flavum | 250 | ||
Enterococcus hirae | 250 | ||
Micrococcus luteus | 250 | ||
Staphylococcus aureus | 125 | ||
Staphylococcus citreus | 500 | ||
Staphylococcus roseus | 125 | ||
Escherichia. coli | 500 | ||
Salmonella typhimurium | 750 | ||
Lawsone from Lawsonia inermis | Bacillus subtilis | Activity at 1000 µg/disc | [35] |
Staphylococcus aureus | No activity | ||
Escherichia coli | No activity | ||
Pseudomonas aeruginosa | No activity | ||
Plumbago indica from root extracts | Cutibacterium acnes (formerly Propionibacterium acnes) | 12.5 | [33] |
Staphylococcus aureus | 12.5 | ||
Staphylococcus epidermidis | 0.78 | ||
Naphthoquinones from Caesalpinia sappan | Clostridium perfringens | Activity observed | [30] |
Bacillus bifidum | Activity observed | ||
Bacillus. breve | No significant activity | ||
Lactobacillus casei | Minute activity | ||
Escherichia coli | Minute activity |
Type of Naphthoquinone | Antibacterial Activity Against | MIC (µg/mL) | Reference |
---|---|---|---|
Plumbagin | Mycobacterium tuberculosis | 4 | [56] |
Mycobacterium smegmatis | 4 | ||
Lawsone | Mycobacterium tuberculosis | >16 | |
Mycobacterium smegmatis | >32 | ||
Lawsone methyl ether | Staphylococcus aureus (MRSA) | 62.5–125 | [57] |
Lawsone derivatives | Staphylococcus aureus (MRSA) | 32–128 & >128 | [58] |
Staphylococcusaureus (MSSA) | 0.6 –128 & >128 | ||
Lapachol | Staphylococcus aureus | 1.25 mM | [59] |
Lapachol, nor lapachol | Staphylococcus aureus (MRSA) | 30–500 & >500 | [60] |
Imidazole derivatives of 1,4-naphthoquinone | Staphylococcus aureus | 8–512 | [61] |
Bacillus subtilis | 32–512 | ||
Pseudomonas aeruginosa | 8–256 | ||
Proteus vulgaris | 16–256 | ||
Escherichia coli | 32–256 | ||
1,4-naphthoquinone derivatives | Staphylococcus aureus | 4–256 | [62] |
Bacillus subtilis | 128–512 | ||
Pseudomonas aeruginosa | 32–512 | ||
Proteus vulgaris | 128–512 | ||
Escherichia coli | 256–512 | ||
Phenylamino-phenylthio derivatives of 1,4-naphthoquinone (no. of derivatives synthesized) | Staphylococcus aureus | 31.25–500 | [53] |
Listeria monocytogenes | 62.5–500 | ||
Pseudomonas aeruginosa | 62.5–500 | ||
Escherichia coli | 15.6–500 | ||
Klebsiella pneumoniae | 62.5–500 | ||
Sulfide derivatives of 1,4-naphthoquinone | Staphylococcus aureus | 7.8–250 & >250 | [24] |
Escherichia coli | 31.3–250 & >250 | ||
Menadione | Staphylococcus aureus | 128 | [63] |
Pseudomonas aeruginosa | 64 | ||
Escherichia coli | 128 | ||
Klebsiella pneumoniae | 128 | ||
Arylsulfanylmethyl-[1,4]-naphthoquinone derivatives | Staphylococcus aureus | 32–256 | [64] |
Staphylococcus epidermidis | 16–256 | ||
Staphylococcus simulans | 32–256 | ||
Escherichia coli | 256 (less activity) | ||
Enterococcus faecalis | 32–256 | ||
1,4-naphthoquinone substituted at positions 2 and 3 | Staphylococcus aureus | 7.8–500 | [65] |
Salmonella bongori | 125–500 | ||
Pseudomonas aeruginosa | 125–500 | ||
Proteus vulgaris | 250–500 | ||
Escherichia coli | 125–500 | ||
Klebsiella pneumoniae | 62.5–500 | ||
Enterococcus faecalis | 125–500 | ||
Enterobacter cloacae | 250–500 | ||
Shikonin derivatives | Staphylococcus aureus | 1.1–45.4 | [66] |
Bacillus subtilis | 2–50 & >50 | ||
Escherichia coli | 3.1–50 & >50 | ||
Pseudomonas aeruginosa | 4–50 & >50 | ||
Naphthoquinone derivatives | Staphylococcus aureus | 16–256 | [19] |
Pseudomonas aeruginosa | 64–256 | ||
Escherichia coli | 64–256 | ||
Enterococcusfaecalis | 64–256 | ||
2-bromo-5-hydroxy-1,4-NQ | Staphylococcus aureus | 16 | |
Juglone | Staphylococcus aureus | 32–256 | [67] |
Staphylococcus epidermidis | 128 | ||
Bacillus cereus | 256 | ||
Salmonella enterica | 256 | ||
Listeria monocytogenes | 256 | ||
Pseudomonas aeruginosa | 128 | ||
Escherichia coli | 128 | ||
Enterococcus feacalis | 256 | ||
Vibrio alginolyticus | 256 | ||
Nitrogen and sulfur derivatives of 1,4-naphthoquinone | Bacillus subtilis | 1.4–19.3 | [68] |
Proteus vulgaris | 2.7–39 | ||
Plumbagin, juglone, lawsone, menadione and their analogues | Staphylococcusaureus (MRSA) | 3.9–125 | [69] |
Pseudomonas aeruginosa | No significant activity | ||
Menadione | Staphylococcus aureus | 3.1 | [70] |
Bacillus anthracis | 6.25 | ||
Streptococcus pyogenes | 25 | ||
Streptococcus agalactiae | 6.25 | ||
1,4-naphthoquinone | Staphylococcus aureus | 6.25 | |
Bacillus anthracis | 12.5 | ||
Streptococcus pyogenes | 50 | ||
Streptococcus agalactiae | 12.5 | ||
2-hydroxy, 1,4 naphthoquinone (Lawsone) and its 2-hydroxynaphthoquinone derivatives | Staphylococcus aureus | 16–512 & >512 | [71] |
Listeria monocytogenes | 512 & >512 | ||
Pseudomonas aeruginosa | 512 & >512 | ||
Escherichia coli | 512 & >512 | ||
Enterococcus faecalis | 256–512 | ||
Acinetobacter baumannii | 512 & >512 | ||
Salmonella typhimurium | 512 & >512 | ||
Plumbagin derivatives | Mycobacterium smegmatis | 13.3–30.4 | [72] |
Mycobacterium tuberculosis | 15.6–77.4 | ||
Nitrogen, sulfur groups substitution at 2, 3 positions of 1,4-naphthoquinone | Staphylococcus aureus | 6.25–50 & >50 | [73] |
Escherichia coli | 6.25–50 & >50 | ||
Klebsiella pneumoniae | 1.56–50 & >50 | ||
5-Hydroxy-2-methyl-1,4-NQ | Clostridium perfringens | Antibacterial activity observed however MIC values are not mentioned specifically for the test organisms | [30] |
1,4-naphthoquinone | Lactobacillus casei | ||
Bifidobacterium bifidum | |||
Bifidobacterium breve | |||
Clostridium perfringens | |||
Escherichia coli | |||
1,2-naphthoquinone | Clostridium perfringens | ||
Bifidobacterium bifidum | |||
Bifidobacterium breve | |||
5-Amino-8-Hydroxy-1,4-NQ | Staphylococcus aureus | 50 | [74] |
1,4-naphthoquinone | Staphylococcus aureus | 10 | |
(L)-a-amino acid methyl ester, heteroalkyl and aryl substituted1,4-naphthoquinone derivatives | Staphylococcus aureus | 12.5–50 & >50 | [54] |
Streptococcus faecalis | 12.5–50 & >50 | ||
Klebsiella pneumoniae | 6.25–50 & >50 | ||
Escherichia coli | 12.5–50 & >50 | ||
Pseudomonas aeruginosa | 50 & >50 |
This entry is adapted from the peer-reviewed paper 10.3390/coatings11040434