Chemical Analysis and Biological Activity of the Essential Oils of Two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis
Abstract
:1. Introduction
2. Results and Discussion
2.1. Essential oil analysis
Compounda | RIb | RA (%)c in N. chinensis | RA (%)c in V. officinalis |
---|---|---|---|
α-Pinene | 927 | t | 14.81 |
Camphene | 941 | - | 6.51 |
p-Cymene | 1010 | 0.11 | - |
D-Limonene | 1014 | - | 6.56 |
Eucalyptol | 1017 | 0.52 | - |
γ-Terpinene | 1047 | t | - |
Terpinene-4-ol | 1175 | t | - |
O-Methylthymol | 1235 | t | - |
O-Methylcarvacrol | 1245 | 0.15 | - |
Bornyl acetate | 1289 | - | 6.73 |
1,2,3-Trimethylindene | 1324 | 0.14 | - |
β-Patchoulene | 1388 | 0.63 | 2.32 |
β-Elemene | 1396 | 0.24 | 0.83 |
10-Epicyperene | 1407 | 0.24 | - |
β-Maaliene | 1418 | 6.70 | - |
β-Caryophyllene | 1426 | - | 1.17 |
Aristolene | 1427 | 3.74 | - |
trans-α-Farnesene | 1440 | - | 0.34 |
α-Guaiene | 1442 | - | 3.62 |
Calarene | 1444 | 25.31 | - |
Epizonarene | 1450 | 0.90 | - |
α-Caryophyllene | 1461 | - | 1.90 |
β-Humulene | 1464 | - | 8.19 |
α-Gurjunene | 1465 | 5.72 | - |
α-Elemene | 1468 | - | 1.21 |
Selina-4,11-diene | 1481 | - | 0.42 |
trans-β-Ionone | 1491 | 3.81 | - |
β-Helmiscapene | 1493 | - | 1.11 |
δ-Selinene | 1501 | - | 2.68 |
α-Bulnesene | 1501 | 1.38 | 7.10 |
Bornyl isovalerate | 1521 | - | 1.31 |
α-Panasinsene | 1526 | 0.47 | 3.21 |
δ-Amorphene | 1529 | 0.52 | - |
1,2-Diisopropylbenzene | 1572 | 0.62 | - |
α-Selinene | 1577 | 7.32 | - |
Spathulenol | 1587 | 6.28 | - |
Globulol | 1593 | 2.96 | - |
1,2-Dimethyl-4-formyl-1-cyclohexene | 1617 | - | 1.34 |
Patchoulol | 1672 | 5.87 | 16.75 |
Valeranone | 1685 | 5.78 | - |
Aristolone | 1776 | 13.35 | - |
Total identified | 92.76 | 88.11 | |
Monoterpene hydrocarbons | 0.11 | 27.88 | |
Oxygenated monoterpenes | 0.67 | 9.38 | |
Sesquiterpene hydrocarbons | 53.17 | 34.10 | |
Oxygenated sesquiterpenes | 34.24 | 18.14 |
2.2. Antimicrobial activity
Test microorganism | N. chinensis oil | V. officinalis oil | Positive control a | |||
---|---|---|---|---|---|---|
MIC (μg/mL) | IC50 (μg/mL) b | MIC (μg/mL) | IC50 (μg/mL) b | MIC (μg/mL) | IC50 (μg/mL) b | |
A. tumefaciens | 62.5 | 36.93 ± 0.51 | 62.5 | 40.00 ± 0.53 | 15 | 8.34 ± 0.09 |
E. coli | 150 | 100.23 ± 0.76 | 200 | 131.88 ± 3.20 | 20 | 10.47 ± 0.31 |
P. lachrymans | 300 | 236.06 ± 1.62 | 100 | 60.05 ± 0.38 | 15 | 9.01 ± 0.09 |
S. typhimurium | 400 | 263.16 ± 2.25 | 200 | 144.11 ± 2.70 | 120 | 91.46 ± 0.55 |
X. vesicatoria | 100 | 54.25 ± 0.83 | 125 | 78.16 ± 1.09 | 20 | 11.62 ± 0.19 |
B. subtilis | 125 | 91.95 ± 0.09 | 62.5 | 48.74 ± 0.65 | 10 | 4.98 ± 0.06 |
S. aureus | 200 | 110.62 ± 2.19 | 200 | 123.39 ± 0.66 | 100 | 78.60 ± 0.61 |
S. haemolyticus | 100 | 67.13 ± 0.69 | 62.5 | 47.37 ± 0.82 | 15 | 7.75 ± 0.16 |
C. albicans | 400 | 374.72 ± 2.46 | 200 | 165.74 ± 1.18 | 900 | 713.13 ± 1.49 |
M. oryzae | 500 | 296.51 ± 2.75 | 200 | 142.59 ± 0.77 | 100 | 38.44 ± 0.56 |
2.3. Antioxidant activity
Sample | DPPH inhibition IC50 b (μg/mL) | β-Carotene bleaching IC50 b (μg/mL) | Ferrozine-Fe2+ complex formation IC50 b (μg/mL) |
---|---|---|---|
N. chinensis oil | 637.47 ± 4.89 | 240.56 ± 0.66 | 231.89 ± 2.66 |
V. officinalis oil | 493.40 ± 4.93 | 181.18 ± 2.82 | 235.44 ± 5.18 |
Positive control a | 25.66 ± 0.42 | 31.46 ± 0.68 | 18.46 ± 0.08 |
3. Experimental
3.1. Plant materials
3.2. Solvents and chemicals
3.3. Preparation of the essential oils
3.4. Oil analysis
3.5. Antimicrobial activity
3.5.1. Antibacterial activity assay
3.5.2. Antifungal activity assay
3.6. Antioxidant activity
3.6.1. DPPH radical scavenging assay
3.6.2. β-Carotene-linoleic acid bleaching assay
3.6.3. Metal chelating activity on ferrous ions (Fe2+)
4. Conclusions
Acknowledgements
- Sample Availability: Samples of the essential oils are available from the authors.
References
- Tripathi, P.; Dubey, N.K. Exploitation of natural products as an alternative strategy to control postharvest fungal rotting of fruit and vegetables. Postharvest Biol. Technol. 2004, 32, 235–245. [Google Scholar] [CrossRef]
- Burt, S. Essential oils: their antibacterial properties and potential applications in foods – a review. Int. J. Food Microbiol. 2004, 94, 223–253. [Google Scholar] [CrossRef]
- Bakkali, F.; Averbeck, S.; Averbeck, D.; Idaomar, M. Biological effects of essential oils – a review. Food Chem. Toxicol. 2008, 46, 446–475. [Google Scholar] [CrossRef]
- Dudareva, N.; Negre, F.; Nagegowda, D.A.; Orlova, I. Plant volatiles: recent advances and future perspectives. Crit. Rev. Plant Sci. 2006, 25, 417–440. [Google Scholar] [CrossRef]
- Rajendran, S.; Sriranjini, V. Plant products as fumigants for stored-product insect control. J. Stored Prod. Res. 2008, 44, 126–135. [Google Scholar] [CrossRef]
- Zhou, L.; Wedge, D.E. Agricultural application of higher plants for their antimicrobial potentials in China. In Crop Protection Research Advance; Burton, E.N., Williams, P.V., Eds.; Nova Science Publishers: New York, USA, 2008; pp. 213–233. [Google Scholar]
- Palmeira-de-Oliveira, A.; Salgueiro, L.; Palmeira-de-Oliveira, R.; Martinez-de-Oliveira, J.; Pina-Vaz, C.; Queiroz, J.A.; Rodrigues, A.G. Anti-Candida activity of essential oils. Mini-Rev. Med. Chem. 2009, 9, 1292–1305. [Google Scholar] [CrossRef]
- Bell, C.D. Preliminary phylogeny of Valerianaceae (Dipsacales) inferred from nuclear and chloroplast DNA sequence data. Mol. Phylogenet. Evol. 2004, 31, 340–350. [Google Scholar] [CrossRef]
- Lu, A.; Chen, S. Flora Reipublicae Popularis Sinicae; Science Press: Beijing, China, 1986; Tomus 73. [Google Scholar]
- Itokawa, H.; Masuyama, K.; Morita, H.; Takeya, K. Cytotoxic sesquiterpenes from Nardostachys chinensis. Chem. Pharm. Bull. 1993, 41, 1183–1184. [Google Scholar] [CrossRef]
- Lee, S.J.; Choi, Y.H.; Choi, B.T. Inhibitory effects of aqueous extracts from Nardostachys chinensis on α-melanocyte stimulating hormone-induced melanogenesis in B16F10 cells. Integr. Biosci. 2006, 10, 233–236. [Google Scholar] [CrossRef]
- Letchamo, W.; Ward, W.; Heard, B.; Heard, D. Essential oil of Valeriana officinalis L. cultivars and their antimicrobial activity as influenced by harvesting time under commercial organic cultivation. J. Agric. Food Chem. 2004, 52, 3915–3919. [Google Scholar] [CrossRef]
- Pavlovic, M.; Kovacevic, N.; Tzakou, O.; Couladis, M. The essential oil of Valeriana officinalis L. growing wild in western Serbia. J. Essent. Oil Res. 2004, 16, 397–399. [Google Scholar] [CrossRef]
- Ashnagar, A.; Naseri, N.G.; Abadi, A.G.A. Isolation and identification of the major chemical compounds found in the essential oil obtained from the roots of valerian plant. Int. J. Chem. Sci. 2006, 4, 739–746. [Google Scholar]
- Raal, A.; Arak, E.; Orav, A.; Kailas, T.; Muurisepp, M. Variation in the composition of the essential oil of commercial Valeriana officinalis L. roots from different countries. J. Essent.Oil Res. 2008, 20, 524–529. [Google Scholar] [CrossRef]
- Huang, B.; Qin, L.; Liu, Y.; Zhang, Q.; Rahman, K.; Zheng, H. Chemical composition and hypnotic activities of the essential oil from roots of Valeriana officinalis var. latifolia in China. Chem. Nat. Compd. 2009, 45, 560–561. [Google Scholar] [CrossRef]
- Huang, B.; Qin, L.; Chu, Q.; Zhang, Q.; Gao, L.; Zheng, H. Comparison of headspace SPME with hydrodistillation and SFE for analysis of the volatile components of the roots of Valeriana officinalis var. latifolia. Chromatographia 2009, 69, 489–496. [Google Scholar] [CrossRef]
- Seidler-Lozykowska, K.; Mielcarek, S.; Baraniak, M. Content of essential oil and valerenic acids in valerian (Valeriana officinalis L.) roots at the selected developmental phases. J. Essent. Oil Res. 2009, 21, 413–416. [Google Scholar] [CrossRef]
- Tanaka, K.; Komatsu, K. Comparative study on volatile components of Nardostachys rhizome. J. Nat. Med. 2008, 62, 112–116. [Google Scholar] [CrossRef]
- Huang, B.; Qin, L.; Chu, Q.; Zhang, Q.; Gao, L.; Zheng, H. Comparison of headspace SPME with hydrodistillation and SFE for analysis of the volatile components of the roots of Valeriana officinalis var. latifolia. Chromatographia 2009, 69, 489–496. [Google Scholar] [CrossRef]
- Tan, M.; Zhou, L.; Qin, M.; Li, D.; Jiang, W.; Wang, Y.; Hao, X. Chemical composition and antimicrobial activity of the flower oil of Russowia sogdiana (Bunge) B. Fedtsch. (Asteraceae) from China. J. Essent. Oil Res. 2007, 19, 197–200. [Google Scholar] [CrossRef]
- Goel, D.; Singh, V.; Ali, M.; Mallavarupu, G.R.; Kumar, S. Essential oils of petal, leaf and stem of the antimalarial plant Artemisia annua. J. Nat. Med. 2007, 61, 187–191. [Google Scholar]
- Tanaka, K.; Komatsu, K. Comparative study on volatile components of Nardostachys rhizome. J. Nat. Med. 2008, 62, 112–116. [Google Scholar] [CrossRef]
- Tabanca, N.; Wedge, D.E.; Wang, X.; Demirci, B.; Baser, K.H.C.; Zhou, L.; Cutler, S.J. Chemical composition and antifungal activity of Angelica sinensis essential oil against three Colletotrichum species. Nat. Prod. Commun. 2008, 3, 1073–1078. [Google Scholar]
- Gong, Y.; Huang, Y.; Zhou, L.; Shi, X.; Guo, Z.; Wang, M.; Jiang, W. Chemical composition and antifungal activity of the fruit oil of Zanthoxylum bungeanum Maxim. (Rutaceae) from China. J. Essent. Oil Res. 2009, 21, 174–178. [Google Scholar] [CrossRef]
- Bisht, D.S.; Padalia, R.C.; Joshi, S.C.; Singh, K.K.; Mathela, C.S. Sesquiterpene hydrocarbons rich essential oil of Stachys sericea Wall. J. Essent. Oil Bearing Plants 2008, 11, 586–590. [Google Scholar]
- Elaissi, A.; Marzouki, H.; Medini, H.; Khouja, M.L.; Farhat, F.; Lynene, F.; Harzallah-Skhiri, F.; Chemli, R. Variation in volatile leaf oils of 13 Eucalyptus species harvested from Souinet Arboreta (Tunisia). Chem. Biodivers. 2010, 7, 909–921. [Google Scholar] [CrossRef]
- Magina, M.D.A.; Dalmarco, E.M.; Wisniewski, A.; Simionatto, E.L.; Dalmarco, J.B.; Pizzolatti, M.G.; Brighente, I.M.C. Chemical composition and antibacterial activity of essential oils of Eugenia species. J. Nat. Med. 2009, 63, 345–350. [Google Scholar]
- Langfied, R.D.; Scarano, F.J.; Heitzman, M.E.; Kondo, M.; Hammond, G.B.; Neto, C.C. Use of a modified microplate bioassay method to investigate antibacterial activity in the Peruvian medicinal plant Peperomia galioides. J. Ethnopharmacol. 2004, 94, 279–281. [Google Scholar] [CrossRef]
- Abe, K.; Matsuki, N. Measurement of cellular 3 -(4,5 - dimethylthiazol - 2 - yl) - 2,5 –diphenyl tetrazolium bromide (MTT) reduction activity and lactate dehydrogenase release using MTT. Neurosci. Res. 2000, 38, 325–329. [Google Scholar] [CrossRef]
- Sakuma, M. Probit analysis of preference data. Appl. Entomol. Zool. 1998, 33, 339–347. [Google Scholar]
- Liu, H.; Wang, J.; Zhao, J.; Lu, S.; Wang, J.; Jiang, W.; Ma, Z.; Zhou, L. Isoquinoline alkaloids from Macleaya cordata active against plant microbial pathogens. Nat. Prod. Commun. 2009, 4, 1557–1560. [Google Scholar]
- Wang, J.; Liu, H.; Zhao, J.; Gao, H.; Zhou, L.; Liu, Z.; Chen, Y.; Sui, P. Antimicrobial and antioxidant activities of the root bark essential oil of Periploca sepium and its main component 2-hydroxy-4-methoxybenzaldehyde. Molecules 2010, 15, 5807–5817. [Google Scholar]
- Ono, M.; Oda, E.; Tanaka, T.; Iida, Y.; Yamasaki, T.; Masuoka, C.; Ikeda, T.; Nohara, T. DPPH radical-scavenging effect on some constituents from the aerial parts of Lippia triphylla. J. Nat. Med. 2008, 62, 101–106. [Google Scholar]
- Ebrahimabadi, A.H.; Ebrahimabadi, E.H.; Djafari-Bidgoli, Z.; Kashi, F.J.; Mazoochi, A.; Batooli, H. Composition and antioxidant and antimicrobial activity of the essential oil and extracts of Stachys inflata Benth from Iran. Food Chem. 2010, 119, 452–458. [Google Scholar]
- Oke, F.; Aslim, B.; Ozturk, S.; Altundag, S. Essential oil composition, antimicrobial and antioxidant activities of Satureja cuneifolia Ten. Food Chem. 2009, 112, 874–879. [Google Scholar] [CrossRef]
- Yamaguchi, F.; Ariga, T.; Yoshimira, Y.; Nakazawa, H. Antioxidant and anti-glycation of carcinol from Garcinia indica fruit rind. J. Agric. Food Chem. 2000, 48, 180–185. [Google Scholar] [CrossRef]
- Okoh, O.; Sadimenko, A.; Afolayan, A. Comparative evaluation of the antibacterial activities of the essential oils of Rosmarinus officinalis L. obtained by hydrodistillation and solvent free microwave extraction methods. Food Chem. 2010, 120, 308–312. [Google Scholar] [CrossRef]
© 2010 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 license (http://creativecommons.org/licenses/by/3.0/).
Share and Cite
Wang, J.; Zhao, J.; Liu, H.; Zhou, L.; Liu, Z.; Wang, J.; Han, J.; Yu, Z.; Yang, F. Chemical Analysis and Biological Activity of the Essential Oils of Two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis. Molecules 2010, 15, 6411-6422. https://doi.org/10.3390/molecules15096411
Wang J, Zhao J, Liu H, Zhou L, Liu Z, Wang J, Han J, Yu Z, Yang F. Chemical Analysis and Biological Activity of the Essential Oils of Two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis. Molecules. 2010; 15(9):6411-6422. https://doi.org/10.3390/molecules15096411
Chicago/Turabian StyleWang, Jihua, Jianglin Zhao, Hao Liu, Ligang Zhou, Zhilong Liu, Jingguo Wang, Jianguo Han, Zhu Yu, and Fuyu Yang. 2010. "Chemical Analysis and Biological Activity of the Essential Oils of Two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis" Molecules 15, no. 9: 6411-6422. https://doi.org/10.3390/molecules15096411