Analysis of Essential Oils of Flowers

8/3/2019 Analysis of Essential Oils of Flowers

http://slidepdf.com/reader/full/analysis-of-essential-oils-of-flowers 1/7

ANALYSIS OF ESSENTIAL OILS OF FLOWERS, RHIZOMES

AND SEEDS OF ZINGIBER RUBENS ROXB

Trinh Dinh Chinh

1

Hoang Thi Nhu Hanh2

1Chemical Department, College of pedagogy, Hue university

2Postgraduate student of College of pedagogy, Hue university

32 Le Loi street, Hue city, Viet Nam

Abstract

The essential oils from flowers, rhizomes and seeds of Zingiber rubens Roxb were

extracted. The essential oils were extracted using the hydrodistillation method and analysed

by GC-MS. The yeild of volatile constituents (mL/100g) of flowers, rhizomes and seeds

were 0.015, 0.075 and 0.094, respectively. The flowers essential oil contained trans--

caryophyllene (22.38%), 2--pinene (19.22%) and bicyclogermacrene (10.88%) as major

compound whereas the seeds essential oil were largely dominated by 2--pinene (33.74%),

-pinene (11.79%) and trans--caryophyllene (11.61%). The essential oil of the rhizomes

contained the major compounds (-) bornyl acetate (18.95%), 2--pinene (17.05%), endo-

borneol (11.35%) and linalool L (11.09%).

Introduction

The pantropical Zingiberaceae is the largest family in the order Zingiberales with 53

genera and over 1300 species[2]. They are distributed throughout tropical Africa, Asia and

America, with its greatest diversity in Southeast Asia. Of the 53 genera and 1300 species

known in the world, at least 24 genera and 115 species are found in Viet Nam[1]

.

Zingiber rubens Roxb is classified under the genera of Zingiber. This plant is from

the Indo-Malaysian region and has been found in many places throughout Southeast Asia.

The paste of the rhizome (10 gm) is given after heating and is also applied to the head for

giddiness. There were several previous studies of this plant. The study by Wimolpun

Rungprom (1990) reported that the essential oil of rhizomes of Zingiber rubens Roxb,



obtained by steam distillation, gave the same bluish-green essential oil (0.40% of dried

rhizomes and 0.28% of fresh rhizomes). Essential oil by gas chromatograph-mass

spectrometer (GC-MS) showed that twelve compounds were the main components of the oil

(84.05%). Four of these compounds were identified by computer as -pinene, conphene,

-pinene and compaene. The residue from steam distillation was extracted with acetone by

maceration. Five substances were obtained. Among them, two compounds, stigmasterol

(C29H48O) and -sitosterol (C29H50O), were indentified. The ground dried roots of zingiber

rubens Roxb were extracted with hexane, chloroform and methanol respectively. Three

solid substances were obtained. The first subtances was believed to be the mixture of five

compounds containing long chain aliphatic esters and long chain aliphatic hydrocarbons.

The second substance was the mixture of three triterpenoids with molecular formular

C30H50O. The third substance was believed to be sucrose[3]

.

The aim of this study was to analyze the volatile constituents of essential oils of

Zingiber rubens Roxb from different parts of the plant namely flowers, rhizomes and seeds

by gas chromatography and mass spectrometry. The study of these essential oils may

provide interesting raw material for the application of this plant.

Experimental

Plant material

The fresh Zingiber rubens Roxb was collected at Binh Dien, Huong Tra, Thua Thien

Hue in august, 2009. The plant was identified by Mr Cam, lecture of Hue college of

Agriculture and Forestry, and transported to Natural compounds Laboratory of Hue college

of pedagogy for essential oil extraction.

Hydrodistillation

1 kg of flowers, 400 grams of rhizomes were chopped into small pieces, 160 grams of seeds

were ground into pieces and subjected to hydrodistillation for 3-4 hours. The essential oils

were isolated by extraction of the distillate with n-hexan and its yield was calculated.

GC-MS analysis

The essential oils were analyzed using GC model HP 6890 (America), MS model Agilent

5973 (America).

The constituents were indentified by comparision with published mass spectra database

Wiley – 1998 and Nist – 1998



Results and Discussion

A total of fifty two components were indentified in the essential oils of flowers,

rhizomes and seeds of Zingiber rubens Roxb. Among them, forty one compounds were

indentified in essential oil of seeds, thirty eight compounds were indentified in essential oil

of flowers and thirty nine compounds were indentified in essential oil of rhizomes.

trans--caryophyllene (22.38%), 2--pinene (19.22%) and bicyclogermacrene (10.88%)

were the major compounds of essential oil in flowers of Zingiber rubens Roxb. (-) Bornyl

acetate (18.95%), endo – borneol (11.35%), 2--pinene (17.05%) and linalool L (11.09%)

were the major compounds of essential oil in rhizomes of Zingiber rubens Roxb. 2--pinene

(33.74%), -pinene (11.79%) and trans--caryophyllene (11.61%) were the major

compounds of essential oil in seeds of Zingiber rubens Roxb.

-thujene, -terpinene, trans--ocimene were indentified in the essential oils of both

flowers and seeds except rhizomes. Camphor, -elemene were indentified in the essential

oils of both seeds and rhizomes except flowers. Linalool L, delta-cadinene were indentified

in the essential oils of both flowers and rhizomes except seeds.

Monoterpene hydrocarbons dominated the essential oil of seeds of Zingiber rubens

Roxb with 61.03% whereas sesquiterpene hydrocarbons were the major type of compounds

in the essential oil of flowers of Zingiber rubens Roxb with 46.21%. Oxygenated

monoterpene derivatives were the major type of compounds present in the essential oil of

rhizomes of Zingiber rubens Roxb with 53.02%.

As a conclusion, major compounds in the essential oils depend on the part of plant studied.

Chemical CompoundsPercentage (%)

Seeds Flowers Rhizomes

Monoterpene hydrocarbons 61.30 31.24 35.34Tricyclene - - 0.31

-Thujene 1.22 0.17 -

-Pinene 11.79 5.63 5.73

Camphene 0.3 0.45 7.88

Sabinene 1.39 1.23 0.83

2--pinene 33.74 19.22 17.05

-Myrcene 0.82 0.58 0.48



-Phellandrene 0.46 - -

-terpinene 0.95 0.14 -

p-cymene 2.16 0.5 0.15

Limonene 1.68 1.16 2.37

trans--ocimene 0.29 1.09 -

-terpinene 6.34 0.81 0.22

-terpinolene 0.16 0.26 0.32

Oxygenated monoterpene derivatives 3.84 16.38 53.02

1,8-cineole 0.36 4.76 7.42

Linalool L - 7.88 11.09

Camphor 0.17 - 0.81

Endo-borneol 0.15 0.75 11.35

Terpinen-4-ol 2.04 0.37 0.87

-terpineol - 1.19 2.27

Myrtenol 0.69 1.09 -

Fenchyl acetate - - 0.26

(-)-Bornyl acetat 0.43 0.34 18.95Sesquiterpene hydrocarbons 14.87 46.21 5.19

-elemene 0.3 - 0.66

-Gujurnene - 0.6 0.65

trans--caryophyllene 11.61 22.38 0.19

-humulene 1.21 2.58 0.19

Aromadendrene - 2.07 0.27

Germacrene B - - 0.7

-cubebene - 0.69 -

-Chamigrene - - 0.12

-Guaiene - - 0.17

Valencene 0.69 - -

Ledene - 0.39 0.4

Bicyclogermacrene - 10.88 0.33



Delta-guaiene - 0.43 -

-Bisabolene 0.39 - -

-Farnesene - 1.09 -

(+)-delta-selinene - - 0.19

Neoisolongifolene - 2.6 -

Alloaromadendrene 0.17 - 0.83

-selinene - - 0.25

-selinene 0.5 - -

(-)-Isoledene - 0.32 -

Isolongifolene - 0.55 0.24

-amorphene - 0.53 -

Delta-cadinene - 0.87 -

Cycloheptane, 4-methylene-1-methyl-2-(2-

methyl-1-propen-1-yl)-1-vinyl- 0.23 -

Oxygenated sesquiterpene derivatives 2.7 - -

Santalol 0.24 - -

Caryophyllene oxide 2.46 - -Miscellaneous compounds 0.47 - -

1,2,3,5-tetramethyl benzene 0.29 - -

Acetic acid 0.18 - -

Total identified constituents 83.18 93.83 93.55

Total non-identified constituents 16.82 6.17 6.45



References

1. Pham Hoang Ho (1993), Cay co Viet Nam quyen III , Mekong publisher, Montréal.

2. W. John Kress, Linda M. Prince and Kyle J. Williams (2002), “The Phylogeny

and a new classification of the Gingers (Zingiberaceae): Evidence from molecular

data”, American Journal of Botany 89(11): 1682-1696, 2002.

3. Wimolpun Rungprom (1990), “Chemical constituents of Zingiber rubens Roxb”,

Department of chemistry Faculty of science chulalongkorn University Thailand.

0

10

20

30

40

50

60

70

Monoterpene

hydrcarbons

Oxygenated

monoterpene

hydrocarbons

Sesquiterpene

hydrocarbons

Oxygenated

sesquiterpene

hydrocarbons

Miscellaneous

compounds

Seeds

Flowers

Rhizomes

(1) (2) (3) (4)

(5) (6)

The Major Chemical Constituents of Essential oils of flowers, rihzomes and seeds

of Zingiber rubens Roxb

(1) trans--caryophyllene ; (2) 2--pinene ; (3) -pinene ; (4) Endo-borneol ;

(5) Bicyclogermacrene ; (6) Linalool L

Figure 1. Chemical Compounds of the Essential oils of Zingiber rubens Roxb



Documents

Analysis of Essential Oils of Flowers