Table 1 Characterization of eighty-three flavonoid derivatives from young leaves of 21 soybean cultivars using UPLC-DAD-QToF/MS.

From: Comprehensive characterization of flavonoid derivatives in young leaves of core-collected soybean (Glycine max L.) cultivars based on high-resolution mass spectrometry

Peak No

Individual flavonoids

Abbreviation

RT

(min)

Molecular Formula

ESI(+)-QToF/MS (experimental ions, m/z)

[M + H]+

error (ppm)

Fragmentation

1a

quercetin 3-O-(2″,6″-di-O-glucosyl)galactoside

Q 3-O-(2″,6″-di-O-glu)gal

9.03

C33H40O22

789.2092

1.0

827[M + K]+, 811[M + Na]+, 789[M + H]+, 627[M + H-glu]+, 465[M + H-2glu]+,303[M + H-2glu-gal]+

2a

quercetin 3-O-(2″,6″-di-O-glucosyl)glucoside

Q 3-O-(2″,6″-di-O-glu)glu

9.06

C33H40O22

789.2099

1.9

827[M + K]+, 811[M + Na]+, 789[M + H]+, 627[M + H-glu]+, 465[M + H-2glu]+,303[M + H-3glu]+

3a

quercetin 3-O-(2″-O-rhamnosyl-6″-O-glucosyl)galactoside

Q 3-(2″-O-rham-6″-O-glu)gal

10.02

C33H40O21

773.2138

0.4

811[M + K]+, 795[M + Na]+, 773[M + H]+, 627[M + H-rham]+, 611[M + H-glu]+, 465[M + H-rham-glu]+, 303[M + H-rham-glu-gal]+

4a

kaempferol 3-O-(2″,6″-di-O-glucosyl)glucoside

K 3-O-(2″,6″-di-O-glu)glu

10.38

C33H40O21

773.2139

0.5

811[M + K]+, 795[M + Na]+, 773[M + H]+, 611[M + H-glu]+, 449[M + H-2glu]+,287[M + H-3glu]+

5a

quercetin 3-O-(2″-O-rhamnosyl-6″-O-glucosyl)glucoside

Q 3-O-(2″-O-rham-6″-O-glu)glu

10.41

C33H40O21

773.2139

0.5

811[M + K]+, 795[M + Na]+, 773[M + H]+, 627[M + H-rham]+, 611[M + H-glu]+, 465[M + H-rham-glu]+, 303[M + H-rham-2glu]+

6

quercetin 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)galactoside

Q 3-O-(2″-O-glu-6″-O-rham)gal

10.43

C33H40O21

773.2138

0.4

811[M + K]+, 795[M + Na]+, 773[M + H]+, 627[M + H-rham]+, 611[M + H-glu]+, 465[M + H-rham-glu]+, 303[M + H-rham-glu-gal]+

7

quercetin 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)glucoside

Q 3-O-(2″-O-glu-6″-O-rham)glu

10.65

C33H40O21

773.2136

0.2

811[M + K]+, 795[M + Na]+, 773[M + H]+, 627[M + H-rham]+, 611[M + H-glu]+, 465[M + H-rham-glu]+, 303[M + H-rham-2glu]+

8

quercetin 3-O-(2″-O-glucosyl)galactoside

Q 3-O-(2″-O-glu)gal

11.16

C27H30O17

627.1548

−1.2

665[M + K]+, 649[M + Na]+, 627[M + H]+, 465[M + H-glu]+, 303[M + H-glu-gal]+

9c

daidzein 7-O-glucoside (daidzin)

D 7-O-glu

11.25

C21H20O9

417.1181

0.2

455[M + K]+, 439[M + Na]+,417[M + H]+, 255[M + H-glu]+

10

kaempferol 3-O-(2″-O-rhamnosyl-6″-O-glucosyl)galactoside

K 3-O-(2″-O-rham-6″-O-glu)gal

11.35

C33H40O20

757.2194

0.7

795[M + K]+, 779[M + Na]+, 757[M + H]+, 611[M + H-rham]+, 595[M + H-glu]+, 449[M + H-rham-glu]+, 287[M + H-rham-glu-gal]+

11c

quercetin 3-O-(2″-O-glucosyl)glucoside (quercetin 3-O-sophoroside)

Q 3-O-(2″-O-glu)glu

11.39

C27H30O17

627.1545

−1.7

665[M + K]+, 649[M + Na]+, 627[M + H]+, 465[M + H-glu]+, 303[M + H-2glu]+

12a

isorhamnetin 3-O-(2″-O-rhamnosyl-6″-O-glucosyl)galactoside

I 3-O-(2″-O-rham-6″-O-glu)gal

11.54

C34H42O21

787.2293

0.2

825[M + K]+, 809[M + Na]+, 787[M + H]+, 641[M + H-rham]+, 625[M + H-glu]+, 479[M + H-rham-glu]+, 317[M + H-rham-glu-gal]+, 302[M + H-rham-glu-gal-CH3]+

13a

quercetin 3-O-(2″,6″-di-O-rhamnosyl)galactoside

Q 3-O-(2″,6″-di-O-rham)gal

11.55

C33H40O20

757.2190

0.6

795[M + K]+, 779[M + Na]+, 757[M + H]+, 611[M + H-rham]+, 465[M + H-2rham]+, 303[M + H-2rham-gal]+

14

quercetin 3-O-(4″,6″-di-O-rhamnosyl)galactoside

Q 3-O-(4″,6″-di-O-rham)gal

11.71

C33H40O20

757.2189

0.4

795[M + K]+, 779[M + Na]+, 757[M + H]+, 611[M + H-rham]+, 465[M + H-2rham]+, 303[M + H-2rham-gal]+

15a

isorhamnetin 3-O-(2″-O-rhamnosyl-6″-O-glucosyl)glucoside

I 3-O-(2″-O-rham-6″-O-glu)glu

11.79

C34H42O21

787.2289

−0.3

825[M + K]+, 809[M + Na]+, 787[M + H]+, 641[M + H-rham]+, 625[M + H-glu]+, 479[M + H-rham-glu]+, 317[M + H-rham-2glu]+, 302[M + H-rham-2glu-CH3]+

16

kaempferol 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)galactoside

K 3-O-(2″-O-glu-6″-O-rham)gal

11.83

C33H40O20

757.2159

−3.5

795[M + K]+, 779[M + Na]+, 757[M + H]+, 611[M + H-rham]+, 595[M + H-glu]+, 449[M + H-rham-glu]+, 287[M + H-rham-glu-gal]+

17a

kaempferol 3-O-(2″-O-rhamnosyl-6″-O-glucosyl)glucoside

K 3-O-(2″-O-rham-6″-O-glu)glu

11.84

C33H40O20

757.2189

0.4

795[M + K]+, 779[M + Na]+, 757[M + H]+, 611[M + H-rham]+, 595[M + H-glu]+, 449[M + H-rham-glu]+, 287[M + H-rham-2glu]+

18a

quercetin 3-O-(6″-O-glucosyl)galactoside

Q 3-O-(6″-O-glu)gal

11.99

C27H30O17

627.1559

0.5

665[M + K]+, 649[M + Na]+, 627[M + H]+, 465[M + H-glu]+, 303[M + H-glu-gal]+

19c

glycitein 7-O-glucoside (glycitin)

Gy 7-O-glu

12.07

C22H22O10

447.1286

0.1

485[M + K]+, 469[M + Na]+,447[M + H]+, 285[M + H-glu]+, 270[M + H-glu-CH3]+

20a,c

quercetin 3-O-(6″-O-glucosyl)glucoside (quercetin 3-O-gentiobioside)

Q 3-O-(6″-O-glu)glu

12.15

C27H30O17

627.1550

−0.9

665[M + K]+, 649[M + Na]+, 627[M + H]+, 465[M + H-glu]+, 303[M + H-2glu]+

21

kaempferol 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)glucoside

K 3-O-(2″-O-glu-6″-O-rham)glu

12.16

C33H40O20

757.2160

−3.4

795[M + K]+, 779[M + Na]+, 757[M + H]+, 611[M + H-rham]+, 595[M + H-glu]+, 449[M + H-rham-glu]+,

287[M + H-rham-2glu]+

22a,b

isorhamnetin 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)galactoside (soyanin I)

I 3-O-(2″-O-glu-6″-rham)gal

12.36

C34H42O21

787.2283

−1.1

825[M + K]+, 809[M + Na]+, 787[M + H]+, 641[M + H-rham]+, 625[M + H-glu]+, 479[M + H-rham-glu]+,

317[M + H-rham-glu-gal]+

23a,b

isorhamnetin 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)glucoside (soyanin II)

I 3-O-(2″-O-glu-6″-O-rham)glu

12.36

C34H42O21

787.2281

−1.3

825[M + K]+, 809[M + Na]+, 787[M + H]+, 641[M + H-rham]+, 625[M + H-glu]+, 479[M + H-rham-glu]+,

317[M + H-rham-2glu]+

24

quercetin 3-O-(2″-O-rhamnosyl)galactoside

Q 3-O-(2″-O-rham)gal

12.40

C27H30O16

611.1613

1.0

649[M + K]+, 633[M + Na]+, 611[M + H]+, 465[M + H-rham]+, 303[M + H-rham-gal]+

25a

quercetin 3-O-(2″-O-rhamnosyl)glucoside (quercetin 3-O-neohesperidoside)

Q 3-O-(2″-O-rham)glu

12.68

C27H30O16

611.1612

0.9

649[M + K]+, 633[M + Na]+, 611[M + H]+, 465[M + H-rham]+, 303[M + H-rham-glu]+

26

kaempferol 3-O-(2″-O-glucosyl)galactoside

K 3-O-(2″-O-glu)gal

12.75

C27H30O16

611.1602

−0.8

649[M + K]+, 633[M + Na]+, 611[M + H]+, 449[M + H-glu]+, 287[M + H-glu-gal]+

27

kaempferol 3-O-(2″,6″-di-O-rhamnosyl)galactoside

K 3-O-(2″,6″-di-O-rham)gal

12.80

C33H40O19

741.2240

0.5

779[M + K]+, 763[M + Na]+, 741[M + H]+, 595[M + H-rham]+, 449[M + H-2rham]+, 287[M + H-2rham-gal]+

28

kaempferol 3-O-(2″-O-glucosyl)glucoside (kaempferol 3-O-sophoroside)

K 3-O-(2″-O-glu)glu

12.99

C27H30O16

611.1602

−0.8

649[M + K]+, 633[M + Na]+, 611[M + H]+, 449[M + H-glu]+, 287[M + H-2glu]+

29

kaempferol 3-O-(4″,6″-di-O-rhamnosyl)galactoside

K 3-O-(4″,6″-di-O-rham)gal

13.11

C33H40O19

741.2259

0.3

779[M + K]+, 763[M + Na]+, 741[M + H]+, 595[M + H-rham]+, 449[M + H-2rham]+, 287[M + H-2rham-gal]+

30a

kaempferol 3-O-(6″-O-glucosyl)galactoside

K 3-O-(6″-O-glu)gal

13.27

C27H30O16

611.1610

0.6

649[M + K]+, 633[M + Na]+, 611[M + H]+, 449[M + H-glu]+, 325[glu + gal + H]+, 287[M + H-glu-gal]+

31

isorhamnetin 3-O-(2″-O-glucosyl)galactoside

I 3-O-(2″-O-glu)gal

13.30

C28H32O17

641.1705

−1.1

679[M + K]+, 663[M + Na]+, 641[M + H]+, 479[M + H-glu]+, 317[M + H-glu-gal]+

32a

isorhamnetin 3-O-(2″-O-glucosyl)glucoside (isorhamnetin 3-O-sophoroside)

I 3-O-(2″-O-glu)glu

13.30

C28H32O17

641.1705

−0.7

679[M + K]+, 663[M + Na]+, 641[M + H]+, 479[M + H-glu]+, 317[M + H-2glu]+

33a,b

isorhamnetin 3-O-(2″,6″-di-O-rhamnosyl)galactoside (soyanin III)

I 3-O-(2″,6″-di-O-rham)gal

13.37

C34H42O20

771.2345

0.4

809[M + K]+, 793[M + Na]+, 771[M + H]+, 625[M + H-rham]+, 479[M + H-2rham]+, 317[M + H-2rham-gal]+

34a,b

isorhamnetin 3-O-(4″,6″-di-O-rhamnosyl)galactoside (soyanin IV)

I 3-O-(4″,6″-di-O-rham)gal

13.59

C34H42O20

771.2342

0.0

809[M + K]+, 793[M + Na]+, 771[M + H]+, 625[M + H-rham]+, 479[M + H-2rham]+, 317[M + H-2rham-gal]+

35

quercetin 3-O-(6″-O-rhamnosyl)galactoside (quercetin 3-O-robinobioside)

Q 3-O-(6″-O-rham)gal

13.59

C27H30O16

611.1611

0.7

649[M + K]+, 633[M + Na]+, 611[M + H]+, 465[M + H-rham]+, 303[M + H-rham-gal]+

36a

genistein 7-O-(6″-O-apiosyl)glucoside (6″-O-apiosylgenistin)

Gn 7-O-(6″-O-api)glu

13.69

C26H28O14

565.1555

0.6

603[M + K]+, 587[M + Na]+, 565[M + H]+, 433[M + H-api]+, 271[M + H-api-glu]+

37

kaempferol 3-O-(2″-O-rhamnosyl)galactoside

K 3-O-(2″-O-rham)gal

13.83

C27H30O15

595.1658

0.1

633[M + K]+, 617[M + Na]+, 595[M + H]+, 449[M + H-rham]+, 287[M + H-rham-gal]+

38c

quercetin 3-O-(6″-O-rhamnosyl)glucoside (quercetin 3-O-rutinoside, rutin)

Q 3-O-(6″-O-rham)glu

13.95

C27H30O16

611.1603

−0.6

649[M + K]+, 633[M + Na]+, 611[M + H]+, 465[M + H-rham]+, 303[M + H-rham-glu]+

39c

kaempferol 3-O-(6″-O-glucosyl)glucoside (kaempferol 3-O-gentiobioside)

K 3-O-(6″-O-glu)glu

14.01

C27H30O16

611.1607

0.1

649[M + K]+, 633[M + Na]+, 611[M + H]+, 449[M + H-glu]+, 325[2glul + H]+, 287[M + H-2glu]+

40c

quercetin 3-O-galactoside (hyperoside)

Q 3-O-gal

14.04

C21H20O12

465.1032

1.0

503[M + K]+, 487[M + Na]+, 465[M + H]+, 303[M + H-gal]+

41a

kaempferol 3-O-(2″-O-glucosyl-6″-O-rhamnosyl)galactoside dimethyl ester

K 3-O-(2″-O-glu-6″-O-rham)gal DME

14.06

C35H44O20

785.2136

−46.2

823[M + K]+, 807[M + Na]+, 785[M + H]+, 639[M + H-rham]+, 287[M + H-rham-glu-gal-2CH3]+

42a,b

isorhamnetin 3-O-(2″,6″-di-O-rhamnosyl)glucoside (soyanin V)

I 3-O-(2″,6″-di-O-rham)glu

14.14

C34H42O20

771.2350

1.0

809[M + K]+, 793[M + Na]+, 771[M + H]+, 625[M + H-rham]+, 479[M + H-2rham]+, 317[M + H-2rham-glu]+

43a

kaempferol 3-O-(2″-O-rhamnosyl)glucoside (kaempferol 3-O-neohesperidoside)

K 3-O-(2″-O-rham)glu

14.22

C27H30O15

595.1657

−0.1

633[M + K]+, 617[M + Na]+, 595[M + H]+, 449[M + H-rham]+, 287[M + H-rham-glu]+

44a

isorhamnetin 3-O-(6″-O-glucosyl)galactoside

I 3-O-(6″-O-glu)gal

14.27

C28H32O17

641.1712

0.0

679[M + K]+, 663[M + Na]+, 641[M + H]+, 479[M + H-glu]+, 317[M + H-glu-gal]+ 302[M + H-glu-gal-CH3]+

45a

genistein 7-O-(2″-O-apiosyl)glucoside (2″-O-apiosylgenistin)

Gn 7-O-(2″-O-api)glu

14.37

C26H28O14

565.1553

0.2

603[M + K]+, 587[M + Na]+, 565[M + H]+, 433[M + H-api]+, 271[M + H-api-glu]+

46c

quercetin 3-O-glucoside (isoquercitrin)

Q 3-O-glu

14.46

C21H20O12

465.1032

1.0

503[M + K]+, 487[M + Na]+, 465[M + H]+, 303[M + H-glu]+

47

isorhamnetin 3-O-(2″-O-rhamnosyl)galactoside

I 3-O-(2″-O-rham)gal

14.46

C28H32O16

625.1769

0.9

663[M + K]+, 647[M + Na]+, 625[M + H]+, 479[M + H-rham]+, 317[M + H-rham-gal]+

48c

luteolin 7-O-glucoside (cynaroside)

L 7-O-glu

14.48

C21H20O11

449.1080

0.4

449[M + H]+, 287[M + H-glu]+

49c

genistein 7-O-glucoside (genistin)

Gn 7-O-glu

14.63

C21H20O10

433.1128

−0.3

471[M + K]+, 455[M + Na]+, 433[M + H]+, 271[M + H-glu]+

50a

daidzein 4'-O-(6″-O-malonyl)glucoside

D 4'-O-(6″-O-mal)glu

14.66

C24H22O12

503.1183

−0.2

541[M + K]+, 525[M + Na]+, 503[M + H]+, 255[M + H-mal-glu]+

51a

isorhamnetin 3-O-(6″-O-glucosyl)glucoside (isorhamnetin 3-O-gentiobioside)

I 3-O-(6″-O-glu)glu

14.67

C28H32O17

641.1711

−0.2

679[M + K]+, 663[M + Na]+, 641[M + H]+, 479[M + H-glu]+, 317[M + H-2glu]+ 302[M + H-2glu-CH3]+

52a

kaempferol 3-O-(2″-O-glucosyl)galactoside dimethyl ester

K 3-O-(2″-O-glu)gal DME

14.90

C29H34O16

639.1558

−56.6

677[M + K]+, 661[M + Na]+, 639[M + H]+, 287[M + H-glu-gal-2CH3]+

53a

kaempferol 3-O-(2″-O-glucosyl)glucoside dimethyl ester

K 3-O-(2″-O-glu)glu DME

15.03

C29H34O16

639.1559

−56.4

677[M + K]+, 661[M + Na]+, 639[M + H]+, 287[M + H-2glu-2CH3]+

54

kaempferol 3-O-(6″-O-rhamnosyl)galactoside (kaempferol 3-O-robinobioside, biorobin)

K 3-O-(6″-O-rham)gal

15.03

C27H30O15

595.1658

0.1

633[M + K]+, 617[M + Na]+, 595[M + H]+, 449[M + H-rham]+, 287[M + H-rham-gal]+

55a,c

isorhamnetin 3-O-(2″-O-rhamnosyl)glucoside (isorhamnetin 3-O-neohesperidoside, calendoflavoside)

I 3-O-(2″-O-rham)glu

15.13

C28H32O16

625.1767

0.6

663[M + K]+, 647[M + Na]+, 625[M + H]+, 479[M + H-rham]+, 317[M + H-rham-glu]+

56a

tectorigenin 7-O-glucoside (tectoridin)

T 7-O-glu

15.37

C22H22O11

463.1239

0.9

501[M + K]+, 485[M + Na]+, 463[M + H]+, 301[M + H-glu]+, 286[M + H-glu-CH3]+

57a,c

kaempferol 3-O-galactoside (trifolin)

K 3-O-gal

15.67

C21H20O11

449.1083

1.0

487[M + K]+, 471[M + Na]+, 449[M + H]+, 287[M + H-gal]+

58c

kaempferol 3-O-(6″-O-rhamnosyl)glucoside (kaempferol 3-O-rutinoside, nicotiflorin)

K 3-O-(6″-O-rham)glu

15.95

C27H30O15

595.1657

−0.1

633[M + K]+, 617[M + Na]+, 595[M + H]+, 449[M + H-rham]+, 287[M + H-rham-glu]+

59c

daidzein 7-O-(6″-O-malonyl)glucoside (6″-O-malonyldaidzin)

D 7-O-(6″-O-mal)glu

16.09

C24H22O12

503.1185

0.2

541[M + K]+, 525[M + Na]+, 503[M + H]+, 255[M + H-mal-glu]+

60

isorhamnetin 3-O-(6″-O-rhamnosyl)galactoside (isorhamnetin 3-O-robinobioside)

I 3-O-(6″-O-rham)gal

16.12

C28H32O16

625.1764

0.1

663[M + K]+, 647[M + Na]+, 625[M + H]+, 479[M + H-rham]+, 317[M + H-rham-gal]+

61

luteolin 7-O-(2″-O-malonyl)glucoside

L 7-O-(2″-O-mal)glu

16.24

C24H22O14

535.1089

1.3

573[M + K]+, 557[M + Na]+, 535[M + H]+, 287[M + H-mal-glu]+

62c

isorhamnetin 3-O-(6″-O-rhamnosyl)glucoside (isorhamnetin 3-O-rutinoside, narcissin)

I 3-O-(6″-O-rham)glu

16.48

C28H32O16

625.1761

−0.3

663[M + K]+, 647[M + Na]+, 625[M + H]+, 479[M + H-rham]+, 317[M + H-rham-glu]+

63c

kaempferol 3-O-glucoside (astragalin)

K 3-O-glu

16.49

C21H20O11

449.1084

1.2

487[M + K]+, 471[M + Na]+, 449[M + H]+, 287[M + H-glu]+

64a,c

isorhamnetin 3-O-galactoside (cacticin)

I 3-O-gal

16.60

C22H22O12

479.1191

1.5

517[M + K]+, 501[M + Na]+, 479[M + H]+, 317[M + H-gal]+

65c

apigenin 7-O-glucoside (cosmosiin)

Ap 7-O-glu

16.95

C21H20O10

433.1133

0.9

455[M + Na]+, 433[M + H]+, 271[M + H-glu]+

66a,c

isorhamnetin 3-O-glucoside

I 3-O-glu

17.05

C22H22O12

479.1188

0.8

517[M + K]+, 501[M + Na]+, 479[M + H]+, 317[M + H-glu]+

67

chrysoeriol 7-O-glucoside (thermopsoside)

C 7-O-glu

17.70

C22H22O11

463.1237

0.5

485[M + Na]+, 463[M + H]+, 301[M + H-glu]+, 286[M + H-glu-CH3]+

68a

luteolin 7-O-(6″-O-malonyl)glucoside

L 7-O-(6″-O-mal)glu

17.98

C24H22O14

535.1084

0.3

557[M + Na]+, 535[M + H]+, 287[M + H-mal-glu]+

69a

genistein 4'-O-(6″-O-malonyl)glucoside

Gn 4'-O-(6″-O-mal)glu

18.12

C24H22O13

519.1136

0.5

557[M + K]+, 541[M + Na]+, 519[M + H]+, 271[M + H-mal-glu]+

70c

genistein 7-O-(6″-O-malonyl)glucoside (6″-O-malonylgenistin)

Gn -7-O-(6″-O-mal)glu

19.16

C24H22O13

519.1130

−0.6

557[M + K]+, 541[M + Na]+, 519[M + H]+, 271[M + H-mal-glu]+

71a

tectorigenin 7-O-(6″-O-malonyl)glucoside (6″-O-malonyltectoridin)

T 7-O-(6″-O-mal)glu

19.71

C25H24O14

549.1237

−0.3

587[M + K]+, 571[M + Na]+, 549[M + H]+, 301[M + H-mal-glu]+, 286[M + H-glu-CH3]+

72

afromosin 7-O-glucoside

Af 7-O-glu

19.71

C23H24O10

461.1445

0.6

499[M + K]+, 483[M + Na]+, 461[M + H]+, 299[M + H-glu]+, 284[M + H-glu-CH3]+

73c

daidzein

D

20.17

C15H10O4

255.0653

0.4

277[M + Na]+, 255[M + H]+

74a

apigenin 7-O-(6″-O-malonyl)glucoside

Ap 7-O-(6″-O-mal)glu

20.50

C24H22O13

519.1129

−0.8

557[M + K]+, 541[M + Na]+, 519[M + H]+, 271[M + H-mal-glu]+

75a

chrysoeriol 7-O-(6″-O-malonyl)glucoside

C 7-O-(6″-O-mal)glu

21.00

C25H24O14

549.1239

0.0

571[M + Na]+, 549[M + H]+, 301[M + H-mal-glu]+

76c

luteolin

L

22.02

C15H10O6

287.0550

0.0

287[M + H]+

77

formononetin 7-O-(6″-O-malonyl)glucoside (6″-O-malonylononin)

F 7-O-(6″-O-mal)glu

22.68

C25H24O12

517.1344

0.7

555[M + K]+, 539[M + Na]+, 517[M + H]+, 269[M + H-mal-glu]+, 254[M + H-mal-glu-CH3]+

78a

afromosin 7-O-(6″-O-malonyl)glucoside

Af 7-O-(6″-O-mal)glu

22.74

C26H26O13

547.1448

0.3

585[M + K]+, 569[M + Na]+, 547[M + H]+, 299[M + H-mal-glu]+, 284[M + H-mal-glu-CH3]+

79c

genistein

Gn

23.54

C15H10O5

271.0601

0.0

271[M + H]+

80c

apigenin

Ap

23.68

C15H10O5

271.0600

−0.4

271[M + H]+

81a

tectorigenin

T

23.82

C16H12O6

301.0710

1.1

323[M + Na]+, 301[M + H]+, 286[M + H-CH3]+

82c

formononetin

F

24.99

C16H12O4

269.0809

0.2

291[M + Na]+, 269[M + H]+, 254[M + H-CH3]+

83

afromosin

Af

25.22

C17H14O5

299.0914

0.0

337[M + K]+, 321[M + Na]+, 299[M + H]+, 284[M + H-CH3]+

  1. All samples analyzed in positive ESI-ionization mode (m/z [M + H]+) of ToF–MS; [M + Na]+ and [M + K]+ adduct ions presented. Each peak was tentatively determined by comparing elution order, MS fragmentation and NMR confirmation presented in constructed library.
  2. RT = retention time; DME = dimethyl ester; Af = afromosin; Ap = apigenin; C = chrysoeriol; D = daidzein; F = formononetin; Gn = genistein; Gy = glycitein; I = isorhamnetin; K = kaempferol; L = luteolin; Q = quercetin; T = tectorigenin; api = apiose (132 Da); gal = galactose (162 Da); glu = glucose (162 Da); rham = rhamnose (146 Da); mal = malonyl (86 Da).
  3. a, new flavonoid in soybean leaves; b, newly named; c, further confirmed in comparison with authentic standards.