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Table 3 Comparison of phytochemical profile from TI samples obtained in February 2018 (dry season) or September 2018 (rainy season) extracted using different organic solvents

From: Season, storage and extraction method impact on the phytochemical profile of Terminalia ivorensis

Phytochemical class

Phytochemical metabolites

Petroleum ether extract (ng/mg)

Chloroform extract (ng/mg)

Ethyl acetate extract (ng/mg)

Ethanol extract (ng/mg)

Dry season

Rainy season

Dry season

Rainy season

Dry season

Rainy season

Dry season

Rainy season

Acetophenones

3,4,5-trimethoxyacetophenone

2.7 ± 0.6

ND

ND

ND

2.0 ± 0.2

ND

2.1 ± 0.5

ND

 

4-hydroxy-3-methoxyacetophenone

36.4 ± 6.2

0.2 ± 0.1***

4.6 ± 1.1

ND

4.8 ± 1.1

ND

3.9 ± 0.9

ND

 

4-hydroxyacetophenone

10.1 ± 2.1

ND

12.2 ± 2.8

4.1 ± 1.1**

5.3 ± 1.2

8.1 ± 1.8

4.6 ± 1.1

ND

Amines

Dopamine

ND

3.1 ± 0.7

ND

3.0 ± 0.7

ND

7.4 ± 1.8

ND

6.6 ± 1.6

 

Spermidine

20.6 ± 5.1

ND

ND

ND

ND

ND

ND

ND

Benzaldehydes

3,4-dimethoxybenzaldehyde

4.9 ± 1.1

9.3 ± 1.3

1.7 ± 0.4

ND

ND

ND

ND

ND

 

P-hydroxybenzaldehyde

ND

9.9 ± 2.4

34.4 ± 4.7

24.7 ± 5.1

ND

9.0 ± 2.2

6.6 ± 1.3

3.7 ± 0.9

 

Protocatachaldehyde

ND

ND

54.8 ± 13.7

ND

36.7 ± 9.1

ND

114.8 ± 28.7

ND

 

Syringin

21.2 ± 4.2

55.2 ± 6.5*

77.6 ± 14.2

57.2 ± 9.6

1.0 ± 0.1

17.2 ± 3.4***

10.4 ± 2.1

4.8 ± 1.2*

 

Vanillin

132.8 ± 23.7

210.4 ± 23.8

359.6 ± 48.6

179.2 ± 23.3*

7.7 ± 1.4

48.2 ± 8.3*

43.2 ± 6.1

42.3 ± 5.6

Benzenes

1,2-dihydroxybenzene

ND

ND

ND

ND

984 ± 246

ND

ND

ND

 

1,2,3-trihydroxybenzene

ND

ND

ND

ND

ND

ND

64.0 ± 16.0

ND

Benzoic acids

2,3-dihydroxybenzoic acid

14.2 ± 3.5

ND

ND

ND

58 ± 14.5

ND

ND

ND

 

2,4-dihydroxybenzoic acid

18 ± 4.5

ND

ND

ND

ND

ND

ND

ND

 

2,5-dihydroxybenzoic acid

ND

ND

ND

ND

22.1 ± 5.5

ND

ND

ND

 

2,6-dihydroxybenzoic acid

ND

ND

ND

ND

5.2 ± 1.3

ND

ND

ND

 

3,4-dimethoxybenzoic acid

ND

ND

ND

ND

99.6 ± 24.9

ND

ND

ND

 

Anthranilic acid

ND

ND

ND

ND

6.8 ± 1.6

ND

7.6 ± 1.8

ND

 

Benzoic acid

291.6 ± 29.3

165.6 ± 31.1*

620.1 ± 79.7

468.3 ± 72.2

281.6 ± 37.5

218.0 ± 34.6

249.2 ± 31.6

476 ± 49.8*

 

Chlorogenic acid

ND

ND

ND

ND

ND

ND

10.1 ± 2.2

27.2 ± 3.4*

 

Gallic acid

ND

ND

37.9 ± 9.4

ND

3200 ± 512.3

3880 ± 486.8

15,360 ± 4102

2684 ± 245.3***

 

P-anisic acid

31.1 ± 4.8

26.3 ± 5.1

30.1 ± 4.6

18.6 ± 2.3

ND

27.2 ± 6.8

ND

18.4 ± 4.6

 

P-hydroxybenzoic acid

ND

ND

55.6 ± 5.8

1.2 ± 0.4***

6.2 ± 1.8

22.1 ± 3.2

40.8 ± 3.6

7.8 ± 2.2*

 

Protocatechuic acid

ND

ND

19.4 ± 4.8

ND

249.2 ± 25.6

134 ± 18.7*

532 ± 54.8

119.2 ± 32.4**

 

Salicylic acid

25,280 ± 3026

71.2 ± 14.7***

39.1 ± 3.1

57.6 ± 8.2

76.4 ± 16.8

46.4 ± 13.3*

36.1 ± 4.8

50.8 ± 4.9

 

Syringic acid

ND

0.1 ± 0.02

62.4 ± 12.1

37.6 ± 2.5

100.4 ± 21.5

17.1 ± 3.3***

33.7 ± 8.4

ND

 

Vanillic acid

48.4 ± 6.9

39.8 ± 11.4

348.8 ± 47.8

96.4 ± 15.3**

84.8 ± 16.2

44.0 ± 8.1*

100.4 ± 17.3

29.2 ± 7.2***

Cinnamic acids

Caffeic acid

ND

ND

ND

ND

391.6 ± 42.8

23.5 ± 4.1***

303.6 ± 43.4

19.3 ± 4.2***

 

Cinnamic acid

ND

3.3 ± 0.6

ND

5.0 ± 1.2

7.0 ± 1.7

ND

ND

ND

 

Ferulic acid

15 ± 3.6

3.1 ± 0.7**

92.4 ± 8.3

54.4 ± 7.9

516.0 ± 52.7

52.4 ± 8.4***

400.9 ± 76.5

22.2 ± 3.2***

 

P-coumaric acid

ND

ND

11.2 ± 2.2

11.4 ± 2.5

58.8 ± 6.8

54.8 ± 7.1

384.8 ± 34.8

38.8 ± 5.5***

 

Sinapic acid

ND

ND

ND

ND

11.4 ± 2.8

ND

ND

ND

Coumarins

Coumarin

3.0 ± 0.6

ND

ND

ND

ND

ND

ND

ND

Flavonoids

Apigenin

ND

ND

12.7 ± 2.6

9.6 ± 2.9

12.2 ± 2.3

14.9 ± 3.4

13.4 ± 3.2

12.4 ± 3.4

 

Bergapten

ND

ND

1.1 ± 0.2

0.8 ± 0.1

ND

1.7 ± 0.4

ND

ND

 

Biochanin A

ND

14.3 ± 3.3

ND

ND

ND

ND

ND

ND

 

Catechin

ND

ND

25.9 ± 3.4

32.5 ± 5.7

18,800 ± 4286.1

16,280 ± 3621.3

17,920 ± 3532

12,480 ± 2642.4

 

Didymin

ND

9.4 ± 2.5

ND

9.2 ± 2.3

ND

10.1 ± 2.5

ND

10.2 ± 2.5

 

Epicatechin

ND

ND

ND

ND

3204 ± 801

ND

2408 ± 147.7

56.2 ± 14.2***

 

Epigallocatechin

ND

ND

ND

ND

2472 ± 618

ND

1832 ± 458

ND

 

Epigallocatechin gallate

ND

ND

ND

ND

34.3 ± 3.9

165.2 ± 31.4***

1128 ± 122.4

114.4 ± 21.6***

 

Ethylferulate

198.1 ± 49.6

ND

ND

ND

ND

ND

ND

ND

 

Formononetin

ND

3.7 ± 0.9

ND

4.4 ± 1.1

ND

3.8 ± 0.9

ND

3.9 ± 0.9

 

Gallocatechin

ND

ND

ND

ND

5720 ± 652.5

684 ± 55.8***

4960 ± 672.5

456 ± 59.8***

 

Genstein

ND

ND

16.1 ± 2.1

13.2 ± 3.2

14.4 ± 4.1

16.9 ± 3.8

15.4 ± 2.8

15.0 ± 3.2

 

Hesperidin

ND

ND

ND

ND

ND

24.2 ± 6.0

ND

22.8 ± 5.7

 

Hesperitin

ND

17.4 ± 4.5

17.7 ± 3.5

82.6 ± 13.4***

3.3 ± 0.4

55.6 ± 5.1***

2.8 ± 0.3

57.6 ± 4.4***

 

Imperatorin

ND

10.2 ± 2.5

3.5 ± 0.9

3.7 ± 0.7

ND

5.1 ± 1.2

5.6 ± 1.5

4.8 ± 1.4

 

Kaempferol

ND

ND

27.1 ± 6.7

ND

35.0 ± 8.7

ND

56 ± 14

ND

 

Luteolin

ND

ND

ND

ND

31.2 ± 2.5

33.2 ± 4.8

28.1 ± 5.2

31.8 ± 4.5

 

Morin

ND

47.2 ± 11.2

100.4 ± 15.7

208.5 ± 34.2**

ND

82.0 ± 20.5

ND

82.8 ± 20.7

 

Myricetin

ND

ND

ND

ND

138.8 ± 32.3

94.8 ± 19.8

139.2 ± 24.4

94.4 ± 21.2

 

Naringenin

ND

ND

66.4 ± 11.2

77.2 ± 13.6

42.4 ± 6.7

114.8 ± 16.8***

61.6 ± 17.

99.2 ± 15.3**

 

Neohesperidin

ND

ND

ND

10.6 ± 2.6

16.9 ± 2.5

25.9 ± 4.6

32.4 ± 5.7

124 ± 23.5***

 

Niacin

ND

ND

ND

ND

322.8 ± 80.7

ND

54.8 ± 13.7

ND

 

Phloretin

ND

ND

ND

3.8 ± 0.9

40.4 ± 5.2

64 ± 7.3

44.4 ± 5.3

34.1 ± 5.1

 

Phloridzin

1.7 ± 0.4

ND

ND

ND

8.1 ± 1.2

75.2 ± 12.5***

34.0 ± 4.5

58.4 ± 6.2

 

Psoralen

ND

ND

ND

ND

1.3 ± 0.3

ND

3.2 ± 0.7

2.6 ± 0.4

 

Quercetin

ND

ND

31.9 ± 7.9

ND

68.8 ± 9.2

63.2 ± 8.4

90.4 ± 8.7

52.8 ± 6.3*

 

Quercetin-3-glucoside

ND

ND

ND

ND

ND

65.6 ± 16.4

30.1 ± 3.8

51.2 ± 4.4

 

Resveratrol

ND

ND

ND

ND

23.8 ± 5.4

5.1 ± 1.3*

12.7 ± 3.1

ND

 

Tangeretin

6.5 ± 2.1

7.6 ± 2.2

12.8 ± 3.1

9.0 ± 2.7

5.9 ± 1.3

15.1 ± 2.4**

16.5 ± 3.4

13.1 ± 2.8

 

Taxifolin

ND

ND

8.4 ± 2.1

ND

112 ± 25.6

135.6 ± 24.3

100 ± 19.7

111.2 ± 24.4

 

Scopoletin

13.1 ± 3.3

1.5 ± 0.1***

6.3 ± 1.2

41.2 ± 4.4*

30.2 ± 7.5

ND

31.3 ± 7.8

ND

Indoles

Indole

ND

ND

ND

11.4 ± 2.8

ND

ND

ND

ND

 

Indole-3-acetic acid

ND

ND

ND

ND

21.0 ± 5.2

ND

ND

ND

 

Indole-3-pyruvic acid

ND

ND

ND

ND

201.2 ± 31.7

624 ± 121.7***

ND

844 ± 211

Lignans

Indole-3-carboxaldehyde

2.2 ± 0.2

2.6 ± 0.4

2.3 ± 0.4

9.6 ± 1.8*

7.0 ± 1.3

11.2 ± 2.4

17.2 ± 4.2

5.8 ± 1.3**

 

Pinoresinol

ND

18.3 ± 4.5

45.6 ± 5.6

29.9 ± 3.7

ND

ND

ND

ND

 

Secoisolariciresinol

ND

2.0 ± 0.5

468.2 ± 38.4

145.6 ± 23.3***

221.6 ± 39.7

112.8 ± 23.8*

82.8 ± 5.7

82.4 ± 8.2

 

Syringaresinol

ND

ND

444.0 ± 50.2

440.0 ± 46.7

504 ± 126

ND

ND

ND

Phenols

2-hydroxybenzyl alcohol

ND

18.3 ± 4.5

ND

25.4 ± 6.2

ND

ND

ND

ND

 

Hydroxytyrosol

ND

ND

ND

ND

159.2 ± 39.8

ND

ND

ND

Phenylacetic acids

Phenylacetic acids

12.2 ± 4.3

49.6 ± 6.5*

2.4 ± 0.7

34.4 ± 4.9**

37.3 ± 9.3

ND

12.9 ± 3.2

ND

Phenyllactic acids

Phenyllactic acid

ND

ND

ND

ND

40.4 ± 10.1

ND

0.9 ± 0.1

ND

Phenylpropionic acids

4-hydroxyphenylpropionic acid

ND

ND

368.0 ± 96.0

ND

ND

ND

ND

ND

 

4-hydroxy-3-methoxyphenylpropionic acid

ND

1.8 ± 0.4

ND

17.5 ± 4.3

2.8 ± 0.3***

1.6 ± 0.3

ND

ND

Phenylpyruvic acids

4-hydroxyphenylpyruvic acid

540 ± 60.2

2796 ± 306.8***

708.2 ± 65.5

408.3 ± 40.7

5160 ± 1290

ND

ND

608 ± 152

  1. Data are presented as amount ± SD, n = 3, *p < 0.05, **p < 0.01 and ***p < 0.001 as compared to TI sample obtained in the dry season by ANOVA followed by Bonferroni’s post hoc test. ND represent not detected (minimum detectable limit of 0.1 ng/mg)