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Antibacterial Activity of Some Flavonoids and Organic Acids Widely Distributed in Plants

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Antibacterial Activity of Some Flavonoids and Organic Acids Widely Distributed in Plants Journal of Clinical Medicine Article Antibacterial Activity of Some Flavonoids and Organic Acids Widely Distributed in Plants Artur Adamczak 1 , Marcin O˙zarowski 2 and Tomasz M. Karpi ´nski 3,* 1 Department of Botany, Breeding and Agricultural Technology of Medicinal Plants, Institute of Natural Fibres and Medicinal Plants, Kolejowa 2, 62-064 Plewiska, Poland; [email protected] 2 Department of Biotechnology, Institute of Natural Fibres and Medicinal Plants, Wojska Polskiego 71b, 60-630 Pozna´n,Poland; [email protected] 3 Department of Medical Microbiology, Pozna´nUniversity of Medical Sciences, Wieniawskiego 3, 61-712 Pozna´n,Poland * Correspondence: [email protected] Received: 21 November 2019; Accepted: 27 December 2019; Published: 31 December 2019 Abstract: Among natural substances widespread in fruits, vegetables, spices, and medicinal plants, flavonoids and organic acids belong to the promising groups of bioactive compounds with strong antioxidant and anti-inflammatory properties. The aim of the present work was to evaluate the antibacterial activity of 13 common flavonoids (flavones, flavonols, flavanones) and 6 organic acids (aliphatic and aromatic acids). The minimal inhibitory concentrations (MICs) of selected plant substances were determined by the micro-dilution method using clinical strains of four species of pathogenic bacteria. All tested compounds showed antimicrobial properties, but their biological activity was moderate or relatively low. Bacterial growth was most strongly inhibited by salicylic acid (MIC = 250–500 µg/mL). These compounds were generally more active against Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa than Gram-positive ones: Enterococcus faecalis and Staphylococcus aureus. An analysis of the antibacterial effect of flavone, chrysin, apigenin, and luteolin showed that the presence of hydroxyl groups in the phenyl rings A and B usually did not influence on the level of their activity. A significant increase in the activity of the hydroxy derivatives of flavone was observed only for S. aureus. Similarly, the presence and position of the sugar group in the flavone glycosides generally had no effect on the MIC values. Keywords: kaempferol; naringin; orientin; rutin; vitexin; chlorogenic acid; citric acid; malic acid; quinic acid; rosmarinic acid 1. Introduction Screening biological studies of chemical compounds of natural origin allow for assessment of their activity and determine further research stages in order to search for new therapeutic solutions based on active compounds known in plants. This is especially important during the observed increasing resistance of bacteria and fungi to antibiotics. Multidrug resistance (MDR) is a serious threat to human health, but also to crops and animals. MDR is a growing challenge in medicine. Recently, several multinational studies have been carried out to determine the prevalence of herbal medicine use in infections due to pathogenic microorganisms [1,2]. It is considered that extracts of medicinal plants can be an alternative source of resistance modifying substances [2]. It is well known that plant extracts and other herbal products are complex mixtures containing the wide variety of primary and secondary metabolites, and their action may be the result of the synergy of different chemical components. Moreover, these extracts may show various mechanisms of biological and pharmacological activity, i.e., ability to bind to protein domains, modulation of the immune response, J. Clin. Med. 2020, 9, 109; doi:10.3390/jcm9010109 www.mdpi.com/journal/jcm J. Clin. Med. 2019, 8, x FOR PEER REVIEW 2 of 16 J. Clin. Med. 2020, 9, 109 2 of 17 interact with the environment and other organisms, therefore their chemical composition and the mitosis,level apoptosis, of active substances and signal transductioncan be very diverse [2]. However, [3,4]. In itaddition, should be th notede manufacturing that plants process interact of with herbal the environmentmedicinal products and other is very organisms, complex therefore because their it encompasses chemical composition non-standardized and the levelprocesses of active like the substancescultivation can beof veryplants, diverse obtaining [3,4]. the In addition,vegetable the ra manufacturingw material from process various of herbalparts medicinalof the world, productspreparing is very of complex extract, becauseand producing it encompasses a product non-standardized in accordance processeswith local like guidelines the cultivation of the ofgood plants,manufacturing obtaining the practice. vegetable Therefore, raw material it can from be co variousncluded parts that of using the world, pure preparingchemical compounds of extract, of andnatural producing origin a product would be in an accordance interesting with complementar local guidelinesy option of thedue goodto their manufacturing easier therapeutic practice. dosage, Therefore,the study it can of mechanisms be concluded of that the usingpharmacological pure chemical action compounds and monitoring of natural of their origin side would effects. be an interestingA complementarylot of widespread option plant due substances, to their easier including therapeutic alkaloids, dosage, organosulfur the study compounds, of mechanisms phenolic of the pharmacologicalacids, flavonoids, action carotenoids, and monitoring coumarins, of their terpenes, side etannins,ffects. and some primary metabolites (amino acids,A lot ofpeptides, widespread organic plant acids) substances, exhibit antimicrob includingial alkaloids, properties organosulfur [1,5–8]. Am compounds,ong them, flavonoids phenolic are acids,a promising flavonoids, group carotenoids, of bioactive coumarins, substances terpenes, with tannins,low systemic and some toxicity. primary Natural metabolites flavonols, (amino flavones, acids,flavanones, peptides, organicand other acids) compounds exhibit antimicrobial of this class be propertieslong to the [1 ,5common–8]. Among secondary them, flavonoidsmetabolites are found a promisingin various group fruits, of bioactive vegetables, substances and withmedicinal low systemic plants toxicity.[9] showing Natural strong flavonols, antioxidant flavones, and flavanones,anti-inflammatory and other compounds properties of[10,11]. this class Dietary belong polyphenols to the common such secondaryas flavonoids metabolites and phenolic found inacids, variousconsumed fruits, vegetables, in large quantities and medicinal in foods plants of plant [9] showing origin, exhibit strong a antioxidant number of andbeneficial anti-inflammatory effects and play propertiesan important [10,11]. role Dietary in the polyphenols prevention of such chronic as flavonoids and degenerative and phenolic diseases. acids, Not consumed only their inantioxidant large quantitiesand anti-inflammatory in foods of plant origin, activities, exhibit but a number also ofne beneficialuroprotective, effects anticancer, and play an importantimmunomodulatory, role in the preventionantidiabetic, of chronicand anti-adipogenic and degenerative properties diseases. have Not onlybeen their shown antioxidant [12,13]. andBiological anti-inflammatory availability of activities,dietary but polyphenols also neuroprotective, is low as anticancer,compared immunomodulatory,with micro- and macronutrients. antidiabetic, andTheir anti-adipogenic absorption in the propertiessmall haveintestine been shownamounts [12 ,13only]. Biological about 5–10%. availability However, of dietary recent polyphenols studies is lowshowed as compared that these withphytochemicals micro- and macronutrients. exhibit prebiotic Their properties absorption and antimicrobial in the small activity intestine against amounts pathogenic only aboutintestinal 5–10%.microflora However, [13]. recent studies showed that these phytochemicals exhibit prebiotic properties and antimicrobialFlavonoids activity selected against for pathogenicour microbiological intestinal microfloratests are [presented13]. in Figure 1. In the large quantities,Flavonoids they selected occur in for stems our and microbiological leaves, flowers tests as well are presentedas fruits of the in Figurespecies1 .from In thethe largefamilies of quantities,Apiaceae, they Asteraceae, occur in stemsBetulaceae, and leaves,Brassicaceae, flowers Ericaceae, as well asFabaceae, fruits of Hypericaceae, the species from Lamiaceae, the familiesLiliaceae, of Apiaceae, Passifloraceae, Asteraceae, Polygonaceae, Betulaceae, Primulaceae, Brassicaceae, Ericaceae,Ranunculaceae, Fabaceae, Rosaceae, Hypericaceae, Rubiaceae, Lamiaceae,Rutaceae, Liliaceae, Scrophulariaceae, Passifloraceae, Tiliaceae, Polygonaceae, and Violaceae. Primulaceae, Two Ranunculaceae, flavonols: quercetin, Rosaceae, kaempferol, Rubiaceae, and Rutaceae,flavones: Scrophulariaceae, apigenin, luteolin Tiliaceae, belong to and the Violaceae. most ubiquitous Two flavonols: plant flavonoids quercetin, [14]. kaempferol, A glycoside andform of flavones:quercetin—rutin apigenin, luteolin (sophori belongn, rutoside) to the most is ubiquitouspresent in plant the flavonoidshighest concentrations [14]. A glycoside in formbuckwheat of quercetin—rutin(Fagopyrum esculentum (sophorin, Moench), rutoside) isrue present (Ruta ingraveolens the highest L.), concentrationsflower buds of in Styphnolobium buckwheat (Fagopyrum japonicum (L.) esculentumSchott Moench),(Sophora japonica rue (Ruta L.), graveolens apricots,L.), peaches, flower budsand citrus of Styphnolobium fruits [15,16]. japonicum Apigenin(L.) derivatives, Schott (Sophora such as vitexin, isovitexin,
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