Antibacterial Activity of Triterpene Acids and Semi-Synthetic Derivatives against Oral Pathogens

Triterpene acids (ursolic, oleanoic, gypsogenic, and sumaresinolic acids) isolated from Miconia species, along with a mixture of ursolic and oleanolic acids and a mixture of maslinic and 2-α-hydroxyursolic acids, as well as ursolic acid derivatives were evaluated against the following microorganisms: Streptococcus mutans, Streptococcus mitis, Streptococcus sanguinis, Streptococcus salivarius, Streptococcus sobrinus, and Enterococcus faecalis, which are potentially responsible for the formation of dental caries in humans. The microdilution method was used for the determination of the minimum inhibitory concentration (MIC) during the evaluation of the antibacterial activity. All the isolated compounds, mixtures, and semi-synthetic derivatives displayed activity against all the tested bacteria, showing that they are promising antiplaque and anticaries agents. Ursolic and oleanolic acids displayed the most intense antibacterial effect, with MIC values ranging from 30 μg/mL to 80 μg/mL. The MIC values of ursolic acid derivatives, as well as those obtained for the mixture of ursolic and oleanolic acids showed that these compounds do not have higher antibacterial activity when compared with the activity observed with either ursolic acid or oleanolic acid alone. With regard to the structure-activity relationship of triterpene acids and derivatives, it is suggested that both hydroxy and carboxy groups present in the triterpenes are important for their antibacterial activity against oral pathogens.

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Antimicrobial Activity of Kaurane Diterpenes against Oral Pathogens

Zeitschrift für Naturforschung C ◽

10.1515/znc-2008-5-603 ◽

2008 ◽

Vol 63 (5-6) ◽

pp. 326-330 ◽

Cited By ~ 38

Author(s):

Sergio R. Ambrosio ◽

Niege A. J. C. Furtado ◽

Dionéia C. R. de Oliveira ◽

Fernando B. da Costa ◽

Carlos H. G. Martins ◽

...

Keyword(s):

Antimicrobial Activity ◽

Lactobacillus Casei ◽

Periodontal Diseases ◽

Significant Activity ◽

Streptococcus Sobrinus ◽

Methyl Ester Derivative ◽

Structure Activity ◽

Structural Differences ◽

Oral Pathogens ◽

Relationship Of

Two kaurane diterpenes, ent-kaur-16(17)-en-19-oic acid (KA) and 15-β-isovaleryloxy-entkaur- 16(17)-en-19-oic acid (KA-Ival), isolated from Aspilia foliacea, and the methyl ester derivative of KA (KA-Me) were evaluated against oral pathogens. KA was the most active compound, with MIC values of 10 μg mL-1 against the following microorganisms: Streptococcus sobrinus, Streptococcus mutans, Streptococcus mitis, Streptococcus sanguinis, and Lactobacillus casei. However, KA did not show significant activity against Streptococcus salivarius and Enterococcus faecalis, with MIC values equal to 100 and 200 μg mL-1, respectively. Our results show that KA has potential to be used as a prototype for the discovery of new effective anti-infection agents against microorganisms responsible for caries and periodontal diseases. Moreover, these results allow to conclude that minor structural differences among these diterpenes significantly influence their antimicrobial activity, bringing new perspectives to studies on the structure-activity relationship of this type of metabolites with respect to caries and periodontal diseases.

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Antibacterial Activity of the Essential Oil from Rosmarinus offi cinalis and its Major Components against Oral Pathogens

Zeitschrift für Naturforschung C ◽

10.1515/znc-2010-9-1009 ◽

2010 ◽

Vol 65 (9-10) ◽

pp. 588-593 ◽

Cited By ~ 28

Author(s):

Wagner A. Bernardes ◽

Rodrigo Lucarini ◽

Marcos G. Tozatti ◽

Lúzio G. Bocalon Flauzino ◽

Maria G. M. Souza ◽

...

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Essential Oil ◽

Gas Chromatography Mass Spectrometry ◽

Streptococcus Sobrinus ◽

Microdilution Method ◽

Oral Pathogens ◽

Rosemary Oil ◽

Rosmarinus Officinalis L ◽

Total Oil

The essential oil of Rosmarinus officinalis L. (rosemary) was obtained by hydro-distillation and analysed by gas chromatography-mass spectrometry. Sixty-two constituents were identified, representing 98.06% of the total oil content. Oxygenated monoterpenes were the predominant components. The rosemary oil was characterized as having prominent (> 5%) contents of camphor (18.9%), verbenone (11.3%), α-pinene (9.6%), β-myrcene (8.6%), 1,8-cineole (8.0%), and β-caryophyllene (5.1%). The antimicrobial activity of the oil as well as of its major constituents was tested against the following microorganisms: Streptococcus mutans, Streptococcus mitis, Streptococcus sanguinis, Streptococcus salivarius, Streptococcus sobrinus, and Enterococcus faecalis, which are potentially responsible for the formation of dental caries in humans. The microdilution method was used for determination of the minimum inhibitory concentration (MIC) during evaluation of the antibacterial activity. The essential oil displayed low activity against the selected microorganisms. In the present study, the pure major compounds were more active than the essential oil. Among all the microorganisms tested, the pathogen S. mitis was the most susceptible and E. faecalis was the most resistant to the evaluated samples. This is the first report on antimicrobial activity of the major components of rosemary oil against oral pathogens.

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Design, Facile Synthesis, Antibacterial Activity and Structure-Activity Relationship of Novel Di- and Tri-Substituted 1,3,5-Triazines

Letters in Drug Design & Discovery ◽

10.2174/157018012799129846 ◽

2012 ◽

Vol 9 (3) ◽

pp. 329-335 ◽

Cited By ~ 14

Author(s):

Surajit Kumar Ghosh ◽

Ashmita Saha ◽

Bornali Hazarika ◽

Udaya Pratap Singh ◽

Hans Raj Bhat ◽

...

Keyword(s):

Antibacterial Activity ◽

Structure Activity Relationship ◽

Activity Relationship ◽

Facile Synthesis ◽

Structure Activity ◽

Relationship Of

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Synthesis, Antibacterial Activity, and Structure–Activity Relationship of Fusaric Acid Analogs

Bulletin of the Korean Chemical Society ◽

10.1002/bkcs.12230 ◽

2021 ◽

Author(s):

Qing‐Yan Zhang ◽

Fei‐Yu Yang ◽

Shang‐Gao Liao ◽

Bing Wang ◽

Rui Li ◽

...

Keyword(s):

Antibacterial Activity ◽

Fusaric Acid ◽

Structure Activity Relationship ◽

Activity Relationship ◽

Structure Activity ◽

Relationship Of

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Synthesis and SAR of the antistaphylococcal natural product nematophin from Xenorhabdus nematophila

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.47 ◽

2019 ◽

Vol 15 ◽

pp. 535-541

Author(s):

Frank Wesche ◽

Hélène Adihou ◽

Thomas A Wichelhaus ◽

Helge B Bode

Keyword(s):

Natural Product ◽

Activity Relationship ◽

Xenorhabdus Nematophila ◽

Structure Activity ◽

Multiresistant Bacteria ◽

Improper Use ◽

Relationship Of ◽

First Time ◽

Synthetic Derivatives ◽

Fluorescent Derivatives

The repeated and improper use of antibiotics had led to an increased number of multiresistant bacteria. Therefore, new lead structures are needed. Here, the synthesis and an expanded structure–activity relationship of the simple and antistaphylococcal amide nematophin from Xenorhabdus nematophila and synthetic derivatives are described. Moreover, the synthesis of intrinsic fluorescent derivatives, incorporating azaindole moieties was achieved for the first time.

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Variability of the antibacterial potential among analogue diterpenes against Gram-positive bacteria: considerations on the structure–activity relationship

Canadian Journal of Chemistry ◽

10.1139/cjc-2018-0369 ◽

2019 ◽

Vol 97 (7) ◽

pp. 568-575 ◽

Cited By ~ 1

Author(s):

Ana Carolina Ferreira Soares ◽

Priscilla Mendonça Matos ◽

Herbert Júnior Dias ◽

Gabriela de Paula Aguiar ◽

Eliene Silvério dos Santos ◽

...

Keyword(s):

Antimicrobial Agents ◽

Public Health Problem ◽

Antibacterial Activities ◽

Structure Activity Relationship ◽

Activity Relationship ◽

Gram Positive ◽

Structure Activity ◽

Esterification Reactions ◽

Relationship Of ◽

Synthetic Derivatives

The search for new antibacterial agents and a better comprehension of substances with antimicrobial behavior is mandatory nowadays due to the serious public health problem of infection diseases. In the present work, 30 diterpenes were studied, with 2 natural derivatives, named ent-16-kauren-19-oic acid and ent-pimara-8(14),15-dien-19-oic acid, and 28 semi-synthetic derivatives. The natural diterpenes were isolated from Mikania glomerata and Viguiera arenaria, respectively. All diterpenes were submitted to antimicrobial assays against six different Gram-positive microorganisms to better understand the structure–activity relationship of antimicrobial diterpenes. The semi-synthetic derivatives were all obtained from the two natural derivatives by structural modifications, mainly esterification reactions. Both natural derivatives, together with the derivative ent-8(14)-pimaren-19-oic acid, displayed the most relevant antibacterial activities, with minimal inhibitory concentration (MIC) values that were less than 10 μg mL–1 for most pathogens; thus, they were considered promising antimicrobial agents. Moreover, in light of the hypothesis of Urzúa and colleagues, several considerations about the structure–activity relationship of antimicrobial diterpenes could be stated.

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Antibacterial evaluation of Styrax pohlii and isolated compounds

Brazilian Journal of Pharmaceutical Sciences ◽

10.1590/s1984-82502013000400004 ◽

2013 ◽

Vol 49 (4) ◽

pp. 653-658 ◽

Cited By ~ 7

Author(s):

Camila Spereta Bertanha ◽

Susane Hellen Utrera ◽

Valéria Maria Melleiro Gimenez ◽

Milton Groppo ◽

Márcio Luis Andrade e Silva ◽

...

Keyword(s):

Antibacterial Activity ◽

Inhibitory Concentration ◽

Ethanolic Extract ◽

Preliminary Evaluation ◽

Microdilution Method ◽

Aerial Parts ◽

Broth Microdilution Method ◽

Weak Antibacterial Activity ◽

Mic Value

The antibacterial activity of the compounds egonol (1) and homoegonol (2), of the crude ethanolic extract of Styrax pohlii (Styracaceae) aerial parts (EE), and of its n-hexane (HF), EtOAc (EF), n-BuOH (BF), and hydromethanolic (HMF) fractions was evaluated against the following microorganisms: Streptococcus pneumoniae (ATCC 6305), S. pyogenes (ATCC 19615), Haemophilus influenzae (ATCC 10211), Pseudomonas aeruginosa (ATCC 27853), and Klebsiella pneumoniae (ATCC 10031). The broth microdilution method was used for determination of the minimum inhibitory concentration (MIC) during preliminary evaluation of antibacterial activity. The EE yielded MIC values of 400 µg/mL for S. pneumoniae and P. aeruginosa and 300 µg/mL for H. influenzae. The HF and EF fractions exhibited enhanced antibacterial activity, with MIC values of 200 µg/mL against S. pneumoniae, but only EF displayed activity against H. influenzae (MIC 200 µg/mL). The best MIC value with compounds 1 and 2 (400 µg/mL) was obtained for (1) against S. pneumoniae and P. aeruginosa. Therefore, 1 exhibited weak antibacterial activity against these standard strains.

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