Đóng góp mới về nghiên cứu thành phần hóa học loài cơm rượu (glycomis petelotii)

1

i v 
hu (Glycomis petelotii)


Phm Th Thu Huyn


i hc Khoa hc T 
Lu ThS.  ; : 60 44 27
ng dn: PGS.TS. Nguyn Mng
o v: 2012


Abstract.      hc c  c vt -   u
p ch
sinh h hing cha bnh tim m

 .
Vi  n lc ngu    c   
quc t trong ving sinh h sinh hc hii. 

















 , 






.

Keywords. ; a hc; u


Content
MỞ ĐẦU
, 
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





, 























 


 



.

t kho thuc khng l v

t. Do nh
hu,   o 

 mt h ng thc v. Theo s
liu tht Vic 307 h thc vm
c s dc cha b [83]. Nguc v
thuy mng dc. 
tin ph





.
Chi Glycosmis 







 ,  . 















 , 
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










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

 , 

















.
CGlycosmis petelotii i Viu t  [50]. Qua




hong mch chut thc nghi


MeOH Glycosmis petelotii ng cao, 







. 



 



Glycosmis petelotii.
Nhm mu  v  ha
a ch 
"Đo
́
ng go
́
p mơ
́
i vê
̀
nghiên cư
́
u tha
̀
nh phâ
̀
n ho
́
a ho
̣
c loa
̀
i Cơm rươ

̣
u
(Glycosmis petelotii) ở Việt Nam''
vi n
2

1. c ca thc v
2. p ch sinh h t hin
ng cha bnh tim mch .
Vihn lc nguc t
trong ving sinh h sinh hc hin i. 
,  ,
















. Luc nhiu kt qu
mc tin cao.

THỰC NGHIỆM

1.1. Đối tượng
Mi rng Cc Pc th, Vit
nh bc vt hi- Vin
c liu. Mn s C-i Vip chn
Khoa h Vit Nam. Mu ly v c ra sch, loi b n
y  nhi 40
0
n nh ng bt, bo qu

n nh 

 nhi 
t lt b hexan, chlo
cn ching.
 chiy s
khan, lt lc khi s dng.
Cc cp chp  nh bt h
c, s d  khng (ESI-
MS), ph khi cao (HR-ESI-MS), ph cng t ht chi
chiu (1D, 2D-NMR).
 ch
1.2. Xử lý mẫu thực vật và chiết tách
/3) G. petelotii ghin nh t vi
35  nhi t trong n cn metanol (1,27 kg)
n MeOH - H
2

O (t l 1 : 1) vt lt b
 theo th t  n nhexan, cSau khi ct
lot gin chit 

 i.
1.3. Hằng số vật lý và các dữ kiện phổ của các hợp chất phân lập được
Hằng số vật lý và các dữ kiện phổ của hợp chất MC-340
MC  340 (cht mi)
Tng: Demethylglypetelotine
TS-methyl N,N-2-[(1H)-indol-3-ethyl]-thiocarbamate,
CTPT: C
12
H
14
N
2
OS
 Tinh th c trong clorofom, axeton.
 Ph
1
H-NMR (Axeton-d
6
, 500 MHz),  (ppm): 10,02 (1H; s; H-1); 7,60 (1H; d; 8,0
Hz; H-4); 7,38 (1H; d; 8,5 Hz; H-7); 7,29 (1H; br.s; H--2); 7,09 (1H; t;
7,5 Hz; H-6); 7,02 (1H; t; 7,5 Hz; H-5); 3,55 (2H; dt; 6,5; 6,5 Hz; H-
H--
 Ph
13
C-NMR (Axeton-d
6

, 125 MHz)  (ppm): 167 (s; C- u); 137,7 (s; C-8);
128,5 (s; C-9); 123,4 (d; C-2); 122,1 (d; C-6); 119,4 (d; C-5); 119,2 (d; C-4); 113,1 (s; C-3);
112,1 (d; C-7); 42,7 (t; C---
 Ph HR-ESI-MS: 235,09017 ([M+H]
+
); 187,08677 ([M+H-CH
3
SH]
+
)
3

 

: 3420,99 cm
-1


N  H
( 





: N  

, 








-1

=CH ( )
, 1678 cm
-1

C=O
, 1590 cm
-1

NH ( )
, 1467 cm
-1

CH
, 1104
cm
-1

CO  S
, 730 cm
-1

C  S
, 2222,72 cm

-1

Hằng số vật lý và các dữ kiện phổ của hợp chất MC-339 ( trng MC-308)
MC-339 (-308):


: glypetelotine
 S-methyl N,N-2-[(1H)-indol-3-ethyl]-methyl-thiocarbamate,
CTPT: C
13
H
16
N
2
OS
 Tinh th            c trong
clorofom, axeton.
 Ph ESI-MS (+): 272.1 ([M+Na]
+
); HR-ESI-MS (+): 272.09019 ([M+Na]
+
),
201.10204 ([M-CH
3
SH]
+
).
 Ph
1
H-NMR (Axeton-d

6
, 500 MHz),  (ppm): 10,05 (1H; s; H-1); 7,67 (1H; d; 7,5
Hz; H-4); 7,39 (1H; d; 8,0 Hz; H-7); 7,19 (1H; br.s; H-2); 7,11 (1H; t; 7,5 Hz; H-6); 7,04
(1H; t; 7,5 Hz; H-5); 3,66 (2H; br.d; H---
 Ph
13
C-NMR (Axeton-d
6
, 125 MHz)  (ppm): 168.2 (s; C--8); 128,5
(s; C-9); 123,4 (d; C-2); 122,2 (d; C-6); 119,5 (d; C-5); 119,2 (d; C-4); 112,8 (s; C-3); 112,2
(d; C-7); 51,1 (t; C---
Hằng số vật lý và các dữ kiện phổ của hợp chất GPH
1
GPH
1

CTPT: C
29
H
50
O


: -Sitosterol
IUPAC: 17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-
2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol.
  , c trong metanol.
 








140  145
o
C
 


1
H  NMR (500MHz, CDCl
3
)  (ppm): 0,68 (3H; s; CH
3
-18); 1,01 (3H; s; CH
3
-
19); 0,81 (3H; d;7,7 Hz;CH
3
-26); 0,88 (3H;d; 7,7Hz; CH
3
-27); 0,84 (3H; t; 7,3 Hz; CH
3
-29);
0,92 (3H; d; 10Hz; CH
3
-21); 3,53 (1H; m; H-3); 5,35 (1H, d, 5,5 Hz, H -6 )
Hằng số vật lý và các dữ kiện phổ của hợp chất GPH

2
CTPT: C
18
H
34
O
2



: axit oleic
 -9-octadecenoic
 

, , , tan trong n - Hexan.
 







13  14
o
C
 


1

H  NMR ( 500 MHz, CDCl
3
) :  (ppm): 0,88 (3H;t; CH
3
-18); 1,63 (2H; m; H -
17); 2,00 2,01 (2x2H; d; H-8 -11); 2,34 (2H; t; H-2); 5,34 (2H, m, H -9, H-10 )


KẾT QUẢ

T (Glycosmis petelotii) 



GPH
1
( -Sitosterol) ,
GPH
2
( Axit oleic) 

 -Hexan, MC340
(DemethylGlypetelotine) 



1 308 (MC339)
(Glypetelotine)
Hợp chất MC- 340 :



MC – 340 











, xanh tan
c trong clorofom, axeton.


4

1-340
Vị trí
δ
C
(ppm)
δ
H
(ppm)
HMBC (HC)
ROESY
(HH)

1

10,02 (1H; s)


2
123,4 (d)
7,17 (1H; br.s)
C-3; C-8; C-9

3
113,1 (s)



4
119,2 (d)
7,60 (1H; d; 8,0 Hz)
C-3; C-6; C-8
H-6
5
119,4 (d)
7,02 (1H; t; 7,5 Hz)
C-7; C-9

6
122,1 (d)
7,09 (1H; t; 7,5 Hz)
C-4; C-8
H-4

7
112,1 (d)
7,38 (1H; d; 8,5 Hz)
C-5; C-9

8
137,7 (s)



9
128,5 (s)




1’
26,4 (t)
2,97 (2H; t; 7,5 Hz)
C-2; C-3; C-9; C-
H-
2’
42,7 (t)
3,56 (2H; dt; 6,5; 6,5 Hz)
C-3; C--
H-
3’

7,29 (1H; s)



4’
167 (s)
(yu)



5’




6’
11,9 (q)
2,27 (3H; s)
C-











(






) :
N
CH
2
CH
2
N
S
CH
3
O
H
H
H
H
H
H
H
1
2
3
4
5
6
7
8
9

1'
2'
3'
4'
5'
6'













2 



:
5

N
CH
2
CH

2
N
S
CH
3
O
H
H
H
H
H
H
H
1
2
3
4
5
6
7
8
9
1'
2'
3'
4'
5'
6'


















, h-340 


, , 

: S-
methyl N,N-2-[(1H)-indol-3-ethyl]-thiocarbamate. H




Glycosmis petelotii.





: C
12
H
14
N
2
OS ( M = 234).
Hơ
̣
p châ
́
t MC – 339 (trng MC – 308):
MC  339  308 























90% 


1



13
C  NMR. nh MC  308  339 
1 
 c trong
clorofom, axeton.

-339 (308)
Vị
trí
δ
C
(ppm)
δ
H
(ppm)
HMBC
(HC)

COSY
(HH)
NOESY
(HH)
1

10,05 (1H; s)


H-2
2
123,4 (d)
7,19 (1H; br.s)


H--1
3
112.8 (s)




4
119,2 (d)
7,67 (1H; d; 7.5
Hz)
C-6; C-8; C-9
H-5
H-5, H--
5

119,5 (d)
7,04 (1H; t; 7,5
Hz)
C-7; C-9
H-4, H-6
H-4, H-6
6
122,2 (d)
7,11 (1H; t; 7,5
Hz)
C-4; C-8
H-5, H-7
H-5, H-7
7
112,2 (d)
7,39 (1H; d; 8,0
Hz)
C-5; C-9
H-6
H-6
8
137,7 (s)




9
128,5 (s)







1’
51.1 (t)
3.66 (2H; br.d)

H-2
H-4, H-2
2’
24.2 (t)
2.98 (2H; br.d)
C--4
H-1
H-2, H-4, H-1
3’





4’
168.2 (s)




5’






6’
12.8 (q)
2,29 (3H; s)
C-4
-

7’
35,2
2,88(3H; s)
C  
-

6

+ 





, COSY, NOESY, 



, 















, 



















.
N
CH
2
H
2
C
N
S
H
3
C
CH
3
O
H
H
H
H
H
H
1
2
3
4
5
6
7

8
9
1
'
2
'
3
'
4
'
5
'
6
'
7
'
NH
CH
2
CH
2
N
S
CH
3
CH
3
O
H
H

H
H
H
1
2
3
4
5
6
7
8
9
1
'
2
'
3
'
4
'
5
'
6
'
7
'
NH
CH
2
CH

2
N
S
CH
3
CH
3
O
H
H
H
H
H
1
2
3
4
5
6
7
8
1
'
2
'
3
'
4
'
5

'
6
'
7
'
HMBC
COSY
NOESY


Kê
́
t luâ
̣
n: 







308, MC340 

Hơ
̣
p châ
́
t GPH
1

:


















, , 

1


   Sitosterol 













-Hexan.























, 





1
H  NMR 





















  

Sitosterol ( 





)
Kê
́
t luâ
̣
n: GPH
1
   Sitosterol :
HO
2
3
4
5
6
7
8
9
10
1
19
11
12
13
14

15
16
17
18
20
22
23
24
28
29
25
27
28
21


Hơ
̣
p châ
́
t GPH
2
:

















, , , 



2


axit Oleic 












-Hexan.























, 





1
H  








.




















axit
oleic

Kê
́
t luâ
̣
n: GPH
2
 axit oleic :
7

OH
O

Đánh giá hoạt tính sinh ho
̣
c dịch phân bố và dịch chiết của cây Glycosmis petelotii
1. Ảnh hưởng của các chất khảo sát tác dụng gây giãn mạch động mạch chuột đã loại bỏ
lớp tế bào nội mô (-EC) và gây co nhờ dung dịch K60
ng mch chut b loi b lp no co tht trong dung dch
PSS cha 60 mM KCl (K60) cho t cht th ng lic
 u nh ng ca ch ng cong th hin nng
 - phi
 li m lp
li (mean  e.s. (n = 4-7)).


.ang biu din s 
mch ph thuc n cht th 
ng mch chut loi lp t 
nc
bng dung dch PSS cha 60mM KCl

(K60) (n 3-7).
Nhng hot chch chi 
tr Emax c tip tc th  
nng  c ch 50%. 




VIP 11 E
max
(%) , 

IC
50
 .
.5.b th hin s ch
ph thuc n ct th 
Emax  ng mch chut loi lp t 
c bng dung dch PSS cha 60mM KCl (K60) (n =4-7). Tt c t chch chit
th nghi IC
50
trong khong 13  63 g/ml.
0.1 1 10 100
0
50
100
05
[VIP] (g/ml)
10
14

13
11
12
23
16
03
06
Risposta (% di K60)

.5.b. ng biu din s ch ph thuc n ct th 


ng mch chut loi lp t c bng
dung dch PSS cha 60mM KCl (K60) (n =4-7).
ch chit cu petelotii (Glycosmis petelotii Guillt).
Dch chi hin   Emax ph

50

Effect of VIP on K60-induced contraction in rat aorta rings
0.1 1 10 100
0
50
100
VIP0007
VIP0008
VIP0017
VIP0001
VIP0004
VIP0018

VIP0019
VIP0020
VIP0024
VIP0027
VIP0026
VIP0002
VIP0025
VIP0021
VIP0028
VIP0015
VIP0022
VIP0029
VIP009
[drug] g/ml
Risposta (%)
8

Ảnh hưởng của các chất khảo sát tác dụng gây giãn mạch động mạch chuột đã loại bỏ
lớp tế bào nội mô (-EC) và gây co nhờ dung dịch phenylephrine
VIP11 

nhng dch chich cao nhng mch
ch i b lp n t qu th
nghic  H.c ng 3.3
0.1 1 10 100
0
50
100
[VIP] (g/ml)
10

11
14
06
Risposta (% di fenilefrina)

.c. ng biu din s ch ph thuc n ct th 
ng mch chut loi lp t -c bng
(n =3- ng  e.s. (n = 3-6). Ti
tr
Bng 3.3. ng ca dch chit VIP 11   loi b n-
p nbng phenylephrine
VIP
-EC
+EC
IC
50
(µg/ml)
E
max

IC
50
(µg/ml)
E
max

11






 chit VIP 11  hiu qu ch cao, th hin   
3.1 
50
38.1 
Ảnh hưởng của các dịch chiết khảo sát tác dụng gây giãn mạch động mạch chuột, còn
lớp tế bào nội mô (+EC) và gây co nhờ dung dịch phenylephrine
VIP11 

nhng dch chich cao nhng mch
ch p vp t  t qu th
nghi3.5.d ng 3.3.
0.1 1 10 100
0
50
100
[VIP] (g/ml)
10
06
11
14
Risposta (% di fenilefrina)

.d. ng biu din s ch ph thuc n ct th 
ng mch chup t c bng
- ng  e.s. (n = 3-6). Ti
tr
9

VIP11 

 nhng dch chich cao nhng mch
ch p v lp n t qu th
nghi   Bng 2  
50
.
Kt qu cho thy   thuc lp t 
endothelium cells.
Ảnh hưởng của phân đoạn từ dịch chiết tác dụng gây giãn mạch động mạch chuột, đã
loại bỏ lớp tế bào nội mô (-EC) và gây co nhờ dung dịch K60
t VIP11  m nhng dch chiu qu
nht trong s ch chit khch chit methanol tc tip tc
chin v -Hexane,
chloroform, ethylacet gim,
n ching VIP11H, VIP11C,
p tc th nghim hoch c
ng mch chung dung d
-ch ph thuc n ch chi
ng. Kt qu .e
1 10 100
0
50
100
[VIP] (g/ml)
11
11B
11C
11E
11H

11W
14
14B
14C
14E
14W
Risposta (% di K60)

3.5.e. ng biu din s ch ph thuc n cn 
ng mch chut loi lp t -c bng
 ng  e.s. (n =1-2). Ti tri
K60 

Kt qu cho thn chloroform ca dch chi ch
hiu qu nha, kh a dch chi
dch chit tng methanol VIP11.
Kt qu u su cho thy dch chit VIP11 t Glycosmis
petelotii ng mch chu i K60 hoc phenylephrine
 thuc n
 thuc n-independent vasodilato
d ng thuc ch
 u 
ch  thun th (voltage-dependent Ca2+ channels
u khin th th (Receptor-m
n n t

Kết quả sàng lọc trên dòng ung thư gan ngươ
̀
i SK-Hep-1 và ung thư vú MCF-7
  bic hot cht ch













MCF-7 (human breast adenocarcinoma) 


SK-Hep-1 (human liver adenocarcinoma). Kt qu c 





 :
10

 3.4--
Hep-Glypetelotine.
(CI -concentration inhibitory %)
Name
Origin
SK-Hep-1

cytotoxicity
(CI%)
MCF-7
cytotoxicity
ug/ml
CI%
ug/ml
CI%
glypetelotin
Glycosmis
petelotii
0.1
7.606
0.1
-1.71
1
9.975
1
-0.18
10
12.54
10
8.166
 Kt qu cho th c ch 8-12% c hai loi ph.
Sàng lọc trên phép thử Wnt
 hii nhc hot cht ch
u protein Wnt. Kt qu cho thy:
3.5
Stt
Code

Wnt signaling
21
VHKC-0021
0.35

: kt qu th cho thy m protein Wnt.


KÊ
́
T LUÂ
̣
N







 (Glycosmis petelotii) 



 

 hai alkaloid


 , 










 , 




. 



 Sitosterol, Axit
oleic.








t kh , 








Glycosmis
petelotii , ng mch chui b lp t 
n- dung dch K60; ng mch chui
b lp t - dung dch phenylephrine; ch
ng mch chup t  dung dch phenylephrine 
dng mch chui b lp t - dung
dch K60.




















Glycosmis petelotii , 








Clorofom.
 hot 



 ch chi
- gan (SK-Hep-1)  

. Th s/b-catenin
signalling pathway.




11

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


 (2012), c
c m (Brucea mollis p (Glycosmis
stenocarpa (Drake) Guillaum)  Vit Nam, 





, 





.
4. Nguyn M           u
(Glycosmis petelotii Cinnamonmum balansae y
Carya tonkinensis Lecomte)  Vit Nam, Luc, Vic.
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p nhTp chc hc, s 8, tr. 5-7.
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



 , 



 2, 










, 

2, Tr. 1286.
7. 
Tr. 1286.

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