Isolation of a Marker Olean-12-en-28-butanol Derivative from Viscum continuum E. Mey. Ex Sprague and the Evaluation of Its Antioxidant and Antimicrobial Potentials
Abstract
:1. Introduction
2. Results
2.1. Evaluation of the Purity of the Isolated Compound by TLC and UPLC-MS Analysis
2.2. Elucidation of the Structure of D4 from Its 1D and 2D NMR Data
2.3. In Vitro Quantitative Antimicrobial (MIC) Analysis of D4 Isolated from South African Mistletoe Extract
2.4. In Vitro Antioxidant Potentials of D4
2.4.1. DPPH Radical Scavenging Activity
2.4.2. Hydrogen Peroxide Radical Scavenging Activity
2.4.3. Reducing Power Activity of D4
2.4.4. Concentration Half Minimum (IC50) Potential of D4
3. Discussion
4. Materials and Methods
4.1. Plant Extraction
4.2. UPLC-MS and NMR Instrumentation Used for Structural Elucidation
4.3. Nuclear Magnetic Resonance (NMR)
4.4. Isolation from the Dichloromethane Extract
4.5. Biological Activity Assays of D4
4.5.1. In Vitro Quantitative Antimicrobial (MIC) of D4
4.5.2. DPPH Free Radical Scavenging Activity of the Mistletoe Extracts
4.5.3. Hydrogen Radical Scavenging Activity
4.5.4. Ferric Chloride Reducing Power Assay
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
- Ochocka, J.R.; Piotrowski, A. Biologically active compounds from European mistletoe (Viscum album L.). Can. J. Plant Pathol. 2010, 24, 21–28. [Google Scholar] [CrossRef]
- Szurpnicka, A.; Zjawiony, J.K.; Szterk, A. Therapeutic potential of mistletoe in CNS-related neurological disorders and the chemical composition of Viscum species. J. Ethnopharmacol. 2019, 231, 241–252. [Google Scholar] [CrossRef] [PubMed]
- Bashar, A.; Juvik, O.J.; Dupont, F.; Francis, G.W.; Fossen, T. Novel aminoalkaloids from European mistletoe (Viscum album L.). Phytochem. Lett. 2012, 5, 677–681. [Google Scholar]
- Choudhary, M.I.; Maher, S.; Begum, A.; Abbaskhan, A.; Ali, S.; Khan, A. Characterization and Antiglycation Activity of Phenolic Constituents from Viscum album (European Mistletoe). Chem. Pharm. Bull. 2010, 58, 980–982. [Google Scholar] [CrossRef] [PubMed]
- Omeje, E.O.; Khan, M.P.; Osadebe, P.O.; Tewari, D.; Khan, M.F.; Dev, K.; Chattopadhyay, N. Analysis of constituents of the eastern Nigeria mistletoe, Loranthus micranthus linn revealed presence of new classes of osteogenic compounds. J. Ethnopharmacol. 2014, 151, 643–651. [Google Scholar] [CrossRef] [PubMed]
- Agbo, M.O.; Lai, D.; Okoye, F.B.; Osadebe, P.O.; Proksch, P. Antioxidative polyphenols from Nigerian mistletoe Loranthus micranthus (Linn.) parasitizing on Hevea brasiliensis. Fitoterapia 2013, 86, 78–83. [Google Scholar] [CrossRef] [PubMed]
- Silhavy, T.J.; Kahne, D.; Walker, S. The bacterial cell envelope. Cold Spring Harb Perspect Biol. 2010, 2, a000414. [Google Scholar] [CrossRef] [PubMed]
- Bassey, K.; Mamabolo, P.; Cosa, S. An Andrographolide from Helichrysum caespitium (DC.) Sond. Ex Harv., (Asteraceae) and Its Antimicrobial, Antiquorum Sensing, and Antibiofilm Potentials. Biology 2021, 10, 1224. [Google Scholar] [CrossRef] [PubMed]
- Salar, R.K.; Sharma, P.; Purewal, S.S. In vitro antioxidant and free radical scavenging activities of stem extract of Euphorbia trigona Miller. CELLMED 2015, 5, 14.1–14.6. [Google Scholar] [CrossRef]
- Song, C.; Wei, X.Y.; Qiu, Z.D.; Gong, L.; Chen, Z.Y.; Ma, Y.; Yang, B. Exploring the resources of the genus Viscum for potential therapeutic applications. J. Ethnopharmacol. 2021, 277, 114233. [Google Scholar] [CrossRef] [PubMed]
- Castellano, J.M.; Ramos-Romero, S.; Perona, J.S. Oleanolic Acid: Extraction, Characterization and Biological Activity. Nutrients 2022, 14, 623. [Google Scholar] [CrossRef] [PubMed]
- Yang, Y.; Chen, M.; Sha, C. Triterpenoids, and triterpenoid saponins of Viscum liquidambaricolum. Zhongguo Zhong Yao Za Zhi 2011, 36, 162–165. [Google Scholar] [PubMed]
- Jung, M.J.; Yoo, Y.C.; Lee, K.B.; Kim, J.B.; Song, K.S. Isolation of epi-oleanolic acid from Korean mistletoe and its apoptosis-lnducing activity in tumor cells. Arch. Pharmacal Res. 2004, 27, 840–844. [Google Scholar] [CrossRef]
- Vuyolwethu, K. Extraction, Isolation and Characterization of Oleanolic Acid and Its Analogues from Syzygium Aromaticum (Cloves) and Evaluation of Their Biological Activities. Ph.D. Dissertation, University of Fort Hare, Alice, South Africa, 2019. [Google Scholar]
- Gibbons, S. Anti-staphylococcal plant natural products. Nat. Prod. Rep. 2004, 21, 263–277. [Google Scholar] [CrossRef] [PubMed]
- Lin, M.; Han, P.; Li, Y.; Wang, W.; Lai, D.; Quinoa, L.Z. Secondary Metabolites and Their Biological Activities or Functions. Molecules 2019, 24, 2512. [Google Scholar] [CrossRef]
- Nicoletti, M. The Antioxidant Activity of Mistletoes (Viscum album and Other Species). Plants 2023, 12, 2707. [Google Scholar] [CrossRef] [PubMed]
- Vlad, D.C.; Popescu, R.; Dumitrascu, V.; Cimporescu, A.; Vlad, C.S.; Vágvölgyi, C.; Krisch, J.; Dehelean, C.; Horhat, F.G. Phytocomponents identification in mistletoe (Viscum album) young leaves and branches, by GC-MS and antiproliferative effect on HEPG2 and MCF7 cell lines. Farmacia J. 2004, 2016, 82–86. [Google Scholar]
- Adeosun, I.J.; Baloyi, I.T.; Cosa, S. Anti-biofilm and associated anti-virulence activities of selected phytochemical compounds against Klebsiella pneumoniae. Plants 2022, 11, 1429. [Google Scholar] [CrossRef] [PubMed]
- Hlophe, S.; Bassey, K. Phytochemical Profiling, and Antioxidant Potentials of South African and Nigerian Loranthus micranthus Linn.: The African Mistletoe Exposé. Plants 2023, 12, 2016. [Google Scholar] [CrossRef] [PubMed]
Position | 13C NMR OF D4 | 1H (Multiplicity) |
---|---|---|
1 | 32.63 (CH2) | 1.76 (dt, J = 27.4, 13.6, 4.2 Hz |
2 | 27.19 (CH2) | 1.66 (m) |
3 | 79.05 (CH) | 3.24 (dd, J = 11.4, 4.4 Hz |
4 | 46.53 (CQ) | - |
5 | 38.41 CH) | 0.94 (m) |
6 | 23.40 (CH2) | 1.89 (m) |
7 | 22.93 (CH2) | 1.67 (m) |
8 | 45.89 (CH) | 1.24 (m) |
9 | 37.10 (CH) | 1.41 (m) |
10 | 39.29 (CQ) | - |
11 | 25.93 (CH2) | 1.11 (dt, J = 14.5, 4.90 Hz)) |
12 | 122.66 (CH) | 5.32 (t, J = 3.7 Hz) |
13 | 143.59 (CQ) | - |
14 | 33.81 (CQ) | - |
15 | 27.69 (CH2) | 1.78 (m) |
16 | 23.57 (CH2) | 1.95 (dt, J = 10.0, 4.7 Hz) |
17 | 41.00 (CQ) | 2.82 (m) |
18 | 41.61 (CH) | 2.88 (m) |
19 | 38.76 (CH2) | 1.63 (m) |
20 | 32.45 (CH) | 1.84 (m) |
21 | 30.67 (CH2) | 1.30 (m) |
22 | 28.10 (CH2) | 1.02 |
23 | 15.53 (CH3) | 0.81 (s) |
24 | 15.32 (CH3) | 0.93 (s) |
25 | 18.30 (CH3) | 1.59 (s) |
26 | 17.14 (CH3) | 0.79 (s) |
27 | 1.01 (CH3) | 0.09 (s) |
28 | 183.14 (CQ) | - |
29 | 33.06 (CH2) | 1.67 (m) |
30 | 47.64 (CH2) | 1.55 (dt, J = 14.2, 5.3 Hz) |
31 | 55.24 (CH2) | 0.79 (d, J = 8.9 Hz) |
MIC (mg/mL) | |||||
---|---|---|---|---|---|
Analytes | Pseudomonas aeruginosa | Streptococcus pyogenes | Staphylococcus aureus | Bacillus subtilis | Escherichia coli |
D4 | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Ciprofloxacin | 0.0039 | 0.0039 | 0.0078 | 0.0156 | 0.0039 |
IC50 Values in mg/mL | |||
---|---|---|---|
Analytes | DPPH Scavenging | H2O2 Scavenging | Fe+3 Reducing Power |
D4 | 0.398 | 0.701 | 0.533 |
Gallic acid | 0.175 | 0.793 | 0.284 |
BHT | 0.072 | 0.329 | 0.422 |
MS Conditions | ||
---|---|---|
Detector | Waters® Synapt G2QTOF | |
Calibration mass range | 50–1200 m/z | |
Capillary voltage | ESI+ 2.6 KV; ESI− 2.4 KV | |
Ionization mode | Both ESI+ and ESI− | |
Source temperature | 120 °C | |
Sampling cone | 20 V | |
Extraction cone | 4.0 V | |
Desolvation temperature | 300 °C | |
Cone gas flow | 20.0 L/Hr | |
Desolvation gas flow | 600.0 L/Hr | |
Data management | MassLynxTM (version 4.1 UNIFI) | |
UPLC Conditions | ||
System | Waters Acquity UPLC | |
Column | Kinetex® 1.7 µm EVO C18 100 Å (2.1 mm ID × 100 mm length) | |
Injection volume | 5 µl | |
Column temperature | 50 °C | |
Sample temperature | 8 °C | |
Flow rate | 0.3 mL/min | |
Mobile phase A | Water + 0.1% formic acid | |
Mobile phase B | Acetonitrile 0.1% formic acid | |
Gradient | ||
Time (min) | %A | %B |
Initial | 97.0 | 3.0 |
0.10 | 97.0 | 3.0 |
14.00 | 0 | 100.00 |
16.00 | 0 | 100.00 |
16.50 | 97.0 | 3.0 |
20.00 | 97.0 | 3.0 |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Mapfumari, S.; Matseke, B.; Bassey, K. Isolation of a Marker Olean-12-en-28-butanol Derivative from Viscum continuum E. Mey. Ex Sprague and the Evaluation of Its Antioxidant and Antimicrobial Potentials. Plants 2024, 13, 1382. https://doi.org/10.3390/plants13101382
Mapfumari S, Matseke B, Bassey K. Isolation of a Marker Olean-12-en-28-butanol Derivative from Viscum continuum E. Mey. Ex Sprague and the Evaluation of Its Antioxidant and Antimicrobial Potentials. Plants. 2024; 13(10):1382. https://doi.org/10.3390/plants13101382
Chicago/Turabian StyleMapfumari, Sipho, Buang Matseke, and Kokoette Bassey. 2024. "Isolation of a Marker Olean-12-en-28-butanol Derivative from Viscum continuum E. Mey. Ex Sprague and the Evaluation of Its Antioxidant and Antimicrobial Potentials" Plants 13, no. 10: 1382. https://doi.org/10.3390/plants13101382