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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 and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour. ad
b
Nantiya Joycharat , Sonesay Thammavong , Supayang Piyawan cd
e
Voravuthikunchai , Patimaporn Plodpai , Watcharapong c
Mitsuwan , Surasak Limsuwan
ad
& Sanan Subhadhirasakul
af
a
Faculty of Traditional Thai Medicine, Prince of Songkla University, Songkhla 90112, Thailand b
Natural Products Research Center of Excellence, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand c
Faculty of Pharmacy, University of Health Sciences, 7444, Lao PDR, Laos d
Department of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand e
Department of Pest Management, Faculty of Natural Resources, Prince of Songkla University, Songkhla 90112, Thailand f
Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand Published online: 17 Jun 2014.
To cite this article: Nantiya Joycharat, Sonesay Thammavong, Supayang Piyawan Voravuthikunchai, Patimaporn Plodpai, Watcharapong Mitsuwan, Surasak Limsuwan & Sanan Subhadhirasakul (2014) Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour., Natural Product Research: Formerly Natural Product Letters, 28:23, 2169-2172, DOI: 10.1080/14786419.2014.924934 To link to this article: http://dx.doi.org/10.1080/14786419.2014.924934
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.
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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, 2014 Vol. 28, No. 23, 2169–2172, http://dx.doi.org/10.1080/14786419.2014.924934
SHORT COMMUNICATION Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour.
Downloaded by [North Dakota State University] at 01:23 28 October 2014
Nantiya Joycharatab*, Sonesay Thammavongc, Supayang Piyawan Voravuthikunchaidb, Patimaporn Plodpaie, Watcharapong Mitsuwand, Surasak Limsuwanab and Sanan Subhadhirasakulaf a
Faculty of Traditional Thai Medicine, Prince of Songkla University, Songkhla 90112, Thailand; bNatural Products Research Center of Excellence, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand; cFaculty of Pharmacy, University of Health Sciences, 7444 Lao PDR, Laos; dDepartment of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand; e Department of Pest Management, Faculty of Natural Resources, Prince of Songkla University, Songkhla 90112, Thailand; fFaculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand (Received 17 April 2014; final version received 13 May 2014) The stem-derived essential oil of Aglaia odorata Lour. was obtained by hydrodistillation using a Clevenger-type system. Gas chromatography – mass spectrometry analysis of the oil revealed the identification of 39 compounds, representing 76.4% of the oil; germacrene D (20.3%), a-humulene (17.1%), ahimachalene (12.7%) and b-caryophyllene (10.2%) were the major components. Arturmerone (1) and eichlerialactone (2) were isolated from the stem oil and ethanolic stem extract of this plant species, respectively. Antimicrobial activities of the oil and ethanol extract were tested against both Gram-positive and Gram-negative bacterial strains including Bacillus cereus ATCC 11778, Staphylococcus aureus ATCC 25923, Acinetobacter baumannii ATCC 19606 and Escherichia coli ATCC 25922, as well as three rice fungal pathogens Bipolaris oryzae, Pyricularia oryzae and Rhizoctonia solani using broth microdilution method. The oil and 1 exhibited significant antifungal activity against the three rice pathogens tested, whereas 2 exhibited good antibacterial activity against both the Gram-positive pathogens tested. Keywords: Aglaia odorata; antimicrobial activity; ar-turmerone; essential oil; rice pathogens
1. Introduction Aglaia odorata Lour. (Thai name: Prayong) of the Meliaceae family is an ornamental tree that has long been recommended in Thai traditional medicine as a tonic, febrifuge and a remedy for menorrhagia during the menopause (Medical Registration Division 1998). The different parts of A. odorata (leaves, twigs, flowers and roots) have been reported to contain biologically active classes of substances, including flavaglines and bisamides. Some metabolites belonging to flavagline and bisamide groups have been described previously to exhibit anticancer, antimicrobial and insecticidal activities (Greger et al. 2001; Inada et al. 2001; Joycharat et al. 2008). Despite the notable chemical compositions and biological potential of the aforementioned plant parts of A. odorata, knowledge in these areas and studies on the stem of this species are scarce. To the best of our knowledge, antimicrobial activities of compounds or
*Corresponding author. Email: [email protected] q 2014 Taylor & Francis
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N. Joycharat et al.
Downloaded by [North Dakota State University] at 01:23 28 October 2014
extracts of some members of Aglaia have been previously published against a limited number of phytopathogens (Joycharat et al. 2010; Plodpai et al. 2013), but no information is available on the essential oil of A. odorata. The purpose of this work was to investigate the chemical composition and antimicrobial activities of the essential oil and the ethanol extract from the stem of A. odorata against the three economically important rice pathogens, Bipolaris oryzae, Pyricularia oryzae and Rhizoctonia solani, and four bacterial pathogens of medical importance, Bacillus cereus ATCC 11778, Staphylococcus aureus ATCC 25923, Acinetobacter baumannii ATCC 19606 and Escherichia coli ATCC 25922. In addition, antimicrobial efficacy of both isolated compounds, ar-turmerone (1) and eichlerialactone (2), was also determined in parallel experiments. 2. Results and discussion 2.1 Chemical constituents of the stem essential oil of A. odorata The yield of hydrodistilled essential oil from the stem of A. odorata was 0.07%. The essential oil was obtained as a pale yellow liquid with distinct aromatic odour and soluble in petroleum ether. In total, 39 components could be identified corresponding to 76.4% of the stem oil derived from this plant species. Gas chromatography – mass spectrometry (GC –MS) analysis of the oil (Table S1) indicates that the stem-derived oil of A. odorata was dominated by sesquiterpenoids, particularly sesquiterpene hydrocarbons accounting for 73.1%. The principal sesquiterpene components of the oil are germacrene D (20.3%), a-humulene (17.1%), a-himachalene (12.7) and b-caryophyllene (10.2%). Oxygenated sesquiterpenes were also identified in the oil but only in minor amounts (3.1%) with the most significant being ar-turmerone (2.3%). Monoterpene hydrocarbons were present in very small amounts, totalling no more than 0.1%. Further isolation and purification of the stem oil of A. odorata yielded one major aromatic sesquiterpene compound (Figure S1), ar-turmerone (1), already identified by GC – MS in this study. Compound 1 has been previously reported to be the component of Curcuma oil (Singh et al. 2011). This work reported the isolation of 1 from the genus Aglaia for the first time. To the best of our knowledge, only the essential oils from the flowers and leaves of A. odorata have been analysed for their chemical compositions (Lin et al. 1984; Weyerstahl et al. 1999). In comparison to the previously analysed oils of A. odorata, sesquiterpenoid remains the dominant group in stem-, flower-, and leaf-derived oils, suggesting A. odorata oil to be sesquiterpene-rich chemotype. 2.2 Isolation and purification of the stem ethanol extract of A. odorata Chromatographic separation of the ethanol extract of A. odorata stem afforded one main component belonging to the 3,4-secodammarane-type triterpenoid (Figure S1), eichlerialactone (2). This compound has all the 13C resonances similar to its 20R isomer (isoeichlerialactone) recently reported from Aglaia forbesii seed except for the significantly different C-21 signal commonly used to distinguish between 20R and 20S isomers of dammarane-type triterpenoids possessing a tetrahydrofuryl side chain (Joycharat et al. 2010). The present findings demonstrated for the first time the isolation of eichlerialactone (2) from the stem of A. odorata. 2.3 Antimicrobial activities of stem oil, ethanolic stem extract and the isolated compounds The in vitro antimicrobial activities of the essential oil, ethanol extract and the isolated compounds 1 and 2 from A. odorata stem against a total of seven microorganisms, including B. cereus ATCC 11778, S. aureus ATCC 25923, A. baumannii ATCC 19606, E. coli ATCC 25922, B. oryzae, P. oryzae and R. solani, were listed (Table S2). The stem oil of A. odorata exhibited the strongest antifungal activity as compared to those of ethanol extract and eicherialactone (2)
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with minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) values of 0.0625 – 0.5 and 0.25 –1 mg mL21, respectively. The isolated compound from the oil, ar-turmerone (1), exhibited good activity against all the tested fungal pathogens with MIC values ranging from 0.0625 to 0.25 mg mL21 whereas it exhibited no activity against both the Gram-positive bacterial strains tested. Eicherialactone (2) possessed significant antimicrobial activity against some pathogens especially B. cereus ATCC 11778 and P. oryzae with the same MIC value of 0.25 mg mL21. The negative control (1% DMSO) did not show an inhibitory effect on any of the tested microorganisms. The isolated sesquiterpene 1 could be among the active components of the stem oil of A. odorata. Previous report on antifungal activity of essential oils rich in ar-turmerone (1) content has been already established (Singh et al. 2011). Furthermore, the antimicrobial activity of the oil from A. odorata stem can be attributed to the presence of germacrene D, a-humulene, a-himachalene and b-caryophyllene which constituted a high amount in this oil. It has been reported that these compounds containing oils have been considered to display relatively good antimicrobial activity (Sabulal et al. 2006; Aguiar et al. 2013; Meccia et al. 2013). A positive correlation between sesquiterpene content of the oils and the pathogenic fungi inhibition was observed and reported (Chang et al. 2008). Our finding was in accordance with the literature data of the antimicrobial activity of essential oils rich in sesquiterpene content. 3. Conclusion The results described here can be considered as the first study on the chemical composition and antimicrobial activity of the stem essential oil of A. odorata Lour. against some important bacterial and fungal pathogens. In addition, our finding reported for the first time the isolation of ar-turmerone (1) from Aglaia species as well as the antimicrobial efficacy of eicherialactone (2) against some pathogens including B. cereus ATCC 11778 and P. oryzae. Regarding a comparably good antifungal potential of 1 in this study, we suggest the feasibility of its application in agriculture or food industry but further work is needed to examine the suitability in practical applications. Supplementary material Experimental details relating to this work are available online, alongside Tables S1 and S2 and Figure S1. Acknowledgements This article was supported by research grant from the Prince of Songkla University, project number TTM540629S. The authors are grateful to the Petroleum and Petrochemical College, Chulalongkorn University, Thailand, for performing part of the GC – MS experiment.
References Aguiar GP, Carvalho CE, Dias HJ, Reis EB, Martins MH, Wakabayashi KA, Groppo M, Martins CH, Cunha WR, Crotti AE. 2013. Antimicrobial activity of selected essential oils against cariogenic bacteria. Nat Prod Res. 27:1668–1672. Chang HT, Cheng YH, Wu CL, Chang ST, Chang TT, Su YC. 2008. Antifungal activity of essential oil and its constituents from Calocedrus macrolepis var. formosana Florin leaf against plant pathogenic fungi. Bioresour Technol. 99:6266– 6270. Greger H, Pacher T, Brem B, Bacher M, Hofer O. 2001. Insecticidal flavaglines and other compounds from Fijian Aglaia species. Phytochemistry. 57:57–64. Inada A, Nishino H, Kuchide M, Takayasu J, Mukainaka T, Nobukuni Y, Okuda M, Tokuda H. 2001. Cancer chemopreventive activity of odorine and odorinol from Aglaia odorata. Biol Pharm Bull. 24:1282 –1285.
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Joycharat N, Greger H, Hofer O, Saifah E. 2008. Flavaglines and triterpenoids from the leaves of Aglaia forbesii. Phytochemistry. 69:206–211. Joycharat N, Plodpai P, Panthong K, Yingyongnarongkul B, Voravuthikunchai SP. 2010. Terpenoid constituents and antifungal activity of Aglaia forbesii seed against phytopathogens. Can J Chem. 88:937–944. Lin Z, Hua Y, Gu Y. 1984. Studies on the chemical constituents of the essential oils from the leaves of Aglaia odorata. Acta Bot Sin. 26:76–81. Meccia G, Quintero P, Rojas LB, Usubillaga A, Velasco J, Diaz T, Diaz C, Vela´squez J, Toro M. 2013. Chemical composition of the essential oil from the leaves of Carapa guianensis collected from Venezuelan Guayana and the antimicrobial activity of the oil and crude extracts. Nat Prod Commun. 8:1641–1642. Medical Registration Division. 1998. Traditional medicine textbook (Thai drug). Office of the Permanent Secretary for Public Health, Ministry of Public Health, Bangkok. Plodpai P, Petcharat V, Chuenchit S, Chakthong S, Joycharat N, Voravuthikunchai SP. 2013. Desmos chinensis: a new candidate as natural antifungicide to control rice diseases. Ind Crops Prod. 42:324–331. Sabulal B, Dan M, John JA, Kurup R, Pradeep NS, Valsamma RK, George V. 2006. Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: chemical characterization and antimicrobial activity. Phytochemistry. 67:2469–2473. Singh S, Sankar B, Rajesh S, Sahoo K, Subudhi E, Nayak S. 2011. Chemical composition of turmeric oil (Curcuma longa L. cv. Roma) and its antimicrobial activity against eye infecting pathogens. J Essent Oil Res. 23:11– 18. Weyerstahl P, Marschall H, Son PT, Giang PM. 1999. Constituents of the flower essential oil of Aglaia odorata Lour. from Vietnam. Flavour Frag J. 14:219–224.
Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour. ad
b
Nantiya Joycharat , Sonesay Thammavong , Supayang Piyawan cd
e
Voravuthikunchai , Patimaporn Plodpai , Watcharapong c
Mitsuwan , Surasak Limsuwan
ad
& Sanan Subhadhirasakul
af
a
Faculty of Traditional Thai Medicine, Prince of Songkla University, Songkhla 90112, Thailand b
Natural Products Research Center of Excellence, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand c
Faculty of Pharmacy, University of Health Sciences, 7444, Lao PDR, Laos d
Department of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand e
Department of Pest Management, Faculty of Natural Resources, Prince of Songkla University, Songkhla 90112, Thailand f
Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand Published online: 17 Jun 2014.
To cite this article: Nantiya Joycharat, Sonesay Thammavong, Supayang Piyawan Voravuthikunchai, Patimaporn Plodpai, Watcharapong Mitsuwan, Surasak Limsuwan & Sanan Subhadhirasakul (2014) Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour., Natural Product Research: Formerly Natural Product Letters, 28:23, 2169-2172, DOI: 10.1080/14786419.2014.924934 To link to this article: http://dx.doi.org/10.1080/14786419.2014.924934
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 [North Dakota State University] at 01:23 28 October 2014
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, 2014 Vol. 28, No. 23, 2169–2172, http://dx.doi.org/10.1080/14786419.2014.924934
SHORT COMMUNICATION Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour.
Downloaded by [North Dakota State University] at 01:23 28 October 2014
Nantiya Joycharatab*, Sonesay Thammavongc, Supayang Piyawan Voravuthikunchaidb, Patimaporn Plodpaie, Watcharapong Mitsuwand, Surasak Limsuwanab and Sanan Subhadhirasakulaf a
Faculty of Traditional Thai Medicine, Prince of Songkla University, Songkhla 90112, Thailand; bNatural Products Research Center of Excellence, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand; cFaculty of Pharmacy, University of Health Sciences, 7444 Lao PDR, Laos; dDepartment of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand; e Department of Pest Management, Faculty of Natural Resources, Prince of Songkla University, Songkhla 90112, Thailand; fFaculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand (Received 17 April 2014; final version received 13 May 2014) The stem-derived essential oil of Aglaia odorata Lour. was obtained by hydrodistillation using a Clevenger-type system. Gas chromatography – mass spectrometry analysis of the oil revealed the identification of 39 compounds, representing 76.4% of the oil; germacrene D (20.3%), a-humulene (17.1%), ahimachalene (12.7%) and b-caryophyllene (10.2%) were the major components. Arturmerone (1) and eichlerialactone (2) were isolated from the stem oil and ethanolic stem extract of this plant species, respectively. Antimicrobial activities of the oil and ethanol extract were tested against both Gram-positive and Gram-negative bacterial strains including Bacillus cereus ATCC 11778, Staphylococcus aureus ATCC 25923, Acinetobacter baumannii ATCC 19606 and Escherichia coli ATCC 25922, as well as three rice fungal pathogens Bipolaris oryzae, Pyricularia oryzae and Rhizoctonia solani using broth microdilution method. The oil and 1 exhibited significant antifungal activity against the three rice pathogens tested, whereas 2 exhibited good antibacterial activity against both the Gram-positive pathogens tested. Keywords: Aglaia odorata; antimicrobial activity; ar-turmerone; essential oil; rice pathogens
1. Introduction Aglaia odorata Lour. (Thai name: Prayong) of the Meliaceae family is an ornamental tree that has long been recommended in Thai traditional medicine as a tonic, febrifuge and a remedy for menorrhagia during the menopause (Medical Registration Division 1998). The different parts of A. odorata (leaves, twigs, flowers and roots) have been reported to contain biologically active classes of substances, including flavaglines and bisamides. Some metabolites belonging to flavagline and bisamide groups have been described previously to exhibit anticancer, antimicrobial and insecticidal activities (Greger et al. 2001; Inada et al. 2001; Joycharat et al. 2008). Despite the notable chemical compositions and biological potential of the aforementioned plant parts of A. odorata, knowledge in these areas and studies on the stem of this species are scarce. To the best of our knowledge, antimicrobial activities of compounds or
*Corresponding author. Email: [email protected] q 2014 Taylor & Francis
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N. Joycharat et al.
Downloaded by [North Dakota State University] at 01:23 28 October 2014
extracts of some members of Aglaia have been previously published against a limited number of phytopathogens (Joycharat et al. 2010; Plodpai et al. 2013), but no information is available on the essential oil of A. odorata. The purpose of this work was to investigate the chemical composition and antimicrobial activities of the essential oil and the ethanol extract from the stem of A. odorata against the three economically important rice pathogens, Bipolaris oryzae, Pyricularia oryzae and Rhizoctonia solani, and four bacterial pathogens of medical importance, Bacillus cereus ATCC 11778, Staphylococcus aureus ATCC 25923, Acinetobacter baumannii ATCC 19606 and Escherichia coli ATCC 25922. In addition, antimicrobial efficacy of both isolated compounds, ar-turmerone (1) and eichlerialactone (2), was also determined in parallel experiments. 2. Results and discussion 2.1 Chemical constituents of the stem essential oil of A. odorata The yield of hydrodistilled essential oil from the stem of A. odorata was 0.07%. The essential oil was obtained as a pale yellow liquid with distinct aromatic odour and soluble in petroleum ether. In total, 39 components could be identified corresponding to 76.4% of the stem oil derived from this plant species. Gas chromatography – mass spectrometry (GC –MS) analysis of the oil (Table S1) indicates that the stem-derived oil of A. odorata was dominated by sesquiterpenoids, particularly sesquiterpene hydrocarbons accounting for 73.1%. The principal sesquiterpene components of the oil are germacrene D (20.3%), a-humulene (17.1%), a-himachalene (12.7) and b-caryophyllene (10.2%). Oxygenated sesquiterpenes were also identified in the oil but only in minor amounts (3.1%) with the most significant being ar-turmerone (2.3%). Monoterpene hydrocarbons were present in very small amounts, totalling no more than 0.1%. Further isolation and purification of the stem oil of A. odorata yielded one major aromatic sesquiterpene compound (Figure S1), ar-turmerone (1), already identified by GC – MS in this study. Compound 1 has been previously reported to be the component of Curcuma oil (Singh et al. 2011). This work reported the isolation of 1 from the genus Aglaia for the first time. To the best of our knowledge, only the essential oils from the flowers and leaves of A. odorata have been analysed for their chemical compositions (Lin et al. 1984; Weyerstahl et al. 1999). In comparison to the previously analysed oils of A. odorata, sesquiterpenoid remains the dominant group in stem-, flower-, and leaf-derived oils, suggesting A. odorata oil to be sesquiterpene-rich chemotype. 2.2 Isolation and purification of the stem ethanol extract of A. odorata Chromatographic separation of the ethanol extract of A. odorata stem afforded one main component belonging to the 3,4-secodammarane-type triterpenoid (Figure S1), eichlerialactone (2). This compound has all the 13C resonances similar to its 20R isomer (isoeichlerialactone) recently reported from Aglaia forbesii seed except for the significantly different C-21 signal commonly used to distinguish between 20R and 20S isomers of dammarane-type triterpenoids possessing a tetrahydrofuryl side chain (Joycharat et al. 2010). The present findings demonstrated for the first time the isolation of eichlerialactone (2) from the stem of A. odorata. 2.3 Antimicrobial activities of stem oil, ethanolic stem extract and the isolated compounds The in vitro antimicrobial activities of the essential oil, ethanol extract and the isolated compounds 1 and 2 from A. odorata stem against a total of seven microorganisms, including B. cereus ATCC 11778, S. aureus ATCC 25923, A. baumannii ATCC 19606, E. coli ATCC 25922, B. oryzae, P. oryzae and R. solani, were listed (Table S2). The stem oil of A. odorata exhibited the strongest antifungal activity as compared to those of ethanol extract and eicherialactone (2)
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with minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) values of 0.0625 – 0.5 and 0.25 –1 mg mL21, respectively. The isolated compound from the oil, ar-turmerone (1), exhibited good activity against all the tested fungal pathogens with MIC values ranging from 0.0625 to 0.25 mg mL21 whereas it exhibited no activity against both the Gram-positive bacterial strains tested. Eicherialactone (2) possessed significant antimicrobial activity against some pathogens especially B. cereus ATCC 11778 and P. oryzae with the same MIC value of 0.25 mg mL21. The negative control (1% DMSO) did not show an inhibitory effect on any of the tested microorganisms. The isolated sesquiterpene 1 could be among the active components of the stem oil of A. odorata. Previous report on antifungal activity of essential oils rich in ar-turmerone (1) content has been already established (Singh et al. 2011). Furthermore, the antimicrobial activity of the oil from A. odorata stem can be attributed to the presence of germacrene D, a-humulene, a-himachalene and b-caryophyllene which constituted a high amount in this oil. It has been reported that these compounds containing oils have been considered to display relatively good antimicrobial activity (Sabulal et al. 2006; Aguiar et al. 2013; Meccia et al. 2013). A positive correlation between sesquiterpene content of the oils and the pathogenic fungi inhibition was observed and reported (Chang et al. 2008). Our finding was in accordance with the literature data of the antimicrobial activity of essential oils rich in sesquiterpene content. 3. Conclusion The results described here can be considered as the first study on the chemical composition and antimicrobial activity of the stem essential oil of A. odorata Lour. against some important bacterial and fungal pathogens. In addition, our finding reported for the first time the isolation of ar-turmerone (1) from Aglaia species as well as the antimicrobial efficacy of eicherialactone (2) against some pathogens including B. cereus ATCC 11778 and P. oryzae. Regarding a comparably good antifungal potential of 1 in this study, we suggest the feasibility of its application in agriculture or food industry but further work is needed to examine the suitability in practical applications. Supplementary material Experimental details relating to this work are available online, alongside Tables S1 and S2 and Figure S1. Acknowledgements This article was supported by research grant from the Prince of Songkla University, project number TTM540629S. The authors are grateful to the Petroleum and Petrochemical College, Chulalongkorn University, Thailand, for performing part of the GC – MS experiment.
References Aguiar GP, Carvalho CE, Dias HJ, Reis EB, Martins MH, Wakabayashi KA, Groppo M, Martins CH, Cunha WR, Crotti AE. 2013. Antimicrobial activity of selected essential oils against cariogenic bacteria. Nat Prod Res. 27:1668–1672. Chang HT, Cheng YH, Wu CL, Chang ST, Chang TT, Su YC. 2008. Antifungal activity of essential oil and its constituents from Calocedrus macrolepis var. formosana Florin leaf against plant pathogenic fungi. Bioresour Technol. 99:6266– 6270. Greger H, Pacher T, Brem B, Bacher M, Hofer O. 2001. Insecticidal flavaglines and other compounds from Fijian Aglaia species. Phytochemistry. 57:57–64. Inada A, Nishino H, Kuchide M, Takayasu J, Mukainaka T, Nobukuni Y, Okuda M, Tokuda H. 2001. Cancer chemopreventive activity of odorine and odorinol from Aglaia odorata. Biol Pharm Bull. 24:1282 –1285.
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Joycharat N, Greger H, Hofer O, Saifah E. 2008. Flavaglines and triterpenoids from the leaves of Aglaia forbesii. Phytochemistry. 69:206–211. Joycharat N, Plodpai P, Panthong K, Yingyongnarongkul B, Voravuthikunchai SP. 2010. Terpenoid constituents and antifungal activity of Aglaia forbesii seed against phytopathogens. Can J Chem. 88:937–944. Lin Z, Hua Y, Gu Y. 1984. Studies on the chemical constituents of the essential oils from the leaves of Aglaia odorata. Acta Bot Sin. 26:76–81. Meccia G, Quintero P, Rojas LB, Usubillaga A, Velasco J, Diaz T, Diaz C, Vela´squez J, Toro M. 2013. Chemical composition of the essential oil from the leaves of Carapa guianensis collected from Venezuelan Guayana and the antimicrobial activity of the oil and crude extracts. Nat Prod Commun. 8:1641–1642. Medical Registration Division. 1998. Traditional medicine textbook (Thai drug). Office of the Permanent Secretary for Public Health, Ministry of Public Health, Bangkok. Plodpai P, Petcharat V, Chuenchit S, Chakthong S, Joycharat N, Voravuthikunchai SP. 2013. Desmos chinensis: a new candidate as natural antifungicide to control rice diseases. Ind Crops Prod. 42:324–331. Sabulal B, Dan M, John JA, Kurup R, Pradeep NS, Valsamma RK, George V. 2006. Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: chemical characterization and antimicrobial activity. Phytochemistry. 67:2469–2473. Singh S, Sankar B, Rajesh S, Sahoo K, Subudhi E, Nayak S. 2011. Chemical composition of turmeric oil (Curcuma longa L. cv. Roma) and its antimicrobial activity against eye infecting pathogens. J Essent Oil Res. 23:11– 18. Weyerstahl P, Marschall H, Son PT, Giang PM. 1999. Constituents of the flower essential oil of Aglaia odorata Lour. from Vietnam. Flavour Frag J. 14:219–224.
