全 文 :2016
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Vol41,No.9 May,2016
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UPLCQTOFMS
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StudyonchemicalconstituentsinLysinotuswilsonibyUPLCQTOFMS
HUJun1,ZHANGQuan1,QIMengdie1,KANGLiping2,NANTiegui2,YANGJian2,
YUANYuan2,ZHANZhilai2,LIUYong1,HUANGLuqi2
(1BeijingUniversityofChineseMedicine,Beijing100102,China;
2ChinaAcademyofChineseMedicalSciences,NationalResourceCenterforChineseMateriaMedica,
StateKeyLaboratoryBreedingBaseofDaodiHerbs,Beijing100700,China)
[Abstract] TheUltrahighPerformanceLiquidChromatographyQuadrupoleTimeofflightMassSpectrometry(UPLCQTOF
MS)wasappliedtoanalyzethechemicalcomponentsinLysinotuswilsoniAWatersACQUITYUPLCBEHC18Scolumn(21
mm×100mm,17μm)wasusedwithagradientelutionofacetonitrilewatercontaining01% formicacidThemassspectrom
etryequippedwithionizationsourcewasusedandthedatawascolectedinnegativeionmodeResultsshowedthat57compo
nentswereidentifiedas42phenylethanoidglycosides,5benzylalcoholglycosides,6flavonoidsand4othercomponentsAmong
them,43compoundswerefirstlyidentifiedinGensneriaceaeandonebenzylalcoholglycosidemaybeanewcompoundWehave
quitecompletelyidentifiedthecomponentsinLwilsoniforthefirsttime,whichmaylaythefoundationforfurtherstudyand
utilizationofthemedicinalplant
[Keywords] UPLCQTOFMS;Lysinotuswilsoni;chemicalconstituents
doi:104268/cjcmm20160916
·8561·
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·9561·
2016
y
5
z À
41
ÁÀ
9
}
Vol41,No.9 May,2016
q
1
Àv¶x(S
UPLCQTOFMS
¡¢TKUÌVWuv¶Iq
(A)
75~155min
uv¶Iq
(B)
Fig1 WholebasepeakionschromatogramofLysionotuswilsonibyUPLCQTOFMS(A)andwholebasepeakionschromatogramin
75155min(B)innegativeionmode
32
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2(3,4di
hydroxyphenyl)ethyl3OβDglucopyranosyl6O(2,
3,4,5tetrahydroxycyclopentyl)4[(2E)3(3,4di
hydroxyphenyl)2propenoate]βDglucopyranoside,
rashomosideA
î
2(3,4dihydroxyphenyl)ethylOD
apioβDfuranosyl(1→ 3)O[βDglucopyranosyl
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βDGlucopyranoside,14ÓrashomosideA,18Ó2(3,
4dihydroxyphenyl)ethylODapioβDfuranosyl(1→
3)O[βDglucopyranosyl(1→6)]4[(2E)3(3,4
dihydroxyphenyl)2propenoate]βDglucopyranoside,
3
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·0661·
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UPLCQTOFMS
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Table1 UPLCQTOFMSqualitativeanalysisofchemicalconstitutentsinLysinotuswilsoni(Negativeionmode)
No
tR
/min
]`«¡ ¡¶(
ë+²
/nm
[M-H]-
nº }s
Masseror
ZJ
7
1 259 chlorogenicacidisomers C16H18O9 215,323 3531000 3530973 27 191055 7,179036 3,
1610241,1350465
2 357 chlorogenicacidisomers C16H18O9 217,324 3531000 3530973 27 191055 7,179036 3,
1610241,1350465
3 387 chlorogenicacid C16H18O9 217,325 3531000 3530973 27 191055 7,179036 3,
1610241,1350465
4 500 4methoxyphenyl4OβL
glucopyranosylβDgalactopyr
anoside
C19H28O12 215,282 4471534 4471503 31 3010317,1790363,1610241
5 573 decafeoylacteoside C20H30O12 215,326 4611646 4611623 23 3151083,1790363,1610267
6 682 pauciflosideorisomers C33H42O19 217,327 7411891 7411878 13 579192 4,447153 4,
3151192,1790363,1610246
7 693 5″deacetylcissosideⅢ C26H28O15 255,343 5792681 5792653 28 4770971,4471534,3000291,
2710251,2550282,1610246
8 699 3[(6deoxyαLmannopyr
anosyl)oxy]2(3,4dihydroxy
phenyl)7[(3OβDglucopyr
anosylβDxylopyranosyl)oxy]
5hydroxy4H1benzopyran4
one
C32H38O20 255,343 7411891 7411878 13 5791831,3000255,
2710218,2550282,1610246
9 740 quercetin3,6OαLarabi
nopyranosylβDgalactopyrano
side
C26H28O16 255,353 5951328 5951299 29 4630916,4450790,3000255,
2710251,2550282,2430290
10 1017 2(3,4dihydroxyphenyl)eth
yl6[(2Z)3(3,4dihydroxy
phenyl)2propenoate]βDglu
copyranoside
C23H26O11 217,327 4771389 4771397 -08 3151083,1790363,1610241
11 774 calceolariosideBorisomers C23H26O11 217,326 4771389 4771397 -08 3151119,1790363,1610241
12 941 2(3,4dihydroxyphenyl)eth
yl2OβDxylopyranosyl4
[(2E)3(3,4dihydroxyphe
nyl)2propenoate]βDgluco
pyranoside
C28H34O15 217,327 6091804 6091819 -15 4471534,3151083,
1790363,1610241
13 818 2(3,4dihydroxyphenyl)eth
yl3OβDglucopyranosyl6O
(2,3,4,5tetrahydroxycyclopen
tyl)4[(2E)3(3,4dihydroxy
phenyl)2propenoate]βDglu
copyranoside
C34H44O20 215,330 7712348 7712348 0 609180 4,447157 7,
3151156,1790363,1610267
14 825 rashomosideA C34H44O20 215,330 7712348 7712348 0 609180 4,447157 7,
3151156,1790363,1610267
15 891 isorhamnetin3O(βDapio
furanosyl(1→ 3)βDglucopy
ranoside)
C27H30O16 253,343 6091450 6091456 -06 475123 9,399003 9,
3000291,2710251,2550315,
1790369,1610272
16 898 sinocrassosideC1 C27H30O16 265,343 6091440 6091456 -16 4771418,3000291,2710251,
2550315,1790369,1610272
17 913 2(3,4dihydroxyphenyl)3
(βLgalactopyranosyloxy)5,7
dihydroxy4H1benzopyran4
one
C21H20O12 265,343 4630887 4630877 10 300025 5,271025 1,
2550282,1790341,1610220
·1661·
2016
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Vol41,No.9 May,2016
K
1
No
tR
/min
]`«¡ ¡¶(
ë+²
/nm
[M-H]-
nº }s
Masseror
ZJ
7
18 928 2(3,4dihydroxyphenyl)ethyl
ODapioβDfuranosyl(1→3)
O[βDglucopyranosyl(1→6)]
4[(2E)3(3,4dihydroxyphe
nyl)2propenoate]βDglucopy
ranoside
C34H44O20 217,329 7712348 7712348 0 6091804,4471577,3151156,
1790363,1610267
19 812 2(3,4dihydroxyphenyl)ethyl
2ODapioβDfuranosyl4
[(2E)3(3,4dihydroxyphenyl)
2propenoate]βDglucopyrano
side
C28H34O15 217,326 6091854 6091819 35 4471534,3151803,1790363,
1610267
20 962 paucifloside C33H42O19 217,328 7412227 7412242 -15 5791924,4471534,3151083,
1790363,1610241
21 1038 calceolariosideC C28H34O15 217,329 6091823 6091819 04 4471490,3151083,1790363,
1610241
22 990 plantamajoside1) C29H36O16 217,326 6391920 6391925 -05 4771642,3151083,1790363,
1610241
23 758 2hydroxy4(hydroxylmethyl)
phenyl6[3(4hydroxy3meth
oxyphenyl)2propenoate]βD
glucopyranoside
C23H26O11 217,326 4771389 4771397 -08 3151119,1790363,1610241
24 975 calceoralariosideE C28H33O15 217,328 6091804 6091819 -15 4471490,3151083,1790363,
1610241
25 1482 chionosideA C35H46O20 217,328 7852483 7842504 -21 6232231,4771597,3151119,
1790363,1610241
26 1064 raduloside C38H50O23 217,328 8732694 8732665 -31 7112334,5791924,4471490,
3151119,1790363,1610241
27 1082 forsythosideB1) C34H44O19 217,330 7552409 7552399 10 5932062,4471534,315,179,
161
28 1108 calceolariosideB1) C23H26O11 217,326 4771389 4771397 -08 3151119,1790363,1610241
29 1139 chionosideF C40H54O24 217,327 9172897 9172927 -30 7552272,5932062,4471534,
3151119,1790363,1610241
30 1159 acteoside1) C29H36O15 217,329 6231996 6231976 20 4611682,3151083,1790363,
1610241
31 1177 2(3,4dihydroxyphenyl)ethyl
3O(6deoxyαLgalactopyrano
syl)4[(2E)3(3,4dihydroxy
phenyl)2propenoate]βDglu
copyranoside
C29H36O15 217,326 6231996 6231976 20 4611682,3151083,1790363,
1610241
32 1181 2(3,4dihydroxyphenyl)ethyl
3OβDglucopyranosyl6O(2,
3,4,5tetrahydroxycyclopentyl)4
[(2E)3(4hydroxy3methoxy
phenyl)2propenoate]βDglu
copyranoside
C35H46O20 217,328 7852483 7852504 -21 6232231,4771597,3151083,
1790363,1610241
33 1189 lunarifolioside C39H52O23 217,329 8872838 8872821 17 7252476,5932062,4471534,
3151119,1790363,1610241
34 1199 maruboside C39H52O23 217,329 8872838 8872821 17 7252476,5932062,4471534,
3151119,1790363,1610241
·2661·
1É
:
ê
UPLCQTOFMS
()TKUÌVW$_«¡¡¢
K
1
No
tR
/min
]`«¡ ¡¶(
ë+²
/nm
[M-H]-
nº }s
Masseror
ZJ
7
35 1219 lysionotosideorisomers C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
36 1261 lysionotoside C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
37 1276 lysionotosideorisomers C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
38 1282 lysionotosideorisomers C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
39 1332 lysionotosideorisomers C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
40 1356 lagotisideA C29H36O16 217,329 6231996 6231976 20 4611682,3151083,1790363,
1610241
41 1369 integrifoliosideA C35H46O19 218,329 7692541 7692555 -14 7552385,6231996,5932081,
4471461,3151093,1790369,
1610246
42 1396 betonyosideF C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
43 1386 samioside C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
44 1660 2″Oβapiosylverbascoside C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
45 1457 myricoside C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
46 1474 chionosideB C36H48O20 217,328 7992614 7992661 -47 7552328,5932112,461163
8,3151047,1790336,1610241
47 1048 (1S)2(3,4dihydroxyphe
nyl)1hydroxyethylO6deoxy
αLmannopyranosyl(1→3)O
[6deoxyαLmannopyranosyl
(1→6)]4[(2E)3(3,4di
hydroxyphenyl)2propenoate]β
Dglucopyranoside
C35H46O20 217,328 7852483 7852504 -21 6232231,4771597,3151119,
1790363,1610241
48 1486 verpectosideB C35H46O20 218,329 7852458 7852504 -46 6232130,4611682,3151047,
1790336,1610241
49 1500 2(4hydroxyphenyl)ethylO6
deoxyαLmannopyranosyl(1→
3)O[βDxylopyranosyl(1→
6)]4[(2E)3(3,4dihydroxy
phenyl)2propenoate]βDglu
copyranoside
C34H44O18 218,330 7392451 7392449 02 5772132,4451683,2991139,
1790336,1610241
50 1521 2(3,4dihydroxyphenyl)ethyl
6O(6deoxyαLmannopyrano
syl)4[3(3,4dihydroxyphe
nyl)2propenoate]βDglucopy
ranoside
C29H36O16 217,329 6231996 6231976 20 4611682,3151083,1790363,
1610241
51 1557 2(4hydroxyphenyl)ethylO6
deoxyαLmannopyranosyl(1→
3)O[βDxylopyranosyl(1→
6)]4[(2E)3(3,4dihydroxy
phenyl)2propenoate]βDglu
copyranosideisomers
C34H44O18 218,327 7392451 7392449 02 5772132,4451683,2991139,
1790336,1610241
·3661·
2016
y
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41
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9
}
Vol41,No.9 May,2016
K
1
No
tR
/min
]`«¡ ¡¶(
ë+²
/nm
[M-H]-
nº }s
Masseror
ZJ
7
52 1597 cistantubulosideB2 C35H46O19 218,329 7692541 7692555 -14 7552385,6231996,5932081,
4471461,3151093,1790369,
1610246
53 1627 2(4hydroxyphenyl)ethylO6
deoxyαLmannopyranosyl(1→
3)O[βDxylopyranosyl(1→
6)]4[(2E)3(3,4dihydroxy
phenyl)2propenoate]βDglu
copyranosideisomers
C34H44O18 218,327 7392451 7392449 02 5932132,4611683,2991139,
1790336,1610241
54 1416 forsythosideF C34H44O19 217,329 7552408 7552399 09 5932062,4471534,3151119,
1790363,1610241
55 1704 verpectosideA C35H46O19 218,329 7692541 7692555 -14 7552385,6231996,6072363,
5932081,4471461,3151093,
1790369,1610246
56 1794 salsasideB C28H34O13 217,329 5771904 5771921 -17 4311116,4151584,2691030,
1610267
57 1881 PG1 C33H42O17 218,329 7092331 7092234 -03 5472055,4311201,4151638,
2691039,1791039,1610246,
1330296
ë
:1)
ÏaÏ\`«¡
。
_ª¨
10,11,23
#
28
졶v¶µÆÓ
m/z47723[M-H]-,
gº1Ó¦¡Ezó
,
J
7Ó
31511[M-H-C5H8O4]
-,m/z
17903[M-H-C5H8O4-174]
-
Ó9¯«¬
8¼
m/z16102[M-H-C5H8O4-191]
-
Ó9¯:-«¬8¼
,
$_ª¨
28
ÏaÏÓ
calceolariosideB。
áª^»
[10
12]
gºLÓ
2(3,4dihydroxyphenyl)ethyl6
[(2Z)3(3,4dihydroxyphenyl)2propenoate]β
Dglucopyranoside,calceolariosideA,2hydroxy4
(hydroxymethyl)phenyl6[3(4hydroxy3me
thoxyphenyl)2propenoate]βDglucopyranoside,
st
4
C_ª¨
Clogp
¡^Ó
-05,02,12,
14,
áªÖµ?Ægº_ª¨
10
Ó
2(3,4di
hydroxyphenyl)ethyl6[(2Z)3(3,4dihydroxy
phenyl)2propenoate]βDglucopyranoside,11Ó
calceolariosideA,
_ ª ¨
23
Ó
2hydroxy4
(hydroxymethyl)phenyl6[3(4hydroxy3me
thoxyphenyl)2propenoate]βDglucopyranoside。
_ª¨
28
?/Ýq
2。
_ª¨
12,19,21
#
24
졶v¶µÆÓ
m/z
60918[M-H]-,
gº1¢Ó¦¡Ezó
,
J
q
2 CalceolariosideB
?/ݬ
(
Àv¶x(
)
Fig2 ThepossiblefragmentationpathwayofcalceolariosideB
(negativeionmode)
7
m/z44715[M-H-C9H8O3]
-,31511[M-
H-C9H8O3-C5H8O4]
-,17903,16102
Ó«¬8
¼v¶
。
ò^»
[1316]
gº_ª¨1
Ó
2(3,4dihydroxyphenyl)ethyl2OβDxylopyrano
syl4[(2E)3(3,4dihydroxyphenyl)2propeno
ate]βDglucopyranoside,2(3,4dihydroxyphenyl)
ethyl2ODapioβDfuranosyl4[(2E)3(3,4di
hydroxyphenyl)2propenoate]βDglucopyranoside,
calceolariosideC
î
calceoralariosideE,
st
4
C_ª
¨
Clogp
¡^Ó
-26,-20,-15,-02,
áªÖ
µ?Ægºgº_ª¨
12
Ó
2(3,4dihydroxyphe
·4661·
1É
:
ê
UPLCQTOFMS
()TKUÌVW$_«¡¡¢
nyl)ethyl2OβDxylopyranosyl4[(2E)3(3,4di
hydroxyphenyl)2propenoate]βDglucopyranoside,
19
Ó
2(3,4dihydroxyphenyl)ethyl2ODapioβD
furanosyl4[(2E)3(3,4dihydroxyphenyl)2prope
noate]βDglucopyranoside,21Ó calceolariosideC,
24
Ó
calceoralariosideE,
$_ª¨
12
#
19
Ó
¼}¤Ú&$mÝ
。
_ª ¨
22
ì ¡ ¶ v ¶ µ Ó
m/z63919
[M-H]-,
J
7
m/z47716[M-H-C9H8
O3]
-,31511[M-H-C9H8O3-C6H10O5]
-,17903,
16102
Ó«¬8¼v¶
,
òÏaÏ_ª
¨
22
Ó
plantamajoside,
?/ݪ«q
3。
q
3 Plantamajoside
?/ݬ
(
Àv¶x(
)
Fig3 Thepossiblefragmentationpathwayofplantamajoside(negativeionmode)
_ª¨
25,32,47
#
48
졶v¶µÆÓ
m/z
78524[M-H]-,
gº1Ó¦¡Ezó
,
J
7Ó
62322[M-H-C9H8O3]
-,47716[M-H-
C9H8O3-C6H10O5]
-,31511[M-H-C9H8O3-
C6H10O5-C6H10O5]
-,17903,16102
Ó«¬8
¼v¶
。
ò^»
[1720]
1Ó
chionoside
A,2(3,4dihydroxyphenyl)ethyl3OβDglucopyr
anosyl6O(2,3,4,5tetrahydroxycyclopentyl)4
[(2E)3(4hydroxy3methoxyphenyl)2propeno
ate]βDglucopyranoside,(1S)2(3,4dihydroxy
phenyl)1hydroxyethylO6deoxyαLmannopyrano
syl(1→ 3)O[6deoxyαLmannopyranosyl(1→
6)]4[(2E)3(3,4dihydroxyphenyl)2propeno
ate]βDglucopyranosideî verpectosideB,st4C
_ª¨
Clogp
¡^Ó
-38,-37,-27,-19,
á
ªÖµ?Ægº_ª¨
25
Ó
chionosideA,32
Ó
2(3,4dihydroxyphenyl) ethyl3OβDglucopyrano
syl6O(2, 3, 4, 5tetrahydroxycyclopentyl)
4[(2E)3(4hydroxy3methoxyphenyl)2propeno
ate]βDglucopyranoside,47Ó (1S)2(3,4di
hydroxyphenyl )1hydroxyethylO6deoxyαLman
nopyranosyl(1→3)O[6deoxyαLmannopyranosyl
(1→6)]4[(2E)3(3,4dihydroxyphenyl)2pro
penoate]βDglucopyranoside,48Ó verpectosideB,
4
C_ª¨Æ¤=VW&$¼}mÝ
。
_ª¨
26
졶v¶µÓ
m/z87326[M-
H]-,
J
7Ó
71123[M-H-C9H8O3]
-,57919
[M-H-C9H8O3-C5H8O4]
-,44716[M-H-
C9H8O3-C5H8O4-C5H8O4]
-,31511[M-H-C9H8O3-
C5H8O4-C5H8O4-C5H8O4]
-,17903,16102
Ó«
¬8¼v¶
。
ò^»
[21]
gº_ª¨
26
Ó
raduloside,
Ú_ª¨¤=VW&$¼}mÝ
。
_ª¨
27,35~39,42~45
#
54
졶v¶µ
Ó
m/z75524[M-H]-,
gºÓ¦¡Ezó
,
J
7Ó
59320[M-H-C9H8O3]
-,44716[M-
HC9H8O3-C6H10O4]
-,31511[M-H-C9H8O3-
·5661·
2016
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41
ÁÀ
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}
Vol41,No.9 May,2016
C6H10O4-C5H8O4]
-,17903,16102
Ó«¬8
¼v¶
。
òÏaÏ_ª¨
27
Ó
forsyth
osideB,
ò^»
[3,2225]
gº_ª¨
36,42~45,54
Ó
lysionotoside,betonyosideF,samioside,2″Oβ
apiosylverbascoside,myricoside,forsythosideF,
st
_ª¨
27,36,42~45,54
Clogp
¡^Ó
-50,
-39,-32,-29,-23,-15,-13,
áªÖµ
?Ægº_ª¨
36
Ó
lysionotoside,35,37~39
Ó
¦¡Ezó
,42
Ó
betonyosideF,43
Ó
samioside,44
Ó
2″Oβapiosylverbascoside,45Ó myricoside,54
Ó
forsythosideF。
$_ª¨
27,42~44,54
¤=
VW&$¼}mÝ
。
_ª¨
29
졶v¶µÓ
m/z91728[M-
H]-,
J
7Ó
75524[M-H-C6H10O5]
-,
59320[M-H-C6H10O5 -C9H8O3]
-,44716
[M-H-C6H10O5-C9H8O3-C6H10O4]
-,31511
[M -H -C6H10O5 -C9H8O3 -C6H10O4 -
C5H8O4]
-,17903,16102
Ó«¬8¼v
¶
。
ò^»
[26]
gº_ª¨
29
Ó
chionosideF,
Ó¼}¤Ú&$mÝ
。
_ª¨
30,31,40,50
졶v¶µÓ
m/z
62319[M-H]-,
gº1Ó¦¡Ezó
,
J
7Ó
46116[M-H-C9H8O3]
-,31511[M-H-
C9H8O3-C6H10O4]
-,17903,16102
Ó«¬8
¼v¶
。
òÏaÏ_ª¨
30
Ó
acte
oside,
ò^»
[2729]
gº_ª¨Ó
2(3,4di
hydroxyphenyl)ethyl3O(6deoxyαLgalactopyrano
syl)4[(2E)3(3,4dihydroxyphenyl)2propeno
ate]βDglucopyranoside,lagotisideAî2(3,4di
hydroxyphenyl)ethyl6O(6deoxyαLmannopyrano
syl)4[3(3,4dihydroxyphenyl)2propenoate]βD
glucopyranoside,
st
4
C_ª¨
Clogp
¡^Ó
-38,-37,-27,-19,
áªÖµ?Ægº_ª
¨
31
Ó
2(3,4dihydroxyphenyl)ethyl3O(6deoxy
αLgalactopyranosyl)4[(2E)3(3,4dihydroxy
phenyl)2propenoate]βDglucopyranoside,40 Ó
lagotisideA,50
Ó
2(3,4dihydroxyphenyl)ethyl6O
(6deoxyαLmannopyranosyl)4[3(3,4dihydroxy
phenyl)2propenoate]βDglucopyranoside,_ª¨
31,40,50
Ó¼}¤Ú&$mÝ
。
_ª¨
33~34
졶v¶µÓ
m/z88728
[M-H]-,
gºÓ¦¡Ezó
,
J
7Ó
72524[M-H-C9H8O3]
-,59321[M-H-
C9H8O3-C5H8O4]
-,44716[M-H-C6H10O5-
C9H8O3-C5H8O4-C6H10O4]
-,31511[M-H-C6
H10O5-C9H8O3-C5H8O4-C6H10O4-C5H8O4]
-,
17903,16102
Ó«¬8¼v¶
。
ò^»
[3031]
gºÓ
lunarifolioside
î
maruboside,
st
2
C_ª¨
Clogp
¡^Ó
-23,-12,
áªÖ
µ?Ægº_ª¨
33
Ó
lunarifolioside,34
Ó
mar
ruboside,
ÆÓ¼}¤Ú&$mÝ
。
_ª¨
46
졶v¶µÓ
m/z79926[M-
H]-,
J
7Ó
75524[M-H-CH3CHO]
-,
59321[M-H-CH3CHO-C9H8O3]
-,46116[M-
H-CH3CHO-C9H8O3-C5H8O4]
-,31511[M-H
-CH3CHO-C9H8O3 -C5H8O4 -C6H10O4]
-,
17903,16102
Ó«¬8¼v¶
。
ò^»
[32]
gº_ª¨
46
Ó
chionosideB,
Ó¼}¤Ú&
$mÝ
。
_ª¨
41,52
#
55
졶v¶µÓ
m/z
76926[M-H]-,
gºÓ¦¡Ezó
,
J
7Ó
75524[M-H-CH2]
-,62319[M-H-
CH2-C5H8O4]
-,59320[M - H - CH2 -
C9H8O3]
-,44714[M -H-CH2 -C9H8O3 -
C5H8O4]
-,31511[M-H-CH2-C9H8O3-C5H8
O4-C5H8O4]
-,17903,16102
Ó«¬8¼
v¶
。
ò^»
[3335]
gºÓ
integrifoliosideA,
cistantubulosideB2î verpectosideA,st 3C_ª
¨
Clogp
¡^Ó
-33,-24,-11,
áªÖµ?Æ
gº_ª¨
41
Ó
integrifoliosideA,52
Ó
cistantubu
losideB2,55ÓverpectosideA,ÆÓ¼}¤Ú&$
mÝ
。
322
7§«¡
_ª¨
49,51
#
53
ì¡
¶v¶µÓ
m/z73924[M-H]-,
gºLÓ¦¡
Ezó
,
J
7Ó
57721[M-H-C9H8O3]
-,
44516[M -H-C9H8O3 -C5H8O4]
-,29919
[M-H-C9H8O3-C5H8O4-C6H10O4]
-,17903,
16102
Ó«¬8¼v¶
。
st
3
C_ª¨
Clogp
¡^Ó
-23,-14,-11
qò^»
[36]
g
º_ª¨
49
Ó
2(4hydroxyphenyl)ethylO6deoxy
αLmannopyranosyl(1→ 3)O[βDxylopyranosyl
(1→6)]4[(2E)3(3,4dihydroxyphenyl)2prope
noate]βDglucopyranoside,_ª¨51,53Ó¦¡E
·6661·
1É
:
ê
UPLCQTOFMS
()TKUÌVW$_«¡¡¢
zó
。
_ª ¨
56
ì ¡ ¶ v ¶ µ Ó
m/z57719
[M-H]-,
J
7Ó
43111[M-H-C6H10O4]
-,
41516[M-H-C9H8O3]
-,26910[M-H-
C9H8O3-C6H10O4]
-,17903,16102
Ó«¬8
¼v¶
。
ò^»
[37]
gº_ª¨
56
Ó
sal
sasideB,
ÆÓ¼}¤Ú&$mÝ
。
_ª¨
57
졶v¶µÓ
m/z70923
[M-H]-,
J
7 Ó
54721[M -H -
C9H8O3]
-,41512[M-H-C9H8O3-C5H8O4]
-,
26910[M-H-C9H8O3-C6H10O4]
-,17903,
16102
Ó«¬8¼v¶
。
Ú_ª¨ÓD_
ª¨
,
Ú¼Ó
PG1,
?ázq
4。
q
4 PG1
?áz
Fig4 ThepossiblestructureofcomponentPG1
323
(㧫¡
Àv¶x(S
,
(ã-§_
ª¨t-©
[M-H]-,[M-H-
c
]-
v¶
,
E
/-©~¼v¶
(YO
-),
Æ/-©~Mw
v¶
([YO
- -H]-·)。
c3P·Þ
(
3O,
7O
3P
)
#cJãú(
(1→2Jãî1→6J
ã
)
+Ï(ã§_ª¨/ݼÈÉ-©ØÙ
,
YO
-,[YO
-H·]
âÏ^
,
¦O+Ï«
JÖÝ[ôOÈÉ~¼-©ØÙ
,
WÍI
ê_ª¨gº]`
。
_ª¨
7
졶v¶µÓ
m/z57926[M-
H]-,
J
7Ó
44715[M-H-C5H8O4]
-,
30102YO
-,30002[YO
- -H]-,
«
JÖÝ
27102,25502,16102。
ò^»
[38]
gº_ª¨
7
Ó
5″deacetylcissosideⅢ,Ó¼}¤=VW&$
mÝ
。
_ª¨
8
졶v¶µÓ
m/z74118[M-
H]-,
J
7Ó
57918[M-H-C6H10O5]
-,
30102YO
-,30002[YO
- -H]-,
«
JÖÝ
27102,25502,17901,16102。
ò^»
[39]
g
º_ª¨
8
Ó
3[(6deoxyαLmannopyranosyl)
oxy]2(3,4dihydroxyphenyl)7[(3OβDgluco
pyranosylβDxylopyranosyl)oxy]5hydroxy4H1ben
zopyran4one,
Ó¼}¤=VW&$mÝ
。
_ª¨
9
졶v¶µÓ
m/z59512[M-
H]-,
J
7Ó
46309[M-H-C5H8O4]
-,
30102YO
-,30002[YO
- -H]-,
«
JÖÝ
27102,25502,17901,16102。
ò^»
[40]
g
º_ª¨
9
Ó
quercetin3,6OαLarabinopyranosyl
βDgalactopyranoside,Ó¼}¤=VW&$mÝ。
_ª¨
15~16
졶v¶µÆÓ
m/z60914
[M-H]-,
gºÓ¦¡Ezó
,
J
7Ó
47512[M-H-C6H10O5]
-,30102YO
-,30002
[YO
- -H]-,
«
JÖÝ
27102,25502,
17901,16102。
ò^»
[4142]
gº_ª¨
15
Ó
isorhamnetin3O(βDapiofuranosyl(1→3)βD
glucopyranoside),16
Ó
sinocrassosideC1
Ó¼}¤=
VW&$mÝ
。
_ª¨
17
졶v¶µÓ
m/z46308[M-
H]-,
J
7ÓB
30102YO
-,30002[YO
- -
H]-,
«
J Ö Ý
27102,25502,17901,
16102。
ò^»
[43]
gº_ª¨
17
Ó
2(3,4
dihydroxyphenyl)3(βLgalactopyranosyloxy)5,7
dihydroxy4H1benzopyran4one,
Ú«¡Ó¼}¤=
VW&$mÝ
。
324
¤§m_ª¨
_ª¨
1~3
졶v
¶µÆÓ
m/z35309[M-H]-,
gºÓ¦¡Ez
ó
,
K¼B⦼v¶
,m/z19105
Ó9¯«
¬8ÿ¼
,m/z17903[M-H-174]-
Ó9
¯«¬8¼
m/z16102[M-H-191]-
Ó9
¯:-«¬8¼
,
áª^»
[44]
gº_ª¨
3
Óð^
,
_ª¨
1~2
Ó¦¡Ezó
,
$ð^
Ó¼}¤=VW&$mÝ
。
_ª¨
4
졶v¶µÓ
m/z44715[M-
H]-,m/z30103[M-H-146]-,
«
JÖÝ
179,161
¼v¶
,
ò^»
[45]
2Ä_ª¨
4
Ó
4methoxyphenyl4OβLglucopyranosylβDgalacto
pyranoside,
Ú_ª¨Ó¼}¤=VW&$mÝ
。
·7661·
2016
y
5
z À
41
ÁÀ
9
}
Vol41,No.9 May,2016
4
s
õ¼}ê
UPLCQTOFMS
()ÏTK
UÌVW$_«¡n¡¢
,
Ê]`â
57
±«
¡
,
$B
42
C7§«¡
,5
C7§
«¡
,6
C(㧫¡
,4
C¤§m_ª¨
,
$B
43
C_ª¨Ó=VW&$¼}mÝ
,
q9:gºâ
1
CD7§_ª¨
。
7§«¡û[§¼B/A6_
ª¨
,
¼B,Î
、
,ÿ
、
,qï
、
,¢£
、
,-_
、
c£
»Áɯ
[4650],
sÂ,-_·!.ÓV¹
。
õ
¡TKUÌVW$áB7§«
¡
,
Ï_,}#z8ãô,ÏT
KUÌVW°¨²>rmʯ¼Bnpd
。
[
uv=w
]
[1]
$%,ÜDE
$%$,²>._
[M]
23
:
&Öm
÷
,1994:1177.
[2] LiuY,WagnerH,BauerRNevadensinglycosidesfromLysionotus
pauciflorus[J]Phytochemistry,1996,42(4):1203
[3] LiuY,WagnerH,BauerRPhenylpropanoidsandflavonoid
glycosidesfromLysionotuspauciflorus[J]Phytochemistry,1998,
48(2):339
[4] LiuP,DengRX,DuanHQ,etalPhenylethanoidglycosides
fromtherootsofPhlomisumbrosa[J]JAsianNatProdRes,
2009,11(1):69
[5] Juliao,LisieuxdeS,Piccineli,etalPhenylethanoidglycosides
fromLantanafucatawithinvitroantiinflammatoryactivity[J]J
NatProd,2009,72(8):1424
[6] LiuY,SeligmannO,WagnerH,etalPaucifloside,anewpheny
lpropanoidglycosidefromLysionotuspauciflorus[J]NatProd
Let,1995,7(1):23
[7] Zubair,Muhammad,NybomH,etalDetectionofgeneticand
phytochemicaldiferencesbetweenandwithinpopulationsof
PlantagomajorL(plantain)[J]SciHorticAmsterdam,2012,
136:9
[8] Porter,ElaineAK,GeofreyCV,etalPhenylethanoidglyco
sidesintepalsofMagnoliasalicifoliaandtheiroccurencein
flowersofMagnoliaceae[J]Phytochemistry,2015,117:185
[9] LiCT,LiuYQ,Abdula,etalDeterminationofphenylethanoid
glycosidesinLagotisbrevitubaMaximbyhighperformanceliq
uidchromatographyelectrosprayionizationtandem massspec
trometry[J]AnalLet,2014,47(11):1862
[10] WanJF,YuanJQ,MeiZN,etalPhenolicglycosidesfromBos
chniakiahimalaica[J]ChinChemLet,2012,23(5):579
[11] JaiswalR,KuhnertNIdentificationandcharacterizationofthe
phenolicglycosidesofLagenariasicerariaStand(BotleGourd)
fruitbyliquidchromatographytandemmassspectrometry[J]J
AgrFoodChem,2014,62(6):1261
[12] ZhaoJ,GuoJ,ZhangY,etalChemicalconstituentsfromthe
rootsandstemsofStauntoniabrachyantheraHandMazzandtheir
bioactivities[J]JFuncFoods,2015,14:374
[13] YangJH,KondratyukTP,JermihovKC,etalBioactivecom
poundsfromthefernLepisoruscontortus[J]JNatProd,2011,74
(2):129
[14] MathuramV,PatraA,KunduABAphenylpropanoidglycoside
fromNyctanthesarbortristis[J]JIndChemSoci,1997,74(8):
653
[15] Phakeovilay,ChiobouaphongD,WannapornS,etalPhenyle
thanoidandflavoneglycosidesfromRueliatuberosaL[J]J
NatMed,2013,67(1):228
[16] XiaYG,YangBY,LiangJK,etalCafeoylphenylethanoidgly
cosidesfromunripefruitsofForsythiasuspensa[J]ChemNat
Comp,2015,51(4):656
[17] CaiH,XieZY,LiuGH,etalIsolation,identificationandac
tivitiesofnaturalantioxidantsfrom Calicarpakwangtungensis
Chun[J]PLoSONE,2014,9(3):e930001
[18] ZubairM,NybomHA,MariaR,etalDetectionofgeneticand
phytochemicaldiferencesbetweenandwithinpopulationsof
PlantagomajorL(plantain)[J]SciHorti(Amsterdam),
2012,136:9
[19] ZhouZL,ZhangHLPhenolicandiridoidglycosidesfromthe
rhizomesofCyperusrotundusL[J]MedChemRes,2013,22
(10):4830
[20] Jensen,SorenRA,DirkCO,etalVeronica:iridoidsandcorno
sideaschemosystematicmarkers[J]BiochemSystEcol,2005,
33(10):1031
[21] BarosJ,MarconiRM,RenataRS,etalAntiinflammatoryand
antioxidantactivitiesofLantanaradulaSwartzanditsphenyle
thanoidglycosides[J]JMedPlantsRes,2014,8(47):1354
[22] StanoevaJP,StefovaM,StefkovGK,etalChemotaxonomiccon
tributiontotheSideritisspeciesdilemmaontheBalkans[J].Bio
chemSystEcol,2015,61:477
[23] NazemiyehH,ShoebM,MovahhedinN,etalPhenoliccom
poundsandtheirglycosidesfromStachysschtschegleevi(Lami
aceae)[J]BiochemicalSystEcol,2006,34(9):721
[24] ZhangJY,LiC,CheYY,etalLTQOrbitrapbasedstrategyfor
traditionalChinesemedicinetargetedclassdiscovery,identifica
tionandherbomicsresearch:acasestudyonphenylethanoidgly
cosidesinthreediferentspeciesofHerbaCistanches[J]RSC
Advances,2015,5(98):80816
[25] SinaphetB,NoiarsaP,RujirawatS,etalDolichandroside,anew
phenolictriglycosidefromDolichandroneserulata(DC)Seem
[J]JNatMed,2006,60(3):251
[26] TaskovaRM,KokubunT,RyanKG,etalPhenylethanoidand
iridoidglycosidesintheNewZealandsnowhebes(Veronica,
Plantaginaceae)[J]ChemPharmBul,2010,58(5):703
[27] SuoMR,OhtaT,TakanoF,etalBioactivephenylpropanoidgly
cosidesfromTabebuiaavelanedae[J]Molecules,2013,18:
·8661·
1É
:
ê
UPLCQTOFMS
()TKUÌVW$_«¡¡¢
7336
[28]
:µ
,
;B
,
ºA
\,ùKUßL$
1
CD7§
_ª¨
[J]
$%$,-.
,2009,34(16):2054
[29] HuangQ,QiaoXB,XuXJPotentialsynergismandinhibitorsto
multipletargetenzymesofXuefuZhuyuDecoctionincardiacdis
easetherapeutics:acomputationalapproach[J]BioorgMed
ChemLet,2007,17(6):1779
[30] Jabeen,B,Riaz,N,Saleem,M,etalIsolationofnaturalcom
poundsfromPhlomisstewartishowingαglucosidaseinhibitory
activity[J]Phytochemistry,2013,96:443
[31] SahpazS,HennebeleT,BaileulFMaruboside,anewpheny
lethanoidglycosidefromMarubiumvulgareL[J]NatProd
Let,2002,16(3):195
[32] TaskovaRM,KokubunT,RyanKG,etalPhenylethanoidand
iridoidglycosidesintheNewZealandsnowhebes(Veronica,
Plantaginaceae)[J]ChemPharmBul,2010,58(5):703
[33] KirmizibekmezH,PiacenteS,PizzaC,etalIridoidandphenyle
thanoidglycosidesfromPhlomisnisoliandPcapitata[J].
ChemSci,2004,59(5):609
[34] MorikawaT,PanY,NinomiyaK,etalAcylatedphenylethanoid
oligoglycosideswithhepatoprotectiveactivityfromthedesertplant
Cistanchetubulosa[J]BioorMedChem,2010,18(5):1882
[35] SaracogluI,HarputUS,InoueM,etalNewphenylethanoidgly
cosidesfromVeronicapectinatavarglandulosaandtheirfree
radicalscavengingactivities[J]ChemPharmBul,2002,50
(5):665
[36] ZhouFY,SheJ,WangYGSynthesisofabenzylprotectedana
logofarenarioside,atrisaccharidephenylpropanoidglycoside
[J].CarbohydrRes,2006,341(15):2469
[37] LeiL,JiangY,LiuXM,etalNewglycosidesfromCistanche
salsa[J]HelvChimActa,2007,90(1):79
[38] XuFMM,HisashiH,HirokiS,etalStructuresofnewflavonoids
andbenzofurantypestilbeneanddegranulationinhibitorsofrat
basophilicleukemiacelsfromtheBrazilianherbalmedicineCis
sussicyoides[J]ChemPharmBul,2009,57(10):1089
[39] YadavaRN,SatnamiDKChemicalconstituentsfromCasia
occidentalisLinn[J]IndianJChemBOrgChemMedChem,
2011,50B(8):1112
[40] BagriAK,KurmazBV,LitvinenkoVINewbiosideofquerce
tin[J]KhimPrirSoedin,1966,2(2):85
[41]
!%z
,
z¡
,
@I
,
É
LöL(ã§_«¡
[J]
$L,
,2011,42(8):1490
[42] MaCY,HuLM,FuQY,etalSeparationoffourflavonoidsfrom
Rhodiolaroseabyonlinecombinationofsamplepreparationand
countercurentchromatography[J]JChromatograA,2013,
1306:12
[43] LiuMM,ZhouL,HePL,etalDiscoveryofflavonoidderivatives
asantiHCVagentsviapharmacophoresearchcombiningmolecu
lardockingstrategy[J]EuroJMedChem,2012,52:33
[44] AdhikariB,DevkotaHP,JoshiKR,etalTwonewdiacetylene
glycosides:bhutkesosideAandBfromtherootsofLigusticopsis
walichiana[J]. NatProd Res, 2015, doi:101080/
1478641920151118635
[45] TanikawaT,FridmanM,ZhuWJ,etalUsingbiologicalperform
ancesimilaritytoinformdisaccharidelibrarydesign[J]JAm
ChemSoc,2009,131(14):5075
[46] HuXP,ShaoMM,SongX,etalAntiinfluenzavirusefectsof
crudephenylethanoidglycosidesisolatedfromLigustrumpurpuras
censviainducingendogenousinterferonγ[J]JEthnopharmacol,
2015,179:128
[47] MorikawaT,NinomiyaK,KuramotoH,etalPhenylethanoidand
phenylpropanoidglycosideswithmelanogenesisinhibitoryactivity
fromtheflowersofNarcisustazetavarchinensis[J]JNat
Med,2016,70(1):89
[48] GaoY,ZongCJ,LiuF,etalEvaluationoftheintestinaltrans
portofaphenylethanoidglycosiderichextractfromCistanchede
serticolaacrosstheCaco2celmonolayermodel[J]PLoSONE,
2015,10(2):e01164901
[49] WangYJ,ZhouSM,XuG,etalInterferenceofphenylethanoid
glycosidesfromCistanchetubulosawiththeMTTassay[J].Mol
ecules,2015,20(5):8060
[50] EncaladaMA,RehechoS,AnsorenaDi,etalAntiproliferative
efectofphenylethanoidglycosidesfromVerbenaoficinalisLon
coloncancercellines[J]LWTFoodSciTechnol,2015,63
(2):1016
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