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Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Chemical constituents, anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau ab
ab
Shi-Jun Liu , Zhi-Xin Liao , Chao Liu
ac
c
& Jin-Yue Sun
a
Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P.R. China b
Click for updates
Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing 211189, P.R. China c
Institute of Agro-Food Science and Technology, Shandong Academy of Agricultural Sciences, 202 Gongye North Road, Jinan 250100, P.R. China Published online: 08 Jan 2015.
To cite this article: Shi-Jun Liu, Zhi-Xin Liao, Chao Liu & Jin-Yue Sun (2015): Chemical constituents, anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.997728 To link to this article: http://dx.doi.org/10.1080/14786419.2014.997728
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions
Natural Product Research, 2015 http://dx.doi.org/10.1080/14786419.2014.997728
SHORT COMMUNICATION Chemical constituents, anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau Shi-Jun Liuab, Zhi-Xin Liaoab*, Chao Liuac and Jin-Yue Sunc
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
a
Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P.R. China; bJiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing 211189, P.R. China; cInstitute of Agro-Food Science and Technology, Shandong Academy of Agricultural Sciences, 202 Gongye North Road, Jinan 250100, P.R. China (Received 2 November 2014; final version received 8 December 2014)
The chemical constituent of the essential oil from Anaphalis lacteal was determined; 31 compounds, representing 93.91% of the total oil, were identified by gas chromatography– mass spectrometry analysis. Three Gram-positive bacteria species, three Gram-negative bacteria species and four fungi were used to determine antimicrobial activity; the results revealed that the essential oil had a remarkable antimicrobial effect against bacteria and a susceptive effect against fungus. The oil also possessed more efficient free-radical scavenging activities than butylated hydroxytoluene (BHT) with 50% inhibitory concentration (IC50) value 31 mg/mL (40 mg/mL for BHT). MTT assay illustrated that the oil expressed certain effect in inhibiting the growth of HeLa and Hep-6 cancer cells. Keywords: Anaphalis lacteal; compositae; chemical constituents; anticancer; antimicrobial; antioxidant activities
1. Introduction The genus Anaphalis consists of 80 species of herbaceous plants mainly distributed in Asia tropical and subtropical areas, 50 of which were discovered in China. Anaphalis lacteal, one species of the genus Anaphalis, was distributed abundantly in Qinghai-Tibet Plateau at an altitude between 2000 and 3400 m. As a Tibetan folk medicine, A. lacteal has long been used for invigorating the circulation of blood, relieving headache and haemostasia (Jiangsu New Medical Collage 1977). In addition, A. lacteal was also reported to have strong activities in curing chronic bronchitis (Yuan et al. 2004). Flavonoids, triterpenoids and steroids were typical
*Corresponding author. Email: [email protected] q 2015 Taylor & Francis
2
S.-J. Liu et al.
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
chemical constituents of A. lacteal, and have been considered responsible for the pharmacological activities of this plant (Bao et al. 2009). Because of its special fragrance, dry grass of A. lacteal was widely used as pillow filling by aboriginal inhabitants of Qinghai province (Flora of China Editorial Committee 1979). However, there were few reports about the essential oil of A. lacteal. In this paper, we describe the chemical composition, potential anticancer, antioxidant and antimicrobial activities of the oil. The whole plant of A. lacteal material (grass) was collected at the altitude of 3300 m from Beishan forest park of Huzhu County (Qinghai Province, China) in July 2012.
2. Results and discussion The obtained oil showed a pale yellow colour and a fragrance of frankincense. Gas chromatography – mass spectrometry was used for analysing the oil, and the compounds were identified on the basis of comparison of their retention index and mass spectra with published data (Adams 2001) and National Institute of Standards and Technology 05 MS (NIST) library data. Thirty-one different components were identified, comprising 93.91% of the total oil. The identified compounds with their retention time and their percentage are listed in Table S1. The results of antimicrobial activity assay of three Gram-positive bacteria, three Gram-negative bacteria and four fungi showed that the essential oil had similar antibacterial activity for Gram-positive bacterium as well as Gram-negative bacterium (See Table 1). Antioxidant activity of the oil was assayed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. As expected, DPPH radical scavenging activities were altered in line with different concentrations of the oil and butylated hydroxytoluene (BHT), as shown in Figure 1. In addition, the IC50 is a parameter often used to evaluate the antioxidant activity (Ye et al. 2013). In our study, the essential oil exhibited an IC50 value of 31 mg/mL, and BHT of 40 mg/mL. The scavenging activity of A. lacteal oil was found stronger than that for BHT at the same concentration. In addition, the effect of different concentrations of the oil on HeLa cell and Hep-6 cell was studied for the first time (See Table 2).
Table 1. Antimicrobial activity of the essential oil against all tested microorganisms. Inhibition zones diameter (mm) Tested microorganism Gram positive Staphylococcus aureus Bacillus subtilis Bacillus cereus Gram negative Escherichia coli Salmonella typhimurium Pseudomonas aeruginosa Fungi Aspergillus niger Saccharomyces cerevisiae Penicillium Fusarium oxysporum Note: Values are mean (n ¼ 3). a Positive control.
Sample
Ampicillina
MIC mg/mL
13 ^ 0.9 16 ^ 0.2 14 ^ 0.8
18 ^ 0.2 18 ^ 0.8 19 ^ 0.7
6.25 6.25 6.25
13 ^ 0.5 14 ^ 0.3 15 ^ 0.6
14 ^ 0.6 15 ^ 0.2 20 ^ 0.4
12.50 6.25 6.25
6 ^ 0.1 11 ^ 0.4 9 ^ 0.7 11 ^ 0.2
14 ^ 0.8 15 ^ 0.3 17 ^ 0.2 17 ^ 0.3
– 3.12 3.12 6.25
Natural Product Research
3
Scavenging activity (%)
100 80 60 40 20 sample BHT
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
0 0
20
40
60
80
100
120
Concentration (ug/ml)
Figure 1. DPPH radical scavenging activity of sample and BHT. Table 2. Cytotoxicity assay of the A. lacteal essential oil on Hela and Hep-6 cell. OD means Cell line
Cytotoxicity (%)
Concentration mg/mL
HeLa
Hep-6
HeLa
Hep-6
0.07 0.7 7 70 140 – 7
2.06 1.96 1.74 1.53 1.07 2.15 0.54
2.24 1.99 1.79 1.50 0.98 2.26 0.54
4.02 8.78 19.29 28.73 50.44 0 75.03
0.93 11.83 20.87 33.64 56.74 0 75.98
Essential oil
DMSO Sophocarpidinea Note: Values are mean (n ¼ 3). a Positive control.
Supplementary material Experimental details relating to this paper are available online, alongside Figures S1 –S3 and Table S1. Funding This work was funded by the State Key Laboratory Cultivation Base for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China [grant number CMEMR2014-B04].
References Adams RP. 2001. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy. Carol Stream, IL: Allured Publishing Corporation. Bao JY, Lu YC, Bai HS. 2009. Quantitative and qualitative analysis on flavonoids in Anaphalis lacteal maxin. J Mol Sci. 25:72–74. Flore of China Editorial Committee. 1979. Flore of China. Vol. 75. Beijing: The First Edition of Science Press. Jiangsu New Medical Collage. 1977. Chinese medicine dictionary. Shanghai: People’s Publishing Press. Ye CL, Dai DH, Hu WL. 2013. Antimicrobial and antioxidant activities of essential oil from onion. Food Control. 30:48–53. Yuan YP, Liu ZP, Jin DQ. 2004. The animal experiments study about the treatment of bronchitis for Anaphalis lacteal. Chin J Comp Med. 16:388–389.
Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Chemical constituents, anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau ab
ab
Shi-Jun Liu , Zhi-Xin Liao , Chao Liu
ac
c
& Jin-Yue Sun
a
Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P.R. China b
Click for updates
Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing 211189, P.R. China c
Institute of Agro-Food Science and Technology, Shandong Academy of Agricultural Sciences, 202 Gongye North Road, Jinan 250100, P.R. China Published online: 08 Jan 2015.
To cite this article: Shi-Jun Liu, Zhi-Xin Liao, Chao Liu & Jin-Yue Sun (2015): Chemical constituents, anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.997728 To link to this article: http://dx.doi.org/10.1080/14786419.2014.997728
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions
Natural Product Research, 2015 http://dx.doi.org/10.1080/14786419.2014.997728
SHORT COMMUNICATION Chemical constituents, anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau Shi-Jun Liuab, Zhi-Xin Liaoab*, Chao Liuac and Jin-Yue Sunc
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
a
Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P.R. China; bJiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, Southeast University, Nanjing 211189, P.R. China; cInstitute of Agro-Food Science and Technology, Shandong Academy of Agricultural Sciences, 202 Gongye North Road, Jinan 250100, P.R. China (Received 2 November 2014; final version received 8 December 2014)
The chemical constituent of the essential oil from Anaphalis lacteal was determined; 31 compounds, representing 93.91% of the total oil, were identified by gas chromatography– mass spectrometry analysis. Three Gram-positive bacteria species, three Gram-negative bacteria species and four fungi were used to determine antimicrobial activity; the results revealed that the essential oil had a remarkable antimicrobial effect against bacteria and a susceptive effect against fungus. The oil also possessed more efficient free-radical scavenging activities than butylated hydroxytoluene (BHT) with 50% inhibitory concentration (IC50) value 31 mg/mL (40 mg/mL for BHT). MTT assay illustrated that the oil expressed certain effect in inhibiting the growth of HeLa and Hep-6 cancer cells. Keywords: Anaphalis lacteal; compositae; chemical constituents; anticancer; antimicrobial; antioxidant activities
1. Introduction The genus Anaphalis consists of 80 species of herbaceous plants mainly distributed in Asia tropical and subtropical areas, 50 of which were discovered in China. Anaphalis lacteal, one species of the genus Anaphalis, was distributed abundantly in Qinghai-Tibet Plateau at an altitude between 2000 and 3400 m. As a Tibetan folk medicine, A. lacteal has long been used for invigorating the circulation of blood, relieving headache and haemostasia (Jiangsu New Medical Collage 1977). In addition, A. lacteal was also reported to have strong activities in curing chronic bronchitis (Yuan et al. 2004). Flavonoids, triterpenoids and steroids were typical
*Corresponding author. Email: [email protected] q 2015 Taylor & Francis
2
S.-J. Liu et al.
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
chemical constituents of A. lacteal, and have been considered responsible for the pharmacological activities of this plant (Bao et al. 2009). Because of its special fragrance, dry grass of A. lacteal was widely used as pillow filling by aboriginal inhabitants of Qinghai province (Flora of China Editorial Committee 1979). However, there were few reports about the essential oil of A. lacteal. In this paper, we describe the chemical composition, potential anticancer, antioxidant and antimicrobial activities of the oil. The whole plant of A. lacteal material (grass) was collected at the altitude of 3300 m from Beishan forest park of Huzhu County (Qinghai Province, China) in July 2012.
2. Results and discussion The obtained oil showed a pale yellow colour and a fragrance of frankincense. Gas chromatography – mass spectrometry was used for analysing the oil, and the compounds were identified on the basis of comparison of their retention index and mass spectra with published data (Adams 2001) and National Institute of Standards and Technology 05 MS (NIST) library data. Thirty-one different components were identified, comprising 93.91% of the total oil. The identified compounds with their retention time and their percentage are listed in Table S1. The results of antimicrobial activity assay of three Gram-positive bacteria, three Gram-negative bacteria and four fungi showed that the essential oil had similar antibacterial activity for Gram-positive bacterium as well as Gram-negative bacterium (See Table 1). Antioxidant activity of the oil was assayed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. As expected, DPPH radical scavenging activities were altered in line with different concentrations of the oil and butylated hydroxytoluene (BHT), as shown in Figure 1. In addition, the IC50 is a parameter often used to evaluate the antioxidant activity (Ye et al. 2013). In our study, the essential oil exhibited an IC50 value of 31 mg/mL, and BHT of 40 mg/mL. The scavenging activity of A. lacteal oil was found stronger than that for BHT at the same concentration. In addition, the effect of different concentrations of the oil on HeLa cell and Hep-6 cell was studied for the first time (See Table 2).
Table 1. Antimicrobial activity of the essential oil against all tested microorganisms. Inhibition zones diameter (mm) Tested microorganism Gram positive Staphylococcus aureus Bacillus subtilis Bacillus cereus Gram negative Escherichia coli Salmonella typhimurium Pseudomonas aeruginosa Fungi Aspergillus niger Saccharomyces cerevisiae Penicillium Fusarium oxysporum Note: Values are mean (n ¼ 3). a Positive control.
Sample
Ampicillina
MIC mg/mL
13 ^ 0.9 16 ^ 0.2 14 ^ 0.8
18 ^ 0.2 18 ^ 0.8 19 ^ 0.7
6.25 6.25 6.25
13 ^ 0.5 14 ^ 0.3 15 ^ 0.6
14 ^ 0.6 15 ^ 0.2 20 ^ 0.4
12.50 6.25 6.25
6 ^ 0.1 11 ^ 0.4 9 ^ 0.7 11 ^ 0.2
14 ^ 0.8 15 ^ 0.3 17 ^ 0.2 17 ^ 0.3
– 3.12 3.12 6.25
Natural Product Research
3
Scavenging activity (%)
100 80 60 40 20 sample BHT
Downloaded by [University of Saskatchewan Library] at 20:59 27 January 2015
0 0
20
40
60
80
100
120
Concentration (ug/ml)
Figure 1. DPPH radical scavenging activity of sample and BHT. Table 2. Cytotoxicity assay of the A. lacteal essential oil on Hela and Hep-6 cell. OD means Cell line
Cytotoxicity (%)
Concentration mg/mL
HeLa
Hep-6
HeLa
Hep-6
0.07 0.7 7 70 140 – 7
2.06 1.96 1.74 1.53 1.07 2.15 0.54
2.24 1.99 1.79 1.50 0.98 2.26 0.54
4.02 8.78 19.29 28.73 50.44 0 75.03
0.93 11.83 20.87 33.64 56.74 0 75.98
Essential oil
DMSO Sophocarpidinea Note: Values are mean (n ¼ 3). a Positive control.
Supplementary material Experimental details relating to this paper are available online, alongside Figures S1 –S3 and Table S1. Funding This work was funded by the State Key Laboratory Cultivation Base for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China [grant number CMEMR2014-B04].
References Adams RP. 2001. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy. Carol Stream, IL: Allured Publishing Corporation. Bao JY, Lu YC, Bai HS. 2009. Quantitative and qualitative analysis on flavonoids in Anaphalis lacteal maxin. J Mol Sci. 25:72–74. Flore of China Editorial Committee. 1979. Flore of China. Vol. 75. Beijing: The First Edition of Science Press. Jiangsu New Medical Collage. 1977. Chinese medicine dictionary. Shanghai: People’s Publishing Press. Ye CL, Dai DH, Hu WL. 2013. Antimicrobial and antioxidant activities of essential oil from onion. Food Control. 30:48–53. Yuan YP, Liu ZP, Jin DQ. 2004. The animal experiments study about the treatment of bronchitis for Anaphalis lacteal. Chin J Comp Med. 16:388–389.
