Nano physical and thermochemical parameters investigation of

essential oils Ginger (Zingiberene and Gingerol)

M. Mahmodi Hashemi 1* , M. Sheikhi 2
1. Department of Chemistry, Science and Research Branch, Islamic Azad University,
Tehran, Iran(mhashemi@edu.sharif)
2. Ph.D Student, Science and Research Branch, Islamic Azad University, Tehran, Iran

ABSTRACT
Ginger is a well known spice and flavoring agent which has also been used in traditional
medicine in many countries. Ginger contains essential oils including gingerol and
zingiberene. It also contains pungent principles such as zingerone, and shogaol. In the
paper six theoretical methods were used to calculation of physical parameters and
thermodynamic parameters in the gas phase for gingerol and zingiberene. Used to
Gaussian98, NMR, NBO and Freq calculations by using HF method with 6-31G, 631G* and 6-31+G basis set and B3LYP, BLYP and B3PW91 methods with 6-31G basis
set. Chemical shift was drown curve for all of the atoms in each molecule. By Freq
calculations determined he thermochemical parameters including Entropy(S),
Energy(E), Enthalpy(H), Gibbs free energy(G), CV and LnQ. Used to NMR calculations
determined physical parameters such as Atomic charges, Chemical Shift Anisotropy(),
Asymmetry parameter(), Chemical Shift anisotropy(), Dipole orientation ,
Isotropic , Anisotropic and NMR determinan for gingerol and zingiberene. Also the
natural bond orbital(NBO) analysis has been performed which seem edquite informative
to show some important atomic and structural features. Also we obtained Shielding
value for the each atom with GaussView program (GIAO Magnetic shielding).
Keywords: Ginger; gingerol; zingiberene; zingerone; shagaol; NBO analysis; Nano
physical parameters; Freq; thermochemical parameters; gas phase; GIAO.

INTRODUCTION
It has been know from ancient times
that essential oil from aromatic and
medicinal plants possess biological
activity, antibacterial, antifungal and
antioxidant properties. Due to the
growing interest in the use of essential
oils in both the food and the
pharmaceutical industries, a sestematic
study on these plant extracts for
different purposes viz flavouring,
keeping away the pests, and in
perfumery 1 .

Ginger (Zingier officinale Roscoe;

family Zingiberaceae) is a well known
spice and flavoring agent.
(a) Classification of Ginger:
Kingdom : Plantae
Division : Angiosperma
Class : Monocotyledoneae
Order : Scitaminaea
Family :Zingiberaceae
Genus : Zingiber
Species : officinale

(b) Vernacular names:

Sanskrit : Adrakam, Ardraka
Hindi : Adrak,Sunthi,Sonth
Kannada : Sunthi
Marathi : Nisam
Gujarati :Sunt
English : Ginger
(c) Part used : Rhizome
(d)
Botanical
description:
A
herbaceous rhizomatous perennial,
reaching up to 90 cm in height under
cultivation. Rhizomes are aromatic,
thick lobed, pale yellowish, bearing
simple alternate distichous narrow
oblong lanceolate leaves. The herb
develops several lateral shoots in
clumps, which begin to dry when the
plant matures. Leaves are long and 2-3
cm broad with sheathing bases, the
blade gradually tapering to a point.
Inflorescence solitary, lateral radical
pedunculate oblongcylindrical spikes.
Flowers are rare, rather small, calyx
superior, gamosepalous, three toothed,
open splitting on one side, corolla of
three subequal oblong to lanceolate
connate greenish segments 2 .
(e) Geographical distribution: The
plant is widely cultivated all over India,
Bangladesh, Taiwan, Jamaica and
Nigeria. This perennial grows in warm
climates 3 .
(f) Traditional use: Ginger is
carminative, pungent, stimulant, used
widely for indigestion, stomachache,
malaria and fevers. It is chiefly used to
cure diseases due to morbidity of Kapha
and Vata. Ginger with lime juice and
rock salt increases appetite and
stimulates the secretion of gastric juices.
It is said to be used for abdominal pain,
anorexia, arthritis, atonic dyspepsia,
bleeding, cancer, chest congestion,
chicken
pox,
cholera,
chronic
bronchitis, cold extremities, colic,
colitis, common cold, cough, cystic
fibrosis, diarrhoea, difficulty in
breathing, dropsy, fever, flatulent,
indigestion, disorders of gallbladder,

hyperacidity,
hypercholesterolemia,
hyperglycemia, indigestion, morning
sickness, nausea, rheumatism, sore
throat, throat ache, stomach ache and
vomiting. Ginger forms an important
constituent of many pharmacopoeial
Ayurvedic formulations 3,4 .
(g) Anatomy of the Rhizome:
The ginger rhizome has the following
chemical composition:
60% starch,
10% proteins,
10% fats,
5% fibers,
6% inorganic material,
10% residual moisture,
1-4% essential oil 6 .
The percentage of essential oil varies
with geographic origin.
Scraped rhizome with buff external
surface showing longitudinal striations
and occasional loose fibers, outer
surface dark brown and more or less
covered with cork which shows
conspicuous, narrow, longitudinal and
transverse ridges; the cork readily
exfoliates from lateral surfaces but
persists between branches. Smoothed
transversely cut surface exhibiting a
narrow cortex separated by an
endodermis from a much wider stele,
numerous
widely
scattered
fibrovascular
bundles,
abundant
scattered oleoresin cells with yellow
contents. Starch abundant in the thinwalled ground tissue, as flattened, ovate
to subrectangular, transversely straited,
simple granules, each with the hilum in
a projection towards one end. Pigments
cells with dark reddishbrown contents
occurring either singly in the ground
tissue or in axial rows accompanying
the vascular bundles. Vessels with spiral
or reticulate thickening in the scattered
vascular bundles are found. Irregularly
shaped thin-walled fibers with delicate,
transverse septa, yielding only slightly
the reaction characteristic of lignin.
Sclereids and calcium oxalate crystals
absent 7,8 .
2

(h) Pharmacology and Clinical

Studies
Anti-emetic Activity: Early animal
studies had demonstrated the antiemetic property of fresh ginger 9 , but it
was the clinical work of Mowrey and
Clayson which generated a wider
interest in this use of ginger 10 . They
compared the effects of 1.88g of dried
powdered
ginger,
100mg
dimenhydrinate
(Dramamine)
and
placebo on the symptoms of motion
sickness in 36 healthy subjects who
reported very high susceptibility to
motion sickness. Motion sickness was
induced by placing the blind folded
subject in a tilted rotating chair. Ginger
was found to be superior to
dimenhydrinate
and
placebo
in
preventing
the
gastrointestinal
symptoms of motion sickness and the
authors postulated a local effort in the
gastrointestinal tract for ginger. This
was particularly likely since it was
given as a powder only 25 minutes
before the test. The gingerols and
shogaols were subsequently identified
as the main anti-emetic compounds in
ginger 11 .
Improvement of digestive function:
Early Chinese and Japanese research
found that oral and intragastric
application of fresh ginger decoction
produced a stimulant action on gastric
secretion1. German scientists found that
chewing 9g of crystallised ginger had a
profound effect on saliva production 12
. Amylase activity was also increased
and the saliva was not more watery,
although it contained slightly less
mucroprotein. Intraduodenal doses of
ginger extract increased bile secretion in
rats. Total secretion of bile solids was
also increased, but not to the same
extent as bile flow. 6-gingerol and 10gingerol were identified as the active
components 13 . Fresh ginger also
contains a proteolytic enzyme 14 .
Ginger, in conjunction with other
pungent Ayurvedic herbs, increased the

bioavailability of a number of drugs by

promoting their absorption and/or
protecting them from being metabolized
in their first passage through the liver 9
. Oral doses of 6-shogaol accelerated
intestinal transit in rats 15 . Also an
extract of ginger, and isolated 6-shogaol
and gingerols, enhanced gastrointestinal
motility in mice after oral doses 16 .
Anti-ulcer Activity: Ginger and 6gingerol inhibited experimental gastric
ulcers in rats 17,18 . Fresh ginger
decocted in water resulted in
symptomatic improvement in 10
patients with peptic ulcers 9 .
Antiplatelet Activity: Srivastava and
co-workers found that aqueous extract
of ginger inhibited platelet aggregation
induced by ADP, epinephrine, collagen
and arachidonic acid in vitro 19 . Ginger
acted by inhibiting thromboxane
synthesis 20,21 . It also inhibited
prostacyclin synthesis in rat aorta 19 .
The antiplatelet action of 6-gingerol
was also mainly due to the inhibition of
thromboxane formation 22 .
Anti-inflammatory Activity: Ginger
extract inhibited carrageenan-induced
paw swelling and was as active as
aspirin 23 . Essential oil of ginger
inhibited chronic adjuvant arthritis in
rats 24 .
Ginger and its pungent components are
dual inhibitors of arachiodonic acid
metabolism. That is, they inhibit both
cyclooxygenase
(prostaglandin
synthetase) and lipoxygenase enzymes
of the prostaglandin and leukotriene
biosynthetic pathways 23,25-30 .
Antipyretic Activity: Ginger extract
given orally reduced fever in rats by
38%, while the same dose of aspirin
was effective by 44% 23 . The
antipyretic activity of 6-shogaol and 6gingerol has also been observed 15 .
Cardiovascular
Effects:
Ginger
exerted a powerful positive inotropic
effect on isolated guinea pigs left atria
31 . Gingerols were identified as the
active components 31,32 .
3

Antioxidant Activity: Extracts of

ginger have pronounced antioxidant
activity comparable to that of synthetic
antioxidant preservatives 33 .
Other Effects: Ginger extract exhibited
a prolonged hypoglycaemic activity in
rabbits 23 . Antihepatotoxic activities of
gingerols and shogaols were observed
using
carbon
tetrachloride
and
galactosamine induced cytotoxicity in
cultured rat hepatocytes 34 . Injection of
6-shogaol showed an intense antitussive
action
in
comparison
with
dihydrocodeine phosphate 15 .
Pharmacokinetics: After injection,
90% of 6-gingerol was bound to serum
protein and elimination was mainly via
the liver 35 . Oral or intraperitoneal
dosage of zingerone resulted in the
urinary excretion of metabolites within
32 hours, mainly as glucuronide and/or
sulphate conjugates. Appreciable biliary
excretion (40% in 12 hours) also
occurred 36 .
(i) Toxicity and Adverse Reactions:
The mutagenic activity of ginger
extracts has been observed in several
strains 30,37 . As a result of component
fractionation of ginger juice, it was
found that 6- gingerol was a potent
mutagen 38 . When mutagenicity of
gingerol or shogaol was tested in the
presence of zingerone, it was observed
that zingerone suppressed the mutagenic
activity of bothcompounds 30,39 .

Ginger extract caused no mortality at

doses of up to 2.5g/kg in mice
(equivalent to about 75g/kg of fresh
rhizome) 23 . This low acute toxicity
was confirmed in a separate study,
which also found that ginger extract at
100mg/kg per day for three months
caused no signs of chronic toxicity 40 .
Topical application of ginger may cause
contact dermatitis in sensitive patients
41 .
(j) Phytochemistry: Ginger has been
reported to contain usually 1-3% of
volatile oil, pungent principles viz.,
gingerols and shogaols and about 6-8
lipids and others. Ginger oil contains
Zingibereneand bisaboline as major
constituents along with other sesqui and
monoterpenes.
Ginger
oleoresin
contains mainly the pungent principles
gingerols and shogaols as well as
zingiberone. Shogaols have recently
been found to be twice as pungent as
gingerols 9-12 .
(k) Active
Shogaols.

principles:

Gingerols,

Figure 1 and 2 show Zingiber officinal

Plant and Zingiber officinal rhizome. Also
Figure 3 show general structure of
Gingerols and Figure 4 show Structure of
Zingiberene.

Figure 1. Zingiber officinal Plant.

Figure 2. Zingiber officinal rhizome.

HO

CH3 O
(CH2)n- CH3

HO

Figure 3. General structure of Gingerols

compounds .

(n=1, 2, 3, 4, 6, 8, 10) for specific

CH3
H

CH3
CH3

H
CH3

Figure 4. Structure of Zingiberene.

Methods Of Computations:
Stage 1: Start ChemDraw and construct
molecules. Save the results as a
ChemDraw file .
Stage 2: Reopen this file using Chem3D
and perform an energy minimization.
Then save the results as a gjc file.
Stage 3: Reopen this file using
Gaussian98 and the calculations were
performed using the Gaussian98
program suite. Gaussian is one of the
most widely used quantum chemical

program packages for molecular

applications, and is used both in
industry and in many scientific areas in
academia. we have calculated the
geometric parameters of the compounds
in the ground state the using the
Hartree-Fock (HF) 42 , Beckes threeparameter hybrid method 43 with the
Lee, Yang, and Parr correlation
functional methods
44
(B3LYP),
Beckes exchange functional in
5

combination with the Lee, Yang and

Parr correlation functional methods
(BLYP)
44,45 , Becke's three
parameter
exchange
functional
combined with gradient corrected
correlation functional of Perdew and
Wang's 1991 (B3PW91) 43,44 , and 631G, 6-31G* and 6-31+G basis set. The
calculation that you ask Gaussian to
perform is distributed between many
processors to get the answer faster. If
you want to optimize a geometry, it
means that you want Gaussian to adjust
the bond lengths, angles, and dihedrals
to find the lowest energy conformation
of the molecule. The command to tell
Gaussian to optimize the molecular
geometry is opt.
The Gaussian
program does semi-empirical and ab
initio calculations. In ab initio
calculations the important integrals are
done directly from first principles. First
principles means that the integrals are
done either using closed formulas or by
doing the integrals numerically. The
particular ab initio method that works
best for calculating NMR properties.
Finding a good geometry is called
geometry optimization, so OPT are
used as the keyword. The calculation
will generate an output file called
filename.out.The
output
file
(filename.out) contains a lot of
information about the calculation and
the results. The content depends on
what type of calculation that has been
performed and on what print options
that was specified. The units are usually
Hartree (atomic unit) for energy and
ngstrm for distance. There are
several different pieces of data that you
may need from this. The important
informationes are the Hartree Fock
energy(E), the Mulliken charges,
Distance matrix(angstroms), Dipole
moment(Debye) and Atomic charge.
Distance matrix value is determined
the using Matlab program.
We used Gaussian98 at the NMR shift
calculation using the HF, B3LYP,

BLYP, B3PW91 methods and 6-31G, 631G* and 6-31+G basis set 47 . There
for NMR are used as the keyword.
The calculation will generate an output
file called NMR.out. The output file
(NMR.out) contains a lot of information
about the NMR shift calculation and are
listed in the GIAO Magnetic shielding
tensor (ppm), such as Isotropic(ppm)
and Anisotropic(ppm). As the usig the
X, Y and z with Matlab program is
solved determinan 3*3 and is
calculated.
Molecular
orbital
calculations can be used to get good
estimates for chemical shifts. Then
using the Excel program draw the
diagrams which shows Anisotropy for
each of the atom.
In the part of GIAO Magnetic
shielding tensor (ppm) the using the
Isotropic(ppm), Anisotropic(ppm)
and Eigenvalues(11, 22, 33) are
calculated parameters such as , and
48 .
A full NBO analysis is obtained in
Gaussian when using the POP=NBO
keyword. NBO analysis did using the
HF, B3LYP, BLYP, B3PW91 methods
and 6-31G, 6-31G* and 6-31+G basis
set and the output is obtaind for each of
the molecule.The main listing of NBOs,
displaying the form and occupancy of
the complete set of NBOs that span the
input AO space and for each orbital
gives the type of orbital and the
occupancy. We were extaracted just
BD for 2-center bond and BD* for 2center antibond from NBO.output 49 .
We obtained Shielding value for the
each atom with GaussView program
(GIAO Magnetic shielding).
Geometry optimization in the gas phase
for Zingiberene and Ginger were
performed at the HF level with the631G, 6- 31+G, 6-31G* basis sets and
B3LYP, BLYP,B3PW91 level with the
6-31G basis set used to Gaussian
program and keyword Freq. The
enthalpies, free energies, entropies
obtained in gas phase.
6

Discussion:
In this work, we calculated parameters
such as atomic charges, energy (),
chemical
shift
anisotropy
(),
asymmetry parameter (), chemical
shift anisotropy (), dipole orientation
, isotropic , anisotropic , NMR
determinan,
distance
matrix
determinan, NBO calculations and
magnetic shielding (GIAO)
for

zingiberene and gingerol using the HF

method with 6-31G,6-31G* and 631+G basis set and B3LYP, BLYP and
B3PW91 methods with 6-31G basis
set. At in work, in molecule(1) (Figure
5). HF/6-31G method and in
molecule(2) (Figure 6) with B3LYP/631G, BLYP/6-31G and B3PW91/631G any response is obtaned.

14

H 3C

13

12
11

15
25 CH3

10

H H

H 30

16 H

CH 3

5
H19

1
4

H3 C

18

3
H17

Figure 5. Molecule 1 Zingiberene or (S)-2-methyl-5((R)-6-methylhept-5-en-2-yl)cyclohexa1,3-diene )

H22

H19

7O
2

H21

15
13

11
8O
H3C

4
H20

18

14

12

5
10

16 O

32

Figure 6. Molecule 2 gingerol

methoxyphenyl)heptan-3-one

H35

17

n=1

This parameters are shown in Table 1

and 2. At present, in this section, we
considered this parameters.
As
shown
in
Table
1,
in
molecule(1)(zingiberene), with HF/631G and HF/6-31G*, C14 has greatest
negative Atomic charge value and H17
has greatest positive Atomic charge
value. With B3LYP/6-31G, C14 has

or

(S)-5-hydroxy-1-(4-hydroxy-3-

greatest negative Atomic charge value

and H25 has greatest positive Atomic
charge value. With BLYP/6-31G, C7
has greatest negative Atomic charge
value and C12 has greatest positive
Atomic charge value and with
B3LPW91/6-31G, C7 has greatest
negative Atomic charge value and H25
has greatest positive Atomic charge
7

value. In molecule(2), with HF/6-31G,

HF/6-31+G and HF/6-31G*, C12 has
greatest positive Atomic charge value
and O7 has greatest negative Atomic
charge value.
As pointed in Table 1, for molecule(1),
with HF/6-31G and HF/6-31G*, C2 has
greatest negative Chemical shift
anisotropy () value and C13 has
greatest positive Chemical shift
anisotropy () value. While with
B3LYP/6-31G,
BLYP/6-31G
and
B3LPW91/6-31G, C3 has greatest
negative Chemical shift anisotropy ()
value and C2 has greatest positive
Chemical shift anisotropy () value. For
molecule(2) with HF/6-31G, HF/631+G and HF/6-31G*, O7 has greatest
negative Chemical shift anisotropy ()
value and O16 has greatest positive
Chemical shift anisotropy () value.
As pointed in Table 1, in molecule(1),
for the atoms is shown in table has the
positive amounts. With HF/6-31G and
HF/6-31G* Asymmetry parameter ()
value for C4 is the greatest value and for
H17 is the smallest value. With
B3LYP/6-31G, for C4 is the greatest
value and for H18 is the smallest value.
Also BLYP/6-31G and B3LPW91/631G, for C12 is the greatest value and

for H18 is the smallest value. In

molecule(2), with HF/6-31G, for C14
is the greatest value and for C9 is the
smallest value, while with HF/6-31+G,
for O8 is the greatest value and for C9
is the smallest value. Also with HF/631G* for C14 is the greatest value and
for H21 is the smallest value.
The results from Table 1 indicate that in
molecule(1) HF/6-31G and HF/6-31G*,
Chemical shift anisotropy () value for
C13 is greatest positive value and for C2
is greatest negative value. With others
methods, C2 has greatest positive value
for Chemical shift anisotropy () and
C3 has greatest negative value for
Chemical shift anisotropy ().
Dipole orientation (Dipole moment) that
reported in Table 1, at the molecule(1)
for B3PW91/6-31G level is the greatest
value and for HF/6-31G* level is the
smallest
value.
While
at
the
molecule(2), Dipole orientation (Dipole
moment) for HF/6-31+G level is the
greatest value and for HF/6-31G* level
is the smallest value.
(kcal/mol) that reported in Table 1,
for two molecule at HF/6-31G is zero.
for molecule(1) with B3LYP
method and for molecule(2) with HF/631G* has greatest negative value.

Table 1. Values of parameters like atomic charges, (kcal/mol), chemical shift (), asymmetry parameter (), chemical shift anisotropy (), dipole
moment for active site of studied moleculars obtained using different methods.

-104.22

-156.34

0.616

-0.15

-86.67

-130.01

0.796

-0.13

-80.62

-120.93

0.834

-0.17

-86.34

-129.52

0.825

0.06

-120.90

-181.35

0.814

0.12

106.93

160.40

0.972

0.15

103.05

154.57

0.919

0.10

107.05

160.57

0.967

C(3)

-0.18

-122.49

-183.74

0.662

-0.19

-115.45

-173.17

0.643

-0.12

-101.67

-152.51

0.817

-0.11

-95.95

-143.92

0.846

-0.15

-101.54

-152.32

0.836

C(4)

-0.16

-121.73

-49.573

0.873

-0.19

-115.49

-43.61

0.841

-0.11

99.93

149.90

0.983

-0.08

94.78

142.17

0.959

-0.13

100.64

150.97

0.952

C(7)

-0.47

21.94

32.91

0.434

-0.50

20.11

30.16

0.483

-0.47

23.43

35.15

0.482

-0.44

23.77

35.66

0.502

-0.54

23.29

34.93

0.429

C(11)

-0.19

-111.75

-167.63

0.495

-0.21

-105.89

-158.84

0.495

-0.13

-91.54

-21.65

0.595

-0.11

-85.89

-128.84

0.615

-0.15

-91.63

-137.45

0.605

C(12)

0.04

-120.35

2.89

0.800

0.06

-113.86

-170.79

0.799

0.14

-98.26

-147.40

0.978

0.17

93.18

139.77

0.969

0.11

-98.22

-147.33

0.981

C(13)

-0.48

26.63

39.95

0.478

-0.50

24.75

37.13

0.528

-0.46

27.96

41.95

0.443

-0.43

28.25

42.37

0.442

-0.53

27.76

41.64

0.404

C(14)

-0.48

15.76

23.65

0.537

-0.51

14.43

21.65

0.485

-0.46

16.14

24.21

0.712

-0.43

16.22

24.33

0.754

-0.53

16.12

24.18

0.745

C(15)

-0.45

15.95

23.93

0.470

-0.49

14.72

22.09

0.492

-0.41

17.77

26.66

0.552

-0.38

18.35

27.52

0.569

-0.48

17.40

26.10

0.560

H(16)

0.17

-2.88

-4.33

0.363

0.17

-3.12

-4.68

0.482

0.11

-2.52

-3.78

0.843

0.08

2.4787

3.71805

0.908

0.14

-2.59

-3.88

0.634

H(17)

0.18

3.33

4.99

0.271

0.18

3.60

5.40

0.304

0.11

2.91

4.36

0.318

0.08

2.8322

4.2483

0.340

0.14

2.81

4.22

0.344

H(18)

0.18

2.93

4.40

0.309

0.18

2.71

4.06

0.474

0.12

3.01

4.52

0.080

0.09

3.0397

4.5596

0.168

0.15

2.90

4.35

0.044

H(19)

0.16

4.69

7.04

0.724

0.16

4.22

6.34

0.804

0.11

3.50

5.25

0.624

0.09

2.98

4.46995

0.685

0.14

3.84

5.77

0.595

H(25)

0.16

-4.41

-6.62

0.658

0.16

-4.09

-6.13

0.679

0.12

-3.89

-5.84

0.738

0.10

-3.5501

-5.3251

0.739

0.15

-4.17

-6.25

0.771

H(30)

0.15

4.54

6.81

0.614

0.16

4.68

7.03

0.620

0.10

4.43

6.65

0.438

0.07

4.3858

6.5788

0.396

0.13

4.34

1.07

0.495

C(2)

0.34

91.40

137.10

0.859

0.25

91.06

136.60

0.872

0.35

90.52

135.78

0.786

C(3)

0.36

91.03

136.55

0.716

-0.05

91.29

136.94

0.716

0.36

83.90

125.85

0.760

C(9)

-0.12

52.74

79.11

0.080

-0.28

54.62

81.94

0.092

-0.16

48.57

72.85

0.096

C(12)

0.51

154.13

231.20

0.391

0.85

156.40

234.61

0.355

0.55

125.46

188.20

0.346

C(13)

-0.39

22.47

33.71

0.903

-0.61

22.23

33.345

0.872

-0.41

19.61

29.42

0.718

C(14)

0.16

22.10

33.15

0.990

-0.33

22.55

33.83

0.933

0.15

-20.00

-30.00

0.918

H(19)

0.19

-3.66

-5.49

0.360

0.23

-3.53

-5.30

0.471

0.19

-4.39

-6.590

0.394

H(20)

0.22

6.00

9.00

0.427

0.26

6.02

9.04

0.349

0.21

6.28

9.43

0.442

H(21)

0.20

3.95

5.93

0.960

0.23

4.13

6.20

0.839

0.20

-4.44

6.54

-1.019

H(22)

0.41

11.53

17.29

0.501

0.49

10.97

16.46

0.498

0.45

11.67

17.51

0.638

H(32)

0.21

3.39

5.09

3.394

0.24

3.50

5.26

0.945

0.20

-3.24

-4.87

0.907

H(35)

0.39

9.66

14.49

0.256

0.45

9.68

14.53

0.323

0.43

10.14

15.21

0.230

O(7)

-0.79

-28.23

-42.35

0.702

-0.77

-31.01

-46.51

0.750

-0.75

52.42

78.63

0.772

O(8)

-0.76

66.31

99.46

0.986

-0.46

68.47

102.71

0.988

-0.66

-30.40

-45.60

0.530

O(16)

-0.56

760.42

1140.63

0.578

-0.49

742.53

1113.80

0.557

-0.54

647.87

971.80

0.585

O(17)

-0.76

59.64

89.47

0.463

-0.63

57.90

86.85

0.697

-0.75

65.10

97.66

0.195

3.2960

-218.8411

3.9893

-14.1001

3.8896

0.2457

-0.24

-2385.5156

0.2539

-2605.3197

0.2024

0.833

-143.0398

0.638

-191.43

-163.32

-127.62

-108.88

0.02

-0.21

0.2608

C(1)
C(2)

Dipole
moment

E(kcal/mol)

0.2697

-2474.9231

Atomic charge

Dipole
moment

E(kcal/mol)

Atomic charge

Dipole
moment

Atomic charge

Dipole
moment

B3PW91

6-31G
E(kcal/mol)

Atomic charge

Dipole
moment

BLYP

6-31G*
E(kcal/mol)

Atomic charge

Atomic charge

Name

Molecule 1
Molecule 2

Dipole
moment

Atoms

6-31+G
E(kcal/mol)

6-31G

Basis set

Parameters

B3LYP

HF

E(kcal/mol)

Method

Table 2 .Values of parameters like isotropic (iso) , anisotropic (aniso) shielding and NMR determinan for active site of studied moleculars obtained using
different methods.

Anisotropy
(ppm)

B3PW91
Isotropic
(ppm)

Anisotropy
(ppm)

Isotropic
(ppm)

Anisotropy
(ppm)

Anisotropy
(ppm)

BLYP
6-31G

83.99

126.39

-3.47e+05

76.02

116.81

-1.30e+05

72.18

110.89

-8.83e+04

78.71

118.24

-9.41e+04

73.08

164.54

-7.32e+05

64.21

160.40

-4.41e+05

60.11

154.57

-3.52e+05

67.61

160.57

-4.32e+05

C(3)

77.93

172.56

-7.84e+05

77.78

142.32

-6.34e+05

70.00

138.59

-4.01e+05

66.72

132.88

-3.30e+05

72.64

139.85

-3.81e+05

C(4)

72.15

171.00

-7.35e+05

71.88

159.48

-6.28e+05

66.63

149.90

-3.54e+05

63.90

142.17

-2.82e+05

69.37

150.97

-3.27e+05

C(7)

186.84

32.91

6.45e+06

181.00

30.16

5.87e+06

171.99

35.15

5.01e+06

165.91

35.66

4.49e+06

175.03

34.93

5.29e+06

C(11)

79.08

125.33

-5.70e+05

78.27

118.74

-4.56e+06

69.89

109.54

-2.73e+05

66.31

104.06

-2.20e+05

72.62

110.34

-2.52e+05

C(12)

75.07

162.53

-7.20e+05

75.10

153.63

-5.92e+05

65.98

145.78

-3.50e+05

61.60

139.77

-2.78e+05

69.57

145.94

-3.34e+05

C(13)

182.50

39.95

5.98e+06

176.80

37.13

5.44e+06

167.73

41.95

4.60e+06

161.73

42.37

4.13e+06

170.76

41.64

4.88e+06

C(14)

190.74

23.65

6.90e+06

148.66

21.65

6.26e+06

176.75

24.21

5.48e+06

171.05

24.33

4.96e+06

179.50

24.18

5.74e+06

C(15)

190.33

23.93

6.85e+06

184.18

22.09

6.21e+06

176.56

26.66

5.45e+06

170.43

27.52

4.90e+06

179.98

26.10

5.78e+06

H(16)

27.76

2.95

2.12e+04

27.35

3.47

2.02e+04

27.25

3.48

2.01e+04

27.06

3.71

1.96e+04

27.15

3.17

1.98e+04

H(17)

27.20

4.99

1.99e+04

27.00

5.40

1.94e+04

26.65

4.36

1.87e+04

26.48

4.24

1.84e+04

26.52

4.22

1.85e+04

H(18)

26.95

4.40

1.94e+04

26.66

4.06

1.88e+04

26.55

4.52

1.85e+04

26.38

4.55

1.81e+04

26.44

4.35

1.83e+04

H(19)

32.36

7.04

3.33e+04

31.69

6.34

3.13e+04

31.10

5.25

2.98e+04

30.67

4.47

2.86e+04

31.05

2.77

2.95e+04

H(25)

32.30

5.49

3.31e+04

31.53

5.15

3.09e+04

30.72

5.08

2.85e+04

30.24

4.63

2.73e+04

30.66

5.54

2.83e+04

H(30)

27.93

6.81

2.13e+04

27.61

7.03

2.05e+04

27.23

6.65

1.97e+04

26.99

6.57

1.92e+04

27.14

6.51

1.96e+04

C(2)

59.74

137.10

-1.87e+05

60.31

136.60

-1.88e+05

58.13

135.78

-1.49e+05

C(3)

58.49

136.55

-1.18e+05

58.10

136.94

-1.20e+05

59.78

125.85

-8.59e+04

C(9)

153.04

79.11

3.30e+06

152.89

81.94

3.27e+06

147.98

72.85

3.00e+06

C(12)

-17.03

231.20

1.08e+06

-18.20

234.61

1.17e+06

2.18

188.20

4.07e+05

C(13)

158.96

33.71

3.94e+06

158.71

33.34

3.92e+06

154.83

29.42

3.66e+05

C(14)

140.57

33.15

2.71e+06

139.89

33.83

2.65e+06

138.12

28.78

2.58e+06

H(19)

27.01

3.73

1.94e+04

26.75

3.90

1.88e+04

26.43

4.58

1.80e+04

H(20)

25.91

9.00

1.67e+04

25.74

9.04

1.63e+04

25.61

9.43

1.60e+04

H(21)

26.41

5.93

1.80e+04

26.27

6.20

1.77e+04

25.88

6.54

1.68e+04

H(22)

22.53

17.29

2.61e+04

30.41

16.46

2.54e+04

29.92

17.51

2.35e+04

(ppm)

(ppm)

Isotropic
(ppm)

-8.63e+05

(ppm)

-4.21e+05

175.48

(ppm)

133.80

73.27

Isotropic
(ppm)

85.53

C(2)

(ppm)

Isotropic
(ppm)

Anisotropy
(ppm)

B3LYP
6-31G*

C(1)

Atoms

Isotropic
(ppm)

Parameters

Anisotropy
(ppm)

HF
6-31+G

6-31G
(ppm)

Molecule 2

Molecule 1

Name

Method
Basis set

H(32)

29.54

5.09

2.54e+04

29.37

5.26

2.50e+04

29.07

4.64

2.42e+04

H(35)

34.39

14.49

3.84e+04

34.09

14.53

3.73e+04

33.64

15.21

3.57e+04

O(7)

265.91

36.05

1.86e+07

266.30

40.71

1.87e+07

271.48

34.89

1.98e+07

O(8)

301.68

99.46

2.62e+07

297.96

102.71

2.51e+07

322.68

78.63

3.28e+07

O(16)

-353.82

1140.63

1.99e+08

-337.20

1113.80

1.86e+08

-239.97

971.80

1.15e+08

O(17)

302.25

89.47

2.68e+07

298.39

86.85

2.57e+07

309.02

97.66

2.86e+07

10

As shown in Table 2, in molecule(1)

with HF/6-31G, B3LYP/6-31G and
BLYP/6-31G iso( Isotropic(ppm) ) for
carbon atoms, C14 is greatest value and
whit HF/6-31G* and B3PW91/6-31G
C15 is greatest value, but for hydrogen
atoms in all methods H19 has greatest
value. In molecule(2) with HF/6-31G,
HF/6-31+G and HF/6-31G*, iso for
carbon atoms C13 has greatest value, for
hydrogen atoms H35 has greatest value
and for oxygen atoms O16 has negative
greatest value.
In molecule(1), aniso( Anisotropic
(ppm) ) with HF/6-31G, HF/6-31G,
B3LYP/6-31G,
BLYP/6-31G
and
B3PW91/6-31G for carbon atoms, C2
has greatest value and C14 has smallest
value. Also for hydrogen atoms, with
HF/6-31G, H19 has greatest value and
with
HF/6-31G,
B3LYP/6-31G,
BLYP/6-31G and B3PW91/6-31G, H30
has greatest value. In molecule(2) aniso
with HF/6-31G for carbon atoms, C2
has greatest value, and with HF/6-31+G
and HF/6-31G* C12 has greatest value.
For hydrogen atoms, with HF/6-31G,
HF/6-31+G HF/6-31G* H22 has greatest
value and H19 as smallest value, and for
oxygen atoms, O16 has greatest value.
Table 3 show share of orbitals contribute
in the bonds (BD for 2-center bond and
BD* for 2-center antibonding ).
According to Tables 3, in molecule(1)
with HF/6-31G method, for the C2-C7

bond, polarization coefficients of this

bond C2= 0.7123 and C7= 0.7019
reported, that sizes of these coefficients
show the importance of the hybrid s C2
in the formation of the bond. For the C2C7 bond with other methods values of
coefficients show the importance of the
hybrid s C2 in the formation of the
bond. In the C12-C13 and C12-C14 bonds
with HF/6-31G and HF/6-31G*
polarization coefficients of this bonds
show the importance of the hybrid s
C12 in the formation of the bond, while
with B3LYP/6-31G, BLYP/6-31G and
B3PW91/6-31Gpolarization coefficients
of this bonds show the importance of
the hybrid s C13 and C14 in the
formation of the bond. In the C-H
bonds polarization coefficients show the
importance of the hybrid s C in the
formation of the bond. In molecule(2)
with HF/6-31G, HF/6-31+G, HF/631G* methods, polarization coefficients
of the C-O bonds show the importance
of the hybrid s O in the formation of
this bond. Also polarization coefficients
of the C-H bonds show the importance
of the hybrid s C in the formation of
this bond. With HF/6-31G, HF/6-31+G,
HF/6-31G*
methods,
polarization
coefficients of the C2-C3 and C13-C14
bonds show the importance of the
hybrid s C2 in the formation of C2-C3
bond and importance of the hybrid s
C13 in the formation of C13-C14 bond.

11

Table 3. Relative natural bond orbital( NBO) for several active bond in studied molecules by : HF method with 6-31G,6-31G* and 6-31+G basis set and B3LYP, BLYP and B3PW91 methods
with 6-31G basis set.
Method

HF

Basis set

Molecule 1

Name

Parameter

Bond

+ 0.7019 sp

0.7129 sp

2.87

+ 0.7047 sp

2.74

0.7096 sp

2.91

+ 0.7059 sp

2.57

0.7086 sp

1.52

+ 0.7110 sp

1.54

0.7033 sp

0.7167 sp + 0.6974 sp

0.7095 sp

C8 C15

0.7083 sp

C11 C12

0.7032 sp

2.31

+ 0.7057 sp

2.27

+ 0.7065 sp

C12 C13

0.7085 sp

C12 C14

0.7078 sp

O8 C9

0.7092 sp

2.53

0.7084 sp

1.75

1.92

+ 0.7029 sp

2.85

+ 0.6979 sp

3.11

+ 0.8177 sp

2.97

+ 0.8160 sp

0.7113 sp

2.74

+ 0.6939 sp

3.14

+ 0.8202 sp

2.97

+ 0.8165 sp

2.55

0.8329 sp

2.66

0.7162 sp

1.82

0.5756 sp

2.03

0.5781 sp

4.04

+ 0.5535 sp

2.54

0.8347 sp

2.38

+ 0.6173 s

0.7878 sp

2.37

+ 0.6101 s

0.7931 sp

2.36

+ 0.6157 s

0.7891 sp

C4 H20

0.7924 sp

C6 H21

0.7880 sp

2.37

1.32

+ 0.8146 sp

0.5584 sp + 0.8296 sp

1.84

+ 0.7059 sp

1.53

+ 0.7111 sp

2.49 0.00

0.7067 sp

2.51 0.00

0.7059 sp

d
d

+ 0.6210 s
+ 0.6299 s
1.78 0.00

2.29

+ 0.6143 s

0.7835 sp

0.7031 sp

+ 0.7083 sp

+ 0.7054 sp

2.87

+ 0.7061 sp

1.53

+ 0.7111 sp

2.47

0.7062 sp

2.49

0.7055 sp

+ 0.6103 s

0.7914 sp

0.7824 sp

+ 0.6228 s

1.57

0.7029 sp

+ 0.7087 sp

3.49

+ 0.6116 s

0.7088 sp

2.25

0.7841 sp

2.65

2.55

+ 0.7080 sp

+ 0.6194 s

0.7912 sp

0.7093 sp

2.30

2.36

3.48

2.73

0.7139 sp + 0.7002 sp

+ 0.7036 sp

2.87

+ 0.7049 sp

2.87

+ 0.7054 sp

1.54

+ 0.7113 sp

2.46

0.7069 sp

2.49

0.7061 sp

2.25

+ 0.7081 sp

3.47

+ 0.6113 s

0.7956 sp

0.7814 sp

+ 0.6129 s
+ 0.6240 s

1.57

+ 0.7073 sp

0.7878 sp

2.66

2.54

2.30

+ 0.6207 s

0.7901 sp

2.71

0.7143 sp + 0.6999 sp

2.36

3.47

2.47

2.47

2.49

2.35

+ 0.6159 s

3.49

+ 0.6058 s

3.48

+ 0.6068 s

2.65

+0.6194 s

0.7949 sp

0.7851 sp

2.66 0.01

1.75 0.01

1.99 0.01

3.68 0.02

+ 0.8191 sp

0.7863 sp

1,57

2.25

2.89

2.15

0.00

+ 0.7061 spd

2.91 0.01

+ 0.6091 s

0.7081 sp

0.7106 sp

+ 0.8211 sp

2.29

2.55

+ 0.7075 sp

+ 0.7043 sp

0.7088 sp

2.47

2.99 0.01

2.45 0.01

2.91

Bonding

2.16

+ 0.7035 sp

+ 0.6926 sp

0.7099 sp

2.30

0.7922 sp

2.47

0.7145 sp + 0.6996 sp

+ 0.6206 s

+ 0.5552 sp

2.42 0.00

+ 0.6238 s

2.43 0.00

+ 0.6178 s

2.41 0.00

+ 0.6214 s

0.00

2.30 0.00

0.00

0.5491 spd

2.88

3.50 0.01

0.7816 sp

99.99

0.7031 sp

0.5731 sp

+ 0.7036 sp

0.7851 sp

+ 0.6160 s

+ 0.8347 sp

1.54 0.00

2.67 0.00

0.8317 sp

2.83

+ 0.6258 s

0.00

0.5737 sp

1.40

0.7038 sp

+ 0.7039 sp

0.7081 spd

2.07

99.99

0.5507 sp

0.7107 sp

0.5708sp

+ 0.8110 sp

Bonding

2.16

2.36 0.01

1.76 0.00

1.88

2.36

2.51 0.00

+ 0.7058 sp

2.29

0.5851 sp

0.7106 sp

2.28 0.00

0.7213 sp

+ 0.5507 sp

+ 0.7050 sp

2.66

4.15

2.68 0.00

0.7767 sp

+ 0.7029 sp

0.7103 sp

0.00

2.67 0.01

1.77

2.32 0.00

0.7838 sp

1.73

2.50 0.00

+ 0.6989 spd

3.49 0.01

+ 0.6247 s

0.7028 sp + 0.7114 sp

0.7867 sp

C12 O16

0.7113 sp

0.5800 sp

0.00

0.7153 spd

2.51

+ 0.7036 sp

C1 H19

C12 O16

+ 0.7109 sp

+ 0.6149 s

0.7106 sp

0.5773 sp

1.51 0.00

1.71

C3 O8

+ 0.7056 sp

0.7841 sp

0.7809 sp

0.5721 sp

2.63

C2 O7

2.89 0.01

+ 0.6145 s

0.7886 sp

0.7201 sp

+ 0.7046 sp

3.43

3.42

C13 C14

0.7800 sp

0.7889 sp

C5 C6

2.84 0.00

C5 H19

C2 C3

+ 0.7013 sp

+ 0.6209 s

0.7839 sp

C11 H30

2.34

C1 H16

Bonding

2.16 0.00

B3PW91

6-31G

Bonding

2.52

C5 C6

BLYP

6-31G*

Bonding

2.16

0.7123 sp

C11 C12

6-31+G

Bonding

C2 C7

C8 H25

Molecule 2

6-31G

B3LYP

1.10 0.01

+ 0.8195 sp

+ 0.8358 spd

12

Table 4 show of GIAO Magnetic

shielding for some of atoms. As shown
value. While with B3LYP/6-31G and
BLYP/6-31G from carbon atoms C14
has greatest Shielding value and C2 has
smallest
Shielding
value,
with
B3PW91/6-31G from carbon atoms C15
has greatest Shielding value and C2 has
Degeneracy value is same, also from
carbon atoms C14 has greatest Shielding
value and C4 has smallest Shielding in
Table 4, in molecule(1), with HF/6-31G
and HF/6-31G*, all atoms In
molecule(2), in three methods of HF/631G, HF/6-31+G and HF/6-31G* all
atoms have same Degeneracy value.
signals are for atoms C1, C2, C3, C4, C11
and C12 (carbons of double bonds), also
smallest signals are for atoms H16, H17
and H18 (hydrogens of double bonds).
Figure 8 show that in molecule(2) at all
methods biggest signal is watched for
the atom C12 and O16 (C=O : carbonyl)
and smallest signal is for H19.
atoms, H35 has greatest Shielding
value and H20 has smallest Shielding
value. For oxygen atoms with HF/631G and HF/6-31+G, O17 has greatest
positive Shielding value and O16 has
negative Shielding value, but with
HF/6-31G*, O8 has greatest positive
Shielding value and O16 has negative
Shielding value.
With HF/6-31G, HF/6-31+G and HF/631G* for carbon atoms, C13 has greatest
Shielding value and C12 has smallest
Shielding value, also for hydrogen
Figures 7,8 are the diagrams which
shows Anisotropy (ppm) for each of the

Table 5 show thermochemical parameters

for molecule(1) and molecule(2) whit
different methods in gas phase. Also Figure
9 show comparison of thermochemical
parameters
in
molecule(1)
and
molecule(2). Molecule(1) response whit
five methods HF/6-31G, HF/6-31G*,
B3LYP/6-31G,
BLYP/6-31G
and
B3PW91/6-31G, but molecule(2) response
whit three method HF/6-31G, HF/6-31+G
and HF/6-31G*.
Also Figure 9 show comparison of
thermochemical parameters in molecule(1)
and molecule(2). According to Tables 5
and Figure 9, s for molecule(2)
(Gingerol) is more than molecule(1)
(Zingiberene), but E, H and G of
molecule(2) are lower than molecule(1).
According to Tables 5, CV(cal/molK) for
molecule(2) is greater than molecule(1),
also LnQ value for molecule(1) is more
negative than molecule(2).

atom at the molecule1 (Zingiberene) and

molecule2 (Gingerol) for each of the

atom, respectedly. As shown in

Figure7, in molecule(1) at all methods
biggest BLYP/6-31G, B3PW91/6-31G
for hydrogen atoms, H19 has greatest
Shielding value and H18 has smallest
Shielding value.
smallest Shielding value. Also with
HF/6-31G, HF/6-31G*, B3LYP/6-31G,
13

Table 4. Ralative GIAO Magnetic shielding for active site of studied moleculars obtained using different
methods.
Method

HF

B3LYP

Shielding
(ppm)

Degeneracy

Degeneracy

84

73.27

C(3)

77.93

C(4)

72.16

C(7)

186.74

C(11)

B3PW91

6-31G
Degeneracy

Shielding
(ppm)

Shielding
(ppm)

Shielding
(ppm)

76.03

72.19

78.72

73.08

64.22

60.12

67.62

77.79

70

66.73

72.64

71.88

66.63

63.90

69.37

181.02

172

165.94

175

79.09

78.28

69.89

66.32

72.62

C(12)

75.07

75.10

65.98

61.6

69.58

C(13)

182.51

176.81

167.74

161.74

170.78

C(14)

190.74

184.66

176.8

171.1

179.5

C(15)

190.38

184.18

176.5

170.44

179.99

H(16)

27.76

27.36

27.56

27.06

27.15

H(17)

27.21

27

26.66

26.48

26.53

H(18)

26.95

26.66

26.55

26.38

26.44

H(19)

32.36

31.69

31.11

30.67

31.06

H(25)

32.30

31.53

30.72

30.24

30.66

H(30)

27.93

27.61

27.23

27

27.14

C(2)

59.74

60.3

58.13

C(3)

58.5

58.1

59.78

C(9)

153.05

152.9

148

C(12)

-17.03

-18.2

2.18

C(13)

159

158.71

154.8

C(14)

140.58

139.6

138.13

H(19)

27.01

26.75

26.44

H(20)

25.92

25.75

25.61

H(21)

26.41

26.27

25.88

H(22)

30.78

30.42

29.92

H(32)

29.54

29.37

29.07

H(35)

34.39

34.09

33.65

O(7)

265.92

266.31

270.15

O(8)

301.68

298

322.7

O(16)

-354.19

-338.2

-240

O(17)

302.25

298.4

309.5

Atoms

Parameter

Shielding
(ppm)

BLYP

6-31G*
Degeneracy

6-31+G
Degeneracy

6-31G

Degeneracy

Molecule 2

Molecule 1

Name

Basis set

Shielding
(ppm)

C(1)

85.53

C(2)

14

14

H3 C

12

10

H H

16 H

5
H19

1
7
H3 C

H 30

8
6

CH3

11

15
25 CH3

13

4
2
3

18

H17

Molecule 1 (Zingiberene)

Figure 7. diagrams which shows Anisotropy (ppm) for each of the atom at the molecule1
(Zingiberene).

15

H22

H19

7O
2

H21

15
13

11
8O
H 3C

12

5
4
H20

18

14

10

16 O

32

17

H 35

Molecule 2 (Gingerol)

Figure 8. diagrams which shows chemical shifts for each of the atom at the molecule2
(Gingerol).

16

Table 5. Relative thermochemical parameters (entropy S cal/molK, E Kcal/mol, enthalpy H

Kcal/mol, Gibbs free energy G Kcal/mol, CV cal/molK and LnQ), of benzimidazoles obtained
in gas phases.

E(Kcal/mol)

CV(cal/molK
)

H(Kcal/mol)

G(Kcal/mol)

Ln (Q)

6-31G

Molecule 1

133.412

248.981

59.831

249.573

209.796

-354.093

Molecule 2

147.631

228.529

67.246

229.121

185.105

-312.419

6-31+G

Molecule 1

Molecule 2

148.243

227.920

67.524

228.512

184.313

-311.084

6-31G*

Molecule 1

134.058

248.231

60.594

248.823

208.854

-352.504

Molecule 2

146.632

228.448

67.452

229.040

185.322

-312.786

B3LYP

Basis
set

Molecule 1

136.366

234.658

64.274

235.250

194.593

-328.433

Molecule 2

BLYP

Metho
d

Molecule 1

136.603

235.155

64.225

235.747

195.019

-329.153

Molecule 2

Molecule 1

137.939

228.439

66.260

229.031

187.904

-317.145

Molecule 2

Parameter

B3PW91

6-31G

HF

Molecule

S(cal/molK)

Figure 9. Comparison of entropy S cal/ (molK), energy E kcal/mol, Gibbs free energy G kcal/mol,
enthalpy H kcal/mol of Molecules 1(Zingiberene) and Molecule2(Gingerol) in gas phases obtained
using HF/6-31G, HF/6-31+G, HF/6-31G*, B3LYP/6-31G, BLYP/6-31G and B3PW91/6-31G levels.

17

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20