Antimicrobial Potential of Aqueous Extract of Giant Sword Fern and Ultra-High-Performance Liquid Chromatography–High-Resolution Mass Spectrometry Analysis
Abstract
:1. Introduction
2. Results
2.1. Antivibrio Activity
2.2. Antiparasitic Activity
2.3. Physio-Chemical Parameters
2.4. Metabolites Detected in the Aqueous Extract of GSF
3. Discussion
4. Materials and Methods
4.1. Sample Collection and Extraction
4.2. Vibrio Strains and Stock Preparation
4.3. Antivibrio Activity
4.4. Parasitic Leech Collection
4.5. Antiparasitic Activity
4.6. Liquid Chromatography
4.7. Data Acquisition
4.8. Data Analysis
4.9. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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No. | Groups | Diameter of Inhibition Zone (mm) Mean ± S.D |
---|---|---|
1 | Oxytetracycline (positive control) | 55.0 ± 1.0 |
2 | V. alginolyticus | 0 |
3 | V. anguillarum | 0 |
4 | V. harveyi | 0 |
5 | V. parahaemolyticus | 19.5 ± 2.50 * |
No. | Group | Time Till Death (mins) Mean ± S.D | Death Percentage |
---|---|---|---|
1 | Normal control | >720.00 ± 00 | 0 |
2 | Positive control (Formalin 0.25%) (v/v) | 3.62 ± 0.42 * | 100 |
3 | GSF aqueous extract (25 mg/mL) | 43.89 ± 3.97 *# | 100 |
4 | GSF aqueous extract (50 mg/mL) | 27.26 ± 4.65 *#$ | 100 |
5 | GSF aqueous extract (100 mg/mL) | 11.30 ± 2.42 *#$^ | 100 |
No. | Water Parameters | Concentrations | ||||
---|---|---|---|---|---|---|
Groups | Normal Control | Positive Control (Formalin 0.25%) (v/v) | GSF Aqueous Extract (mg/mL) | |||
(25) | (50) | (100) | ||||
1 | Temperature (°C) | 25.6 | 25.9 | 25.9 | 24.9 | 24.9 |
2 | pH | 7.77 | 7.30 | 5.59 | 5.38 | 5.08 |
3 | Salinity (ppt) | 30.0 | 30.9 | 31 | 31 | 31 |
4 | Dissolved oxygen (mg/L) | 7.2 | 6.7 | 7.0 | 7.1 | 7.1 |
Name | R. Time (mins) | Formula | Mass Error (ppm) | Calc. Molecular Mass | Database | Matching Score * | Class |
---|---|---|---|---|---|---|---|
(4R)-4-but-2-yn-1-yl-l-glutamic acid (1) | 3.45 | C9H13NO4 | 0.01 | 199.0845 | ChemSpider | 63.3 | Amino acid |
Isoleucine (2) | 1.43 | C6H13NO2 | 1.11 | 131.0948 | mzCloud | 99.1 | Amino acid |
Tyrosine (3) | 1.07 | C9H11NO3 | 1.05 | 181.0741 | mzCloud | 99.0 | Amino acid |
(1E)-1-Phenyl-1-penten-3-one (4) | 7.73 | C11H12O | −0.14 | 160.0888 | ChemSpider | 60.0 | Aromatic |
(1R,2S,3R,4R)-3-[(Cyclopentylmethyl)amino]-4-phenyl-1,2-cyclopentanediol (5) | 10.01 | C17H25NO2 | −0.26 | 275.1885 | mzCloud | 87.0 | Aromatic |
1-(1H-Benzo[d]imidazol-2-yl)ethan-1-ol (6) | 3.02 | C9H10N2O | 0.50 | 162.0794 | mzCloud | 81.0 | Aromatic |
4-(4-{4-[(7-oxo-6-Propionylnonyl)oxy] phenoxy}butyl)-3,5-heptanedione (7) | 7.52 | C29H44O6 | 1.08 | 488.3143 | ChemSpider | 56.8 | Aromatic |
4-Indolecarbaldehyde (8) | 6.12 | C9H7NO | −0.40 | 145.0527 | mzCloud | 94.7 | Aromatic |
4-Methoxycinnamaldehyde (9) | 5.38 | C10H10O2 | −0.71 | 162.0680 | ChemSpider | 52.4 | Aromatic |
7-Benzoylheptanoic acid (10) | 7.61 | C14H18O3 | −0.14 | 234.1256 | ChemSpider | 73.7 | Aromatic |
Amylcinnamaldehyde (11) | 7.46 | C14H18O | 0.88 | 202.1359 | ChemSpider | 66.0 | Aromatic |
Cinnamaldehyde (12) | 4.37 | C9H8O | 0.21 | 132.0575 | ChemSpider | 60.0 | Aromatic |
Cinnamic acid (13) | 7.13 | C9H8O2 | 0.41 | 148.0525 | ChemSpider | 50.0 | Aromatic |
Heptanophenone (14) | 6.60 | C13H18O | 0.45 | 190.1359 | ChemSpider | 69.8 | Aromatic |
Indole-3-acrylic acid (15) | 5.67 | C11H9NO2 | −0.01 | 187.0633 | mzCloud | 98.3 | Aromatic |
Jasmonal (16) | 11.62 | C14H18O | 0.65 | 202.1359 | ChemSpider | 73.7 | Aromatic |
N-{2-[(4-methylphenyl)thio]pyridin-3-yl}-2-phenylacetamide (17) | 4.82 | C20H18N2OS | −0.13 | 334.1139 | mzCloud | 90.9 | Aromatic |
Psoralen (18) | 4.77 | C11H6O3 | 0.13 | 186.0317 | mzCloud | 81.5 | Aromatic |
Valerophenone (19) | 6.81 | C11H14O | 0.13 | 162.1045 | ChemSpider | 53.6 | Aromatic |
Abscisic acid (20) | 10.09 | C15H20O4 | −0.70 | 264.1360 | mzCloud | 82.7 | Cyclic ketone |
1,2-Dimethyl-4-oxo-1,4-dihydro-3-pyridinyl β-d-glucopyranoside (21) | 4.28 | C13H19NO7 | −0.25 | 301.1161 | ChemSpider | 52.9 | Cyclic ketone |
12-oxo Phytodienoic acid (22) | 8.15 | C18H28O3 | −0.47 | 292.2037 | ChemSpider | 75.8 | Cyclic ketone |
4-(1,3-Butadienyl)-3,5,5-trimethylcyclohex-2-en-1-one (23) | 5.00 | C13H18O | 0.38 | 190.1358 | ChemSpider | 51.4 | Cyclic ketone |
(2Z)-11-Methyl-2-dodecenoic acid (24) | 6.06 | C13H24O2 | −0.15 | 212.1776 | ChemSpider | 80.8 | Fatty acyl |
(4E)-4-Undecen-1-yn-3-ol (25) | 4.87 | C11H18O | 0.15 | 166.1358 | ChemSpider | 69.4 | Fatty acyl |
1-Octyn-3-ol (26) | 4.84 | C8H14O | 1.88 | 126.1047 | ChemSpider | 52.6 | Fatty acyl |
2-[3-(Dimethylamino)-3-oxopropyl]-4-oxopentanedioic acid (27) | 2.99 | C10H15NO6 | −0.31 | 245.0899 | ChemSpider | 82.1 | Fatty acyl |
2-Amino-1,3,4-octadecanetriol (28) | 21.50 | C18H39NO3 | 0.03 | 317.2930 | mzCloud | 82.8 | Fatty acyl |
5,8-Tetradecadienal (29) | 10.66 | C14H24O | −0.17 | 208.1827 | ChemSpider | 65.4 | Fatty acyl |
9-Aminononanoic acid (30) | 4.31 | C9H19NO2 | 0.95 | 173.1417 | ChemSpider | 53.5 | Fatty acyl |
Decanamide (31) | 10.02 | C10H21NO | 0.69 | 171.1624 | mzCloud | 84.8 | Fatty acyl |
Ethyl (2E,4E)-2,4-undecadienoate (32) | 5.38 | C13H22O2 | 0.92 | 210.1622 | ChemSpider | 54.4 | Fatty acyl |
Tetradeca-2Z,5Z,8Z-trien-1-ol (33) | 10.58 | C14H24O | −0.17 | 208.1827 | ChemSpider | 71.2 | Fatty acyl |
2-(3,4-Dihydroxyphenyl)-8-galactopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one (34) | 5.26 | C21H20O11 | −0.04 | 448.1005 | mzCloud | 85.8 | Flavonoid |
5,6,2’-Trimethoxyflavone (35) | 10.16 | C18H16O5 | −0.74 | 312.0995 | mzCloud | 88.4 | Flavonoid |
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-β-d-galactopyranoside (36) | 6.82 | C30H26O14 | 0.39 | 610.1325 | ChemSpider | 68.6 | Flavonoid |
Afzelin (37) | 6.59 | C21H20O10 | 0.19 | 432.1057 | mzCloud | 95.2 | Flavonoid |
Apigenin (38) | 5.84 | C15H10O5 | −0.38 | 270.0527 | mzCloud | 99.5 | Flavonoid |
Cosmosiin (39) | 5.84 | C21H20O10 | −0.09 | 432.1056 | mzCloud | 99.1 | Flavonoid |
Cynaroside (40) | 5.42 | C21H20O11 | −0.45 | 448.1004 | mzCloud | 81.2 | Flavonoid |
Diosmetin (41) | 6.06 | C16H12O6 | −0.87 | 300.0631 | mzCloud | 96.0 | Flavonoid |
Eriodictyol (42) | 5.64 | C15H12O6 | −0.59 | 288.0632 | mzCloud | 98.4 | Flavonoid |
Homoeriodictyol (43) | 6.34 | C16H14O6 | −0.44 | 302.0789 | mzCloud | 86.3 | Flavonoid |
Kaempferol (44) | 5.98 | C15H10O6 | 0.14 | 286.0478 | mzCloud | 99.1 | Flavonoid |
Kaempferol-3-O-β-glucopyranosyl-7-O-α-rhamnopyranoside (45) | 5.54 | C27H30O15 | 0.61 | 594.1588 | mzCloud | 98.9 | Flavonoid |
Kaempferol-7-O-glucoside (46) | 4.95 | C21H20O11 | 0.23 | 448.1007 | mzCloud | 99.3 | Flavonoid |
Luteolin (47) | 5.42 | C15H10O6 | −0.18 | 286.0477 | mzCloud | 97.6 | Flavonoid |
Naringenin (48) | 6.15 | C15H12O5 | −0.31 | 272.0684 | mzCloud | 94.4 | Flavonoid |
Naringin (49) | 6.08 | C27H32O14 | 0.81 | 580.1797 | mzCloud | 94.4 | Flavonoid |
Prunin (50) | 6.15 | C21H22O10 | 0.49 | 434.1215 | mzCloud | 99.0 | Flavonoid |
Quercetin (51) | 5.72 | C15H10O7 | −0.61 | 302.0425 | mzCloud | 99.4 | Flavonoid |
Quercetin-3β-d-glucoside (52) | 5.72 | C21H20O12 | −0.08 | 464.0954 | mzCloud | 98.2 | Flavonoid |
Quercitrin (53) | 6.16 | C21H20O11 | 0.43 | 448.1008 | mzCloud | 89.3 | Flavonoid |
Rutin (54) | 5.58 | C27H30O16 | 0.55 | 610.1537 | mzCloud | 99.1 | Flavonoid |
Sinensin (55) | 4.79 | C21H22O11 | 0.38 | 450.1164 | mzCloud | 85.6 | Flavonoid |
Taxifolin (56) | 4.36 | C15H12O7 | −0.09 | 304.0583 | mzCloud | 93.5 | Flavonoid |
Tiliroside (57) | 7.23 | C30H26O13 | 0.47 | 594.1376 | mzCloud | 98.9 | Flavonoid |
Trifolin (58) | 5.98 | C21H20O11 | 0.54 | 448.1008 | mzCloud | 84.3 | Flavonoid |
Vicenin-2 (59) | 4.87 | C27H30O15 | 1.48 | 594.1594 | mzCloud | 88.0 | Flavonoid |
Wogonin (60) | 10.12 | C16H12O5 | −0.02 | 284.0685 | mzCloud | 88.2 | Flavonoid |
3-Hexyl-4-methyl-2,5-furandione (61) | 6.18 | C11H16O3 | 0.76 | 196.1101 | ChemSpider | 51.9 | Heterocyclic |
D-(+)-Pyroglutamic Acid (62) | 1.12 | C5H7NO3 | 1.15 | 129.0427 | mzCloud | 96.6 | Heterocyclic |
Loliolide (63) | 6.07 | C11H16O3 | 0.76 | 196.1101 | ChemSpider | 61.1 | Heterocyclic |
Maltol (64) | 3.84 | C6H6O3 | 0.85 | 126.0318 | mzCloud | 99.4 | Heterocyclic |
Zeatin (65) | 3.36 | C10H13N5O | 0.17 | 219.1121 | mzCloud | 89.3 | Heterocyclic |
(4R,6R)-4-Hydroxy-6-{2-[(1S,2S,8aR)-2-methyl-1,2,6,7,8,8a-hexahydro-1-naphthalenyl]ethyl}tetrahydro-2H-pyran-2-one (66) | 11.62 | C18H26O3 | −0.23 | 290.1881 | ChemSpider | 62.5 | Lactone |
Sedanolide (67) | 5.76 | C12H18O2 | 0.70 | 194.1308 | ChemSpider | 56.4 | Lactone |
(3S)-3-{[(Allyloxy)carbonyl]amino}-5-[(2,6-dihydroxybenzoyl)oxy]-4-oxopentanoic acid (68) | 3.67 | C16H17NO9 | −0.28 | 367.0902 | ChemSpider | 55.6 | Phenolic |
2-Hydroxycinnamaldehyde (69) | 3.08 | C9H8O2 | 0.13 | 148.0525 | ChemSpider | 64.3 | Phenolic |
3,4-Dihydroxybenzaldehyde (70) | 4.10 | C7H6O3 | 0.11 | 138.0317 | mzCloud | 85.5 | Phenolic |
3R,5R-Sonnerlactone (71) | 11.00 | C14H18O5 | −0.65 | 266.1153 | ChemSpider | 57.9 | Phenolic |
4-(3,4-Dihydroxyphenyl)-6,7-dihydroxy-2-naphthoic acid (72) | 3.47 | C17H12O6 | −1.15 | 312.0630 | mzCloud | 97.0 | Phenolic |
5,7-Dihydroxy-4-methylcoumarin (73) | 5.02 | C10H8O4 | 0.69 | 192.0424 | mzCloud | 93.8 | Phenolic |
6-Gingerol (74) | 9.71 | C17H26O4 | −0.88 | 294.1829 | ChemSpider | 59.8 | Phenolic |
Caffeic acid (75) | 4.06 | C9H8O4 | −0.34 | 180.0422 | mzCloud | 98.8 | Phenolic |
Esculetin (76) | 4.15 | C9H6O4 | −0.32 | 178.0266 | mzCloud | 99.0 | Phenolic |
Esculin (77) | 4.50 | C15H16O9 | −0.65 | 340.0792 | mzCloud | 94.4 | Phenolic |
Ferulic acid (78) | 5.04 | C10H10O4 | 0.32 | 194.0580 | mzCloud | 95.9 | Phenolic |
Isovanillic acid (79) | 3.64 | C8H8O4 | 0.70 | 168.0424 | mzCloud | 83.9 | Phenolic |
Naringeninchalcone (80) | 6.07 | C15H12O5 | −0.02 | 272.0685 | mzCloud | 96.3 | Phenolic |
N-p-Coumaroyltyrosine (81) | 6.09 | C18H17NO5 | −0.56 | 327.1105 | mzCloud | 99.3 | Phenolic |
o-Coumaric acid (82) | 5.12 | C9H8O3 | 0.49 | 164.0474 | mzCloud | 96.8 | Phenolic |
p-Coumaric acid (83) | 4.67 | C9H8O3 | 0.53 | 164.0474 | mzCloud | 80.6 | Phenolic |
Phyllodulcin (84) | 11.12 | C9H8O2 | −0.30 | 148.0524 | ChemSpider | 55.0 | Phenolic |
Sinapinic acid (85) | 4.56 | C11H12O5 | 1.03 | 224.0687 | mzCloud | 94.7 | Phenolic |
Vanillin (86) | 5.42 | C8H8O3 | 0.64 | 152.0474 | mzCloud | 90.5 | Phenolic |
(-)-Caryophyllene oxide (87) | 7.54 | C15H24O | −0.09 | 220.1827 | mzCloud | 86.5 | Terpenoid |
(+)-ar-Turmerone (88) | 6.74 | C15H20O | 0.92 | 216.1516 | ChemSpider | 76.7 | Terpenoid |
epi-Antheindurolide A (89) | 4.56 | C15H20O4 | 0.57 | 264.1363 | mzCloud | 89.6 | Terpenoid |
Geranylacetone (90) | 6.06 | C13H22O | 0.10 | 194.1671 | ChemSpider | 78.1 | Terpenoid |
Nicotinamide (91) | 1.10 | C6H6N2O | 1.69 | 122.0482 | mzCloud | 94.0 | Vitamin B |
Pyridoxine (92) | 1.08 | C8H11NO3 | 1.41 | 169.0741 | mzCloud | 96.4 | Vitamin B |
Steroidal compound | 6.02 | C27H44O7 | −1.01 | 480.3082 | mzCloud | 94.1 | Steroid |
Name | R. Time (mins) | Formula | Mass Error (ppm) | Calc. Molecular Mass | Database | Matching Score * | Class |
---|---|---|---|---|---|---|---|
N-Acetyltryptophan (93) | 5.69 | C13H14N2O3 | 0.20 | 246.1005 | mzCloud | 98.9 | Aromatic |
{(1R,2R)-2-[(2Z)-5-(Hexopyranosyloxy)-2-penten-1-yl]-3-oxocyclopentyl}acetic acid (94) | 4.70 | C18H28O9 | 0.29 | 388.1734 | mzCloud | 87.8 | Cyclic ketone |
Abscisic acid (95) | 9.52 | C15H20O4 | 0.67 | 264.1363 | mzCloud | 81.2 | Cyclic ketone |
(15Z)-9,12,13-Trihydroxy-15-octadecenoic acid (96) | 8.60 | C18H34O5 | 0.34 | 330.2407 | mzCloud | 92.8 | Fatty acyl |
(9Z,11E,13S,15Z)-13-Hydroxy-9,11,15-octadecatrienoic acid (97) | 11.69 | C18H30O3 | 0.42 | 294.2196 | mzCloud | 82.7 | Fatty acyl |
3-tert-Butyladipic acid (98) | 7.20 | C10H18O4 | −1.72 | 202.1202 | mzCloud | 83.7 | Fatty acyl |
Corchorifatty acid F (99) | 8.17 | C18H32O5 | 0.98 | 328.2253 | mzCloud | 97.8 | Fatty acyl |
Dodecanedioic acid (100) | 6.77 | C12H22O4 | −0.93 | 230.1516 | mzCloud | 97.1 | Fatty acyl |
Tetradecanedioic acid (101) | 10.12 | C14H26O4 | −0.08 | 258.1831 | mzCloud | 85.0 | Fatty acyl |
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside (102) | 5.97 | C27H30O15 | 1.42 | 594.1593 | mzCloud | 83.3 | Flavonoid |
Cynaroside (103) | 6.01 | C21H20O11 | 0.49 | 448.1008 | mzCloud | 82.0 | Flavonoid |
Daidzein (104) | 8.70 | C15H10O4 | −0.31 | 254.0578 | mzCloud | 93.2 | Flavonoid |
Quercetin-3β-d-glucoside (105) | 5.75 | C21H20O12 | 0.62 | 464.0958 | mzCloud | 90.2 | Flavonoid |
(1S,4aS,6S,7aS)-4-[(β-d-Glucopyranosyloxy)methyl]-6-hydroxy-7a-methyl-7-methylene-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl 3-methylbutanoate (106) | 7.79 | C22H34O10 | −0.14 | 458.2151 | ChemSpider | 55.6 | Heterocyclic |
1-Caffeoyl-β-d-glucose (107) | 5.43 | C15H18O9 | 0.95 | 342.0954 | ChemSpider | 73.3 | Phenolic |
3-[3-(β-d-Glucopyranosyloxy)-2-hydroxyphenyl]propanoic acid (108) | 4.34 | C15H20O9 | 0.62 | 344.1109 | mzCloud | 80.8 | Phenolic |
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate (109) | 3.51 | C9H10O7S | −0.35 | 262.0146 | ChemSpider | 50.0 | Phenolic |
4-(3,4-Dihydroxyphenyl)-6,7-dihydroxy-2-naphthoic acid (110) | 5.97 | C17H12O6 | 0.62 | 312.0636 | mzCloud | 99.5 | Phenolic |
Caffeoylglycolic acid (111) | 5.51 | C11H10O6 | −1.13 | 238.0475 | ChemSpider | 75.0 | Phenolic |
Esculin (112) | 4.18 | C15H16O9 | 0.23 | 340.0795 | mzCloud | 95.5 | Phenolic |
Salvianolic acid B (113) | 6.62 | C36H30O16 | 1.80 | 718.1547 | mzCloud | 90.5 | Phenolic |
2-[(2S,4aR,8aS)-2-Hydroxy-4a-methyl-8-methylenedecahydro-2-naphthalenyl]acrylic acid (114) | 9.99 | C15H22O3 | −0.20 | 250.1568 | mzCloud | 86.4 | Polycyclic |
Dendronobiloside B (115) | 7.31 | C21H38O8 | 1.47 | 418.2573 | ChemSpider | 59.1 | Terpenoid |
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Venmathi Maran, B.A.; Palaniveloo, K.; Mahendran, T.; Chellappan, D.K.; Tan, J.K.; Yong, Y.S.; Lal, M.T.M.; Joning, E.J.; Chong, W.S.; Babich, O.; et al. Antimicrobial Potential of Aqueous Extract of Giant Sword Fern and Ultra-High-Performance Liquid Chromatography–High-Resolution Mass Spectrometry Analysis. Molecules 2023, 28, 6075. https://doi.org/10.3390/molecules28166075
Venmathi Maran BA, Palaniveloo K, Mahendran T, Chellappan DK, Tan JK, Yong YS, Lal MTM, Joning EJ, Chong WS, Babich O, et al. Antimicrobial Potential of Aqueous Extract of Giant Sword Fern and Ultra-High-Performance Liquid Chromatography–High-Resolution Mass Spectrometry Analysis. Molecules. 2023; 28(16):6075. https://doi.org/10.3390/molecules28166075
Chicago/Turabian StyleVenmathi Maran, Balu Alagar, Kishneth Palaniveloo, Thivyalaxmi Mahendran, Dinesh Kumar Chellappan, Jen Kit Tan, Yoong Soon Yong, Mohammad Tamrin Mohamad Lal, Elliecpearl Jasca Joning, Wei Sheng Chong, Olga Babich, and et al. 2023. "Antimicrobial Potential of Aqueous Extract of Giant Sword Fern and Ultra-High-Performance Liquid Chromatography–High-Resolution Mass Spectrometry Analysis" Molecules 28, no. 16: 6075. https://doi.org/10.3390/molecules28166075