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Compounds isolated from hexane fraction of Alternanthera brasiliensis show synergistic activity against methicillin resistant Staphylococcus aureus

  • Enitan Omobolanle Adesanya ORCID logo EMAIL logo , Mubo Adeola Sonibare , Edith Oriabure Ajaiyeoba and Samuel Ayodele Egieyeh
Published/Copyright: July 1, 2021
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Physical Sciences Reviews
From the journal Physical Sciences Reviews Volume 8 Issue 8

Abstract

Methicillin resistant Staphylococcus aureus (MRSA) has been classified as a “serious threat” by the centre for Disease Control, USA. Alternanthera brasiliensis plant, usually found on wasteland, belongs to the family Amaranthaceae. It is traditionally used for wound healing and has shown antimicrobial effect. Yet, this plant has not been fully explored for its antibacterial activity. Hence, this study evaluated isolated compounds from this plant for its activity against MRSA infections. The leaves extracts and fractions were prepared and concentrated in vacuo using a rotatory evaporator. Isolated compounds were obtained through vacuum liquid chromatographic (VLC) techniques and structurally elucidated with various spectroscopic techniques. Anti-MRSA assay of the fraction and compounds were evaluated by agar-well diffusion and broth-dilution methods while checkerboard assay was used to determine the fractional inhibitory concentration index (FICi). The Gas Chromatography-Mass Spectrometry (GCMS) and High Performance Liquid Chromatography (HPLC) analysis revealed fatty acid and carboxylic acid components like hexadecanoic acid, bis (2-ethylhexyl) phthalate and Fettsäure. The compounds AbHD1 and AbHD5 were identified as hexadecanoic acid and di (ethylhexyl) phthalate. Anti-MRSA assay shows that A. brasiliensis hexane fraction (AbHF) and the compounds had zones of inhibitions (Zi) ranging from 7.3 ± 0.5 to 17.5 ± 0.5 mm with minimum inhibitory concentrations (MIC) between 1.22 × 10−5 – 2.5 mg/mL. Synergistic effects were observed between AbHF and erythromycin, AbHF and ampicillin and AbHF and ciprofloxacin with FICi 0.208–0.375 in K1St4 strain while amoxicillin revealed antagonistic effects against M91 strain (4.67). Similarly, hexadecanoic acid and di (ethylhexyl) phthalate showed synergistic behaviour only with ampicillin against K1St4 while the rest were antagonistic. The study revealed that hexadecanoic acid and di (ethylhexyl) phthalate isolated from A. brasiliensis showed synergistic activity in variations against MRSA isolate and strains.

Keywords: Alternanthera brasiliensis ; antibacterial; isolation; methicillin resistant Staphylococcus aureus ; synergistic activity
Corresponding author: Enitan Omobolanle Adesanya, Department of Pharmacognosy, Faculty of Pharmacy, University of Ibadan, Ibadan, Nigeria, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

Appendix
Tabe A1:

Compounds identified from Alternanthera brasiliensis hexane fraction via GCMS analysis.

S/no Retention Time (min) Compound name
1 5.82 Ar-tumerone
2 Phenyl tiglate, 2-(1Z)-propenyl-
3 Tumerone
4 (Z)-.gamma.-Atlantone
5 (E)-.gamma.-Atlantone
6 4.40 Curlone
7 2-Methyl-6-(4-methylenecyclohex-2-en-1-yl)hept-2-en-4-one
8 Benzoic acid, 4-amino-, 4-acetoxy- 2,2,6,6-tetramethyl-1-piperidinyl ester
9 4.71 2-Pentadecanone, 6,10,14-trimethyl
10 2-Undecanone, 6,10-dimethyl-
11 7.09 Neophytadiene
12 Bicyclo[3.1.1]heptane, 2,6,6-trimethyl-
13 Bicyclo [3.1.1] heptane, 2, 6, 6-trimethyl-, (1.alpha. 2. beta., 5.alpha.)
14 1.69 3,7,11,15-Tetramethyl-2-hexadecen-1-ol
15 1,4-Eicosadiene
16 2.89 9-Eicosyne
17 1-Hexadecyne
18 5.93 Hexadecanoic acid, methyl ester
19 17.06 n-Hexadecanoic acid
20 1.84 Methyl 10-trans,12-cis-octadecadienoate
21 9,12-Octadecadienoic acid, methyl ester
22 1.90 11-Octadecenoic acid, methyl ester
23 9-Octadecenoic acid, methyl ester, (E)-
24 9-Octadecenoic acid (Z)-, methyl ester
25 22.34 Phytol
26 1.59 Methyl stearate
27 Heptadecanoic acid, 16-methyl-, methyl ester
28 2.34 2-Methyl-Z,Z-3,13-octadecadienol
29 Cyanoacetylurea
30 1,19-Eicosadiene
31 2.05 4,8,12,16-Tetramethylheptadecan-4-olide
32 2(3H)-Furanone, 5-butyldihydro-4-methyl-
33 5.59 Bis(2-ethylhexyl) phthalate
34 Phthalic acid, di(2-propylpentyl)ester
35 6.69 Squalene
36 Supraene
37 1.40 Cyclotrisiloxane, hexamethyl-
38 Benzo[h]quinoline, 2,4-dimethyl-
39 1-methyl-4-phenyl-5-thioxo-1,2,4-triazolidin-3-one
40 Tetrasiloxane, decamethyl-
Table A2:

HPLC analysis of A. brasiliensis hexane fraction.

S/no Likely component expected
1 Cyclo(polylvaly 1)
2 Cerebroside
3 9-OH-pinoresinol
4 Aureonitol
5 Fetts äure
6 Bastadin 2
7 Herbarin B
8 Indo-3-Carbaldehyde
9 Aloresin A
10 2,3-Dibromoaldsin
11 Septone
12 (E,Z) Paucin
13 (Z)-oct.2-ene 1,3,8-tricarboxylic acid
Table A3:

HSQC assignment of AbHD1.

Position 13C NMR

Experimental		 13C NMR

Reporteda 		1H NMR

Experimental		 1H NMR

Reporteda 		Type of Carbon
1 178.7 178.7 – – C
2 34.1 34.1 2.33 (2H, t, J = 8.0 Hz) 2.33 (2H, t, J = 8.0 Hz) CH2
3 24.9 24.9 1.23–1.40 (2H, m) 1.61 (2H, m) CH2
4 29.1 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
5 29.4 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
6 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
7 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
8 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
9 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
10 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
11 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
12 29.7 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
13 29.4 29.9–29.3 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
14 31.9 32.1 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
15 22.7 22.9 1.23–1.40 (2H, m) 1.28 (2H, m) CH2
16 14.1 14.2 0.86 (3H, t, J = 8.0 Hz) 0.86 (3H, t, J = 8.0 Hz) CH3

  1. m, multiplet; t, triplet; J = coupling constant in Hertz. aReported by Fadzil et al. [14].

Table A4:

HSQC assignment of compound ABHD5 [di(2-ethylhexyl) phthalate].

Position 1H NMR 13C NMR (Observed) 13C NMR (aReported)
1 7.62 (1H, dd, J = 5.6, 3.3 Hz) 128.8, CH 129.1, CH
2 7.45 (1H, dd, J = 5.6, 3.3 Hz) 130.9, CH 131.2, CH
3 7.45 (1H, dd, J = 5.7, 3.3 Hz) 130.9, CH 131.2, CH
4 7.62 (1H, dd, J = 5.7, 3.3 Hz) 128.8, CH 129.1, CH
1′ – 132.5,qC 132.8, qC
2′ – 167.8, qC 168.1, qC
3′ 4.20 (2H, dd, J = 10.9, 5.8 Hz) 68.2, CH2 68.5, CH2
4′ 2.15 (1H, m) 39.4, CH 39.1, CH
5′ 1.10–1.90 (2H, m) 30.4, CH2 30.7, CH2
6′ 1.10–1.90 (2H, m) 29.4, CH2 29.3, CH2
7′ 1.10–1.90 (2H, m) 23.8, CH2 23.3, CH2
8′ 0.80–0.90 (3H, t, J = 6.8 Hz) 14.1, CH3 14.4, CH3
9′ 1.10–1.90 (2H, m) 24.8, CH2 24.1, CH2
10′ 0.80–0.90 (3H, t, J = 6.8 Hz) 10.9, CH3 11.3, CH3
1″ – 132.5,qC 132.8, qC
2″ – 167.8,qC 168.1, qC
3″ 4.20 (2H, dd, J = 10.9, 5.8 Hz) 68.2, CH2 68.5, CH2
4″ 2.15 (1H, m) 39.4,CH 39.1, CH
5″ 1.10–1.90 (2H, m) 30.4, CH2 30.7, CH2
6″ 1.10–1.90 (2H, m) 29.4, CH2 29.3, CH2
7″ 1.10–1.90 (2H, m) 23.8, CH2 23.3, CH2
8″ 0.80–0.90 (3H, t, J = 6.8 Hz) 14.1, CH3 14.4, CH3
9″ 1.10–1.90 (2H, m) 24.8, CH2 24.1, CH2
10″ 0.80–0.90 (3H, t, J = 6.8 Hz) 10.9, CH3 11.3, CH3

  1. aReported by Nair et al. [15]. qC, quaternary carbon; dd, double doublet; m, multiplet; t, triplet.

Figure A1: 1H NMR spectrum of AbHD1.
Figure A1:

1H NMR spectrum of AbHD1.

Figure A2: Proton NMR of AbHD5.
Figure A2:

Proton NMR of AbHD5.

Figure A3: Carbon – 13 NMR of AbHD1.
Figure A3:

Carbon – 13 NMR of AbHD1.

Figure A4: Carbon 13 of AbHD5.
Figure A4:

Carbon 13 of AbHD5.

Figure A5: NOESY of AbHD1.
Figure A5:

NOESY of AbHD1.

Figure A6: NOESY of AbHD5.
Figure A6:

NOESY of AbHD5.

Figure A7: HMQC of AbHD1.
Figure A7:

HMQC of AbHD1.

Figure A8: HMQC of AbHD5.
Figure A8:

HMQC of AbHD5.

Figure A9: Proton NMR of AbHD5.
Figure A9:

Proton NMR of AbHD5.

Figure A10: Carbon 13 of AbHD5.
Figure A10:

Carbon 13 of AbHD5.

Figure A11: NOESY of AbHD5.
Figure A11:

NOESY of AbHD5.

Figure A12: HMQC of AbHD5.
Figure A12:

HMQC of AbHD5.

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Published Online: 2021-07-01

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https://doi.org/10.1515/psr-2020-0113
Keywords for this article
Alternanthera brasiliensis; antibacterial; isolation; methicillin resistant Staphylococcus aureus; synergistic activity

Articles in the same Issue

  1. Frontmatter
  2. Reviews
  3. Influence of lime (CaO) on low temperature leaching of some types of bauxite from Guinea
  4. Ethnobotanical survey, phytoconstituents and antibacterial investigation of Rapanea melanophloeos (L.) Mez. bark, fruit and leaf extracts
  5. Catalytic properties of supramolecular polymetallated porphyrins
  6. Lignin-based polymers
  7. Bio-based polyhydroxyalkanoates blends and composites
  8. Biodegradable poly(butylene adipate-co-terephthalate) (PBAT)
  9. Repurposing tires – alternate energy source?
  10. Theoretical investigation of the stability, reactivity, and the interaction of methyl-substituted peridinium-based ionic liquids
  11. Polymeric membranes for biomedical applications
  12. Design of locally sourced activated charcoal filter from maize cob for wastewater decontamination: an approach to fight waste with waste
  13. Synthesis of biologically active heterocyclic compounds from allenic and acetylenic nitriles and related compounds
  14. Magnetic measurement methods to probe nanoparticle–matrix interactions
  15. Health and exposure risk assessment of heavy metals in rainwater samples from selected locations in Rivers State, Nigeria
  16. Evaluation of raw, treated and effluent water quality from selected water treatment plants: a case study of Lagos Water Corporation
  17. A chemoinformatic analysis of atoms, scaffolds and functional groups in natural products
  18. Hemicyanine dyes
  19. Thermodynamics of the micellization of quaternary based cationic surfactants in triethanolamine-water media: a conductometry study
  20. Compounds isolated from hexane fraction of Alternanthera brasiliensis show synergistic activity against methicillin resistant Staphylococcus aureus
  21. Internal structures and mechanical properties of magnetic gels and suspensions
  22. SPIONs and magnetic hybrid materials: Synthesis, toxicology and biomedical applications
  23. Magnetic field controlled behavior of magnetic gels studied using particle-based simulations
  24. The microstructure of magnetorheological materials characterized by means of computed X-ray microtomography
  25. Core-modified porphyrins: novel building blocks in chemistry
  26. Anticancer potential of indole derivatives: an update
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  32. Naturally occurring heterocyclic anticancer compounds
  33. Part-II- in silico drug design: application and success
  34. Advances in biopolymer composites and biomaterials for the removal of emerging contaminants
  35. Nanobiocatalysts and photocatalyst in dye degradation
  36. 3D tumor model – a platform for anticancer drug development
  37. Hydrogen production via water splitting over graphitic carbon nitride (g-C3N4 )-based photocatalysis
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