Studies on the Isoflavone in Extract of the Flower of Pueraria Lobata by RRLC-Q-TOF MS/MS†

doi:10.7503/cjcu20140168

Abstract

Abstract:

Rapid resolution liquid chromatography-electrospray ionization mass spectrometry(RRLC-ESI-MSⁿ) was applied to identify and differentiate the isoflavone constituents of the flower of Pueraria lobata(Willd.)Ohwi. The data of retention time and molar masses were obtained for the identification of the major isoflavone constituents in the flower of Pueraria lobata(Willd.) Ohwi. The ESI-MSⁿ data of the [M-H]^- provide detailed structural information on the isoflavone. Alopecuroides A has been firstly detected from the Pueraria lobata(Willd.) Ohwi. flower. 28 components were detected in total from the flower of Pueraria lobata(Willd.) Ohwi..

Key words: Pueraria lobata(Willd.) Ohwi., Isoflavone, Rapid resolution liquid chromatography-electrospray ionization mass spectrometry(RRLC-ESI-MSn)

CLC Number:

O657

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.

Figures/Tables 6

References 23

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Compd.	R₁	R₂	R₃	R₄	MF	M_w
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.	R₁	R₂	R₃	R₄	MF	M_w
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.	R₁	R₂	MF	M_w
Quercetin	OH	OH	C₁₅H₁₀O₇	302.0427
Rutin	Oglc-6glc	OH	C₂₇H₃₀O₁₆	610.1534
Nicotiflorin	Oglc-6glc	H	C₂₇H₃₀O₁₅	594.1580

Compd.	R₁	R₂	MF	M_w
Quercetin	OH	OH	C₁₅H₁₀O₇	302.0427
Rutin	Oglc-6glc	OH	C₂₇H₃₀O₁₆	610.1534
Nicotiflorin	Oglc-6glc	H	C₂₇H₃₀O₁₅	594.1580

t_R/min	[M-H]^-, m/z					MS/MS, m/z		Compd.
t_R/min	Mean measured mass			Theoretical exact mass				10⁶ Mass accuracy
2.245	417.1770	417.1707		15.1		MS/MS, m/z	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