DSpace at VNU: Terpinen-4-ol-rich Essential Oil from the Fresh Rhizomes of Zingiber pellitum of Vietnam

This article was downloaded by: [Heriot-Watt University] On: 28 December 2014, At: 20:15 Publisher: Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK Journal of Essential Oil Bearing Plants Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/teop20 Terpinen-4-ol-rich Essential Oil from the Fresh Rhizomes of Zingiber pellitum of Vietnam a a Phan Minh Giang , Phan Tong Son & Wilfried A König b a Faculty of Chemistry, College of Natural Science , Vietnam National University, Hanoi, 19 Le Thanh Tong Street, Hanoi , Vietnam b Institut für Organische Chemie, Universität Hamburg , Martin-Luther-King-Platz 6, D-20146 , Hamburg , Germany Published online: 12 Mar 2013 To cite this article: Phan Minh Giang , Phan Tong Son & Wilfried A König (2011) Terpinen-4-ol-rich Essential Oil from the Fresh Rhizomes of Zingiber pellitum of Vietnam, Journal of Essential Oil Bearing Plants, 14:4, 494-497, DOI: 10.1080/0972060X.2011.10643607 To link to this article: http://dx.doi.org/10.1080/0972060X.2011.10643607 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 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/terms-and-conditions Jeobp 14 (4) 2011 pp 494 - 497 494 Journal of Essential Oil Bearing Plants ISSN Print: 0972-060X Online: 0976-5026 www.jeobp.com Terpinen-4-ol-rich Essential Oil from the Fresh Rhizomes of Zingiber pellitum of Vietnam Phan Minh Giang 1*, Phan Tong Son and Wilfried A König Downloaded by [Heriot-Watt University] at 20:15 28 December 2014 Faculty of Chemistry, College of Natural Science, Vietnam National University, Hanoi, 19 Le Thanh Tong Street, Hanoi, Vietnam Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany Received 15 August 2010; accepted in revised form 07 February 2011 Abstract: The hydrodistilled essential oil from the fresh rhizomes of Zingiber pellitum Gagnep (Zingiberaceae) originating in Vietnam was analyzed by GC and GC-MS The chemical constituents of the oil were identified using MassFinder program which allows two-dimensional search of mass spectra and retention indices of compounds The oil was found to be rich of terpinen-4-ol (35.9 %), p-cymene (19.8 %), and sabinene (7.1 %) Monoterpenoids constituted 80.1 % of the oil Sesquiterpenoids were detected as minor compounds of the oil and the identified compounds consisted of 2.5 % of the oil Key words: Zingiber pellitum, Zingiberaceae, essential oil, terpinen-4-ol, p-cymene, sabinene Introduction: The genus Zingiber (Zingiberaceae) in Asia is represented by forty-five species Eleven Zingiber species are distributed in Vietnam, among which Z officinale Rosc., Z cassumunar Roscoe (syn: Z purpureum Roscoe), Z zerumbet Sm., and Z gramineum Blume are well-known medicinal plants of Vietnam 1,2 Studies of composition of essential oils from Zingiber plants showed that the qualitative and quantitative profiles of the oils were significantly influenced by the collection locations The most studied case is the chemical composition of the rhizome oils of Z officinale Roscoe For example, the GC profiles of the rhizome oil from Nigeria showed zingiberenesesquiphelladrene chemotype 3,4, while the oil from Ecuador occurred as zingiberene-ar-curcumenecamphene chemotype 5, and the oil from Cuba was represented by zingiberene-ar-curcumene-βbisabolene-cadina-1,4-diene chemotype In addition, the observation of very high accumulation of several principal compounds in some Zingiber essential oils studied is also of significant economic interest 7-9 There is no report on the chemical constituents of Z pellitum essential oils and therefore the composition of its rhizome oil was analyzed in this study using GC-MS interpretation program MassFinder 2.3 10 Experimental Plant material: The fresh rhizomes of Z pellitum Gagnep (Zingiberaceae) were collected in *Corresponding author (Phan Minh Giang) E-mail: < phanminhgiang@yahoo.com > © 2011, Har Krishan Bhalla & Sons Phan Minh Giang et al / Jeobp 14 (4) 2011 494 - 497 495 district Huong Son, province Ha Tinh, Vietnam The plant was identified by Mr Nguyen Quoc Binh, a botanical taxonomist at the Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hanoi, Vietnam in September 2003 A voucher specimen (NQB-903) is deposited at the same Institute Downloaded by [Heriot-Watt University] at 20:15 28 December 2014 Oil preparation: The fresh rhizomes were sliced and subjected to hydrodistillation using a Clevenger-type apparatus for h to produce a colourless and pleasant-smelling oil of 0.02 % yield (w/ w) The oil was stored at 4°C for gas chromatography (GC) and gas chromatography - mass spectrometry (GC-MS) analysis GC and GC-MS analysis of the essential oil: A Carlo Erba 5300 Mega gas chromatograph equipped with two fused silica capillary columns (25 m × 0.25 mm i.d., 0.15 μm film thickness) coated with CPSil-5-CB and CPSil-19-CB, respectively, split injection and flame ionization detection (FID) was used for GC analysis The injector and detector temperatures were at 200°C and 250°C, respectively The oven temperature was programmed from 50 to 250°C at 3°C/min The carrier gas was H2 at 1.2 mL/min A Hewlett-Packard HP 5890 gas chromatograph coupled to a VG Analytical 70-250S mass spectrometer was used for GC-MS analysis The GC was fitted with a fused silica capillary column coated with CPSil5-CB (25 m × 0.25 mm i.d., 0.15 μm film thickness) The GC operating conditions were identical with those described above for GC analysis except that helium was used as carrier gas As MS operating parameters the ionization voltage was 70 eV and the ion source temperature was 230oC Compounds of the oil were identified by comparison of the retention indices and mass spectra with those of our authentic samples, obtained under identical experimental conditions Furthermore, the identification of the oil constituents was also carried out by using a computer-supported spectral library MassFinder 2.3 which allowed simultaneous comparison of retention indices and mass spectra 10,11 The relative percentages of the oil components were calculated by peak normalization using the GC CPSil-5-CB capillary column Results and discussion: Twenty-eight components of the oil representing 82.6 % of the oil were identified in this study Twenty-one monoterpenoids including 34.7 % monoterpene hydrocarbons and 45.4 % oxygenated monoterpenoids and seven sesquiterpenoids including % sesquiterpene hydrocarbons and 0.5 % oxygenated sesquiterpenoids were identified Twenty-eight chemical constituents of the oil were listed in Table I Significant percentage of terpinen-4-ol (35.9 %) was detected in the oil p-Cymene (19.8 %) and sabinene (7.1 %) were also the abundant monoterpenoid components Sesquiterpene hydrocarbons of different skeleton types such as daucene (0.2 %), βelemene (0.5 %), aristolochene (1 %), γ-humulene (0.1 %), and germacrene A (0.2 %) were identified β-Caryophyllene oxide (0.3 %) was detected, however, β-caryophyllene was not identified in the oil In previous studies high accumulation of zingiberene (24-29 %) was found in the rhizome oil of Z officinale Roscoe 3-6, β-phellandrene (45.3 %) in the inflorescence oil of Z spectabile Griff 7, linalool (53.3 %) in the rhizome oil of Z roseum Rosc 8, and β-caryophyllene (42.2 %) in the rhizome oil of Z nimmonii (J Graham) Dalzell The very high content of terpinen-4-ol identified in the rhizome oil of Z pellitum may be an important chemical and economic characteristic of the oil Acknowledgements: This work was supported by the VolkswagenStiftung (Partnerschaftsvorhaben “Untersuchung ätherischer Öle Vietnams”) and the National Foundation for Science and Technology Development (NAFOSTED, Hanoi, Vietnam) Phan Minh Giang et al / Jeobp 14 (4) 2011 494 - 497 Downloaded by [Heriot-Watt University] at 20:15 28 December 2014 10 11 496 References Do, T.L (1991) Medicinal Plants and Herbal Remedies of Vietnam Science and Technique, Hanoi Vo, V.C (1997) Dictionary of Vietnamese Medicinal Plants Medicine, Ho Chi Minh city Ekundayo, O., Laakso, I and Hiltunen, R (1988) Composition of ginger (Zingiber officinale Roscoe) volatile oils from Nigeria Flav Frag J 3: 85-90 Onyenekwe, P.C and Hashimoto, S (1999) The composition of the essential oil of dried Nigerian ginger (Zingiber officinale Roscoe) Eur Food Res Technol 209: 407-410 Sacchetti, G., Maietti, S., Muzzoli, M., Scaglianti, M., Manfredini, S., Radice, M and Bruni, R (2005) Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods Food Chem 91: 621-632 Pino, J.A., Marbot, R., Rosado, A and Batista, A (2004) Chemical composition of the essential oil of Zingiber officinale Roscoe L from Cuba J Essent Oil Res 16: 186-188 Zoghbi Mariadas, G.B and Andrade, E.H.A (2005) Volatiles of the Etlingera elatior (Jack) R M Sm and Zingiber spectabile Griff.: two Zingiberaceae cultivated in the Amazon J Essent Oil Res 17: 209-211 Prakash, O., Panta, K and Mathela, C.S (2006) Linalool-rich essential oil from the rhizomes of Zingiber roseum Rosc J Essent Oil Res 18: 638-639 Sabulal, B., Dan, M., John, J.A., Kurup, R., Pradeep, N.S., Valsamma, R.K and George, V (2006) Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: chemical characterization and antimicrobial activity Phytochemistry 67: 2469-2473 Hochmuth, D.H., König, W.A and Joulain, D (2003) MassFinder 2.3 Software & Data Bank, Hamburg Available at: http://www.massfinder.com Joulain, D and König, W.A (1998) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons E.B.-Verlag, Hamburg Phan Minh Giang et al / Jeobp 14 (4) 2011 494 - 497 497 Downloaded by [Heriot-Watt University] at 20:15 28 December 2014 Table I Chemical constituents of the essential oil of the fresh rhizomes of Zingiber pellitum a No Compound 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 α-Thujene α-Pinene Camphene Sabinene β-Pinene Myrcene p-Cymene Limonene γ-Terpinene trans-Sabinene hydrate Terpinolene cis-Sabinene hydrate trans-p-Menth-2-en-1-ol Terpinen-4-ol α-Terpineol cis-Piperitol trans-Piperitol Fenchyl acetate a Bornyl acetate Terpinen-4-ol acetate α-Terpineol acetate Daucene β-Elemene Aristolochene γ-Humulene Germacrene A β-Caryophyllene oxide γ-Bicyclohomofarnesal correct isomer was not identified RI Content (%) 926 935 950 970 974 983 1016 1025 1055 1060 1082 1082 1116 1168 1178 1183 1192 1210 1273 1282 1331 1380 1390 1483 1486 1503 1573 1785 0.1 0.6 0.5 7.1 4.2 0.9 19.8 0.7 0.6 1.1 0.2 1.3 1.4 35.9 1.2 0.1 0.2 0.7 2.1 0.5 0.9 0.2 0.5 1.0 0.1 0.2 0.3 0.2 ... plants of Vietnam 1,2 Studies of composition of essential oils from Zingiber plants showed that the qualitative and quantitative profiles of the oils were significantly influenced by the collection... compounds of the oil and the identified compounds consisted of 2.5 % of the oil Key words: Zingiber pellitum, Zingiberaceae, essential oil, terpinen-4-ol, p-cymene, sabinene Introduction: The genus Zingiber. .. 494 Journal of Essential Oil Bearing Plants ISSN Print: 0972-060X Online: 0976-5026 www.jeobp.com Terpinen-4-ol-rich Essential Oil from the Fresh Rhizomes of Zingiber pellitum of Vietnam Phan