Table 1 Tentative identification and characterization of phytochemical compounds in Phyllanthus niruri leaf and stem using LC-QToF in positive and negative ionization modes.

From: Cytotoxic and chemomodulatory effects of Phyllanthus niruri in MCF-7 and MCF-7ADR breast cancer cells

#

RT (min)

Compound Name

CH2Cl2

MeOH

Chemical class

Molecular Formula

Exact mass

[M + H]+

Fragment ions

[M–H]−

Fragment ions

1

2.4

2-Deoxy-2,3-dehydro-N-acetylneuraminic acid

√

√

Alpha-keto acid sugars

C11H17NO8

291.0954

–

–

290.0882

(290.0881)*

200.0567 [M–H–C3H6O3]−, 128.0356 [M–H–C3H6O3–C3H4O2]−

2

2.6

β-glucogallin

1-O-galloyl-B-D-glucopyranose,

√

√

Phenolic acid glycoside

C13H16O10

332.0743

–

–

331.0678

(331.0671)

211.0246 [M–H-C4H8O4]−, 169.0143 [M–H–C6H10O5]−, 125.0244 [M–H–C6H10O5–CO2]−

3

3.4

Gallic acid

√

√

Phenolic acid

C7H6O5

170.0215

171.0289

(171.0288)

–

169.0146

(169.0142)

125.0245 [M–H–CO2]−, 107.0139 [M–H–CO2–H2O]−

4

3.6

Vanillic acid 4-sulfate

√

√

Phenolic acid

C8H8O7S

247.9991

–

–

246.9922

(246.9918)

203.0019 [M–H–CO2]−, 121.0296 [M–H–CO2–SH2O3]−, 108.0220 [M–H–CO2–SH2O3–CH]−, 96.9604 [H2SO4]−, 80.9656 [H2SO3]−

5

4.07

Sesbanimide A

√*

√

Polyketide alkaloide

C15H21NO7

327.1318

328.1399

(328.1391)

310.1290 [M + H–H2O]+, 250.1655 [M + H–H2O–C2H4O2]+, 232.1550 [M + H–2H2O–C2H4O2]+, 132.0811 [M + H–2H2O–C2H4O2–C4H4O3]+, 120.0810 [M + H–2H2O–C2H4O2–C5H4O3]+

326.1243

(326.1245)

–

6

4.30

Phenylalanine

√

√

Amino acid

C9H11NO2

165.0790

166.0855

(166.0863)

120.0479

164.0719

(164.0717)

–

7

4.44

Caffeoylglucaric acid

√

√

Phenolic acid

C15H16O11

372.0693

–

–

371.0619

(371.0620)

315.0720 [M–H–C2O2]−, 209.0306 [M–H–C2O2–C7H6O]−

8

5.2

Dihydrocaffeic acid 3-O-glucuronide

√

√

Phenolic acid glycoside

C15H18O10

358.0900

–

–

357.0826

(357.0827)

269.0336, 219.0512, 151.0402, 123.0451

9

5.3

Protocatechuic acid

√*

√

Phenolic acid

C7H6O4

154.0266

–

–

153.0194

(153.0193)

–

10

5.75

Dihydro virganin

√*

√

phenolic

C26H24O18

624.0963

–

–

623.0883

(623.0890)

355.0665 [M–H–C9H8O8]−, 234.0405 [M–H–C9H8O8–C7H5O2]−

11

6.3

1,6-Digalloylglucose; D-pyranose-form

√*

√

Phenolic glycoside

C20H20O14

484.0853

–

–

483.0776

(483.0780)

169.0141, 125.0246

12

7.1

Phyllanthusiin B/ Phyllanthusiin G/ Phyllanemblinin C

√*

√

ellagitannins

C41H30O28

970.0924

–

–

969.0850

(969.0851)

925.0955

13

7.7

√*

√

14

9.1

√*

√

15

7.2

Brevifolin carboxylic acid

√

√

Phenol carboxylic acid

C13H8O8

292.0219

–

–

291.0157

(291.0146)

247.0250 [M–H–CO2]−, 219.0294 [M–H–CO2–CO]−, 191.0344 [M–H–CO2–2CO]−, 145.0292, 119.0505

16

7.56

Methyl gallate

√

√

Phenolic acid ester

C8H8O5

184.0372

–

–

183.0298

(183.0299)

124.0167 [M–H–CH3–CO2]−

17

7.8

Geraniin /Phyllanthusiin A/Geraniinic acid B

√

√

ellagitannin

C41H28O27

952.0818

–

–

951.0740

(951.0745)

–

18

9.8

√

√

19

12.2

√

√

20

6.9

Corilagin/1-O-Galloyl-6-O-luteoyl-α-D-glucopyranose

√

√

ellagitannins glycoside

C27H22O18

634.0806

652.1146

(652.1144)

[M + NH4]+

465.0666 [M + H–C7H6O5]+,

633.0743

(633.0733)

463.0517 [M–H–C7H6O5]−, 300.9995, 275.0202

21

8.1

√

√

22

8.8

Phyllanthusiin C

√

√

ellagitannin

C40H30O26

926.1025

–

–

925.0950

(925.0953)

511.0559

23

8.84

3,5,7-Trihydroxyflavone-8-sulfonic acid; 3-O-β-D-Glucopyranoside (Galangin-8-sulfonic acid, glucopyranoside

√

√

Flavnoid = flavone

C21H20O13S

512.0625

–

–

511.0555

(511.0552)

349.0026 [M–H–C6H10O5]−, 319.9996 [M–H–C6H10O5–CHO]−, 290.9974 [M–H–C6H10O5–2CHO]−, 269.0457 (galangin)

24

9.29

Brevifolin

√

√

Phenolic

C12H8O6

248.0015

–

–

247.0252

(247.0248)

219.0295, 191.0345, 145.0290, 117.0342

25

9.5

Phyllanemblinin A

√

√

Ellagitannins

C27H20O17

616.0700

–

–

615.0622

(615.0628)

300.9994, 169.0145

26

9.7

Quercetin-xylosyl-glucoside

√

√

Flavnoid = flavonol

C26H28O16

596.1377

597.1454

(597.1450)

303.0493

595.1299

(595.1305)

300.0272

27

9.90

Methylbrevifolin carboxylate

√

√

Phenolic

C14H10O8

306.0376

307.0453

(307.0448)

183.0921

305.0306

(305.0303)

273.0043 [M–H–CH3OH]−, 245.0085 [M–H–CH3OH–CO]−, 217.0136 [M–H–CH3OH–2CO]−, 201.0186 [M–H–CH3OH–CO–CO2]−, 189.0189 [M–H–CH3OH–3CO]−, 173.0237 [M–H–CH3OH–2CO–CO2]−,

28

10.30

Ellagic acid

√

√

Phenolic acid

C14H6O8

302.0063

–

–

300.9999

(00.9990)

283.9958 [M–H–OH]−, 257.0072 [M–H–CO2]−,

29

10.35

Quercetin-3-O-rutinoside

√

√

Flavnoid = flavonol

C27H30O16

610.1534

611.1611

(611.1607)

303.0501

609.1462

(609.1461)

301.0351

30

10.6

4-O-Brevifolincarbonyl-1-O-galloyl-3,6-O-hexahydroxydiphenoyl-D-glucopyranose

√

√

Phenolic

C40H28O25

908.0920

  

907.0847

(907.0844)

611.0708, 169.0141

31

10.88

Quercetin-O-hexoside

√

√

Flavnoid = flavonol

C21H20O12

464.0955

–

–

463.0877

(463.0877)

300.0257 [M–H–Hex]−, 271.0252 [M–Hex–CH2O]−, 255.0299 [M–Hex–CO–H2O]−, 151.0036

32

11.5

kaempferol 3-O-rutinoside

√

√

Flavnoid = flavonol

C27H30O15

594.1585

595.1661

(595.1657)

287.0556

593.1520

(593.1512)

285.0413

33

11.96

Chebulinic acid

√

√

Ellagitannins

C41H32O27

956.1131

–

–

955.1048

(955.1058)

923.0789 [M–H–CH4O]−, 879.0899 [M–H–CH4O–CO2]−, 611.0708 [M–H–CH4O–CO2–C11H8O8]−, 351.0176 [M–H–CH4O–CO2–C11H8O8–C10H12O8]−, 300.9988 [ellagic acid]−

34

12.72

Phyllanthussiin U

√

√

Ellagitannins

C40H28O26

924.0869

–

–

923.0792

(923.0796)

461.0359, 300.9988 [ellagic acid]

35

13.4

Azelaic acid

√

√

Dicarboxylic acid

C9H16O4

188.1049

–

–

187.0974

(187.0976)

–

36

13.7

3,4,5,7-Tetrahydroxyflavone-8-sulfonic acid

√

√

Flavnoid = flavone

C15H10O9S

366.0046

–

–

364.9973

(364.9973)

285.0403 [M–H–SO3]−

37

14.43

4-Hydroxybenzoic acid

√

√

Phenolic acid

C7H6O3

138.0317

–

–

137.0245

(137.0244)

93.0350 [M–H–CO2]−, 75.0243 [M–H–CO2–H2O]−

38

15.65

3,5,7-Trihydroxyflavone-8-sulfonic acid (Galangin-8-sulfonic acid)

√

√

Flavnoid = flavone

C15H10O8S

350.0096

–

–

349.0032

(349.0024)

269.0456 (galangin)

39

15.97

√

√

40

17.7

Niruriflavone

√

√

Flavnoid = flavone

C16H12O8S

364.0253

–

–

363.0187

(363.0180)

347.9944, 268.0376, 151.0035

41

18.21

Trihydroxy-octadecadienoic acid

√

√

Fatty acid

C18H32O5

328.2250

–

–

327.2175

(327.2177)

285.0797, 215.1289, 171.1027, 85.0299

42

18.40

√

√

43

18.60

√

√

44

18.90

Trihydroxy-octadecanoic acid

√

√

Fatty acid

C18H34O5

330.2406

–

–

329.2332

(329.2333)

 

45

19.75

√

√

46

19.98

√

√

47

21.0

√

√

48

21.4

Nirtetralin

√

√

Lignan

C24H30O7

430.1992

431.2054

(431.2064)

–

–

–

49

22.7

Phyltetralin

√

√

Lignan

C24H32O6

416.2199

417.2278

(417.2272)

151.0755

–

–

50

22.9

Phyllanthin

√

√

Lignan

C24H34O6

418.2355

419.2428

436.2694

(436.2691)

441.2248

(441.2249)

184.0740, 151.0764

–

–

51

23.4

Hypophyllanthin

√

√

Lignan

C24H30O7

430.1992

431.2065

(431.2064)

–

–

–

52

23.5

Niranthin

√

√

Lignan

C24H32O7

432.2148

433.2221

455.2045

(455.2040)

–

–

–

53

23.6

Isolintetralin

√

√

Lignan

C23H28O6

400.1886

401.1961

(401.1958)

151.0751

–

–

  1. Significant values are in bold.
  2. *Theoretical accurate mass; Compound #5, 9–14 are present in low abundances in methylene chloride extracts.
Back to article page