Luận văn Thạc sĩ Khoa học: Nghiên cứu các xanthanolid và các thành phần hóa học khác của cây Ké đầu ngựa (Xanhthium strumarium L., Asteraceae) mọc ở Hà Nội

5,870
410
93
Lu
n v
n Tha

Khoa Hoá h
c

13
Trâ
 
  
50
 
45-
-kappaB-
].
.
O
.
O
OH
.
39
 quiterpen lacton          
Xanthium sibiricum       7,11-2-
hydroxyeremophila-1(10)-en-12,8-olid (40), 7,11-2-hydroxyeremophila-
1(10)-en-12,8-olid (41), 7,11-eremophila-1(10)-en-12,8-olid (42),
7,11-eremophila-1(10),11(13)-dien-12,8-olid (43), 8-epi-xanthatin-1,5-
epoxid (17 tomentosin (18).
;43, 17 18

50
].
O
R
1
O
.
.
R
2
40
R
1
= OH, H
R
2
= CH
3
41
R
1
= OH, H
R
2
= CH
3
42
R
1
= CH
2
R
2
= CH
3
43
R
1
= CH
2
R
2
= CH
2
Lu  n v  n Tha  Khoa Hoá h  c   13 Trâ      50   45- -kappaB- ]. . O . O OH . 39  quiterpen lacton           Xanthium sibiricum       7,11-2- hydroxyeremophila-1(10)-en-12,8-olid (40), 7,11-2-hydroxyeremophila- 1(10)-en-12,8-olid (41), 7,11-eremophila-1(10)-en-12,8-olid (42), 7,11-eremophila-1(10),11(13)-dien-12,8-olid (43), 8-epi-xanthatin-1,5- epoxid (17 tomentosin (18). ;43, 17 18  50 ]. O R 1 O . . R 2 40 R 1 = OH, H R 2 = CH 3 41 R 1 = OH, H R 2 = CH 3 42 R 1 = CH 2 R 2 = CH 3 43 R 1 = CH 2 R 2 = CH 2
Lu
n v
n Tha

Khoa Hoá h
c

14
Trâ
 
    ,9-dihydroxy-8-epi-xanthatin (44) [35]  -
hydroxytomentosin-1,5-epoxit (45) [28]       Xanthium
strumarium (1993).
.
O
.
O
O
.
OH
OH
44
O
O
.
.
.
O
O
OH
45
               
Xanthium strumarium 

n- cây Xanthium strumarium 
   


      

 


10].
y Xanthium strumarium
           
X. strumarium
          
7]. Trong m
Lu  n v  n Tha  Khoa Hoá h  c   14 Trâ       ,9-dihydroxy-8-epi-xanthatin (44) [35]  - hydroxytomentosin-1,5-epoxit (45) [28]       Xanthium strumarium (1993). . O . O O . OH OH 44 O O . . . O O OH 45                 Xanthium strumarium   n- cây Xanthium strumarium                    10]. y Xanthium strumarium             X. strumarium            7]. Trong m
Lu
n v
n Tha

Khoa Hoá h
c

15
Trâ
 
Xanthium spinosum 
       -LOX (IC
50
 
COX-1 (IC
50
-LOX (IC
50

 (46-kappaB [11].
O
H
O
.
.
H
46
dion
    (7-hydroxymethyl-8,8-dimethyl-4,8-dihydro-
benzo[1,4]thiazin-3,5-dion) (47) -(2-O-caffeoyl)--D-glucopyranosid
(48) Xanthium strumarium
32, 42].
S
N
H
O
O
.
.
OH
47
O
OH
OH
OH
O
O
O
OH
OH
S
N
H
O
O
.
.
48
Lu  n v  n Tha  Khoa Hoá h  c   15 Trâ   Xanthium spinosum         -LOX (IC 50   COX-1 (IC 50 -LOX (IC 50   (46-kappaB [11]. O H O . . H 46 dion     (7-hydroxymethyl-8,8-dimethyl-4,8-dihydro- benzo[1,4]thiazin-3,5-dion) (47) -(2-O-caffeoyl)--D-glucopyranosid (48) Xanthium strumarium 32, 42]. S N H O O . . OH 47 O OH OH OH O O O OH OH S N H O O . . 48
Lu
n v
n Tha

Khoa Hoá h
c

16
Trâ
 

(49)Xanthium pungens [8].
O
S
OH
O
OH
CH
3
49
  -)-xanthienopyran (49   
Xanthium strumarium. H
49
    formyl-L-methionyl-L-leucyl-L-phenylalanin  
IC
50
µg/ml [26].
        7-hydroxymetyl-8,8-
dimetyl-4,8-dihydrobenzo[1,4]thiazin-3,5-dion-11-O-[-D-apiofuranosyl-(1->6)-O-
-D-glucopyranosid] (50). C 50     
 apisose].
 (51Xanthium sibiricum
Patr. [20].
Lu  n v  n Tha  Khoa Hoá h  c   16 Trâ    (49)Xanthium pungens [8]. O S OH O OH CH 3 49   -)-xanthienopyran (49    Xanthium strumarium. H 49     formyl-L-methionyl-L-leucyl-L-phenylalanin   IC 50 µg/ml [26].          7-hydroxymetyl-8,8- dimetyl-4,8-dihydrobenzo[1,4]thiazin-3,5-dion-11-O-[-D-apiofuranosyl-(1->6)-O- -D-glucopyranosid] (50). C 50       apisose].  (51Xanthium sibiricum Patr. [20].
Lu
n v
n Tha

Khoa Hoá h
c

17
Trâ
 
50
O
O
O
OH
OH
O
OH
S
N
H
O
O
.
.
OH
OH
OH
51
O
OH
OH
O
OH
S
N
H
O
O
.
.
OH

axit caffeic (52   
Xanthium strumarium2) [32].
OH
O
OH
OH
52
Axit 1,3,5-tri-O-caffeoylquinic (53)  axit 3,5-di-O-
  Xanthium strumarium  A.   
[22].   cây Xanthium strumarium kali-3-
O-caffeoyl quinat (54) axit 1,5-di-O-caffeoyl quinic (55) [13].53
9].
Lu  n v  n Tha  Khoa Hoá h  c   17 Trâ   50 O O O OH OH O OH S N H O O . . OH OH OH 51 O OH OH O OH S N H O O . . OH  axit caffeic (52    Xanthium strumarium2) [32]. OH O OH OH 52 Axit 1,3,5-tri-O-caffeoylquinic (53)  axit 3,5-di-O-   Xanthium strumarium  A.    [22].   cây Xanthium strumarium kali-3- O-caffeoyl quinat (54) axit 1,5-di-O-caffeoyl quinic (55) [13].53 9].
Lu
n v
n Tha

Khoa Hoá h
c

18
Trâ
 
OH
OH
O
O
OH
HOOC
OR
O
O
OH
OH
53 R = Caffeoyl
OR
3
OH
OR
4
O
R
1
O
OR
2
R
1
R
2
R
3
R
4
54 K H caffeoyl H
55 H caffeoyl H caffeoyl
O
OH
OH
.
caffeoyl
  . Y.
        Xanthium strumarium   
  -tri-O-caffeoylquinic (53), axit 1,5-di-O-caffeoylquinic
axit (55), metyl 3,5-di-O-caffeoylquinat (56), axit 3,5-di-O-caffeoylquinic (57), axit
1,3-di-O-caffeoyl quinic (58), axit chlorogenic (59)  meth   
neochlorogenic (60) 3-hydroxy-1-(4-hydroxy-
phenyl)-propan-1-on (61), axit protocatechuic (62)  e (63)  56
cho 
50


[19].
Lu  n v  n Tha  Khoa Hoá h  c   18 Trâ   OH OH O O OH HOOC OR O O OH OH 53 R = Caffeoyl OR 3 OH OR 4 O R 1 O OR 2 R 1 R 2 R 3 R 4 54 K H caffeoyl H 55 H caffeoyl H caffeoyl O OH OH . caffeoyl   . Y.         Xanthium strumarium      -tri-O-caffeoylquinic (53), axit 1,5-di-O-caffeoylquinic axit (55), metyl 3,5-di-O-caffeoylquinat (56), axit 3,5-di-O-caffeoylquinic (57), axit 1,3-di-O-caffeoyl quinic (58), axit chlorogenic (59)  meth    neochlorogenic (60) 3-hydroxy-1-(4-hydroxy- phenyl)-propan-1-on (61), axit protocatechuic (62)  e (63)  56 cho  50   [19].
Lu
n v
n Tha

Khoa Hoá h
c

19
Trâ
 
OR
2
OR
3
OR
4
O
R
5
O
OR
1
R
1
R
2
R
3
R
4
R
5
56 H caffeoyl H caffeoyl OCH
3
57 H caffeoyl H caffeoyl OH
58 caffeoyl caffeoyl H H OH
59 H caffeoyl H H OH
60 H caffeoyl H H OCH
3
O
OH
OH
.
caffeoyl
OH
O
OH
61
OH
O
OH
OH
62
O
OH
OH
OH
OH
O
O
OH
OH
OH
O
OH
OH
OH
OH
63
  2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-on (64)
Xanthium sibiricum Patr. [19].
H
3
CO
O
OH
OH
OH
64
Lu  n v  n Tha  Khoa Hoá h  c   19 Trâ   OR 2 OR 3 OR 4 O R 5 O OR 1 R 1 R 2 R 3 R 4 R 5 56 H caffeoyl H caffeoyl OCH 3 57 H caffeoyl H caffeoyl OH 58 caffeoyl caffeoyl H H OH 59 H caffeoyl H H OH 60 H caffeoyl H H OCH 3 O OH OH . caffeoyl OH O OH 61 OH O OH OH 62 O OH OH OH OH O O OH OH OH O OH OH OH OH 63   2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-on (64) Xanthium sibiricum Patr. [19]. H 3 CO O OH OH OH 64
Lu
n v
n Tha

Khoa Hoá h
c

20
Trâ
 
 glycosid
 kauren glycosid (65
Xanthium pungens [22].
O
ROCO
O
OH
OH
OH
.
OH
.
COOH
HOOC
65 R = CH
2
CH(CH
3
)CH
2
)CH
3
 , ba kauren glycosid  axit -O--D-glucopyranosyl-15-
hydroxy-kaur-16-en-18,19-dicarboxylic (66), 4ʹ-desulphated-carboxyatractylosid
(68)  ʹ-desulphated-atractylosid (70)   ʹ,4ʹ-didesulphated-
carboxyatractylosid (67)  ʹ,4ʹ-didesulphated-atractylosid (69)   
phân cây Xanthium spinosum [36].
O
R''O
O
R'O
OH
OH
.
OH
.
COOH
R
R R' R''
66 COOH H H
67 COOH H -COCH
2
CH(Me)
2
68 COOH SO
3
2-
-COCH
2
CH(Me)
2
69 H H -COCH
2
CH(Me)
2
70 H SO
3
2-
-COCH
2
CH(Me)
2
Lu  n v  n Tha  Khoa Hoá h  c   20 Trâ    glycosid  kauren glycosid (65 Xanthium pungens [22]. O ROCO O OH OH OH . OH . COOH HOOC 65 R = CH 2 CH(CH 3 )CH 2 )CH 3  , ba kauren glycosid  axit -O--D-glucopyranosyl-15- hydroxy-kaur-16-en-18,19-dicarboxylic (66), 4ʹ-desulphated-carboxyatractylosid (68)  ʹ-desulphated-atractylosid (70)   ʹ,4ʹ-didesulphated- carboxyatractylosid (67)  ʹ,4ʹ-didesulphated-atractylosid (69)    phân cây Xanthium spinosum [36]. O R''O O R'O OH OH . OH . COOH R R R' R'' 66 COOH H H 67 COOH H -COCH 2 CH(Me) 2 68 COOH SO 3 2- -COCH 2 CH(Me) 2 69 H H -COCH 2 CH(Me) 2 70 H SO 3 2- -COCH 2 CH(Me) 2
Lu
n v
n Tha

Khoa Hoá h
c

21
Trâ
 

H. 3-
norpinan-2-on 3-O--D-apiofuranosyl---D-glucopyranosid (71), (6Z)-3-
hydroxymethyl-7-methylocta-1,6-dien-3-ol 8-O--D-glucopyranosid (72), (6E)-3-
hydroxymethyl-7-methylocta-1,6-dien-3-ol 8-O--D-glucopyranosid (73), 7-[(-D-
apiofuranosyl---D-glucopyranosyl)oxymethy]-8,8-dimethyl-4,8-
dihydrobenzo[1,4]thiazin-3,5-dion (50   (74    Xanthium
sibiricum Patr. [20].
O
O
OH
OH
OH
O
OH
OH
OH
O
.
.
O
71
O
OH
OH
OH
OH
O
.
OH
.
OH
72
73
O
OH
OH
OH
OH
OH
.
OH
O
.
N
N
N
N
O
OH
OH
OH
NH
2
H
74
Lu  n v  n Tha  Khoa Hoá h  c   21 Trâ    H. 3- norpinan-2-on 3-O--D-apiofuranosyl---D-glucopyranosid (71), (6Z)-3- hydroxymethyl-7-methylocta-1,6-dien-3-ol 8-O--D-glucopyranosid (72), (6E)-3- hydroxymethyl-7-methylocta-1,6-dien-3-ol 8-O--D-glucopyranosid (73), 7-[(-D- apiofuranosyl---D-glucopyranosyl)oxymethy]-8,8-dimethyl-4,8- dihydrobenzo[1,4]thiazin-3,5-dion (50   (74    Xanthium sibiricum Patr. [20]. O O OH OH OH O OH OH OH O . . O 71 O OH OH OH OH O . OH . OH 72 73 O OH OH OH OH OH . OH O . N N N N O OH OH OH NH 2 H 74
Lu
n v
n Tha

Khoa Hoá h
c

22
Trâ
 
1.3Xanthium strarium L.)
1.3
a (Xanthium strumarium L.) -, 
               
Xanthium canadense, X. chinense, X. glabratum     
aceae).
1.2: Xanthium strumarium L.)
    -120 cm  , thân   
nh.


    
Lu  n v  n Tha  Khoa Hoá h  c   22 Trâ   1.3Xanthium strarium L.) 1.3 a (Xanthium strumarium L.) -,                  Xanthium canadense, X. chinense, X. glabratum      aceae). 1.2: Xanthium strumarium L.)     -120 cm  , thân    nh.       