Tp ch Khoa hc 2011:19b 80-84

Trng i hc Cn Th

GP PHN KHO ST THNH PHN HA HC

CA R CAU (ARECA CATECHU L.)
L Thanh Phc v Bnh Nguyn Anh Ho 1

ABSTRACT
From the petroleum ether extracts of the roots of Areca catechu L., collected in Phong
Dien district, Can Tho city, we have isolated two compounds: lupeol (C30H50O) and
lupeol acetate (C32H52O2). The structures of these compounds have been elucidated by
modern spectroscopic methods: MS, 1H-NMR, 13C-NMR, HSQC, COSY and HMBC.
Keywords: Areca catechu L. root, chemical components, lupeol, lupeol acetate.
Title: Contribution to the study on the chemical components of Areca catechu L. root

TM TT
T dch chit petroleum ether ca r cy Cau trng ti huyn Phong in, thnh ph Cn
Th, chng ti c lp c hai hp cht: lupeol (C30H50O) v lupeol acetate
(C32H52O2). Cu trc ha hc cc hp cht ny c xc nh bng cc phng php
quang ph hin i: MS, 1H-NMR, 13C-NMR, HSQC, COSY v HMBC.
T kha: R Cau Areca catechu L., thnh phn ha hc, lupeol, lupeol acetate

1 T VN
Cy Cau c tn khoa hc l Areca catechu L., thuc h Cau (Arecaceae) ( Tt
Li et al., 1995). Theo kinh nghim dn gian v y hc c truyn, ht Cau l ngun
dc liu quan trng cha nhiu bnh nh: sn x mt, sn l, cha vim rut,
bng y trng, b tiu tin; r Cau ni c tc dng b dng ( Huy Bch et
al., 2004). Trn th gii, ht Cau c kt hp vi mt s nguyn liu thin
nhin khc to cht khng oxi ha dng lm m phm, lm thuc chng bnh trm
cm, bnh cao huyt p (Wetwitayaklunga et al., 2006).
Thnh phn ha hc ca ht Cau c nhiu tc gi trong v ngoi nc nghin
cu. Tuy nhin, c rt t bi bo cng b v thnh phn ha hc ca r cy Cau.
xc nh thnh phn ha hc ng thi lm c s khoa hc cho cc bi thuc dn
gian c s dng r Cau, chng ti tin hnh phn lp v xc nh cu trc mt
s hp cht c trong r Cau (Areca catechu L.) trng huyn Phong in, thnh
ph Cn Th.
2 PHNG TIN V PHNG PHP
2.1 Nguyn liu
R Cau non thu hi ti huyn Phong in, thnh ph Cn Th. R Cau c ra
sch, loi b phn su, sy kh nhit 55C n khi lng khng i v xay
nh trc khi s dng.
R Cau c Ths. Ng Thanh Phong, B Mn Sinh, Khoa Khoa hc T Nhin,
i Hc Cn Th nh danh khoa hc l r ca loi Areca catechu L..
1

Khoa Khoa hc T nhin, Trng i hc Cn Th

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2.2 Phng php

- Chit hot cht: bt r Cau (3500 g) c chit ngm kit vi cn ethylic 96
(EtOH) trong 7 ngy, tch ly phn lng em c quay di p sut km thu cao
EtOH th (305 g). Cho phn cao th ha tan trong mt lng nc ct nht nh,
sau chit lng lng ln lt vi cc dung mi petroleum ether (PE), ethyl
acetate (EtOAc), n-butanol (BuOH). Thu gom cc dch trch v sau khi loi dung
mi di p sut km thu c cc cao PE (59 g), cao EtOAc (49 g) v cao BuOH
(56.5 g), tng ng.
- Phn lp cc cht t cao petroleum ether: thc hin sc k ct, cht hp ph l
silica gel, s dng nhng h dung mi gii ly gm PE, EtOAc c phn cc tng
dn. Theo di qu trnh sc k ct bng sc k bn mng vi h dung mi gii ly
l petroleum ether:ethyl acetate, thuc th hin vt l dung dch acid sulfuric 10%
trong ethanol v sy bn mng 110C. Cc phn on th hin ging nhau trn
sc k bn mng c gp li. Tin hnh sc k ct ln 2 vi cc phn on ging
nhau c lp c cht sch.
- Xc nh cu trc ca cc cht c lp c bng cch s dng cc phng
php ph nghim: ph khi lng MS c o trn my MS 5989 B (Hewlett
Pakard), 1H-NMR, 13C-NMR, COSY, HSQC, HMBC. Ph NMR (?) c o trn
my Bruker Advance Model DRX500 (Vin Cng Ngh, 18 Hong Quc Vit,
Cu Giy, H Ni).
- im nng chy (melting point) c o trn my ELECTROTHERMAL Model
9100 ca Anh, dng mao qun khng hiu chnh.
- Silica gel dng cho sc k ct pha thng c ht 0.040-0.063 mm. Sc k lp
mng (TLC) c thc hin trn bn mng trng sn silica gel KG 60 F254. Cc
ha cht tinh khit khc c xut x t Trung Quc.
3 KT QU V THO LUN
3.1 Kt qu sc k ct
T 9.023g cao petroleum ether tin hnh sc k ct nhanh trn silica gel cho 9
phn on. Kt qu sc k ct silica gel i vi cao chit bng petroleum ether
c tm tt trong Bng 1.
Bng 1: Kt qu sc k ct silica gel ca cao petroleum ether

Phn on H dung mi gii ly

PE 100%
1
PE:EtOAc = 99:1
2
PE:EtOAc = 98:2
3
PE:EtOAc = 98:2
4
PE:EtOAc = 95:5
5
PE:EtOAc = 9:1
6
PE:EtOAc = 8:2

Tn m ha

Sc k bn mng

Ghi ch

PE1

Nhiu vt

PE2
PE3
PE4
PE5
PE6

Nhiu vt c 1 vt chnh Kho st

3 vt, c 1 vt chnh
Kho st
Nhiu vt
Nhiu vt
3 vt

PE:EtOAc = 7:3

PE7

Nhiu vt

8
9

PE:EtOAc = 1:1
EtOAc 100%

PE8
PE9

Vt ko di
Vt ko di
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3.2 C lp cc cht tinh khit t cc phn on sc k ct nhanh ca cao

petroleum ether
T cc phn on tng i sch ca sc k ct nhanh cao petroleum ether, phn
on PE2, PE3 c tip tc tinh ch thu c cc cht tinh khit.
3.2.1 Phn on PE2
Phn on PE2 (400 mg), c tinh ch bng cch sc k ct thng vi h dung
mi gii ly PE 100%, PE:EtOAc = 99:1; 98:2. Kt qu phn on PE:EtOAc =
98:2 thu c tinh th hnh kim mu trng c, hin vt mu tm c Rf = 0.78
(PE:EtOAc = 75:25) trn TLC khi dng thuc th l H2SO4 10% trong MeOH.
Hp cht ny c nhit nng chy 169-170C v c k hiu l cht PHUOCHAO02 (55 mg).
Hp cht PHUOC-HAO02
Ph khi va chm electron (EI-MS) cho pic phn t m/z (%): 427 (M-41), m/z 408
(M-AcOH), m/z 249 (M-C16H27), m/z 189 {(249)-AcOH}.
m/z 427
CH2

m/z 408

m/z 189

CH3COO

m/z 181

Hnh 1: C ch phn mnh ph EI-MS ca PHUOC-HAO02

1

Ph H-NMR (500 MHz, CDCl3), (ppm), J (Hz): 0.76 (dd, 1H, J =10.8, 5.8 Hz,
H-5), 0.81 (s, 3H, H-28), 0.82 (s, 9H, H-23, H-24, H-25), 0.91 (s, 3H, H-27), 1.00
(s, 3H, H-26), 1.66 (s, 3H, H-30), 1.82-1.93 (m, 2H, H-21), 2.01 (s, 3H,
CH3COO-),), 2.33 (dt, 1H, J = 11.1, 5.6 Hz, H-19), 4.44 (dd, 1H, J = 10.8, 5.8 Hz,
H-3), 4.54 (br s, 1H, H-29), 4.66 (br s, 1H, H-29).
Ph 13C-NMR (CDCl3), (ppm): 14.5 (C-27), 15.9 (C-24), 16.1 (C-25), 16.4 (C26), 17.9 (C-28), 18.1 (C-6), 19.0 (C-30), 21.3 (CH3COO-), 20.9 (C-11), 23.7 (C2), 25.0 (C-12), 27.4 (C-15), 28.2 (C-23), 29.8 (C-21), 34.2 (C-7), 35.5 (C-16),
37.0 (C-10), 37.7 (C-4), 38.0 (C-13), 38.3 (C-1), 39.9 (C-22), 40.8 (C-8), 42.8 (C14), 42.9 (C-17), 48.0 (C-18), 48.2 (C-19), 50.3 (C-9), 55.3 (C-5), 80.9 (C-3),
109.3 (C-29), 150.9 (C-20), 171.0 (CH3COO-).
Kt hp ph cng hng t ht nhn 2 chiu HSQC v HMBC cho thy
PHUOC-HAO02 thuc nhm terpenoid v c khung sn fernan.
T cc kt qu phn tch ph trn chng ti kt lun cht PHUOC-HAO02 l
lupeol acetate, c cng thc phn t l C32H52O2. Kt qu ny ph hp vi kt qu
cng b ca Arshad Kamal et al. 2001.

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29
CH2
20
19

30
12
11
25

17

28

14

16

CH3COO

22

13

26

21

18

10
3
24

15
27

6
23

Hnh 2: Cng thc cu to ha hc lupeol acetate

Lupeol acetate c tim nng ng dng trong y hc, l mt cht khng vim hiu
qu, c th ngn chn s di chuyn v s pht trin ca ca t bo ung th (Arrieta
et al., 2003) trung ha nc c ca nhiu loi rn cc c nh Daboia russellii,
Naja kaouthia (Ipshita Chatterjee et al., 2006).
3.2.2 Phn on PE3
Phn on PE3 (326 mg), c tinh ch bng cch sc k ct thng vi h dung
mi gii ly PE:EtOAc = 99:1; 98:2. Kt qu phn on PE:EtOAc = 98:2 thu
c cc tinh th hnh kim mu trng c, trn TLC xut hin vt mu tm c Rf =
0.43 (PE:EtOAc = 75:25) khi dng thuc th l H2SO4 10% trong MeOH. K hiu
hp cht ny l PHUOC-HAO03 (44 mg).
Hp cht PHUOC-HAO03
Ph khi va chm electron (EI-MS) cho pic phn t m/z (%): 426 [M+] (49), ng
vi cng thc phn t C30H50O. Cc pic c bn: 411 (23%, M+ - CH3), 218 (73%),
207 (28%), 203 (26%), 189 (27%), 175 (10%), 139 (27%), 95 (100%).
m/z 411
CH2

m/z 207

m/z 189

HO

m/z 218
m/z 139

Hnh 3: C ch phn mnh ph EI-MS ca PHUOC- HAO03

1

Ph H-NMR (500 MHz, CDCl3), (ppm), J (Hz): 0.66 (d, 1H, J = 9.1 Hz, H-5),
0.73 (s, 3H, H-24), 0.76 (s, 3H, H-28), 0.80 (s, 3H, H-25), 0.92 (s, 3H, H-27), 0.94
(s, 3H, H-23), 1.00 (s, 3H, H-26), 1.65 (s, 3H, H-30), 1.821.96 (m, H-21), 2.35
(dt, 1H, J = 10.9, 5.5 Hz, H-19), 3.16 (dd, 1H, J = 10.8, 5.1 Hz, H-3), 4.55 (br s,
1H, H-29), 4.65 (br s, 1H, H-29)
Ph 13C-NMR (CDCl3), (ppm): 14.5 (C-27), 15.3 (C-24), 15.9 (C-25), 16.1 (C26), 18.0 (C-28), 18.3 (C-6), 19.3 (C-30), 20.9 (C-11), 25.1 (C-12), 27.4 (C-2, C15), 28.0 (C-23), 29.7 (C-21), 34.3 (C-7), 35.6 (C-16), 37.1 (C-10), 38.0 (C-13),
38.7 (C-1), 38.8 (C-4), 40.0 (C-22), 40.8 (C-8), 42.8 (C-14), 43.0 (C-17), 48.0 (C18), 48.3 (C-19), 50.4 (C-9), 55.3 (C-5), 79.0 (C-3), 109.3 (C-29), 150.9 (C-20)
Ph DEPT NMR kt hp 13C NMR cho thy c 11 nhm CH2, 6 nhm CH=, 7
nhm CH3, 6C t cp.
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Trng i hc Cn Th

T nhng d kin trn PHUOC-HAO03 c nhn danh l lupeol. Kt qu ny

cng ph hp vi kt qu ca Ali et al., 2007.
29
CH2
20
19

30

26
9

17

28

14
16

HO

22

13

11
25
1

21

18

12

10
3
24

15
27

6
23

Hnh 4: Cng thc cu to ha hc lupeol

Lupeol c th ngn chn s di chuyn v s pht trin ca ca t bo ung th vng

u v c bao gm ung th mi, khoang ming, hng, thanh qun, tuyn gip v
tuyn nc bt. Cn bnh ny thng tn cng ngi chu hn so vi ngi
chu u do mt s tp qun n ung nh ht thuc l, ung ru qu nhiu, n
thc phm bo qun lu ngy nh c mui. Cc bnh ung th ny u rt kh cha
bng phu thut (Mohammad Saleem et al., 2009).
4 KT LUN
phn lp v xc nh cu trc ca: lupeol, lupeol acetate t r Cau. y l
nhng cht c hot tnh sinh hc kh tt nn gii thch c l do ti sao r Cau
c dng cha mt s bnh trong y hc dn gian.
TI LIU THAM KHO
Ali and S.Waseemuddin Ahmed Shehla Imam, Iqbal Azhar, M. Mohtasheemul Hasan, 2007.
Two triterpenes lupanone and lupeol isolated and identified from Tamarindus Indica
Linn, Pak. J. Pharm. Sci., Vol.20(2), 125-127.
Arrieta J., Benitez J., Flores E. et al., 2003. Purification of gastroprotective triterpenoid from
the stem bark of Amphipterygium adstringens; role of prostaglandins, sulfhydryls, nitric
oxide and capsaicin-sensitive neurons. Planta Med 69:905909.
Arshad Kamal et al., 2001. Studies in the chemical constituents of Andrachne aspeara
sprengs (euphorbiaceae), university of Karachi.
Huy Bch, 2004. Cy thuc v ng vt lm thuc Vit Nam, NXB Khoa hc v K
thut, H ni, (I), tr. 350-353.
Tt Li, 1995. Nhng cy thuc v v thuc Vit Nam, NXB Khoa hc v K thut,
tr. 172-174.
Ipshita Chatterjeea, Chakravartyb A.K. and Gomes A., 2006. Daboia russellii and Naja
kaouthia venom neutralization by lupeol acetate isolated from the root extract of Indian
sarsaparilla Hemidesmus indicus R.Br., Journal of Ethnopharmacology, Vol 106, No 1,
38-43.
Mohammad Saleem, Imtiyaz Murtaza, Rohinton S. Tarapore, Yewseok Suh, Vaqar Mustafa
Adhami, Jeremy James Johnson, Imtiaz Ahmad Siddiqui, Naghma Khan, Mohammad
Asim, Bilal Bin Hafeez, Mohammed Talha Shekhani, Benyi Li and Hasan Mukhtar, 2009.
Lupeol inhibits proliferation of human prostate cancer cells by targeting -catenin
signaling, Carcinogenesis, 30(5):808-817.
Wetwitayaklunga P., et al., 2006. The study of antioxidant capacity in various parts of Areca
catechu L., Naresuan University Journal, 14(1), pp. 1-14.

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