ĐH KHOA HO
̣
C TƢ
̣
NHIÊN
ĐH QUÔ
́
C GIA HA
̀
NÔ
̣
I
VIỆN KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM
VIỆN HÓA HỌC
PHM TH THU HUYỀN
ĐO
́
NG GO
́
P MƠ
́
I VÊ
̀

HÀ NỘI - 2012 ĐH QUÔ
́
C GIA HA
̀
NÔ
̣
I ĐH
KHOA HO
̣
C TƢ
̣
NHIÊN
VIỆN KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM
VIỆN HÓA HỌC PHM TH THU HUYÊ
̀
N
ĐO
́


HÀ NỘI - 2012
MỤC LỤC
 1
 3
1.1. Chi Glycosmis 3
 3
 4
 Glycosmis 5
1.1.4Glycosmis 27
(Glycosmis petelotii) 30
 31
 31
 31
 31
 32
2.2. 



 32
2.2.1. 



3.1.3. 


1
: 67
3.1.4. 


2
: 68
3.2. 





 69
 75


-Hep--7 76
3.3.2. 







DANH MỤC SƠ ĐỒ

 Glycosmis petelotii 33
2.2: -Hexan 34








-451 37
2.4:  38

DANH MỤC HÌNH VẼ


- 340 47
3.1.b: 

1H - 



- 340 () 48
3.1.c: 


13
C- 

 340 49
3.1.d: 



 340 49
3.1.e: 





 340 50
3.1.f: 




 340 

 53
3.1.l. 



 340 55
3.1.m. 





 340 

 55
3.1.n. 





 340 (1.8  3.8 ppm) 56
3.2.a. 


1
H-

3.2.g: 





 339 () 61
3.2.h: 



 339 () 62
3.2.i: 



 339 62
3.2.k. 



 339 63
3.2.l: 





 339 () 64


 

(n 3-7) 71
Hình 3.5.b: S  72
Hình 3.5.c: S-EC) 73
Hình 3.5.d: S 74
3.5.e: S  (-EC) 75
DANH MỤC BẢNG BIỂU

1.1. 









1
H-NMR
Proton Nuclear Magnetic
Resonance Spectroscopy
     
proton
13
C- NMR
Carbon -13 Nuclear Magnetic
Resonance Spectroscopy
     
cacbon 13C
DEPT
Distortionless Enhancement by
Polarisation Transfer

HMBC
Heteronuclear Multiple Bond
Correlation

HSQC
Heteronuclear Single Quantum
Coherence

NOESY
Nuclear Overhauser Effect
Spectroscopy

1
H-

Triplet
Q

Quartet
Dd

doublet doublet
Dt

doublet triplet
B

Broad
M

Multiplet
J (Hz)

 HzHz

(ppm = part per million)


CC
Column Chromatography

TLC

Tetrametyl Silan
BuOH

Butanol







2012

1

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

.
 

. Do n
 ,  

 
phong phú          
dân
[83]. 
và phát  






.
Chi Glycosmis 







 ,  .














.
Cây Glycosmis petelotii 
[50]. Qua 



, chúng tôi


 MeOH Glycosmis petelotii g cao, 






 . 




n ho
́
a ho
̣
c loa
̀
i C ơm rƣơ
̣
u
(Glycosmis petelotii) ở Việt Nam''

1.    loài 
2.  
 .






2012

2



 , 


, 

H
   uýt Rutacea chia làm 4 

  Rutoideae,
Toddaloideae, Rhabdodendroideae, Aurantioideae Clausena [72]. Chi Glycosmis là




Aurantioideae (=Citroideae), phân nhóm Clauseneae (Lukaseder
et al., 2009). Phân nhóm Clauseneae có ba chi: Glycosmis, Clausena và Murraya
[68
chi Glycosmis ies
Á [72], [81].



7].
5 loài Glycosmis [7
Glycosmis
]. Các loài 

 Glycosmis 
 
    Glycosmis có tên chung là C      G.
pentaphylla Correa]. Ngoài ra
lá loài G. cymosa và G. citrifolia  d].
          G.
stenocarpa và G. petelotii  hóa
 ], [50

gian. Loài G. pentaphylla 
 

ng [50
G. parviflora 
77G. citrifolia 
G. pentaphylla
G. citrifolia hóa
  

1
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5

bào Dao vùng Ba Vì - Glycosmis lanceolata
G. cyanocarpa 5].
1.1.3. Thành phần hóa học chi Glycosmis
                
Glycosmis [4Glycosmis: G.
angustifolia, G. arborea, G. bilocularis, G. citrifolia*, G. chlorosperma, G.
craibii*, G. crassifolia*, G. cyanocarpa*, G. mauritiana, G. ovoidea*, G.
parviflora*, G. rupestris, G. pentaphylla*, G. cochinchinensis, G. trichanthera*, G.
cf. chlorosperma, G. ex. aff. pseudoracemosa, G. Montana, G. parva, G. petelotii*


) 2 

) 3 [59].
1.1.3.2. Flavonoit
       

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7 1.1: Mvonoid

-  

-          


bi

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




  [78].
G. citrifolia . 
glychalcon-A 4, glychalcol-B 5, glyflavanon-A 6 và glyflavanon-B 7 [76].
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9  
loài G. montana  glymontanin A 8, glymontanin B 9  
dime là montahomobisflavan A 10 và montahomobisflavan B 11 [38]. 1.1.3.3. Coumarin
Coumarin        





  Hordenum sativum        Colchicum
autumnale L.

 . 
 lkaloid          . axit nitric, malic,
sucxinic).   lkaloid          
 






2012

11

 
Alkaloid t Apocynaceae (h
Papaveraceae (h
Fabaceae Solanaceae 00 alkaloid. 
Claviceps purpureaAmanita phalloides.

hu hái.
-
samandarin,
samandaridin, samanin Bufotenin, bufotenidin,
dehydrobufotenin 
 và phong p
       , k      strychnine,

Cc acridon đơn gin:






2012

12



  11 





 6 
Glycosmis.  



 6  : arborinin (15a)
 G. pentaphylla, glycocitrin I (15b), glycocitrin II (15c), 3  O 
metylglycocitrin II (15d), glyfolin (15e)  (15f) 




1,5  diOH ; 3  OCH
3
; 4  CH
2
CH = C (CH
3
)
2
; 10  CH
3

15c
1,3  diOH; 4  CH
2
CH = C (CH
3
)
2
15d
2  OH ; 3  OCH
3
; 4  CH
2
CH = C ( CH
3
)
2
15e
1,6  diOH ; 2,3,4,5  tetra OCH
3

 G. mauritina; 1,3  hydroxyl  10  metyl 
prenylacridon (15i); glycocitrin VI (15j) 



 G. citrifolia  glycocitrin III
(15k), 1,5  dihydroxyl  2,3  dimetoxy  10  metylacridon ( 15l) 



 G.
pentaphylla G. bilocularis 

.

N
O
1
2
3
4
5
6
7
8
9
10
H

15g











(16a) (16b). 
2000  1 



 n V (17)
G. Citrinfolia [36].
1
2
11
6
7
8
9
10
NH
O
O
3
4


 11 monome 






G. citrifolia [4(18a) [54], N  methylseverifolin (18b), 7 
hydroxyl  N  methylserverifolin (18c), citracridon I (18d), 7 –
hydroxynoracronycin (18e), de  N  methyacronycin (18f) de  N 
methylnoracronycin (18g), noracronycin (18h)  (18i). De  N 












G. pentaphylla [17].
15h
1  OH ; 3  OCH
3
; 10  CH
3

4
5
6
12
7
8
9
10
11

18a
1,8  diOH ; 7  OCH
3

18b
1  OH ; 2  CH
2
CH = C (CH
3
)
2
; 12  CH
3

18c
1,7  diOH; 2  CH
2
CH = C (CH
3
)












 G. citrifolia , 
















(19) [73].



 (21),
glycobismin D (22), glycobismin E (23a) [42]  2004 










 2 



 (23b), glycomis (24) [53]. 













O
O
N
O
OH
OH
HO
OH
OMe
OMeMe
Me

22

N
O
O
O
N
O
OH
OH
R
OH
OMe
OMeMe
Me

23a. R = OCH
3














 .  , quinolon,


.
Cc alkaloid dng vng quinolin đơn gin:




9 








[14], glycolon B (26a) [66], glycosolon (26b) [27],   glycosolon (26c) 


[45].












 (25b) 



 G. mauritiana
[58]. Glycophylon (26d)  G.
pentaphylla [9]. 






