Chem. J. Chinese Universities ›› 2014, Vol. 35 ›› Issue (7): 1396.doi: 10.7503/cjcu20140168
• Analytical Chemistry • Previous Articles Next Articles
DAI Yulin1, YU Shanshan1, ZHANG Ying1, HAO Ying1, ZHONG Wei1, YUE Hao1, LIU Shuying1,2,*()
Received:
2014-03-04
Online:
2014-07-10
Published:
2014-05-26
Contact:
LIU Shuying
E-mail:syliu@ciac.jl.cn
Supported by:
CLC Number:
TrendMD:
DAI Yulin, YU Shanshan, ZHANG Ying, HAO Ying, ZHONG Wei, YUE Hao, LIU Shuying. Studies on the Isoflavone in Extract of the Flower of Pueraria Lobata by RRLC-Q-TOF MS/MS†[J]. Chem. J. Chinese Universities, 2014, 35(7): 1396.
Compd. | Structure | R1 | R2 | R3 | R4 | MF | Mw |
---|---|---|---|---|---|---|---|
Irisolidone | OH | OMe | OH | OMe | C17H14O6 | 314.0790 | |
Genistin | Oglc | H | OH | OH | C21H20O10 | 432.1057 | |
Tectoridin | Oglc | OMe | OH | OH | C22H22O11 | 462.1162 | |
Daidzein | OH | H | H | OH | C15H10O4 | 254.0579 | |
Tectorigenin | OH | OMe | OH | OH | C16H12O6 | 300.0634 | |
Genistein | OH | H | OH | OH | C15H10O5 | 270.0528 | |
Biocanin A | OH | H | OH | OMe | C16H12O5 | 284.0685 | |
Kakkatin | OMe | OH | H | OH | C16H12O5 | 284.0685 | |
Glycitein | OH | OMe | H | OH | C16H12O5 | 284.0685 | |
Daidzin | Oglc | H | H | OH | C21H20O9 | 416.1107 | |
Kakkalide | Oglc-6xyl | OMe | OH | OMe | C28H32O15 | 608.1741 | |
6-O-Xylosyl-tectoridin | Oglc-6xyl | OMe | H | OH | C27H30O15 | 594.1585 |
Table 1 Possible isoflavone compounds in Pueraria lobata(Willd.) Ohwi. flower
Compd. | Structure | R1 | R2 | R3 | R4 | MF | Mw |
---|---|---|---|---|---|---|---|
Irisolidone | OH | OMe | OH | OMe | C17H14O6 | 314.0790 | |
Genistin | Oglc | H | OH | OH | C21H20O10 | 432.1057 | |
Tectoridin | Oglc | OMe | OH | OH | C22H22O11 | 462.1162 | |
Daidzein | OH | H | H | OH | C15H10O4 | 254.0579 | |
Tectorigenin | OH | OMe | OH | OH | C16H12O6 | 300.0634 | |
Genistein | OH | H | OH | OH | C15H10O5 | 270.0528 | |
Biocanin A | OH | H | OH | OMe | C16H12O5 | 284.0685 | |
Kakkatin | OMe | OH | H | OH | C16H12O5 | 284.0685 | |
Glycitein | OH | OMe | H | OH | C16H12O5 | 284.0685 | |
Daidzin | Oglc | H | H | OH | C21H20O9 | 416.1107 | |
Kakkalide | Oglc-6xyl | OMe | OH | OMe | C28H32O15 | 608.1741 | |
6-O-Xylosyl-tectoridin | Oglc-6xyl | OMe | H | OH | C27H30O15 | 594.1585 |
Compd. | Structure | R1 | R2 | MF | Mw |
---|---|---|---|---|---|
Quercetin | OH | OH | C15H10O7 | 302.0427 | |
Rutin | Oglc-6glc | OH | C27H30O16 | 610.1534 | |
Nicotiflorin | Oglc-6glc | H | C27H30O15 | 594.1580 |
Table 2 Possible flavonoid compounds in Pueraria lobata(Willd.) Ohwi. flower
Compd. | Structure | R1 | R2 | MF | Mw |
---|---|---|---|---|---|
Quercetin | OH | OH | C15H10O7 | 302.0427 | |
Rutin | Oglc-6glc | OH | C27H30O16 | 610.1534 | |
Nicotiflorin | Oglc-6glc | H | C27H30O15 | 594.1580 |
Fig.1 RRLC profiles of the three reference compounds(A) and the water extracts of Pueraria lobata(Willd.) Ohwi. flower(B) on the molecular ions in negative ion mode (A) 1. Genistin; 2. tectoridin; 3. kakkalide.
tR/min | [M-H]-, m/z | MS/MS, m/z | Compd. | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Mean measured mass | Theoretical exact mass | 106 Mass accuracy | |||||||||
2.245 | 417.1770 | 417.1707 | 15.1 | 152[M-H-C11H20]-, 108[M-H-C13H25]- | Puerarol | ||||||
3.373 | 461.1240 | 461.1242 | 0.4 | 301[M-H-C10H8O2]- | Alopecuroides A | ||||||
3.919 | 623.1607 | 623.1618 | -1.7 | 283[M-H-C12H20O11]- , | 6″-O-Xylosyl-glycitin | ||||||
[M+HCOOH-H]- | [M+HCOOH-H]- | 268[M-H-C12H20O11-CH3]- | |||||||||
4.598 | 491.1180 | 491.1195 | -3.0 | 445[M-H-HCOOH]-, | Sissotrin, glycitin, | ||||||
[M+HCOOH-H]- | [M+HCOOH-H]- | 283[M-H-HCOOH-C6H10O5]- | 3'-oxymethy-puerarin | ||||||||
4.911 | 431.0953 | 431.0984 | 7.1 | 311[M-H-C4H804]- , | Genistin | ||||||
283[M-H-C4H804-CO]- | |||||||||||
5.224 | 593.1508 | 593.1512 | -0.6 | 299[M-H-C17H18O9]- , 284[M-H-C17H18O9-CH3]- | 6″-O-Xylosyl-tectoridin | ||||||
5.658 | 609.1353 | 609.1461 | 17.7 | 285[M-H-C12H20010]-, | Rutin | ||||||
269[M-H-C12H20010-H2O]- | |||||||||||
6.014 | 283.0610 | 283.0612 | -0.7 | 268[M-H-CH3]-, 240[M-H-CH3-CO]-, | BiocaninA, | ||||||
196[M-H-CH3-CO-OH-COH]- | Kakkatin, Glycitein | ||||||||||
6.603 | 461.1106 | 461.1089 | -3.6 | 299[M-H-C6H10O5]-, | Tectoridin | ||||||
284[M-H-C6H10O5-CH3]-, 255[M-H- C6H10O5 -CH3-CO]- | |||||||||||
7.025 | 269.0466 | 269.0455 | -4 | 240[M-H-CO2H]- | Genistein | ||||||
7.461 | 491.1180 [M+HCOOH-H]- | 491.1195 [M+HCOOH-H]- | -3 | 283[M-H-C6H10O5]- | Sissotrin, glycitin, 3'-oxymethy-puerarin | ||||||
8.425 | 298.0844 | 298.0841 | 1.0 | 282[M-H-CH3]- , 267[M-H-CH3-CH3]-, | 3'-Oxymethy-daidzein-7-O-methylether | ||||||
254[M-H-CH3-CH3-H2O]-, | |||||||||||
239[M-H-CH3-CH3-CO]-, | |||||||||||
211[M-H-CH3-CH3-CO-H2O]-, 195[M-H-CH3-CH3-CO-H2O-OH]- | |||||||||||
8.937 | 607.1639 | 607.1668 | -4.7 | 313[M-H-C11H18O9]-, 298[M-H-C11H18O9-CH3] - | Kakkalide | ||||||
9.336 | 253.0522 | 253.0506 | -6.3 | 224[M-H-COH]-, 209[M-H-CO2]-, 135[M-H-C7H2O2]- | Daidzein | ||||||
9.783 | 313.0725 | 313.0718 | -2.2 | 298[M-H-CH3]- , 283[M-H-C2H6]-, | Irisolidone | ||||||
270[M-H-CH3-CO]-, | |||||||||||
255[M-H-CH3-CO-H2O]-, | |||||||||||
239[M-H-CH3-CO2-H2O]-, | |||||||||||
211[M-H-CH3-CO2-H2O-CH3O]- | |||||||||||
10.598 | 475.1246 | 475.1246 | 0 | 313[M-H-C6H10O5]-, | 7-O-Glc-Irisolidone | ||||||
298[M-H-C6H10O5-CH3]- | |||||||||||
11.072 | 299.0557 | 299.0561 | 1.3 | 284[M-H-CH3]-, 255[M-H-CH3-CO]- | Tectorigenin | ||||||
11.354 | 329.2734 | 329.2697 | -11.2 | 211[M-H-C4H6O4]- | 2,3-Dihydroxypropyl- palmitate | ||||||
12.004 | 301.0350 | 301.0354 | 1.3 | 283[M-H-H2O]-, 257[M-H-C2O]- | Quercetin |
Table 3 RRLC-ESI-MS/MS data of the water extract of Pueraria lobata(Willd.) Ohwi. flower in negative ion mode
tR/min | [M-H]-, m/z | MS/MS, m/z | Compd. | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Mean measured mass | Theoretical exact mass | 106 Mass accuracy | |||||||||
2.245 | 417.1770 | 417.1707 | 15.1 | 152[M-H-C11H20]-, 108[M-H-C13H25]- | Puerarol | ||||||
3.373 | 461.1240 | 461.1242 | 0.4 | 301[M-H-C10H8O2]- | Alopecuroides A | ||||||
3.919 | 623.1607 | 623.1618 | -1.7 | 283[M-H-C12H20O11]- , | 6″-O-Xylosyl-glycitin | ||||||
[M+HCOOH-H]- | [M+HCOOH-H]- | 268[M-H-C12H20O11-CH3]- | |||||||||
4.598 | 491.1180 | 491.1195 | -3.0 | 445[M-H-HCOOH]-, | Sissotrin, glycitin, | ||||||
[M+HCOOH-H]- | [M+HCOOH-H]- | 283[M-H-HCOOH-C6H10O5]- | 3'-oxymethy-puerarin | ||||||||
4.911 | 431.0953 | 431.0984 | 7.1 | 311[M-H-C4H804]- , | Genistin | ||||||
283[M-H-C4H804-CO]- | |||||||||||
5.224 | 593.1508 | 593.1512 | -0.6 | 299[M-H-C17H18O9]- , 284[M-H-C17H18O9-CH3]- | 6″-O-Xylosyl-tectoridin | ||||||
5.658 | 609.1353 | 609.1461 | 17.7 | 285[M-H-C12H20010]-, | Rutin | ||||||
269[M-H-C12H20010-H2O]- | |||||||||||
6.014 | 283.0610 | 283.0612 | -0.7 | 268[M-H-CH3]-, 240[M-H-CH3-CO]-, | BiocaninA, | ||||||
196[M-H-CH3-CO-OH-COH]- | Kakkatin, Glycitein | ||||||||||
6.603 | 461.1106 | 461.1089 | -3.6 | 299[M-H-C6H10O5]-, | Tectoridin | ||||||
284[M-H-C6H10O5-CH3]-, 255[M-H- C6H10O5 -CH3-CO]- | |||||||||||
7.025 | 269.0466 | 269.0455 | -4 | 240[M-H-CO2H]- | Genistein | ||||||
7.461 | 491.1180 [M+HCOOH-H]- | 491.1195 [M+HCOOH-H]- | -3 | 283[M-H-C6H10O5]- | Sissotrin, glycitin, 3'-oxymethy-puerarin | ||||||
8.425 | 298.0844 | 298.0841 | 1.0 | 282[M-H-CH3]- , 267[M-H-CH3-CH3]-, | 3'-Oxymethy-daidzein-7-O-methylether | ||||||
254[M-H-CH3-CH3-H2O]-, | |||||||||||
239[M-H-CH3-CH3-CO]-, | |||||||||||
211[M-H-CH3-CH3-CO-H2O]-, 195[M-H-CH3-CH3-CO-H2O-OH]- | |||||||||||
8.937 | 607.1639 | 607.1668 | -4.7 | 313[M-H-C11H18O9]-, 298[M-H-C11H18O9-CH3] - | Kakkalide | ||||||
9.336 | 253.0522 | 253.0506 | -6.3 | 224[M-H-COH]-, 209[M-H-CO2]-, 135[M-H-C7H2O2]- | Daidzein | ||||||
9.783 | 313.0725 | 313.0718 | -2.2 | 298[M-H-CH3]- , 283[M-H-C2H6]-, | Irisolidone | ||||||
270[M-H-CH3-CO]-, | |||||||||||
255[M-H-CH3-CO-H2O]-, | |||||||||||
239[M-H-CH3-CO2-H2O]-, | |||||||||||
211[M-H-CH3-CO2-H2O-CH3O]- | |||||||||||
10.598 | 475.1246 | 475.1246 | 0 | 313[M-H-C6H10O5]-, | 7-O-Glc-Irisolidone | ||||||
298[M-H-C6H10O5-CH3]- | |||||||||||
11.072 | 299.0557 | 299.0561 | 1.3 | 284[M-H-CH3]-, 255[M-H-CH3-CO]- | Tectorigenin | ||||||
11.354 | 329.2734 | 329.2697 | -11.2 | 211[M-H-C4H6O4]- | 2,3-Dihydroxypropyl- palmitate | ||||||
12.004 | 301.0350 | 301.0354 | 1.3 | 283[M-H-H2O]-, 257[M-H-C2O]- | Quercetin |
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