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On: 28 December 2014, At: 20:15
Publisher: Taylor & Francis
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Journal of Essential Oil Bearing Plants
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Terpinen-4-ol-rich Essential Oil from the Fresh Rhizomes of Zingiber pellitum of Vietnam
Phan Minh Giang a , Phan Tong Son a & 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
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Trang 2Terpinen-4-ol-rich Essential Oil from the Fresh
Rhizomes of Zingiber pellitum of Vietnam
Phan Minh Giang 1* , Phan Tong Son 1 and Wilfried A König 2
1 Faculty of Chemistry, College of Natural Science, Vietnam National University,
Hanoi, 19 Le Thanh Tong Street, Hanoi, Vietnam
2 Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
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 zingiberene-sesquiphelladrene chemotype 3,4, while the oil from Ecuador occurred as
zingiberene-ar-curcumene-camphene chemotype 5, and the oil from Cuba was represented by
zingiberene-ar-curcumene-β-bisabolene-cadina-1,4-diene chemotype 6 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
Journal of Essential Oil Bearing Plants
www.jeobp.com
*Corresponding author (Phan Minh Giang) E-mail: < phanminhgiang@yahoo.com > © 2011, Har Krishan Bhalla & Sons
Received 15 August 2010; accepted in revised form 07 February 2011
Trang 3district 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
Oil preparation: The fresh rhizomes were sliced and subjected to hydrodistillation using a
Clevenger-type apparatus for 6 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 2 % 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 %), β-elemene (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 9 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 MinhGianget al / Jeobp 14 (4) 2011 494 - 497 495
Trang 41 Do, T.L (1991) Medicinal Plants and Herbal Remedies of Vietnam Science and Technique,
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2 Vo, V.C (1997) Dictionary of Vietnamese Medicinal Plants Medicine, Ho Chi Minh city.
3 Ekundayo, O., Laakso, I and Hiltunen, R (1988) Composition of ginger (Zingiber officinale
Roscoe) volatile oils from Nigeria Flav Frag J 3: 85-90
4 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.
5 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
6 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.
7 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
8 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.
9 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
10 Hochmuth, D.H., König, W.A and Joulain, D (2003) MassFinder 2.3 Software & Data
Bank, Hamburg Available at: http://www.massfinder.com
11 Joulain, D and König, W.A (1998) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons.
E.B.-Verlag, Hamburg
Trang 5Table I Chemical constituents of the essential oil of the fresh rhizomes of Zingiber pellitum
a correct isomer was not identified
Phan MinhGianget al / Jeobp 14 (4) 2011 494 - 497 497