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

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 

       
 Xanthium strumarium    


c sau.

(Xanthium strumarium 
n-hexan (XSLH, h
XSLDn-
hexan (XSCH XSCD, 0,34 %).
        


 9
 n-  
             
   -MS,
1
H-NMR,
13
-  DEPT).    
  3-hexacosanyl-2-oxacyclopentanon (I), -sitosterol (II), betulin (III),
5,8-epidioxy-(22E,24R)-ergosta-6,22-dien-3-ol (IV), acid tricosanoic (V), N-
(1,3,4-trihydroxyheptadec-2-yl)-2-hydroxypentadecanamid (VIa  N-(1,3,4-
trihydroxy-8Z-eicos-8-en-2-yl)-2-hydroxypentadecanamid (VIb), -sitosterol 3-O-
-D-glucopyranosid (VIIa)   -O--D-glucopyranosid (VIIb)  
; -sitosterol (II), 1-tricosanol (VIII)IX)
.
 I, III, IV, V, VIa, VIb, VIIIIX  
Xanthium strumariumVIa
VIb IX 
cây Artermisia japonica m 2014)id
Lu  n v  n Tha  Khoa Hoá h  c   63 Trâ             Xanthium strumarium       c sau.  (Xanthium strumarium  n-hexan (XSLH, h XSLDn- hexan (XSCH XSCD, 0,34 %).             9  n-                    -MS, 1 H-NMR, 13 -  DEPT).       3-hexacosanyl-2-oxacyclopentanon (I), -sitosterol (II), betulin (III), 5,8-epidioxy-(22E,24R)-ergosta-6,22-dien-3-ol (IV), acid tricosanoic (V), N- (1,3,4-trihydroxyheptadec-2-yl)-2-hydroxypentadecanamid (VIa  N-(1,3,4- trihydroxy-8Z-eicos-8-en-2-yl)-2-hydroxypentadecanamid (VIb), -sitosterol 3-O- -D-glucopyranosid (VIIa)   -O--D-glucopyranosid (VIIb)   ; và -sitosterol (II), 1-tricosanol (VIII)IX) .  I, III, IV, V, VIa, VIb, VIIIIX   Xanthium strumariumVIa VIb IX  cây Artermisia japonica m 2014)id
Lu
n v
n Tha

Khoa Hoá h
c

64
Trâ
 
 th
10
Lu  n v  n Tha  Khoa Hoá h  c   64 Trâ    th 10
Lu
n v
n Tha

Khoa Hoá h
c

65
Trâ
 


1. 2011), 
,Tp 1, 456-458.
2. ,
Minh, 178-179.
3.91), 
4. 
-79.
nh
         Xanthium
spinosumPhytochemistry, 23 (4), 915-916.
       
from Xanthium spinosum, Phytochemistry, 30 (10), 3461-3462.
       
Xanthium pungensPhytochemistry, 29 (7), 2211-2215.
8. Ahmed A. M., Ahmed A. A., Munekazu I., Toshiyuki T. (1995),
   fruits of Xanthium pungens
Terrahedron Letters, 36 (49), 8985-8986.
9. Anjoo K., Ajay    Phytopharmacological review of Xanthium
strumarium L. (Cocklebur)Int. J. Green Pharm., 4 (3), 129-139.
 Preliminary evaluation
of in vitro cytotoxicity and in vivo antitumor activity of Xanthium strumarium in
transplantable tumors in miceAm. J. Chin. Med., 41 (1), 145-162.
11. Bader A., Giner R. M., Martini F., Schinella G. R., Ríos J. L., Braca A., Prieto J.
M. Modulation of COX, LOX and NXanthium spinosum
L. root extract and ziniolideFitoterapia, 91, 284-289.
Lu  n v  n Tha  Khoa Hoá h  c   65 Trâ     1. 2011),  ,Tp 1, 456-458. 2. , Minh, 178-179. 3.91),  4.  -79. nh          Xanthium spinosumPhytochemistry, 23 (4), 915-916.         from Xanthium spinosum, Phytochemistry, 30 (10), 3461-3462.         Xanthium pungensPhytochemistry, 29 (7), 2211-2215. 8. Ahmed A. M., Ahmed A. A., Munekazu I., Toshiyuki T. (1995),    fruits of Xanthium pungens Terrahedron Letters, 36 (49), 8985-8986. 9. Anjoo K., Ajay    Phytopharmacological review of Xanthium strumarium L. (Cocklebur)Int. J. Green Pharm., 4 (3), 129-139.  Preliminary evaluation of in vitro cytotoxicity and in vivo antitumor activity of Xanthium strumarium in transplantable tumors in miceAm. J. Chin. Med., 41 (1), 145-162. 11. Bader A., Giner R. M., Martini F., Schinella G. R., Ríos J. L., Braca A., Prieto J. M. Modulation of COX, LOX and NXanthium spinosum L. root extract and ziniolideFitoterapia, 91, 284-289.
Lu
n v
n Tha

Khoa Hoá h
c

66
Trâ
 
 lactones from the aerial
parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines
Phytochemistry Letters, 5, 685-689.
    new thiazinedione glycoside from the fruit of
Xanthium sibiricumChemistry of Natural Compounds, 49 (5), 977-979.
14. Cermak S. C., Isbell T. A. (2000), Synthesis of -stearolactone from oleic
acid, JAOCS, 74 (3), 243-248.
15. Elmira C., Riscala D.,    anthanolides and a bis-
norxanthanolide from Xanthium cavanillesiiPhytochemistry, 35 (6), 1588-1589.
16       Xanthium
orientalePhytochemistry, 20 (10), 2429-2430.
17. Fer         Xanthium
indicumPhytochemistry, 21 (6), 1441-1443.
18.              
eudesmanes from Artemisia japonica Nat. Prod. Res., doi:
10.1080/14786419.2014.891115.
19               ldose
reductase inhibitory compounds from Xanthium strumarium Arch. Pharm. Res,
36, 1090-1095.
20              our new
glycosides from the fruit of Xanthium sibiricum  Molecules, 18, 12464-
12473.
21             -Tri-O-
caffeoylquinic acid from X, Phytochemistry, 33 (2), 508-509.
22. Jativa C., Xanthium catharticum
J. Nat. Prod., 54 (2), 460-465.
23wo toxic kaurene glycosides from the burrs of
Xanthium pungensJ. Nat. Prod., 53 (2), 451-455.
Lu  n v  n Tha  Khoa Hoá h  c   66 Trâ    lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines Phytochemistry Letters, 5, 685-689.     new thiazinedione glycoside from the fruit of Xanthium sibiricumChemistry of Natural Compounds, 49 (5), 977-979. 14. Cermak S. C., Isbell T. A. (2000), Synthesis of -stearolactone from oleic acid, JAOCS, 74 (3), 243-248. 15. Elmira C., Riscala D.,    anthanolides and a bis- norxanthanolide from Xanthium cavanillesiiPhytochemistry, 35 (6), 1588-1589. 16       Xanthium orientalePhytochemistry, 20 (10), 2429-2430. 17. Fer         Xanthium indicumPhytochemistry, 21 (6), 1441-1443. 18.               eudesmanes from Artemisia japonica Nat. Prod. Res., doi: 10.1080/14786419.2014.891115. 19               ldose reductase inhibitory compounds from Xanthium strumarium Arch. Pharm. Res, 36, 1090-1095. 20              our new glycosides from the fruit of Xanthium sibiricum  Molecules, 18, 12464- 12473. 21             -Tri-O- caffeoylquinic acid from X, Phytochemistry, 33 (2), 508-509. 22. Jativa C., Xanthium catharticum J. Nat. Prod., 54 (2), 460-465. 23wo toxic kaurene glycosides from the burrs of Xanthium pungensJ. Nat. Prod., 53 (2), 451-455.
Lu
n v
n Tha

Khoa Hoá h
c

67
Trâ
 
24. Kim Y. S., Kim J. S.,        Two cytotoxic
sesquiterpene lactones from the leaves of Xanthium strumarium and their in vitro
inhibitory activity on farnesyltransferasePlanta Med., 69 (4), 375-377.
25. Laura S. F., Alejandra O. M., Graciela H. W. (200Anti-ulcerogenic activity
of xanthanolide sesquiterpenes from Xanthium cavanillesii  , J.
Ethnopharmacol., 100, 260-267.
26. Lee C. L., Huang P. C., Hsieh P. W., Hwang T. L., Hou Y. Y. (2008), -)-
Xanthienopyran, a new inhibitor of superoxide anion generation by activated
neutrophils, and further constituents of the seeds of Xanthium strumariumPlanta
Med., 74 (10), 1276-1279.
27Inhibition of melanogenesis
by Xanthium strumarium LBiosci. Biotechnol. Biochem., 76 (4), 767-771.
28           anthanolides from
Xanthium strumariumPhytochemistry, 32 (1), 206-207.
29. Miemanang R. S., 
Paullinomide A: A new cerebroside and a new ceramide from leaves of Paullinia
pinnataZ. Naturforsch, 61b, 1123-1127.
30Biological activities of
xanthatin from Xanthium strumarium Phytother Res., 25 (12), 1883-1890.
31 Xanthium
cavanillesiiNat. Prod. Res., 23 (4), 388-392.
32        Isolation and identification of
phytochemicals from Xanthium strumarium International J. Chem. Tech. Res., 4
(1), 266-271.
33. Parwaiz A., Mohd A., Maheesh P. S., Humaira F., Hamid N. K. (2010),
ts of Corylus colurna J. Phytol., 2 (3),
89-100.
Lu  n v  n Tha  Khoa Hoá h  c   67 Trâ   24. Kim Y. S., Kim J. S.,        Two cytotoxic sesquiterpene lactones from the leaves of Xanthium strumarium and their in vitro inhibitory activity on farnesyltransferasePlanta Med., 69 (4), 375-377. 25. Laura S. F., Alejandra O. M., Graciela H. W. (200Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii  , J. Ethnopharmacol., 100, 260-267. 26. Lee C. L., Huang P. C., Hsieh P. W., Hwang T. L., Hou Y. Y. (2008), -)- Xanthienopyran, a new inhibitor of superoxide anion generation by activated neutrophils, and further constituents of the seeds of Xanthium strumariumPlanta Med., 74 (10), 1276-1279. 27Inhibition of melanogenesis by Xanthium strumarium LBiosci. Biotechnol. Biochem., 76 (4), 767-771. 28           anthanolides from Xanthium strumariumPhytochemistry, 32 (1), 206-207. 29. Miemanang R. S.,  Paullinomide A: A new cerebroside and a new ceramide from leaves of Paullinia pinnataZ. Naturforsch, 61b, 1123-1127. 30Biological activities of xanthatin from Xanthium strumarium Phytother Res., 25 (12), 1883-1890. 31 Xanthium cavanillesiiNat. Prod. Res., 23 (4), 388-392. 32        Isolation and identification of phytochemicals from Xanthium strumarium International J. Chem. Tech. Res., 4 (1), 266-271. 33. Parwaiz A., Mohd A., Maheesh P. S., Humaira F., Hamid N. K. (2010), ts of Corylus colurna J. Phytol., 2 (3), 89-100.
Lu
n v
n Tha

Khoa Hoá h
c

68
Trâ
 
34. Ramisrez E. I., Huang Y., Hick   Xanthatin
and xanthinosin from the burs of Xanthium strumarium L. as potential anticancer
agentsCan. J. Physiol. Pharmacol., 85 (11), 1160-1172.
35           Xanthium
strumariumPhytochemistry, 35 (4), 1080-1082.
36 
from Xanthium spinosumPhytochemistry, 41 (5), 1357-1360.
37. Takeda S., Matsuo K., Yaji K., Okajima M. (2011), -)-Xanthatin selectively
-independent cell death in human breast
cancer MDA-MB-231 cellsChem. Res. Toxicol., 24 (6), 855-865.
38. Toshie T., Yoshitsugu S. (1980), Structures of xantholides A and B, two new
guaianolides from Xanthium canadense Tetrahedron Letters, 21, 1861-1862.
39Anti-allergic rhinitis effect of
caffeoylxanthiazonoside isolated from fruits of Xanthium strumarium L. in rodent
animalsPhytomedicine, 14, 21-26.
40. Yamasaki K., Sholichin M., Kasai R., Tanaka O. (1980),
13
C Nuclear magnetic
resonance of lupane-      , Chem.
Pharm. Bull., 28(3), 1006-1008.
41      Inhibition of lipopolysaccharide-
induced inducible nitric oxide synthase and cyclooxygenase-2 expression by
xanthanolides isolated from Xanthium strumarium Bioorganic & Medicinal
Chemistry Letters, 18, 2179-2182.
42. Ying T. M., Mu C. H., Feng L. H., Hsiu F. C.  Thiazinedione from
Xanthium strumariumPhytochemistry, 48 (6), 1083-1085.
43. Yue M., Chen S. N., Lin Z. W., Sun H. D. (2001), Sterols from the fungus
Lactarium volemus, Phytochemistry, 56, 801-806.
Lu  n v  n Tha  Khoa Hoá h  c   68 Trâ   34. Ramisrez E. I., Huang Y., Hick   Xanthatin and xanthinosin from the burs of Xanthium strumarium L. as potential anticancer agentsCan. J. Physiol. Pharmacol., 85 (11), 1160-1172. 35           Xanthium strumariumPhytochemistry, 35 (4), 1080-1082. 36  from Xanthium spinosumPhytochemistry, 41 (5), 1357-1360. 37. Takeda S., Matsuo K., Yaji K., Okajima M. (2011), -)-Xanthatin selectively -independent cell death in human breast cancer MDA-MB-231 cellsChem. Res. Toxicol., 24 (6), 855-865. 38. Toshie T., Yoshitsugu S. (1980), Structures of xantholides A and B, two new guaianolides from Xanthium canadense Tetrahedron Letters, 21, 1861-1862. 39Anti-allergic rhinitis effect of caffeoylxanthiazonoside isolated from fruits of Xanthium strumarium L. in rodent animalsPhytomedicine, 14, 21-26. 40. Yamasaki K., Sholichin M., Kasai R., Tanaka O. (1980),  13 C Nuclear magnetic resonance of lupane-      , Chem. Pharm. Bull., 28(3), 1006-1008. 41      Inhibition of lipopolysaccharide- induced inducible nitric oxide synthase and cyclooxygenase-2 expression by xanthanolides isolated from Xanthium strumarium Bioorganic & Medicinal Chemistry Letters, 18, 2179-2182. 42. Ying T. M., Mu C. H., Feng L. H., Hsiu F. C.  Thiazinedione from Xanthium strumariumPhytochemistry, 48 (6), 1083-1085. 43. Yue M., Chen S. N., Lin Z. W., Sun H. D. (2001), Sterols from the fungus Lactarium volemus, Phytochemistry, 56, 801-806.
Lu
n v
n Tha

Khoa Hoá h
c

69
Trâ
 

Lu  n v  n Tha  Khoa Hoá h  c   69 Trâ   
Lu
n v
n Tha

Khoa Hoá h
c

70
Trâ
 
PH LC 1: PH
1
H-NMR CA XSLH4.1 (I)
Lu  n v  n Tha  Khoa Hoá h  c   70 Trâ   PH LC 1: PH 1 H-NMR CA XSLH4.1 (I)
Lu
n v
n Tha

Khoa Hoá h
c

71
Trâ
 
PH LC 2: PH
13
C-NMR VÀ DEPT CA XSLH4.1 (I)
Lu  n v  n Tha  Khoa Hoá h  c   71 Trâ   PH LC 2: PH 13 C-NMR VÀ DEPT CA XSLH4.1 (I)
Lu
n v
n Tha

Khoa Hoá h
c

72
Trâ
 
PH LC 3: PH (+)-ESI-MS CA XSLH4.1 (I)
Lu  n v  n Tha  Khoa Hoá h  c   72 Trâ   PH LC 3: PH (+)-ESI-MS CA XSLH4.1 (I)