THNH PHN HA HC CA TINH DU L TRU (PIPER BETLE L.

)
TRNG TI HI DNG

Phm Th Chnh*, Dng Ngha Bang, Phan Thanh Phng,

Khiu Th Tm, Phm Th Thm, L Th Xun, Bi Th Thy
Trng i hc Khoa hc i hc Thi Nguyn

TM TT
Bng phng php chng ct li cun hi nc c bit c hiu ng mui kt hp vi un hi lu,
chng ti tch thnh cng tinh du l tru c trng ti Hi Dng vi hiu sut t 1,01%.
Tinh l tru tch c c t trng cao l d425 =0,963 v chit sut ln nD25 =1,5362. Bng phng
php sc k kh ghp ni khi ph (GC/MS), chng ti khng nh tinh du l tru trng ti Hi
Dng c thnh phn ha hc chnh l eugenol, vi hm lng ln ti 77,24%. T tinh du ny
chng ti s dng phng php sc k ct thng nhi bng silica gel theo phng php nhi
t vi h dung mi ra gii l n-hexan/etyl axetat, 10/1, v/v; phn lp c eugenol tinh khit
v khng nh c cu trc ca n bng cc phng php ph hin i IR, MS, 1H&13C-NMR.
T kha: tru khng, tinh du tru, eugenol, allylbenzen, polyphenol

M U nn hot tnh ca sn phm, nn cn phi

Cy tru (Piper betel L.) c trng khp
ni trong nc ta ly l n tru. N cn
c trng ti nhiu nc khc chu ,
vng nhit i nh Malaysia, Inonexia,
Philipin... Ngoi vic dng l tru nhai vi
cau v vi n tru v bo v rng ming,
dn gian cn dng nc l tru st trng,
chng l lot, chng vim nhim...[1]. Cc
hp cht polyphenol trong l tru c kh nng
chng oxi ha cao, v c ch mt s nguyn
nhn gy bnh lot d dy [4].
Tinh du l tru n cha cadinen, -
lacton, metyl eugenol...[3], theo Nguyn Th
L v cng s, tinh du l tru trng Nam
B cha ch yu l 4-allyl-1,2-
diaxetoxylbenzen (43,21%), phenol- 4-allyl-
2metoxyaxetat (19,44%) v phenol-2-metoxi-
4-(1-propenyl) (19,82%) [2].
Tinh du l tru trng cc a phng pha
Bc cha c s liu cng b v thnh phn
ha hc. Hn na sn phm nc xc ming
c ngun gc t tinh du l tru ca nhiu
cng ty dc phm c bn trn th
trng, chng c sn xut da trn cc
kinh nghim dn gian m cha c tiu chun
kim nghim ha hc v thnh phn chnh to
Tel: 0988113933; Email: chemistry20069@gmail.com
nghin cu k v thnh phn ha hc ca tinh
du l tru, l nhng l do cho nghin cu
ca cng trnh ny.
THC NGHIM V PHNG PHP
NGHIN CU
Mu thc vt
L cy tru (Piper betel L.), c thu hi vo
thng 2 nm 2009 ti Hi Dng. Mu do
phng thc vt, Vin sinh thi v Ti nguyn
Sinh vt thuc Vin Khoa hc Vit Nam gim
nh. Mu sau khi thu hi c lm sch v
phi kh trong iu kin nh sng t nhin,
sau nghin thnh bt mn.
Ha cht v thit b
Cht hp ph dng cho sc k ct l silica
gel (0,040 0,063 mm, Merck). Sc k lp
mng dng bn mng trng sn 60F 254
(Merck). Cc dung mi chit v chy sc k
t loi tinh khit (PA).
Ph cng hng t ht nhn c ghi trn
my Bruker AV 500 MHz i vi ph 1H
v 125,7 MHz i vi 13C-NMR. Ph khi
lng c o trn my Hewlett Packard HP
5890, Serie II. Ph IR c o trn my
Impac 410-Nicolet FT-IR.
Chng ct tinh du
Cho 300 g bt l tru vo bnh ct, 600 ml
dung dch NaCl 15%, lp by tinh du c sn

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Phm Th Chnh v cs Tp ch KHOA HC & CNG NGH 72(10): 48 - 52

100 ml toluen, lp sinh hn, un hi lu 3 gi, 149(38%), 131(22%), 121 (18%), 103 (21%),
tho dung mi trong by, ct ly 1,5 lt nc- 91(20%), 77 (23%), 65(10%), 55(22%); IR
du. Bo ha dch ct bng NaCl, chit dch (Film): maxcm -1: 3517 (OH), 3083 (CH
thu c bng 150 ml toluen, chia lm 3 ln. thm); 2941, 2849 (CH3,CH2); 1594, 1443
Gp dch chit toluen vi toluen ly t by, (C=C, thm); 850 (=CH2); 1H&13C-NMR
lm kh, ct loi toluen thu c 3,03 g tinh (DMSO) (xem Bng 2).
du (hiu sut 1,01%), l cht lng mu vng, KT QU V THO LUN
mi thm d chu, d425 =0,963, nD25 =1,5362. iu ch v phn tch tinh du l tru Hi Dng
Phn tch tinh du bng sc k kh ghp Theo cc ti liu cng b [2,3,4,5], thnh
ni khi ph phn chnh ca tinh du l tru l cc dn xut
Tinh du l tru c phn tch thnh phn ca phenol. Cc dn xut ny c nhit si
bng my GC/MS (Gas Chromatography cao, v vy chng ti dng phng php ct
Mass Spectrometry), trn thit b Hewlet li cun hi nc c bit c hiu ng mui,
Packard 6890 Series GC System vi ct HP-5 un hi lu v by dung mi ct tinh du.
(5% phenyl metyl polysiloxan), Hewlet Kt qu cho thy tinh du l tru vng Hi
Packard HP 5973 Mass Selective Detector. Dng c hiu sut cao 1,01%, tinh du c
c tin hnh vi kh mang He tc mi d chu, c t trng kh ln d425 =0,963
1ml/pht, nhit bung bm mu 2500C, v chit sut nD25 =1,5362. iu ny chng t
theo chng trnh nhit : gi 300C trong
tinh du c thnh phn c nhit si cao
5 pht sau tng 50C/pht n 2700C, gi
chim a s. Qu vy, phn tch tinh du l
nhit ny trong vng 5 pht. iu kin ca
tru Hi Dng bng phng php GC/MS
detector ph khi lng: nhit ngun l
chy theo chng trnh nhit v so snh ph
2300C, in th 70eV, ngun 2A, phn gii
khi lng vi ph khi trn th vin my
1000. Cu trc ca cc thnh phn c xc
nhn dng cc cht vi iu kin c trng
nh bng so snh ph ca thnh phn tinh
lp 90% tr ln. Kt qu hnh 1, bng 1.
du vi ph khi c trong th vin my, nu
trng lp t 90% tr ln c coi nh Bng 1. Thnh phn ha hc ca tinh du l
nhn bit. Kt qu phn tch th hin trn ph tru Hi Dng
GC (Hnh 1) v Bng 1. S Thi gian
Thnh phn
Hm
TT lu (pht) lng (%)
Phn lp thnh phn chnh ca tinh du l tru
1 15,52 Chavicol 7,56
Tin hnh sc k ct 1 g tinh du vi ct di
70 cm v ng knh 2,0 cm, s dng 50 g 2 18,45 Chavicyl axetat 0,58
sili cagel c ht 0,040 0,063 mm, theo 3 18,86 Cha xc nh 0,19
phng php nhi t, dung mi ra gii l 4 19,40 Eugenol 77,24
h n-hexan/etyl axetat 10/1 (v/v) thu c 50 5 20,37 Cha xc nh 0,14
phn on, mi phn on 3 ml. Kho st sc
6 20,76 -Caryophyllen 0,27
k lp mng (SKLM) cc phn on thu
c, gom cc phn on c Rf ging nhau 7 22,56 Cha xc nh 0,62
thnh mt nhm, loi dung mi thu sn phm. 8 23,60 Cha xc nh 1,83
T phn on 10 n phn on 24 thu c 9 23,94 -cadinen 0,17
0,53 g cht lng (T1), hiu sut t 53% so
10 24,18 Eugenyl axetat 8,67
vi cn tinh du, nD25 =1,5401, tan tt trong
4-allyl-1,2-
axeton, benzen, Rf=0,59 (n-hexan/etyl axetat 11 27,51 2,73
diaxetoxybenzen
10/1), EI-MS: M+=164, m/z (%):164 (100%),

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Phm Th Chnh v cs Tp ch KHOA HC & CNG NGH
Hnh 1. Ph GC ca tinh du l tru Hi Dng
Kt qu cho thy tinh du ca l tru Hi
Dng c 11 thnh phn, 7 thnh phn
nhn dng c chim 96,37%, 4 thnh phn
cha xc nh c chim 3,63%. Thnh
phn chnh ca tinh du l eugenol chim n
77,24%, hai thnh phn c hm lng ln na
l eugenyl axetat 8,67% v chavicol 7,56%,
thnh phn 4-allyl-1,2-axetoxybenzen chim
2,73%. R rng thnh phn tinh du ca l
tru Hi Dng rt khc thnh phn tinh du
ca l tru Nam B, tinh du l tru Nam B
c thnh phn chnh l 4-allyl-1,2-
axetoxybenzen 43,21% [3], khng c
chavicol v cng khng c eugenyl axetat.
Thnh phn chnh ca tinh du l tru Hi
Dng cng rt khc vi thnh phn chnh
ca tinh du n , Malaysia [2,3,4]. C s
khc bit trn c th do th nhng v kh
hu, cng c th do phng php iu ch
tinh du. Thnh phn chnh eugenol, chavicol,
eugenyl axetat v 4-allyl-1,2-diaxetoxybenzen
ca tinh du l tru Hi Dng chim
96,37%. Tt c chng u l dn xut ca
phenol, chng c nhit si cao, t trng v
chit sut cao. V eugenol trong tinh du l
tru chim ti 77,24% nn c th ni tinh du
l tru Hi Dng l ngun nguyn liu qu
cho sn xut eugenol.
Phn lp v xc nh cu trc cc thnh
phn ca tinh du
Phn lp tinh du bng sc k ct:
Gi tr ca tinh du tng ln nhiu ln khi
chng ta phn lp c nhiu cht tinh khit
c gi tr v kinh t. V vy chng ti t vn ppm, m, 1H (-CH2-CH=CH2) v H = 5,02
S ha bi Trung tm Hc liu i hc Thi Nguyn
72(10): 48 - 52
phn lp cc cht tinh khit t tinh du l
tru Hi Dng.
Nh phn trn trnh by, 4 thnh phn
chnh ca tinh du l tru Hi Dng l:
eugenol (77,24%), eugenyl axetat (8,67%),
chavicol (7,56%) v 4-allyl-1,2-
diaxetoxylbenzen (2,73%). Bn hp cht ny
c nhit i si cao v cu trc phn t gn
ging nhau nn phng php phn lp tt
nht c th l phng php sc k ct.
Vi h dung mi n-hexan/etyl axetat, 10/1,
v/v; trn ct di 70 cm ng knh 2 cm, cht
hp ph l silica gel 40-63 m, t l cht phn
tch trn cht hp ph l 1/50, nhi ct theo
phng php nhi t. Chng ti phn lp
c mt cht tinh khit t tinh du l tru
Hi Dng, hiu sut 53% k hiu l T1. T1
l cht lng c mi thm d chu, hp dn, Rf
= 0,59 (n-hexan/etyl axetat, 10/1, v/v), hin
mu tm nu vi vanilin/H2SO4 1% v xanh
en vi FeCl3 5%.
Xc nh cu trc ca T1:
T1 l cht lng c mi thm d chu, chit sut
cao nD25 =1,5401. Ph IR ca T1 cho thy nhm
OH = 3517 cm -1, c 1 nhn thm = 3083,
1594, 1443 cm -1; tn hiu ca lin kt C-H no
= 2941, 2849 cm -1; ngoi ra cn c tn hiu
ca nhm metylen u mch =850 cm -1.
T ph 1H&13C-NMR v DEPT cho bit T1
c 10 nguyn t cacbon, trong c 1 nhm
OCH3 H = 3,72 ppm, s, 3H; 1 nhm OH H =
8,80 ppm, s, 1H; 1 nhm allyl: H = 3,25 ppm,
d br, J = 4,8 Hz (-CH2-CH=CH2), H = 5,89
ppm, d br, 2H, J = 7 Hz (-CH2-CH=CH2) v
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Phm Th Chnh v cs Tp ch KHOA HC & CNG NGH 72(10): 48 - 52

c mt nhn thm 3 nhm th cc v ch (tng tc octo-octo v meta-meta); H = 6,63

1,2,4 th hin 3 pic ca proton thm: H =
6,81 ppm, d, 1H, J = 8,0 Hz (tng tc octo-
octo); H = 6,55 ppm, dd, 1H, J = 8,0; 1,8Hz
(tng tc octo-octo v meta-meta); H = 6,63
ppm, d, 1H, J = 1,8 Hz (tng tc meta-meta).
Xc nh cu trc ca T1
T1 l cht lng c mi thm d chu, chit sut
cao nD25 =1,5401. Ph IR ca T1 cho thy nhm
OH = 3517 cm -1, c 1 nhn thm = 3083,
1594, 1443 cm -1; tn hiu ca lin kt C-H no
= 2941, 2849 cm -1; ngoi ra cn c tn hiu
ca nhm metylen u mch =850 cm -1.
T ph 1H&13C-NMR v DEPT cho bit T1
c 10 nguyn t cacbon, trong c 1 nhm
OCH3 H = 3,72 ppm, s, 3H; 1 nhm OH H =
8,80 ppm, s, 1H; 1 nhm allyl: H = 3,25 ppm,
d br, J = 4,8 Hz (-CH2-CH=CH2), H = 5,89
ppm, m, 1H (-CH2-CH=CH2) v H = 5,02
ppm, d br, 2H, J = 7 Hz (-CH2-CH=CH2) v
c mt nhn thm 3 nhm th cc v ch
1,2,4 th hin 3 pic ca proton thm: H =
6,81 ppm, d, 1H, J = 8,0 Hz (tng tc octo-
octo); H = 6,55 ppm, dd, 1H, J = 8,0; 1,8Hz
ppm, d, 1H, J = 1,8 Hz (tng tc meta-meta)
Nh vy t cc d liu ph IR, 1H&13C-NMR
v DEPT cu trc ca T1 c nhn danh l
eugenol (1):
Cu trc ny ca T1 c khng nh li mt
ln na bng cch so snh ph khi ca n
vi ph khi ca eugenol trong th vin my,
kt qu cho thy chng c trng lp 98%
v ph hp vi qui lut phn mnh (2):
KT LUN
Bng phng php ct li cun hi nc c
bit c hiu ng mui, chng ti tch c
tinh du l tru Hi Dng vi hiu sut
1,01%, tinh du c t trng v chit sut cao
d425 =0,963, nD25 =1,5362. Tinh du l tru Hi
Dng c hm lng eugenol rt ln 77,24%.
T tinh du ny chng ti phn lp xc
nh cu trc ca eugenol bng cc phng
php ph hin i.

(2)
S liu ph H& C-NMR xem bng 2:
1 13

Bng 2. D liu ca ph 1H& 13C-NMR ca T1

13 1
S tn C-NMR H-NMR
khung C C (ppm) Nhm c H H (ppm) S H bi J (Hz)
C-1 145,99 C
C-2 146,48 C
C-3 115,83 CH 6,63 1H d 1,8
C-4 132,30 C
C-5 118,83 CH 6,55 1H dd 1,8; 8,0
C-6 112,37 CH 6,81 1H d 8,0
C-1 38,89 CH2 3,25 2H d br 4,8

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Phm Th Chnh Tp ch KHOA HC & CNG NGH 72(10): 48-52

C-2 138,05 CH 5,89 1H m

C-3 115,21 CH2 5,02 2H m 7,0
OCH3 55,68 OCH3 3,72 3H s

TI LIU THAM KHO [4] Lakshmi Arambewela, K.G.A Kumaratunga

1. Tt Li (2005), Nhng cy thuc v v
thuc Vit Nam, Nxb Y hc, tr 118-119.
2. Nguyn Th L, Trn Th Hng Vn, tch tinh du
v carotenoid t l tru (Piper betle L.), Hi ngh
KHCN (ln 9), H Bch Khoa TP H Ch Minh.
3. K. Ghosh and T. K. Bhattacharya (2005),
Chemical Constituents of Piper betle Linn.
(Piperaceae) roots, Molecules, 10, p 798-802.
and Kalyani Dias (2005), Studies on piper betle of
Sri Lanka, J. Natn.Sci.Foundation Sri Lanka, 33(2),
p133-139.
5. T. Nalina and Z.H.A. Rahim (2007), The Crude
Aqueous Extract of Piper betle L. and its
Antibacterial Effect Towards Streptococcus
mutans, American Jounal of Biotechnology and
Biochemistry,3(1),p10-1.

SUMMARY
CHEMICAL CONSTITUENTS OF ESSENTIAL OIL
IN LEAF PIPER BETLE L. HAIDUONG

Pham The Chinh, Dng Nghia Bang, Phan Thanh Phng,

Khieu Thi Tam, Pham Thi Tham, Le Thi Xuan, Bui Thi Thuy
College of Sciences Thai Nguyen University

By method of steam distillation appealing special effects combined with boiling salt reflux, we have
successfully prepared the essential oil of betel leaf grown in Hai Duong to the performance achieved
1.01%. The essential oil of betel leaf is modulated high density (d 425 = 0.963) and nD25 = 1.5362. By
method of gas chromatography mass spectrometry coupling (GC/MS), we have confirmed the betle
oil which is the main chemical ingredient is eugenol, with levels of up to 77.24%. we have used
column chromatography method with solvent cleaning solution is n-hexan/etyl acetate, 10/1, v/v; the
eugenol was isolated and was confirmed the structure by modern spectroscopmetry: IR, MS, 1H &
13
C-NMR.
Keyword: piper betle, betel oil, eugenol, allylbenzene, polyphenol

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Phm Th Chnh Tp ch KHOA HC & CNG NGH 72(10): 48-52

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