Anti-acetylcholinesterase and Antioxidant Activity of Essential Oils from Hedychium gardnerianum Sheppard ex Ker-Gawl
Abstract
:1. Introduction
2. Results and Discussion
2.1. Essential Oil Composition
Components | %b | |||||
---|---|---|---|---|---|---|
Class | RIa | FU | FO | SC | AC | |
α-Pinene | a | 870 | 0.9 | 0.8 | 0.8 | 0.8 |
β-Pinene | a | 920 | 0.8 | 0.7 | 0.7 | 0.7 |
β-Limonene | a | 986 | 0.1 | t | 0.1 | 0.1 |
Eucalyptol | b | 996 | n.d. | n.d. | t | t |
S-3-Carene | a | 1080 | t | n.d. | t | t |
trans-Limonene oxide | b | 1128 | 0.1 | 0.1 | t | 0.1 |
Cymol | f | 1136 | t | 0.1 | 0.1 | t |
m-Cymene | a | 1178 | t | n.d. | 0.1 | t |
Verbenene | a | 1195 | 0.1 | n.d. | t | 0.1 |
Myrtenal | b | 1201 | 0.1 | 0.1 | 0.1 | 0.1 |
α-Copaene | c | 1416 | 0.7 | 0.1 | 0.1 | 0.1 |
β-Elemene | c | 1434 | 0.1 | n.d. | 0.1 | n.d |
trans-Caryophyllene | c | 1465 | 0.5 | 0.4 | 0.6 | 0.4 |
α-Humulene | c | 1501 | 2.7 | 2.2 | 3.3 | 2.1 |
Neoalloocimene | c | 1510 | 1.1 | 1.1 | 1.2 | 1.3 |
(−)-Calamenene | c | 1523 | 0.1 | 0.1 | 0.1 | 0.1 |
β-Selinene | c | 1536 | n.d. | n.d. | 0.1 | 0.1 |
α-Selinene | c | 1545 | 0.8 | 1.4 | 1.4 | 0.8 |
α-Muurolene | c | 1551 | 1.1 | 0.9 | 1.0 | 0.9 |
α-Farnesene | c | 1559 | 1.1 | 0.5 | 0.9 | 0.5 |
γ-Cadinene | c | 1565 | 3.5 | 3.9 | 3.7 | 3.4 |
Cadalin | c | 1576 | 6.4 | 5.0 | 5.9 | 5.0 |
α-Cadinene | c | 1590 | 0.4 | 0.4 | 0.4 | 0.4 |
3-Methoxycinnamaldehyde | f | 1620 | n.d. | 0.1 | 0.4 | 0.3 |
9,10-Dehydroisolongifolene | c | 1632 | 4.8 | 5.6 | 5.0 | 4.8 |
8,9-Dehydroisolongifolene | c | 1637 | n.d | 3.9 | 3.6 | 4.8 |
trans-α-Bisabolene | c | 1653 | 4.2 | 4.2 | 4.5 | 4.0 |
3,4-Dimethyl-3-cyclohexen-1-carboxaldehyde | f | 1664 | 9.0 | 10.2 | 9.0 | 10.5 |
1,2,3,4,4a,7-Hexahydro-1,6-dimethyl-4-(1-methylethyl)-naphthalene | c | 1669 | 2.2 | 2.5 | 2.1 | 2.3 |
(−)-δ-Selinene | c | 1672 | 0.7 | 0.4 | n.d. | n.d. |
Calamene | c | 1680 | n.d. | 2.4 | 2.2 | 3.1 |
(−)-Cedreanol | d | 1694 | 16.3 | 15.8 | 15.2 | 15.9 |
δ -Cadinene | c | 1705 | 16.5 | 14.6 | n.d. | n.d. |
α-Calacorene | c | 1711 | 1.1 | 1.1 | 15.9 | 16.2 |
Guaiazolene | c | 1730 | 0.4 | 0.5 | 0.5 | 0.5 |
(−)-Isoledene | c | 1741 | 0.3 | 0.3 | 0.3 | 0.3 |
11,14,17-Eicosatrienoic acid methyl ester | e | 2116 | 0.1 | n.d. | 0.1 | 0.1 |
Monoterpene hydrocarbons | a | 1.9 | 1.6 | 1.7 | 1.7 | |
Oxygenated monoterpenes | b | 0.2 | 0.1 | 0.2 | 0.2 | |
Sesquiterpenes hydrocarbons | c | 47.8 | 51.5 | 52.7 | 50.9 | |
Oxygenated sesquiterpenes | d | 16.3 | 15.8 | 15.2 | 15.9 | |
Esters | e | 0.1 | n.d. | 0.1 | 0.1 | |
Others | f | 9.0 | 10.4 | 9.5 | 10.9 | |
Total | 75.0 | 79.5 | 79.3 | 79.8 |
2.2. Acetylcholinesterase (AChE) Inhibition Assay
Essential oils/standard | AChE inhibitory activity | ||
---|---|---|---|
IC50 (mg/mL) | KM (mg/mL) | Vmax (ΔAbs415nm/min) | |
Control | - | 0.466 | 0.0587 |
FU | 1.03 a ± 0.14 | 2.605 | 0.0689 |
FO | 1.17 a ± 0.07 | 1.061 | 0.0390 |
AC | 1.17 a ± 0.09 | 1.261 | 0.0312 |
SC | 1.37 a ± 0.27 | 1.01 | 0.0389 |
α-Pinene | 1.43 a ± 0.07 | 0.453 | 0.0477 |
Ursolic acid | 0.19 b ± 0.014 | 2.410 | 0.0579 |
2.3. Characterization of the Inhibition of Acetylcholinesterase
2.4. DPPH Radical Scavenging Assay
Essential oils/standards | DPPH scavenging activity |
---|---|
EC50 (µg/mL) | |
FU | 8.46 a ± 0.90 |
FO | 28.76 c ± 2.60 |
AC | 31.14 c ± 2.70 |
SC | 15.16 b ± 1.50 |
Quercetin | 3.11 ± 0.06 |
Trolox | 5.63 ± 0.09 |
Ascorbic acid | 10.34 ± 0.28 |
BHT | 31.00 ± 0.19 |
2.5. Artemia salina Cytotoxicity Bioassay
Essential oils /Standard | A. salina Bioassay |
---|---|
LC50 (μg/mL) | |
FU | 375.93 a ± 24.91 |
FO | 300.20 ab ± 15.80 |
AC | 504.67 c ± 24.33 |
SC | 379.93 b ± 94.90 |
Berberine Chloride | 4.12 ± 0.02 |
Phenol | 124.45 ± 0.23 |
Caffeine | >1,000 |
Theophylline | >1,000 |
3. Experimental
3.1. Chemicals
3.2. Plant Collection
3.3. Essential Oils Isolation
3.4. Essential Oils Analysis
3.5. Microplate Assay for AChE Activity
3.6. DPPH Radical Scavenging Assay
3.7. Microwell Cytotoxicity Assay using Artemia salina (Brine Shrimp)
3.8. Statistical Analysis
4. Conclusions
Acknowledgements
- Samples Availability: Hedychium gardnerianum essential oils are available from the authors.
References
- Howes, M.R.; Perry, N.S.L.; Houghton, P.J. Plants with Traditional Uses and Activities, Relevant to the Management of Alzheimer’s Disease and Other Cognitive Disorders. Phytother. Res. 2003, 17, 1–18. [Google Scholar] [CrossRef]
- Perry, N.S.L.; Bollen, C.; Perry, E.K.; Ballard, C. Salvia for dementia therapy: Review of pharmacological activity and pilot tolerability clinical trial. Pharmacol. Biochem. Behav. 2003, 75, 651–659. [Google Scholar] [CrossRef]
- Savelev, S.; Okello, E.; Perry, N.S.L.; Wilkins, R.M.; Perry, E.K. Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil. Pharmacol. Biochem. Behav. 2003, 75, 661–668. [Google Scholar] [CrossRef]
- Mattson, M.P. Pathways towards and away from Alzheimer’s disease. Nature 2004, 430, 631–639. [Google Scholar] [CrossRef]
- Giacobini, E. Cholinesterase Inhibitors Stabilize Alzheimer Disease. Neurochem. Res. 2000, 25, 1185–1190. [Google Scholar] [CrossRef]
- Talesa, V.N. Acetylcholinesterase in Alzheimer’s disease. Mech. Ageing Dev. 2001, 122, 1961–1969. [Google Scholar] [CrossRef]
- Khalid, A.; Zaheer-ul-Haq; Ghayur, M.N.; Feroz, F.; Atta-ur-Rahman; Gilani, A.H.; Choudhary, M.I. Cholinesterase inhibitory and spasmolytic potential of steroidal alkaloids. J. Steroid Biochem. Mol. Biol. 2004, 92, 477–484. [Google Scholar] [CrossRef]
- Ndhlala, A.R.; Finnie, J.F.; Staden, J.V. In Vitro Antioxidant Properties, HIV-1 Reverse Transcriptase and Acetylcholinesterase Inhibitory Effects of Traditional Herbal Preparations Sold in South Africa. Molecules 2010, 15, 6888–6904. [Google Scholar] [CrossRef]
- Silva, L.; Ojeda, E.L.; Rodríguez, J.L.L.; Daehler, C. Biological invasions. In Invasive Terrestrial Flora and Fauna of Macaronesia. Top 100 in Azores, Madeira and Canaries; Silva, L., Ojeda, E.L., Rodríguez, J.L.L., Eds.; ARENA: Ponta Delgada, Portugal, 2008; pp. 192–522. [Google Scholar]
- Medeiros, J.R.; Campos, L.B.; Mendonça, S.C.; Davin, L.B.; Lewis, N.G. Composition and antimicrobial activity of the essential oils from invasive species of the Azores, Hedychium gardnerianum and Pittosporum undulatum. Phytochemistry 2003, 64, 561–565. [Google Scholar] [CrossRef]
- Kumrit, I.; Suksamrarn, A.; Meepawpan, P.; Songsri, S.; Nuntawong, N. Labdane-Type Diterpenes from Hedychium gardnerianum with Potent Cytotoxicity against Human Small Cell Lung Cancer Cells. Phytother. Res. 2010, 24, 1009–1013. [Google Scholar]
- Perry, N.B.; Anderson, R.E.; Brennan, N.J.; Douglas, M.H.; Heaney, A.J.; McGimpsey, J.A.; Smallfield, B.M. Essential oils from Dalmation Sage (Salvia officinalis L.): Variations among individuals, plant parts, seasons and sites. J. Agric. Food Chem. 1999, 47, 2048–2054. [Google Scholar]
- Pedro, L.G.; Santos, P.A.; Silva, J.A.; Figueiredo, A.C.M.; Barroso, J.C.; Deans, S.G.; Looman, A.; Scheffer, J.J.C. Essential oils from Azorean Laurus azorica. Phytochemistry 2001, 57, 245–250. [Google Scholar]
- Orhan, B.; Sener, B. Acetylcholinesterase Inhibitors from Natural Resources: Review. J. Pharm. Sci. 2003, 28, 51–58. [Google Scholar]
- Ingkaninan, K.P.; Temkitthawon, P.; Chuenchom, K.; Yuyaem, T.; Thongnoi, W. Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies. J. Ethnopharmacol. 2003, 89, 261–264. [Google Scholar]
- Orhan, I.; Sener, B.; Choudhary, M.I.; Khalid, A. Acetylcholinesterase and butyrylcholinesterase inhibitory activity of some Turkish medicinal plants. J. Ethnopharmacol. 2004, 91, 57–60. [Google Scholar] [CrossRef]
- Adsersen, A.; Gauguin, B.; Gudiksen, L.; Jager, A.K. Screening of plants used in Danish folk medicine to treat memory dysfunction for acetylcholinesterase inhibitory activity. J. Ethnopharmacol. 2006, 104, 418–422. [Google Scholar] [CrossRef]
- Miyazawa, M.; Kakiuchi, A.; Watanabe, H.; Kameoka, H. Inhibition of acetylcholinesterase activity by volatile α,β-unsaturated ketones. Nat. Prod. Lett. 1988, 12, 131–134. [Google Scholar]
- Savelev, S.U.; Okello, E.J.; Perry, E.K. Butyryl- and acetyl-cholinesterase inhibitory activities in essential oils of Salvia species and their constituents. Phytother. Res. 2004, 18, 315–324. [Google Scholar] [CrossRef]
- Loizzo, M.R.; Tundis, R.; Conforti, F.; Menichini, F.; Bonesi, M.; Nadjafi, F.; Frega, N.; Menichini, F. Salvia leriifolia Benth (Lamiaceae) extract demosntrates in vitro antioxidant properties and cholinesterase inhibitory activity. Nutr. Res. 2010, 30, 823–830. [Google Scholar] [CrossRef]
- Barbosa-Filho, J.M.; Medeiros, K.C.P.; Batista, L.M.; Athaude-Filho, F.P.; Silva, M.S.; Cunha, E.V.L.D.; Almeida, J.R.G.S.; Quintans-Júnior, L.J. Natural Products inhibitors of the enzyme acetylcholinesterase. Braz. J. Phamacongn. 2006, 16, 258–285. [Google Scholar]
- Tepe, B.; Daferera, D.; Sokmen, A.; Sokmen, M.; Polissiou, M. Antimicrobial and antioxidant activities of essential oil and various extracts of Salvia tomentosa Miller (Lamiaceae). Food Chem. 2005, 90, 333–340. [Google Scholar] [CrossRef]
- Miguel, M.G. Antioxidant and anti-inflammatory activities of essential oils: A short review. Molecules 2010, 15, 9252–9287. [Google Scholar] [CrossRef]
- Solis, P.N.; Wright, C.W.; Anderson, M.; Gupta, M.P.; Philhipson, J.D. A Microwell Cytotoxicity Assay using Artemia salina (Brine Shrimp). Planta Med. 1993, 59, 250–252. [Google Scholar] [CrossRef]
- Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectrometry, 2nd ed; Allured Publishing Corporation: Carol Stream, IL, USA, 2001. [Google Scholar]
- Ellman, G.L.; Courtney, K.D.; Andres, V.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88–95. [Google Scholar] [CrossRef]
- Blois, M.S. Antioxidant determinations by the use of a stable free radical. Nature 1961, 181, 1199–1200. [Google Scholar] [CrossRef]
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Arruda, M.; Viana, H.; Rainha, N.; Neng, N.R.; Rosa, J.S.; Nogueira, J.M.F.; Barreto, M.d.C. Anti-acetylcholinesterase and Antioxidant Activity of Essential Oils from Hedychium gardnerianum Sheppard ex Ker-Gawl. Molecules 2012, 17, 3082-3092. https://doi.org/10.3390/molecules17033082
Arruda M, Viana H, Rainha N, Neng NR, Rosa JS, Nogueira JMF, Barreto MdC. Anti-acetylcholinesterase and Antioxidant Activity of Essential Oils from Hedychium gardnerianum Sheppard ex Ker-Gawl. Molecules. 2012; 17(3):3082-3092. https://doi.org/10.3390/molecules17033082
Chicago/Turabian StyleArruda, Miguel, Hugo Viana, Nuno Rainha, Nuno R. Neng, José Silvino Rosa, José M. F. Nogueira, and Maria do Carmo Barreto. 2012. "Anti-acetylcholinesterase and Antioxidant Activity of Essential Oils from Hedychium gardnerianum Sheppard ex Ker-Gawl" Molecules 17, no. 3: 3082-3092. https://doi.org/10.3390/molecules17033082