Pomegranate Phytochemicals

The different types of phytochemicals that have been identified from various parts of the pomegranate tree and from pomegranate fruits and seeds are listed in Table 1.1, items 1 to 31, and Figure 1.1a through Figure 1.1m show their chemical structures. The major class of pomegranate phytochemicals is the polyphenols (phenolic rings bearing multiple hydroxyl groups) that predominate in the fruit. Pomegranate polyphenols include flavonoids (flavonols, flavanols, and anthocyanins), condensed tannins (proanthocyanidins), and hydrolyzable tannins (ellagitannins and gallotan-nins). Other phytochemicals identified from the pomegranate are organic and phenolic acids, sterols and triterpenoids, fatty acids, triglycerides, and alkaloids.

The major source of dietary pomegranate phytochemicals is the fruit. Pomegranates are popularly consumed as fresh fruit, as beverages (e.g., juices and wines), as food products (e.g., jams and jellies), and as extracts wherein they are used as botanical ingredients in herbal medicines and dietary supplements. Commercial pomegranate juice (PJ) is obtained by a hydrostatic pressing process of whole fruits whereby two predominant types of polyphenolic compounds are extracted into PJ: flavonoids and hydrolyzable tannins (HTs).32 The flavonoids include flavonols such as luteolin, quercetin, and kaempferol found in the peel extract17 and anthocyanins found in the arils.14,15 Anthocyanins are the water-soluble pigments responsible for the bright red color of PJ. Pomegranate anthocyanins include pelargonidin-3-gluco-side, cyanidin-3-glucoside, delphinidin-3-glucoside, pelargonidin 3,5-diglucoside, cyanidin 3,5-diglucoside, and delphinidin 3,5-diglucoside14,15 (Table 1.1).

HTs are found in the peels (rind, husk, or pericarp), membranes, and piths of the fruit.33 HTs are the predominant polyphenols found in PJ and account for 92%

TABLE 1.1

Phytochemicals Identified from Pomegranates

ID

Name

Formula

MW

Plant Part

Ref.

Ellagitannins and Gallotannins

1

2,3-(S)-HHDP-D-glucosea

C20H18O14

482.35

Bark, peel

1

2

Castalagin

C41H26O26

934.63

Bark

2

3

Casuariin

C34H24O22

784.54

Bark

2

4

Casuarinin

C41H28O26

936.65

Bark, pericarp

2, 3

5

Corilagin

C27H22O18

634.45

Fruit, leaves,

3, 4, 5

pericarp

6

Cyclic 2,4:3,6-bis(4,4',5,5',6,6'-

C41H28O26

936.65

Leaves

6

hexahydroxy[1,1 '-biphenyl]-

2,2'-dicarboxylate) 1-(3,4,5-

trihydroxybenzoate)

b-D-Glucose

7

Granatin A

C34H24O23

800.54

Pericarp

3

8

Granatin B

C34H28O27

952.64

Peel

3, 4

9

Pedunculagin

C34H24O22

784.52

Bark, pericarp

1, 3

10

Punicacortein A

C27H22O18

634.45

Bark

2

11

Punicacortein B

C27H22O18

634.45

Bark

2

12

Punicafolin

C41H30O26

938.66

Leaves

7

13

Punigluconin

C34H26O23

802.56

Bark

2

14

Strictinin

C27H22O18

634.45

Leaves

7

15

Tellimagrandin I

C34H26O22

786.56

Leaves, pericarp

3, 8

16

Tercatain

C34H26O22

786.56

Leaves

8

17

2-O-galloyl-4,6(S,S) gallagoyl-

C41H26O26

934.63

Bark

1

D-glucose

18

5-O-galloyl-punicacortein D

C54H34O34

1222.8

Leaves

9

19

Punicacortein C

C47H26O30

1070.7

Bark

2

20

Punicacortein D

C47H26O30

1070.7

Bark, heartwood

2

21

Punicalin

C34H22O22

782.53

Bark, pericarp

1, 3

22

Punicalagin

C48H28O30

1084.7

Bark, pericarp,

1, 2, 3

peel

23

Terminalin/gallayldilacton

C28H20O16

602.37

Pericarp

3

Ellagic Acid Derivatives

24

Ellagic acid

C14H6O8

302.19

Fruit, pericarp,

3, 10

bark

25

Ellagic acid, 3,3'-di-O-methyl

C16H10O8

330.25

Seed

11

26

Ellagic acid, 3,3', 4'-tri-O-

C17H12O8

344.27

Seed

11

methyl

27

Ellagic acid, 3'-O-methyl-3,

C16H8O8

328.23

Heartwood

5

4-methylene

28

Eschweilenol C

C20H16O12

448.33

Heartwood

5

29

Diellagic acid rhamnosyl(1-4)

C40H30O24

894.65

Heartwood

9

glucoside

(continue<

TABLE 1.1 (continued)

Phytochemicals Identified from Pomegranates

TABLE 1.1 (continued)

Phytochemicals Identified from Pomegranates

ID

Name

Formula

MW

Plant Part

1

Catechin and Procyanidins

3C

(-)-Catechin

C15H1406

29C.27

Juice

12

31

Catechin-(4,8)-gallocatechin

C30H26013

594.52

Peel

13

32

Gallocatechin

C15H1407

3C6.27

Peel

13

33

Gallocatechin-(4,8)-catechin

C3CH26013

594.52

Peel

13

34

Gallocatechin-(4,8)-

C3CH26014

61C.52

Peel

13

gallocatechin

35

Procyanidin B1

C3CH26012

578.52

Juice

12

36

Procyanidin B2

C30H26012

578.52

Juice

12

Anthocyanins and Anthocyanidins

37

Cyanidin

C15H11O6

287.24

Juice

4, 14

38

Cyanidin-3-glucoside

C21H21O11

449.38

Juice

4, 14, 15

39

Cyanidin-3,5-diglucoside

C27H31O16

611.52

Juice

4, 14, 15

4C

Cyanidin-3-rutinoside

C27H31O15

595.53

Juice

12

41

Delphinidin

C15H11O7

3C3.24

Juice

4, 14

42

Delphinidin-3-glucoside

C21H21O12

465.38

Juice

4, 14, 15

43

Delphinidin 3, 5-diglucoside

C27H31O17

627.52

Juice

4, 14, 15

44

Pelargonidin 3-glucoside

C21H21O10

433.38

Juice

4, 14

45

Pelargonidin 3,5-diglucoside

C27H31O15

595.53

Juice

4, 14

Flavonols

46

Apigenin-4'-O-ß-D-glucoside

C21H20O11

448.32

Leaves

16

47

Kaempferol

C15H10O6

286.24

Peel, fruit

17

48

Luteolin

C15H10O6

286.24

Peel, fruit

17

49

Luteolin-3'-O-ß-D-glucoside

C21H20O10

432.11

Leaves

16

5C

Luteolin-4'-O-ß-D-glucoside

C21H20O10

432.11

Leaves

16

51

Luteolin-3'-O-ß-D-Xyloside

C20H18O10

418.C9

Leaves

16

52

Myricetin

C15H10O8

318.C4

Fruit

18

53

Quercetin

C15H10O7

3C2.C4

Peel, fruit

4, 18, 19

54

Quercimeritrin

C21H20O12

464.38

Fruit

4

55

Quercetin-3-O-rutinoside

C27H30O16

61C.52

Fruit

12

56

Quercetin-3,4'-dimethyl ether 7-

C28H32O16

624.54

Bark, peel

19

O-a-L-arabinofuranosyl-(1-6)-

ß-D-glucoside

57

Eriodictyol-7-O-a-L-

C26H30O15

582.51

Leaves

2C

arabinofuranosyl (1-6)-ß-D-

glucoside

58

Naringenin 4'-methylether 7-O-

C27H32O14

58C.53

Leaves

2C

a-L-arabinofuranosyl (1-6)-

ß-D-glucoside

Organic Acids

59

Caffeic acid

C9H8O4

18C.16

Juice

12

6C

Chlorogenic acid

C16H18O9

345.31

Juice

12

TABLE 1.1 (continued)

Phytochemicals Identified from Pomegranates

TABLE 1.1 (continued)

Phytochemicals Identified from Pomegranates

ID

Name

Formula

MW

Plant Part

61

Cinnamic acid

C9H8O2

148.16

Juice

12

62

Citric acid

C6H8O7

192.12

Juice

21

63

o-Coumaric acid

C9H8O3

164.16

Juice

12

64

p-Coumaric acid

C9H8O3

164.16

Juice

12

65

Ferulic acid

C10H10O4

194.18

Juice

12

66

Gallic acid

C7H6O5

170.12

Juice

12

67

L-Malic acid

C4H6O5

134.09

Juice

21

68

Oxalic acid

C2H2O4

90.03

Juice

21

69

Protocatechuic acid

C7H6O4

154.12

Juice

21

70

Quinic acid

C7H12O6

192.17

Juice

12

71

Succinic acid

C4H6O4

118.09

Juice

21

72

Tartaric acid

C4H6O6

150.09

Juice

21

Simple Gallyol Derivatives

73

Brevifolin

C12H8O6

248.19

Leaves

10

74

Brevifolin carboxylic acid

C13H8O8

292.2

Leaves

10

75

Brevifolin carboxylic acid-10-

C13H7KO10S

394.25

Leaves

8

monosulphate

76

1,2,3-Tri-O-galloyl-ß-D-glucose

C27H24O18

636.47

Leaves

10

77

1,2,4-Tri-O-galloyl-ß-D-glucose

C27H24O18

636.47

Leaves

10

78

1,2,6-Tri-O-galloyl-ß-D-glucose

C27H24O18

636.47

Leaves

10

79

1,4,6-Tri-O-galloyl-ß-D-glucose

C27H24O18

636.47

Leaves

10

80

1,3,4-Tri-O-galloyl-ß-D-glucose

C27H24O18

636.47

Leaves

8

81

1,2, 4, 6-Tetra-O-galloyl-ß-D-

C34H28O22

788.57

Leaves

10

glucose

82

1,2,3,4, 6-Pent- O-galloyl-ß-D-

C41H32O26

940.68

Leaves

10

glucose

83

Methyl gallate

C8H8O5

184.15

Heartwood

5

84

3,4,8,9,10-pentahydroxy-

C13H8O7

276.20

Leaves

10

dibenzo[b,d]pyran-6-one

Fatty Acids and Triglycerides

85

Eicosenoic acid

C20H40O2

312.53

Seed oil

22

86

Linoleic acid

C18H32O2

280.45

Seed oil

2

87

Linolenic acid

C18H30O2

278.43

Seed oil

22

88

Oleic acid

C18H34O2

282.46

Seed oil

22

89

Palmitic acid

C16H32O2

256.42

Seed oil

22

90

Punicic acid

C18H30O2

278.43

Seed oil

22

91

Stearic acid

C18H36O2

284.48

Seed oil

22

92

Tri- O-punicylglycerol

C57H92O6

873.34

Seeds

23

93

Di- O-punicyl- O-octadeca-8Z-

C57H92O6

873.34

Seeds

23

11Z-13E-trienylglycerol

94

1-O-trans, cis, trans,

C21H36O4

352.51

Seed oil

24

octadecatrienol glycerol octadecatrienol glycerol

(continued)

TABLE 1.1 (continued)

Phytochemicals Identified from Pomegranates

ID

Name

Formula

MW

Plant Part

Ref.

95

1-0-isopentyl-3-0-octadec-2-

C26H50O4

426.67

Seed oil

24

enoyl glycerol

Sterols and Terpenoids

96

Asiatic acid

C30H48O5

488.7

Seed

25

97

Betulinic acid

C30H48O3

456.70

Seed

26

98

Cholesterol

C27H46O

386.65

Seed oil

27

99

Daucosterol

C35H60O6

576.85

Seed

11

100

Estrone

C18H22O2

270.37

Seed oil

27

101

Estradiol

C18H24O2

272.38

Seed oil

27

102

Estriol

C18H24O3

288.38

Seed oil

27

103

Friedooleanan-3-one

C30H50O

426.72

Bark

28

104

ß-Sitosterol

C29H50O

414.71

Seed oil, leaves,

27, 29

stem

105

Stigmasterol

C29H48O

412.69

Seed oil

27

106

Testosterone

C19H28O2

288.42

Seed oil

27

107

Ursolic acid

C30H48O3

456.70

Seed

29

Alkaloids

108

Hygrine

C8H15NO

141.21

Root bark

30

109

Norhygrine

C7H13NO

127.18

Root bark

30

110

Pelletierine

C8H15NO

141.21

Bark

30

111

N-methyl pelletierine

C9HnNO

155.24

Bark

30

112

Sedridine

C8H17NO

143.23

Bark

30

113

Pseudopelletierine

QH^NO

153.22

Bark

30

114

Nor-pseudopelletierine

C8H13NO

139.19

Bark

30

115

2,3,4,5-tetrahydro-6-propenyl-

C8H13N

123.20

Bark

30

pyridine

116

3,4,5,6-tetrahydro-a-methyl-2-

C8H15NO

141.21

Bark

30

pyridine ethanol

117

1-(2,5-dyihydroxy-phenyl)-

CllHl0ClNO2

223.66

Leaves

16

pyridium chloride

Other Compounds

118

Coniferyl 9-O-[ß-D-

C21H30O12

474.46

Seed

11

apiofuranosyl-(1-6)]-O-ß-D-

glucopyranoside

119

Sinapyl 9-O-[ß-D-

C22H32O13

504.48

Seed

11

apiofuranosyl-(1-6)]-O-ß-D-

glucopyranoside

120

Phenylethyl rutinoside

C20H30O10

430.45

Seed

11

121

Icariside D1

C19H28O10

416.42

Seed

11

122

Mannitol

C6H14O6

182.17

Bark

31

a HHDP = hexahydroxydiphenoyl.

a HHDP = hexahydroxydiphenoyl.

OH Galloyl = "OH

HO OH OH OH

HHDP= HO

HO OH OH OH

OH Galloyl = "OH

5 Galloyl

6 Galloyl 9 H 12 Galloyl

14 Galloyl

16 Galloyl

R2 H

2HHDP4

2hhdp3

Galloyl Galloyl

R3 2HHDP3

HHDP

3hhdp6

Galloyl

Galloyl (a)

Galloyl

R6 H

3HHDP6

4HHDP6

4HHDP6

4hhdp6

HHDP

FIGURE 1.1 Chemical structures of pomegranate phytochemicals; a = ellagitannins and gallotannins; b = ellagic acid derivatives; c = catechins and procyanidins; d = anthocyanins and anthocyanidins; e = organic and phenolic acids; f = simple galloyl derivatives; g = fatty acids and triglycerides; h = sterols and triterpenoids; i = alkaloids; j = other compounds.

of its antioxidant activity.32 The predominant pomegranate HT is punicalagin, which is responsible for about half of the total antioxidant capacity of the juice. The soluble polyphenol content in PJ has been reported to vary within the limits of 0.2 to 1.0%.34 HTs are gallic acid and ellagic acid esters of core molecules that consist of polyols such as sugars. HTs are susceptible to enzymatic and non-enzymatic hydrolysis and are further classified according to the products of hydrolysis: gallotannins yield gallic acid and glucose while ellagitannins yield ellagic acid and glucose.35 This combination of monomers leads to large structural heterogeneity. For instance, pomegranate leaves, bark, and fruit contain more than 18 individual HT structures.127 These structures are classified into gallotannins, ellagitannins (ellagic acid esters of D-glucose with one or more galloyl substitutions) and the more unique gallagoyl esters such as punicalagin and punicalin (Figure 1.1a to Figure 1.1d).

Recently, there has been an increase in the use of pomegranate fruit extracts as botanical ingredients in herbal medicines and dietary supplements. In these extracts, both polyphenol and fatty-acid constituents from various parts of the fruit such as its arils and juice, peels, pericarp and pith, and seeds, may be present. The seeds of pomegranates have been well investigated. For example, pomegranate seed oil

OH OH

o-Hhdp

OH OH

HHDP

HHDP

Galloyl GalloyKO O

,Hhdp

HOOC Y O OH

O-Galloyl O O O

HO O

^HHDP

OH OH

OH OH

OH OH

OH OH

OH OH O

OH OH O

Galloyl

OH OH

HO HO HO HO

HO HO HO HO

OH OH HO

^Galloyl

OH OH HO

FIGURE 1.1 (continued)

OH OH

OH OH

31 Catechin-(4-8)-gallocatechin

33 Gallocatechin (4-8)-catechin

34 Gallocatechin-(4-8)-gallocatechin

35 Epicatechin-(4-8)-catechin

36 Epicatechin-(4-8)-epicatechin

FIGURE 1.1 (continued)

contains levels of >60% of punicic acid, a cis-9, trans-11, cis-13 conjugated linolenic acid.36 Other fatty acids found in pomegranate seed oil include linoleic, oleic, palmitic, stearic, arachidic, and palmitoleic acid.37 In addition, there have been reports of sex hormones such as estrone and coumestrol in pomegranate seeds.37-39 However, a recent paper did not detect the presence of the steroid hormones estone, estradiol, and testosterone in pomegranate seeds, juice, and commercial preparations.

R1

OH

HO

O

■R2

or4

OR3

R1

R2

R3

R4

37

OH

H

H

H

38

OH

H

Glucose

H

39

OH

H

Glucose

Glucose

40

OH

H

Rutinose

H

41

OH

OH

H

H

42

OH

OH

Glucose

H

43

OH

OH

Glucose

Glucose

44

H

H

Glucose

H

45

H

H

Glucose

Glucose

(g)

R2

Ri w1

R3-

Ö-

OH O

R1

R2

R3

59

H

OH

OH

61

H

H

H

63

OH

H

H

64

H

H

OH

65

H

OMe

OH

OH 60

FIGURE 1.1 (continued)

HO OH

HO O

HOOC OH

RoO.

HO OH

HO OH

MeO O 83

MeO O 83

HO OH

HO OH

80 81 82

OR R1

Diet And Exercise Expertise

Diet And Exercise Expertise

Get All The Support And Guidance You Need To Be A Success At Dieting And Exercise. This Book Is One Of The Most Valuable Resources In The World When It Comes To Better Physical Personal Development Through Better Living.

Get My Free Ebook


Post a comment