2-Octylcyclopentanone Inhibits Beta Lactam Resistant Diabetic Wound Pathogens

Main Article Content

Nur Amiera Syuhada Rozman
Tong Woei Yenn
Leong Chean Ring
Syarifah Ab Rashid
Tan Wen-Nee
Jun Wei Lim

Abstract

Microbial infection is a frequent complication of diabetic foot ulcers, with up to 82% of ulcers being infected at the initial stage of diabetes. Furthermore, the emergence of beta lactam resistant pathogens managed to eliminate the use of beta lactam antibiotics as a chemotherapeutic alternative. This further increases the amputation and mortality rate. Hence, the aim of this study is to evaluate antimicrobial efficacy of a ketone derivative 2-octylcyclopentanone against diabetic wound pathogens. The inhibitory activity of the compound was determined using disc diffusion and broth microdilution assay. Generally, 2-octylcyclopentanone showed broad-spectrum antimicrobial activity, particularly against beta lactam resistant pathogens. The compound showed comparably better antimicrobial activity than all reference antibiotics, including chloramphenicol, streptomycin, ampicillin and penicillin. In addition, the same compound also inhibits a clinically isolated Pseudonomas aeruginosa that was resistant to all reference antibiotics. The activity was microbicidal based on the low minimal lethality concentration recorded, particularly on MRSA, P. aeruginosa and Candida utilis. The killing efficiency of the compound was concentration dependent. During kill curve analysis, the inhibitory activity of 2-octylcyclopentanone was concentration and time-dependent. 99.9% of reduction of bacterial growth was observed. MRSA and P. aeruginosa, two significant diabetic wound infections, are totally inhibited by the molecule at a concentration of minimum lethality concentration. In short, 2-octylcyclopentanone exhibited significant inhibitory towards wide range of diabetic wound pathogens. Which is considered crucial since it will provide a safe and effective alternative treatment for diabetic ulcer infection.

Article Details

How to Cite
2-Octylcyclopentanone Inhibits Beta Lactam Resistant Diabetic Wound Pathogens. (2023). Tropical Life Sciences Research, 34(1), 279–291. https://doi.org/10.21315/tlsr2023.34.1.15
Section
Short Communication

References

Baker C D, Federico M J and Accurso F J. (2007). Case report: Skin discoloration following administration of colloidal silver in cystic fibrosis. Current Opinion in Pediatrics 19, 733–735. https://doi.org/10.1097/MOP.0b013e3282f11fee

Basak S S and Candan, F. (2010). Chemical composition and in vitro antioxidant and antidiabetic activities of Eucalyptus camaldulensis Dehnh. essential oil. Journal of the Iranian Chemical Society 7(1): 216–226. https://doi.org/10.1007/bf03245882

Cho H, Uehara T and Bernhardt T G. (2014). Beta-lactam antibiotics induce a lethal malfunctioning of the bacterial cell wall synthesis machinery. Cell 159(6): 1300–1311. https://doi.org/10.1016/j.cell.2014.11.017

Darah I and Lim S H. (2015). In vitro antimicrobial activities of methanolic extract from marine alga Enteromorpha intestinalis. Asian Pacific Journal of Tropical Biomedicine 5(9): 785–788. https://doi.org/10.1016/j.apjtb.2015.07.012

Darah I, Jain K, Lim S H and Wendy R. (2013). Efficacy of pyroligneous acid from Rhizophora apiculata on pathogenic Candida albicans. Journal of Applied Pharmaceutical Science 3: 7–13. https://doi.org/10.21161/mjm.60714

de Souza Araújo E, Pimenta A S, Feijó F M C, Castro R V O, Fasciotti M, Monteiro T V C and de Lima K M G. (2018). Antibacterial and antifungal activities of pyroligneous acid from wood of Eucalyptus urograndis and Mimosa tenuiflora. Journal of Applied Microbiology 124(1): 85–96. https://doi.org/10.1111/jam.13626

El Sawi S A M, Hanafy D M M M and El Alfy T S M A. (2014). Composition of the non-polar extracts and antimicrobial activity of Chorisia insignis HBK leaves. Asian Pacific Journal of Tropical Disease 4(6): 473–479. https://doi.org/10.1016/S2222-1808(14)60609-5

Fazli M, Bjarnsholt T, Kirketerp-Moller K, Jorgensen B, Andersen A S, Krogfelt K A, and Tolker-Nielsen T. (2009). Non-random distribution of Pseudomonas aeruginosa and Staphylococcus aureus in chronic wounds. Journal of Clinical Microbiology 47: 4084–4089. https://doi.org/10.1128/JCM.01395-09

Huang J, Long W, Agrawal P K and Jones C W. (2009). Effects of acidity on the conversion of the model bio-oil ketone cyclopentanone on H?Y zeolites. The Journal of Physical Chemistry C 113(38): 16702–16710. https://doi.org/10.1021/jp905661w

Jacyno J M, Montemurro N, Bates A D and Cutler H G. (1991). Phytotoxic and antimicrobial properties of cyclocolorenone from Magnolia grandiflora L. Journal of Agricultural and Food Chemistry 39(6): 1166–1168. https://doi.org/10.1021/jf00006a036

Kalishwaralal K, Barath M K S, Pandian S R K, Deepak V and Gurunathan S. (2010). Silver nanoparticles impede the biofilm formation by Pseudomonas aeruginosa and Staphylococcus epidermidis. Colloids and Surfaces B: Biointerfaces 79: 340–344. https://doi.org/10.1016/j.colsurfb.2010.04.014

Kingsley A. (2001). A proactive approach to wound infection. Nursing Standard 15: 50–58. https://doi.org/10.7748/ns2001.04.15.30.50.c3012

Kuhbacher A, Burger-Kentischer K and Rupp S. (2017). Interaction of Candida species with the skin. Microorganisms 5: 1–12. https://doi.org/10.3390/microorganisms5020032

Lim S H, Darah I, Jain K and Suraya S. (2011). Gallic acid: an anticandidal compound in hydrolysable tannin extracted from the barks of Rhizophora apiculata Blume. Journal of Applied Pharmaceutical Science 1: 75–79.

Malic S, Hill K E, Hayes A, Percival S L, Thomas D W and Williams D W. (2009). Detection and identification of specific bacteria in wound biofilms using peptide nucleic acid fluorescent in situ hybridization (PNA FISH). Microbiology 155, 2603–2611. https://doi.org/10.1099/mic.0.028712-0

Narres M, Kvitkina T, Claessen H, Droste S, Schuster B, Morbach S and Icks A. (2001). Incidence of lower extremity amputations in the diabetic compared with the non-diabetic population: A systematic review. PloS One 12: 1–28. https://doi.org/10.1371/journal.pone.0182081

Neta M C S, Vittorazi C, Guimarães A C, Martins J D L, Fronza M, Endringer D C and Scherer R. (2016). Effects of ?-caryophyllene and Murraya paniculata essential oil in the murine hepatoma cells and in the bacteria and fungi 24-h time–kill curve studies. Pharmaceutical Biology 55(1): 190–197. https://doi.org/10.1080/13880209.2016.1254251

Olid A S, Sola I, Barajas?Nava L A, Gianneo O D, Bonfill C X and Lipsky B A. (2015). Systemic antibiotics for treating diabetic foot infections. Cochrane Database. Systemic Reviews 4(9): 9601–9605. https://doi.org/10.1002/14651858.CD009061.pub2

Omosa L K, Midiwo J O, Mbaveng A T, Tankeo S B, Seukep J A, Voukeng I K and Kuete V. (2016). Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes. SpringerPlus 5: 901–916. https://doi.org/10.1186/s40064-016-2599-1

Öztürk A M, Tasbakan M, Metin D Y, Yener C, Uysal S, Simsir I Y and Cetinkalp S. (2019). A neglected causative agent in diabetic foot infection: A retrospective evaluation of 13 patients with fungal etiology. Turkish Journal of Medical Sciences 49(1): 81–86. https://doi.org/10.3906/sag-1809-74

Pence M A, Haste N M, Meharena H S, Olson J, Gallo R L, Nizet V and Kristian S A. (2015). Beta-lactamase repressor BlaI modulates Staphylococcus aureus cathelicidin antimicrobial peptide resistance and virulence. PloS One 10(8): e0136605. https://doi.org/10.1371/journal.pone.0136605

Peters B M, Jabra-Rizk M A, Graeme A O, Costerton J W and Shirtliff M E. (2012). Polymicrobial interactions: impact on pathogenesis and human disease. Clinical Microbiology Reviews 25: 193–213. https://doi.org/10.1128/CMR.00013-11

Rovira J, Martí N, Marta S and Jose L D. (2015). Human exposure to trace elements through the skin by direct contact with clothing: Risk assessment. Environmental Research 140: 308–316. https://doi.org/10.1016/j.envres.2015.03.032

Rozman N A S, Tong W Y, Tan W N, Ring L R, Yusof F A B M and Sulaiman B. (2018). Homalomena pineodora, a novel essential oil-bearing plant and its antimicrobial activity against diabetic wound pathogens. Journal of Essential Oil-Bearing Plants 21: 963–971. https://doi.org/10.1080/0972060X.2018.1526129

Scognamiglio J, Jones L, Letizia C S and Api A M. (2012). Fragrance material review on cyclopentanone. Food and Chemical Toxicology 50: 608–612. https://doi.org/10.1016/j.fct.2012.03.027

Serra R, Grande R, Butrico L, Rossi A, Settimio U F, Caroleo B and de Franciscis S. (2015). Chronic wound infections: the role of Pseudomonas aeruginosa and Staphylococcus aureus. Expert Review of Anti-infective Therapy 13: 605–613. https://doi.org/10.1586/14787210.2015.1023291

Silva O and Gomes E T. (2003). Guieranone A, a naphthyl butenone from the leaves of Guiera senegalensis with antifungal activity. Journal of Natural Product 66(3): 447–449. https://doi.org/10.1021/np0204904

Tonari K and Sameshima K. (2000). Antibacterial activity of 3-methylcyclopentanone derivatives in relation to methylenomycins. Journal of Oleo Science 49: 583–590. https://doi.org/10.5650/jos1996.49.583

Tong W Y, Abdullah A Y K, Rozman N A S, Wahid M I A, Hossain M S, Ring L C and Tan W N. (2018). Antimicrobial wound dressing film utilizing cellulose nanocrystal as drug delivery system for curcumin. Cellulose 25(1): 631–638. https://doi.org/10.1007/s10570-017-1562-9

Tong W Y, Ang S N, Darah I and Latiffah Z. (2014). Antimicrobial activity of Penicillium minioluteum ED24, an endophytic fungus residing in Orthosiphon stamineus Benth. World Journal Pharmacy and Pharmaceutical Science 3: 121–132.

Tong W Y, Darah I, Lee K C, Syarifah A R, Leong C R, Tan W N and Muhamad Izham M N. (2017). Antimicrobial efficacy of endophytic Penicillium purpurogenum ED76 against clinical pathogens and its possible mode of action. Korean Journal of Microbiology 53(3): 193–199.