Chemical composition of the leaf oil of Litsea glutinosa (Lour.) C. B.Rob. from Ha Tinh province

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VNU Joumal of Science, Natural Sciences and Technolo gy 26 (2070) 161-7(/.

Chemical composition

of

the

leaf

oil

of

Litsea

glutinosa

(Lour.)

C.

B. Rob.

from

Ha Tinh province

Nguyen

Thi

Hienr, Tran

Dinh

_{rhang2,Do Ngoc Dai3,*, Tran Huy}

_Thai3

'

tFaculty of

Biolog,

Yinh University, lB2 Le Duan, Vinh, Nghe An, vietnam

2Faculty

of chemistry, vinh (Jniversity, 182 Le Duan, vinh, Nghe An, yietnam

3lnstitute

of Ecolog and Biological Resources, Vietnamese Academy of Science and Technologt,

18 _{Hoang Quoc}Viet, Hanoi, Vietnam

Nh{n ngdy I th6ng 3 ndm 2010

Abstract. Fresh leaves of Litsea glutinosa (Lour.) C. B. Rob. from Ha Tinh were steam distilled to
produce an oil in 0'15% yield. The essential oil was analysis by a combination of capillary GC and

GCA4S. Seventy eight compowrds were detected in the oil, of which more than 95.18% were
terpenoids. The major components were (E)-p-ocimene (13.35%), p-caryophyllene (27.20%) and
bicyclogermacrene ( I 8. I 6%).

fyry

: Litsea glutinosa, _{Lauraceae, essential}_oil_{composition, (E)-p-ocimene, p-caryophyllene,}
bicyclogermacrene.

1. Introduction

The

genus

Litsea

is a

member

of

the
Lauraceae and _{comprises more than 400}_species

which

are

distributed

widely

throughout

hopical _{and subtropical Asia, Ausfialia, North}

America

to

subtropical South

America;

73

species _{have been recorded}

_in

_China,_most

_of

them located

in

south and southwest warm

regions

_[];

a5

species have been found in
Vietnam, until now [2].

Litsea glutinosa

is

an evergreen
medium-sized tree.

Its

_{barks and leaves are used as}a

demulcent and mild astringent for diarrhea and

dysentery,

the

roots

are used

for

poulticing

;Co*rp*alng

author. Tel.: 84-38-3855697.
E-mail:

sprains and bruises, and the

oil

extracted from

the seeds is used in the treatrnent of rheumatism

[3].

Some psychopharmacological actions

of

the essential

oil

of Litsea glutinosa (Lour.) C.

B. Rob. have been studies by Menon

K. M.

et

al. [a]. Effect of essential oil of Litsea glutinosa

(Lour.)

C.

B.

Rob.

on

cardiovascular system

and isolated tissues _{have been investigated by}

same authors

_[5].

Flavonoids and aporphine

alkaloids were isolated from Litsea glutinosa

[6, 71.

A

water-soluble arabinoxylan (D-xylose

and L-arabinose in the molar ratio 1.0:3.4) was

isolated from the mucilaginous bark

of

Litsea
glutinosa

_l8l.

Recently, research disclosetl that the MeOH

extract

of

Litsea

glutinosa

bark

effectively

inhibited

both

Gram-positive

and

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162

N.T. Hien et al. I WU lournal of Science, Natural Sciences and Technology 26 (20L0) 1.61.-1.64

negative bacteria.

The

results

justiff

the
reported uses in diarrhea and dysentery _[9].

The BuOH extract

of

the leaves and twigs

of

Litsea

glutinosa

were

shown

to

exhibit

significant

cytotoxic

activity

against human

Hela cell lines.in vitro. Chemical examination

of the BuOH extract of the leaves and tvrigs

of

Litsea glutinosa collected from Xishuangbanna

resulted

in

the isolation

of

two new aporphine

alkaloids, namely litseglutine

A

and

B,

along

with

two

known aporphine alkaloids, boldine

and _{laurolitsine [10].}

In

the

course

of

the

systematic study

of

Litsea

in

Indochina,

monoterpenes,

sesquiterpenes and other components of the leaf

oil

of Litsea glutinosa

fiom

Ha Tinh province

have been investigated.

2.

Experimental

.

1. Soarce- Litsea glutinosa (Lour.)

C.

B.
Rob. (Lauraceae),

is

a shrub tree up

to 7-10'

high, growing in Vietram. The leaves of Litsea
glutinosa were collected

in April

2009;

in

Vu,

Quang National

park,

Ha Tinh

province.

A'

voucher specimen

(NHll0)

was deposited at

the Herbarium of the Faculty of Biology, Vinh

University.

Fresh leaves were shredded and

their

oil

were obtained

by

steam distillation

for

3h

at

normal pressure, according

to

the Viebramese
Pharmacopoeia _[11].The yield of the fresh leaf

oil was 0.I5%.

2. GC- About 15mg of oil, which was dried

with

anhydrous sodium sulfate, was dissolved

in lml

of

n-hexane

(for

spectroscopy or

chromatography).

GC analysis was performed on a HP 6890

Plus Gas chromatograph equipped

with

a

FID

.

and fitted with HP-5MS column

(L:30nrm,ID

:

0.25mm,

film

thickness

:

0.25pm). The

analytical conditions

were:

carrier

gas

Hz,

injector

temperature

(PTV)

250oC, detector

temperature 260oC, temperature programmed

60' (2 min

hold)

to

220o

(10

min

hold)

at

4"Clmin.

3.

GC/IWS-

An

Agilent

Technologies HP
6890

N

Plus Chromatograph was fitted

with

a

fused silica capillary col. HP-5MS column

(L:

30mm,

ID :

0.25mm,

film

thickness

:

0.25pm). The condition of use were the same as

described above

with

He

as ca:rier gas, and

interface

with a

mass spectrometer

HP

5973

MSD

(70eV). Component identification was

carried out

by

comparing MS data

with

those

reported in Library Willey on Chemstation HP,

and

in

some

qnes

substances identified from
oils known composition and also with standard

substances _lI2-171.

3. Results and discussion

Of the more than 90 leaf

oil

components

of

Litsea glutinosa

that

were

separated by
capillary GC

in

this study, 78 were identified
after GC/IMS analysis, representing 95.18%

of

the total (Table 1).

T4bte 1. Volatile leaf components of Litsea
glutinosa (Lour.) C. B. Rob. from Ha Tinh

No Compounds

KI%

FID

tricylene
o-thujene
a-pinene
camphene
sabinene
p-pinene
myrcene
a-phellandrene
63-carene
cr-terpinene
p-cymene
o-cymene

927

trace

931

0.37

939

3.38

953

0.41

976

0.29

980

3.26

990

1.91

1006 0.65

l0l

l

0.50

l0l7

trace

1026 trace

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N.T. Hien et al. / WU lournal of Science, Natural Sciences andTechnology 26 (2010) 151-754 163
limonene
(Z)-B-ocimene
(E)-B-ocimene
y-terpinene
eterpinolene
linalool
nonanal

(E)-4,8-dimethyl- 1,3,7-nonatriene
alloocimene
geijerene
mpnthone
iso-menthone
(Z)-anethol
decanal

octyl acetate

linalyl acetate
2-undecanone
(E)-anethole

bornyl acetate
undecanal
bicycloelemene
ecubebene
neryl acetate
cl-ylangene
GCOpaene
&bourbonene
$cubebene
Selemene
iso-caryopbyllene
dodecanal
$caryophyllene
y-elemene
eguaiene
aromadendrene
3,7-guaiadiene
ehumulene

(+)-epi-bicyclosesquiphellandrene
germacrene D

eamophene
Sselinene
bicyclogermacrene

(E,E)-o.farnesene
y-cadinene
6-cadinene
germacrene B

(E)-nerolidol

bourboneol

germacrene-D4-ol

spathulenol

caryophyllene oxide
cedrol

1032 r.30
1042 2.s4

1053 13.35

l06l

0.12

1090 0.14

1100 tace

ll02

tace
I104 0.41

I128 0.48

ll43

tace

1153 0.66

1163 0.14

I165 1.04

1180 0.20

ll83

trace

l261 0.15

1273 tace

1285 0.24

1289 trace

1290 tace

1327 0.20

1343 0.t4

1362 tr:ace

1374 tace

1376 0.24

1386 0.15 .

1389 0.14

l39l

0.66

1409 0.10

t4t2

0.t8

t4t9

27.20

1433 0.19

1440 tace

1443 trace

1447 0.r0

1454 3.04

t474 0.10

1480 r.48

148s 0.66

1490 0.r0
1499 18.16

1506 0.81

t5t4

0.21

ts2s

0.56

1536 0.82

1558 2.73

1567 trace

1574 0.t0

1577 0.67

t58t

2.21

1598'0.16
ledol
cr-cedrene
r-muurolol
$eudesmol
ecadinol
(Z)-P-asarone

minsulfide
benzylbenzoate
tetadecanal

6,10,

l4-trimethyl2-pentadecanone
n-eicosane
n-heneicosane
phytol
n-docosane
n-heptacosane

1600 0.26

1640 tace

l64l

0.91

l65l

0.13

.1653 _0.13

1676 tace

1742 trace

1760 0.27

1770

e

1829 0.31

2000 tace
2100 tace

2125 0.33

2200 tace

2700 0.19
Note: trace < 0,1; KI = Kovats index

The

monoterpenes represented

the

most

abundant component

with

(E)-p-ocimene
(l 3 .3 5%), o-pinene (3 .38%), p-pinene (3 .260/o),

(Z)-p-ocimene

(2.54%),

myrcene (I.9I%),

limonene (1.30%), (E)-anethol (1.04%) and

other

components

with

content

lower

than

I.00%. Among the sesquitetpenes, there werd

caryophyllene (27.20Vo), bicyclogermacrene

(18.16%),

o-humulene

(3.04o/o), nerolidol

(2.73%),

caryophyllene

oxide

(2.21%),
germacrene

D

(1.48%) and other constituents

with content lower than I.00%.

The

oxygenated compounds

such

its

linalool, nonanal, menthone, iso-menthon e,

(Z)-,

(E)-

anethol, decanal,

octyl

acetate, linalyl

acetAte,

2-undecanone,

bornyl

acetzte,

undecanal,

neryl

acetate, dodecanal,

(E)-nerolidol,

bourboneol,

germacrene-D-4-ol,

spathulenol, caryophyllene oxide, cerdrol, ledol,

r-muurolol, nerolidol, p-eudesmol, o-cadinol,
(Z)-p-asarone,

berzyl

benzoate, tetradecanal,

6,10,14-trimethyl 2-pentadecanone and phytol

have a relatively small content, but contribute to

the charactistic odor of this oil,

This

essential

oil

contains

also

small

amount

of

n-paraffin:

n-eicosane,

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N.T. Hien et al. I WU lournal of Scieace, Natural Sciences and Technology 25 (20L0) 161-164

r64

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Nghi6n

cr?u

thenh

phAn h6a

hgc

tinh

dAu

ld

cdy

Bcri

lcri

nhor

(Litsea glutinosa

(Lour.)

C.

B.

Rob.) d Hd

finh

Nguy6n Thi

Hi6nt,

TrAn

Dinh

ThEng2,D5

Nggc

Dei3,

Tr6n Huy

Th6i3

tKhoa

Sinh hpc, Dqi hpc Vinh, 182 L6 Duiin, Vinh, Nghg An, ViQt Nam

2Khoa

H6a hpc, Dei hpc vinh, 182 L6 Duiin, Vinh, NghQ An, yist Nam

3Yipn

sinh thdi vd Tdi nguyin sinh.vgt, ItiQn Khoa hpcvd c6ng nghs vigt Nam,
18 _{Hodng Qu6c}ViQt, Hd NAi, ViQt Nam

Hdm luqng tinh ddu

fi

16

ciy

Boi loi _nhot

h

_O,ll%;otheo_{nguyOn liQu}_{tuoi. Nghidn}_{cuu thdnh ph6n}

h6a hqc cria tinh

diu

15 c6y Boi ldi nhdt (Litsea glutinosa (Lour.) C. B. Rob.) d He Tinh bdng phuong

phdp s6c ky

qi

(GQ vn sic

kj

khi kh5i prro

_lccnvrs),

hon 90 hqp ctr6t euqc t6ch ra tu tinn

#u,

tron!

t16 78 hqtp chdt ilugc xdc <linh (chiiSm gs,I8yo tdng hdm luqng

tinh

_Thanh_phdn_chinh_cua_tinh

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