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

5,839
410
93
Lu
n v
n Tha

Khoa Hoá h
c

3
Trâ
 

1.1 XANTHIUM 
1.1.1 Xanthium
Chi Xanthium           -

Xanthium spinosum


-
 


 
- 28 µm
      
 -      
-
    
µm.
Xanthium            
         

         Xanthium
xanthos  [9].
Lu  n v  n Tha  Khoa Hoá h  c   3 Trâ    1.1 XANTHIUM  1.1.1 Xanthium Chi Xanthium           -  Xanthium spinosum   -       - 28 µm         -       -      µm. Xanthium                                 Xanthium xanthos  [9].
Lu
n v
n Tha

Khoa Hoá h
c

4
Trâ
 
Xanthium
Chi Xanthium       
X. spinosum L.X. strumarium L.
X. canadens 
X. strumarium     32].   
Xanthium [9]:
Xanthium ambrosioide Hook & Arn
Xanthium argenteum Widder
Xanthium cavanillesii Shouw
Xanthium cloessplateaum D.Z.Ma
Xanthium echinatum Murray
Xanthium inaequilaterum DC.
Xanthium italicum Moretti
Xanthium mongolicum Kitag.
Xanthium orientale L.
Xanthium sibiricum Patrin ex Widder
Xanthium spinosum L.
Xanthium strumarium L.
Xanthium albinum Widder H. Scholz
Xanthium italicum Moretti
Lu  n v  n Tha  Khoa Hoá h  c   4 Trâ   Xanthium Chi Xanthium        X. spinosum L.X. strumarium L. X. canadens  X. strumarium     32].    Xanthium [9]:  Xanthium ambrosioide Hook & Arn  Xanthium argenteum Widder  Xanthium cavanillesii Shouw  Xanthium cloessplateaum D.Z.Ma  Xanthium echinatum Murray  Xanthium inaequilaterum DC.  Xanthium italicum Moretti  Xanthium mongolicum Kitag.  Xanthium orientale L.  Xanthium sibiricum Patrin ex Widder  Xanthium spinosum L.  Xanthium strumarium L. Xanthium albinum Widder H. Scholz Xanthium italicum Moretti
Lu
n v
n Tha

Khoa Hoá h
c

5
Trâ
 
Xanthium spinosum L.
Xanthium sibirisum Patrin ex Widder
1.1: Xanthium
    Xanthium       d 
 Xanthium cavanillesii 
31].

   Xanthium, Xanthium
strumarium Xanthium inaequilaterum DC.;
Xanthium inaequilaterum
 [4].


      (1980)    
antholid A (1), xantholid B (23
  2   Xanthium canadense 
-ray [38].
Lu  n v  n Tha  Khoa Hoá h  c   5 Trâ   Xanthium spinosum L. Xanthium sibirisum Patrin ex Widder 1.1: Xanthium     Xanthium       d   Xanthium cavanillesii  31].     Xanthium, Xanthium strumarium Xanthium inaequilaterum DC.; Xanthium inaequilaterum  [4].         (1980)     antholid A (1), xantholid B (23   2   Xanthium canadense  -ray [38].
Lu
n v
n Tha

Khoa Hoá h
c

6
Trâ
 
H
H
.
.
O
H
H
.
O
1
H
H
.
.
O
H
H
O
R
1
R
2
2
R
1
= H, R
2
= Me
3
R
1
= Me, R
2
= H
Xanthium orientale  4 - 8 
4 568
-epi-xanthanol [16].
.
O
O
.
O
.
4
.
O
O
O
.
5
.
O
O
.
OR
.
OAc
6 R = H
7 R = Ac
8 R = H (2-epi)
Lu  n v  n Tha  Khoa Hoá h  c   6 Trâ   H H . . O H H . O 1 H H . . O H H O R 1 R 2 2 R 1 = H, R 2 = Me 3 R 1 = Me, R 2 = H Xanthium orientale  4 - 8  4 568 -epi-xanthanol [16]. . O O . O . 4 . O O  O . 5 . O O . OR . OAc 6 R = H 7 R = Ac 8 R = H (2-epi)
Lu
n v
n Tha

Khoa Hoá h
c

7
Trâ
 
M
(5)
cây Xanthium cavanillesii [25].
       
50


2
-
 
-lipoxygenase,      
].
Xanthatin, xanthinosin
Xanthium strumarium L. cho 
       -MB-231 AT   -
4].
Xanthium indicum   
             9), isoalan-
tolacton (10), eudesmanolid (11), 8-epimer (12), 8-epi-xanthatin (13), 2-
hydroxytomentosin (14), xanthumin (15), 2-epi-xanthumin (16), 8-epi-xanthatin-
1,5-epoxid (17), tomentosin (18), axit 4-oxo-bedfordia (19  iso-guaien (20)
[17].
O
O
.
.
.
9
O
O
.
H
.
.
10
.
.
O
O
.
H
.
.
11 8
H
12 8
H
Lu  n v  n Tha  Khoa Hoá h  c   7 Trâ   M (5) cây Xanthium cavanillesii [25].         50   2 -   -lipoxygenase,       ]. Xanthatin, xanthinosin Xanthium strumarium L. cho         -MB-231 AT   - 4]. Xanthium indicum                 9), isoalan- tolacton (10), eudesmanolid (11), 8-epimer (12), 8-epi-xanthatin (13), 2- hydroxytomentosin (14), xanthumin (15), 2-epi-xanthumin (16), 8-epi-xanthatin- 1,5-epoxid (17), tomentosin (18), axit 4-oxo-bedfordia (19  iso-guaien (20) [17]. O O . . . 9 O O . H . . 10 . . O O . H . . 11 8  H 12 8  H
Lu
n v
n Tha

Khoa Hoá h
c

8
Trâ
 
.
O
O
.
O
.
13
.
O
O
.
O
.
RO
14 R = H
15 R = Ac
.
O
O
.
O
.
AcO
16
.
O
O
.
O
.
O
H
17
.
O
O
.
O
.
18
.
.
.
H
.
20
N  -meth  -)-xathatin (5 
Xanthium strumarium


 lacton exo-meth
(---8-epi-xathatin (13)  lên
      --       --
-MB-
Lu  n v  n Tha  Khoa Hoá h  c   8 Trâ   . O O . O . 13 . O O . O . RO 14 R = H 15 R = Ac . O O . O . AcO 16 . O O . O . O H 17 . O O . O . 18 . . . O . 19 . . . H . 20 N  -meth  -)-xathatin (5  Xanthium strumarium    lacton exo-meth (---8-epi-xathatin (13)  lên       --       -- -MB-
Lu
n v
n Tha

Khoa Hoá h
c

9
Trâ
 
231, gây ch   -- 

con n37].
Hai sesq    8-epi-xanthatin (13 -epoxid-epi-
xanthatin (17Xanthium strumarium

-- --     
-in vitro
        -  

50
64-58 µM [24].
Xanthium spinosum 5, 6, 7,
13, 14, 15      1,5-epoxy-1,5-dihydroxanthatin (21), 1,5-
epoxy-1,5-dihydroxanthatin (22), desacetyl xanthiuminol (23  2-hydroxy-4-O-
acetyl-desacetylxanthanol (24) [5-6       
ses    4-O--D-glucopyranosyl-11,13-dihydro-8-epi-
desacetyl xanthiuminol (25)  2-O--D-glucopyranosyl-11,13-dihydro-8-epi-
desacetyl xanthiuminol (26)  [36].
Lu  n v  n Tha  Khoa Hoá h  c   9 Trâ   231, gây ch   --   con n37]. Hai sesq    8-epi-xanthatin (13 -epoxid-epi- xanthatin (17Xanthium strumarium  -- --      -in vitro         -    50 64-58 µM [24]. Xanthium spinosum 5, 6, 7, 13, 14, 15      1,5-epoxy-1,5-dihydroxanthatin (21), 1,5- epoxy-1,5-dihydroxanthatin (22), desacetyl xanthiuminol (23  2-hydroxy-4-O- acetyl-desacetylxanthanol (24) [5-6        ses    4-O--D-glucopyranosyl-11,13-dihydro-8-epi- desacetyl xanthiuminol (25)  2-O--D-glucopyranosyl-11,13-dihydro-8-epi- desacetyl xanthiuminol (26)  [36].
Lu
n v
n Tha

Khoa Hoá h
c

10
Trâ
 
.
O
O
.
O
.
O
21
1
,5
-epoxy
22
1
,5
-epoxy
.
O
O
.
.
HO
HO
23
.
O
O
.
.
AcO
HO
24
O
O
.
.
OR''
.
H
H
R'O
R'
R''
25 H
26 H
O
OH
CH
3
OH
OH
OH
O
OH
CH
3
OH
OH
OH
quiterpen lactonXanthium pungens
 xanthipugolid (27), pungiolid A (28), pungiolid B (29),
2-acetoxy-4,5-epoxyxanthanolid-1,4-endoperoxid (30), 1,5-epoxy-11,13-
dihydrotomentosin (31) axit 4-hydroxyseudoguai-11(13)-en-12-oic (32) [7].
Lu  n v  n Tha  Khoa Hoá h  c   10 Trâ   . O O . O . O 21 1  ,5  -epoxy 22 1  ,5  -epoxy . O O . . HO HO 23 . O O . . AcO HO 24 O O . . OR'' . H H R'O R' R'' 25 H 26 H O OH CH 3 OH OH OH O OH CH 3 OH OH OH quiterpen lactonXanthium pungens  xanthipugolid (27), pungiolid A (28), pungiolid B (29), 2-acetoxy-4,5-epoxyxanthanolid-1,4-endoperoxid (30), 1,5-epoxy-11,13- dihydrotomentosin (31) axit 4-hydroxyseudoguai-11(13)-en-12-oic (32) [7].
Lu
n v
n Tha

Khoa Hoá h
c

11
Trâ
 
.
O
.
O
O
27
.
O
O
.
.
OH
H
O
O
O
.
O
.
28 1
-OH, 5

29 1',5'-epoxid
.
O
O
.
O
OAc
O
O
.
30
.
O
O
.
O
.
O
31
.
COOH
.
H
OH
.
32
-hydroxy-1-p-methoxybenzoyloxydauc-2-en (33a
xanthanolid    Xanthium catharticum (   
 11,13-dihydro-8-
epi-xanthantin (34), 1,5-epoxid-1,5,11,13-tetrahydro-8-epi-xanthatin (35),
1,5-epoxid (36quiterpen guaianolid ziniolid (1)
1 [22].
Lu  n v  n Tha  Khoa Hoá h  c   11 Trâ   . O . O O 27 . O O . . OH H O O O . O . 28 1  -OH, 5  29 1',5'-epoxid . O O . O OAc O O . 30 . O O . O . O 31 . COOH . H OH . 32 -hydroxy-1-p-methoxybenzoyloxydauc-2-en (33a xanthanolid    Xanthium catharticum (     11,13-dihydro-8- epi-xanthantin (34), 1,5-epoxid-1,5,11,13-tetrahydro-8-epi-xanthatin (35), 1,5-epoxid (36quiterpen guaianolid ziniolid (1) 1 [22].
Lu
n v
n Tha

Khoa Hoá h
c

12
Trâ
 
O
CH
3
OH
.
.
O
OCH
3
33
.
O
O
.
.
HO
H
H
34
.
O
O
.
O
.
O
H
H
1
5
35 1
,5
-epoxid
36 1
,5
-epoxid
    y Xanthium cavanillesii, Elmira  
bis-norxanthanolid (37i
13-dihydroxanthumin (38) [15].
.
O
O
.
O
O
37
.
O
O
.
.
O
AcO
38
Ba sesquiterpenoid xanthatin (5), xanthinosin (4   -oxo-bedfordia
(39Xanthium strumarium
Lu  n v  n Tha  Khoa Hoá h  c   12 Trâ   O CH 3 OH . . O OCH 3 33 . O O . . HO H H 34 . O O . O . O H H 1 5 35 1  ,5  -epoxid 36 1  ,5  -epoxid     y Xanthium cavanillesii, Elmira   bis-norxanthanolid (37i 13-dihydroxanthumin (38) [15]. . O O . O O 37 . O O . . O AcO 38 Ba sesquiterpenoid xanthatin (5), xanthinosin (4   -oxo-bedfordia (39Xanthium strumarium