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. 2019 Nov 6;9(6):357–392. doi: 10.1007/s13659-019-00222-3

Table 2.

Chemical constituents isolated from the genus Terminalia and the studied plant organs

No. Compounds Plants Organs References
Triterpenes (86)
 1 2α,3β,19α-Trihydroxyolean-12-en-20-oic acid 3-O-β-d-galactosyl-(1 → 3)-β-d-glucoside T1 R [3]
 2 2α,3β,19α-Trihydroxyolean-12-en-28-oic acid methylester 3β-O-rutinoside T1 R [53]
 3 2α,3β,19β,23-Tetrahydroxyolean-12-en-28-oic acid 3β-O-β-d-galactosyl-(1 → 3)-β-d-glucoside-28-O-β-d-glucoside T1 R [52]
 4 3-Acetylmaslinic acid T1 RB [54]
 5 Arjunic acid

T1

T4

T17

T25

T28

T32

T44

B

SB, F

F

SB

B

B

R

[55, 74]

[60, 79, 124]

[146]

[130]

[132]

[145]

[133]

 6 Arjunoside I T4 SB [61]
 7 Arjunoside II T4 SB [61]
 8 Arjunoside III T4 R [62, 63]
 9 Arjunoside IV T4 R [62, 63]
 10 Arjunetin

T1

T4

T8, T16, T17, T20, T39

B

B, L, S, R, F

B, L, S, R, F

[55, 74]

[23, 67]

[23]

 11 Oleanolic acid

T1

T9

T4, T16, T20

T8, T17

T39

T28

T36

H

L

B, L, S, R, F

B, L, S, R

L, S, R, F

B

B

[56]

[97]

[23]

[23]

[23]

[132]

[140]

 12 Ursolic Acid

T4, T16, T20

T8, T17

T39

B, L, S, R, F

L, S, R

B, L, S, F

[23]

[23]

[23]

 13 Maslinic acid

T1

T9

T17

T36

H

L

F

B

[56]

[97]

[21, 116]

[140]

 14 2α,3α,24-Trihydroxyolean-11,13(18)-dien-28-oic acid T33 SB [158]
 15 Terminoside A T4 B [58]
 16 Arjungenin

T4

T25

T12

T8, T16, T20, T39

T17

T25

T28

T32

T33

T44

SB,L,R,F

R

B

B, L, S, R, F

B, L, S, R, F

R, SB

B

B

SB

RB

[23, 60, 70, 74]

[60]

[99]

[23]

[23, 146]

[69, 130]

[132]

[145]

[158]

[133, 152]

 17 Hypatic acid T25 R [69]
 18 Arjunglucoside I

T4

T17

T50

T32

B, R

F

R

B

[70, 74, 78]

[146]

[72]

[145]

 19 Sericoside

T4

T25

T28

T44

T32

T50

B

SB

B

R, L, SB

B

R

[71]

[130]

[76, 131]

[43, 133, 149]

[145]

[72]

 20 Crataegioside

T4

T17

B

F

[75]

[146]

 21 23-O-neochebuloylarjungenin 28-O-β-d-glycosyl ester T17 F [146]
 22 23-O-4′-epi-neochebuloylarjungenin T17 F [146]
 23 23-O-galloylarjunic acid

T39

T32

B

B

[144]

[145]

T17 F [146]
 24 Quercotriterpenoside I T32 B [145]
T17 F [146]
 25 Sericic acid

T28

T32

T44

B

B

R

[132]

[145]

[150]

 26 24-Deoxy-sericoside T32 B [138]
 27 Arjunolic acid

T1

T4

T7

T9

T8

T16, T17, T20, T39

T34

T36

B, H

B, H, L, S, R, F

RB

L

B, L, S, R

B, L, S, R, F

L

B

[55, 56, 74]

[23, 77, 78, 91]

[97]

[23]

[23]

[23, 144]

[35]

[140]

 28 Terminolic acid

T1

T17

T7, T16, T31

T25

T32

H

F

H

H, Rl

H, B

[56]

[146]

[128]

[128]

[128, 145]

 29 Arjunglucoside II

T4

T17

B

F

[70, 74]

[146]

 30 23-O-galloylarjunolic acid T17 F [146]
 31 23-O-galloylarjunolic acid 28-O-β-d-glucosyl ester T17 F [146]
 32 23-O-galloylterminolic acid 28-O-β-d-glucosyl ester T17 F [146]
 33 Arjunolitin T4 SB [80]
 34 Terminolitin T4 F [80]
 35 Arjunglucoside III T4 B [74]
 36 Methyl oleanate T4 R, F [80, 124]
 37 Olean-3α,22β-diol-12 en-28-oic acid 3-O-β-d-glucosyl-(1 → 4)-β-d-glucoside T4 B [81, 84]
 38 Arjunetoside T4 R, SB [82]
 39 Olean 3β,6β,22α-triol-12en-28-oic acid-3-O-β-d-glucosyl-(1 → 4)-β-d-glucoside T4 B [84]
 40 2α,19α,Dihydroxy-3-oxo-olean-12-en-28-oic acid-28-O-β-d-glucoside T4 R [85]
 41 Ivorengenin A (2α,19α,24-trihydroxy-3-oxoolean-12-en-28-oic acid) T28 B [132]
 42 Chebuloside I T17 F [115]
 43 Chebuloside II

T17

T32

F

B

[115]

[138]

 44 Arjunglucoside

T17

T44

T33

F

R, SB

SB

[115]

[133]

[158]

 45 Glaucescic acid (2α,3α,6α,23-tetrahydroxyolean-2-en-28-oic acid) T25 R [69]
 46 Glaucinoic acid (2α,3β,19α,24-tetrahydroxyolean-12-en-30-oic acid) T25 SB [130]
 47 Termiarjunoside I (olean-1α,3β,9α,22α-tetraol-12-en-28-oic acid-3-β-d-glucoside) T4 SB [156]
 48 Termiarjunoside II (olean-3α,5α,25-triol-12-en-23,28-dioic acid-3α-d-glucoside) T4 SB [156]
 49 β-Amyrin

T25

T36

SB

B

[129]

[140]

 50 Ivorenoside A T28 B [131]
 51 Ivorenoside B T28 B [131]
 52 Ivorenoside C T28 B [131]
 53 Ivorengenin B (4-oxo-19α-hydroxy-3,24-dinor-2,4-secoolean-12-ene-2,28-dioic acid) T28 B [132]
 54 1α,3β-Hydroxyimberbic acid 23-O-α-l-4-acetylrhamnoside T47 SB [48]
 55 1α,3β,3,23-Trihydroxy-olean-12-en-29-oate-23-O-α-[4-acetoxyrhamnosyl]-29-α-rhamnoside T47 SB [48]
 56 2α,3β-Dihydroxyolean-12-en-28-oic acid 28-O-β-d-glucoside T48 SB [49]
 57 2α,3β,21β-Trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucoside T48 SB [49]
 58 2α,3β,29-Trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucoside T48 SB [49]
 59 2α,3β,23,27-Tetrahydroxyolean-12-en-28-oic acid 28-O-β-d-glucoside T48 SB [49]
 60 Terminaliaside A ((3β,21β,22α)-3-O-(3′-O-angeloylglucosyl)-21,22-dihydroxy-28-O-sophorosyl-16-oxoolean-12-ene) T50 R [72]
 61 2, 3, 23-Trihydroxylolean-12-ene T7 RB [91]
 62 2α,3β,23-Trihydroxylolean-12-en-28-oic acid T48 SB [49]
 63 23-O-galloylpinfaenoic acid 28-O-β-d-glucosyl ester T17 F [146]
 64 Pinfaenoic acid 28-O-β-d-glucosyl ester

T4

T17

B

F

[76]

[146]

 65 2α,3β-Dihydroxyurs-12,18-dien-28-oic acid 28-O-β-d-glucosyl ester T4 B [76]
 66 Quadranoside VIII T4 B [76]
 67 Kajiichigoside F1 T4 B [76]
 68 2α,3β,23Trihydroxyurs-12,19-dien-28-oic acid 28-O-β-d-glucosyl ester T4 B [76]
 69 α-Amyrin T7 RB [91]
 70 2α,3β,23-Trihydroxy-urs-12-en-28-oic acid T34 L [35]
 71 2α-Hydroxyursolic acid

T34

T17

L

F

[35]

[115, 116]

 72 Ursolic acid T11 L [35]
 73 2α-Hydroxymicromeric acid T17 F [115, 116]
 74 Betulinic acid

T1

T11

T12

T4, T16, T17, T20, T39

T8

T25

T28

T36

B

L

B

B, L, S, R, F

B, L, S, R

SB

B

B

[55]

[35]

[99]

[23]

[23]

[129]

[132]

[140]

 75 Terminic acid T4 R, H [57, 62]
 76 Lupeol

T4

T25

T44

SB

SB

SB, R

[80]

[129]

[43]

 77 Monogynol A T12 B [99]
 78 Triterpenes

T25

T44

SB

R, SB

[129]

[133]

 79 Friedelin

T4

T7

T25

T34

F

RB

SB

SB

[83]

[93]

[129, 130]

[35]

 80 Maslinic lactone T1 H [56]
 81 Terminalin A T25 SB [129]
 82 Arjunaside A T4 B [68]
 83 Arjunaside B T4 B [68]
 84 Arjunaside C T4 B [68]
 85 Arjunaside D T4 B [68]
86 Arjunaside E T4 B [68]
Mono- (14) and sesqui- (4) terpendoids
 87 α-Pinene T9 L [13]
 88 Sabinene T9 L [13]
 89 Myrcene T9 L [13]
 90 β-Pinene T9 L [13]
 91 1,8-Cineole T9 L [13]
 92 Linalool T9 L [13]
 93 Menthone T9 L [13]
 94 γ-Terpineol T9 L [13]
 95 α-Terpineol T9 L [13]
 96 Limonene T9 L [13]
 97 Neral T9 L [13]
 98 Geraniol T9 L [13]
 99 Thymol T9 L [13]
 100 Isomenthone T9 L [13]
 101 β-Copaene T9 L [13]
 102 β-Caryophyllene T9 L [13]
 103 Caryophyllene T9 L [13]
 104 α-Humulene T9 L [13]
Hydrolysable (89) and condensed tannins (2)
 105 1,2,3,6-Tetra-O-galloyl-β-d-glucose T17 F [159]
 106 Gallotannin (1,2,3,4,6 penta galloyl glucose)

T4

T17

T19

T30

T45, T46

SB, L

F

F

R

L

[86]

[21, 118, 119]

[120]

[133]

[133]

 107 1,3,4,6-Tetra-O-galloyl-β-d-glucose T17 F [159]
 108 2,3,4,6-Tetra-O-galloyl-d-glucose

T3

T4

F

SB, L

[154]

[86]

 109 1,2,6-Tri-O-galloyl-β-d-glucose T31 R [101]
 110 Sanguiin H-1 T14 L [102]
 111 1,6-Di-O-galloyl-β-d-glucose

T3

T17

T40

F

F

B

[154]

[21, 119]

[41]

 112 1,3,6-Tri-O-galloyl-β-d-glucose

T3

T40

T19

T17

F

B

F

F

[154]

[41]

[120]

[159]

 113 Methyl 3,6-di-O-galloyl-β-d-glucoside T40 B [41]
 114 4,6 Bis hexahydroxydiphenyl-1-galloyl-glucose T4 SB, L [86]
 115 Sanguiin H-4 T14  L [18, 102]
 116 Corilagin

T3

T31

T16

T17

T19

T24

T32

F

R

L, B

F

F

F

L

[154]

[101]

[41, 106, 107]

[21, 118, 119, 159]

[120]

[126]

[135, 136]

 117 Tercatain

T16

T17

B, L

F

[41, 106, 107]

[159]

 118 1,3-Di-O-galloyl-β-d-glucose T17 F [159]
 119 2,3-O-(S)-HHDP-d-glucose

T3

T14

T4

T16

T40

T36

F

L

B

B, L

B

L

[154]

[102]

[104]

[41, 107]

[41]

[38]

 120 2,3-(S)-HHDP-6-O-galloyl-d-glucose

T3

T4

T40

T32

F

B

B

B

[154]

[104]

[41]

[137]

 121 3,6-Di-O-galloyl-d-glucose

T3

T40

T17

F

B

F

[154]

[41]

[159]

 122 3,4-Di-O-galloyl-d-glucose T3 F [154]
 123 6-O-galloyl-d-glucose T17 F [159]
 124 3,4,6-Tri-O-galloyl-d-glucose T17 F [159]
 125 Tellimagrandin I

T35

T17

L

F

[139]

[159]

 126 Gemin D T17 F [159]
 127 Arjunin

T4

T17

L

F

[65, 86]

[115]

 128 Punicalin

T3

T4

T14

T40

T16

T17

T28

T49

F

L, B

L

B

L

L, F

SB

L

[154]

[65, 86, 104]

[102]

[41]

[106, 107]

[21, 155]

[29]

[149]

 129 Casuarinin

T4

T16

T17

L, B

B

F

[88, 104]

[41]

[21, 118, 119]

 130 Casuariin T4 B [90, 104]
 131 Terchebulin

T3

T4

T7

T12

T17

T31

F

B

SB

B

F

W

[154]

[90, 104]

[92]

[100]

[21]

[134]

 132 Castalagin

T4

T16, T40

B

B

[90, 104]

[41]

 133 Grandinin T16, T40 B [41]
 134 Castalin T16, T40 B [41]
 135 α/β-Punicalagin

T3

T7

T4

T11

T12

T31

T14

T16

T17

T40

T19

T28

T32

T35

T36

T38

F

SB

B

L

B

R

L

B

L, F

B

F

SB

B

L

L

L

[154]

[92]

[104]

[35]

[100]

[101]

[18, 103]

[41]

[21, 106, 119, 155]

[41]

[120]

[29]

[137]

[139]

[38]

[39]

 136 1-α-O-galloylpunicalagin T14  L [18, 102, 103]
 137 6′-O-methyl neochebulagate T17 F [159]
 138 Dimethyl neochebulagate T17 F [159]
 139 Neochebulagic acid T17 F [159]
 140 Dimethyl 4′-epi-neochebulagate T17 F [159]
 141 Methyl chebulagate T17 F [159]
 142 Chebulagic acid

T3

T4

T8

T17

T16

T39

T20

T19

T32

T35

F

B, L, S

F, B, L, S

F, B, L, S, R

F, B, L, S, R

F, B, L, S, R

F, B, L, R

F

L

L

[154]

[23]

[23]

[23, 96]

[3, 4, 9, 21, 110]

[23]

[23]

[120]

[135, 136]

[139]

 143 Chebulinic acid

T3

T4, T8, T16, T20, T39

T17

T32

T35

F

F, B, L, S, R

F, B, L, S, R

L

L

[154]

[23]

[3, 4, 21, 110, 119, 155]

[23]

[110, 135, 139]

 144 Chebulanin

T34, T11

T17

L

F

[35]

[21, 119, 155, 159]

 145 1,3-Di-O-galloyl-2,4-chebuloyl-β-d-glucose T3 F [154]
 146 1,6-Di-O-galloyl-2,4-chebuloyl-β-d-glucose T17 F [155, 159]
 147 2-O-galloylpunicalin

T14

T40

T32

T49

L

B

B

L

[18]

[41]

[137]

[149]

 148 1-Desgalloyleugeniin

T14

T16

L

L

[102]

[107]

 149 Eugeniin T14  L [102]
 150 Rugosin A T14  L [102]
 151 1(α)-O-galloylpedunculagin T14  L [102]
 152 Praecoxin A T14  L [102]
 153 Calamansanin T14  L [102]
 154 Calamanin A T14  L [102]
 155 Calamanin B T14  L [102]
 156 Calamanin C T14  L [102]
 157 Terflavin C

T4

T14

T17

B

L

L

[104]

[103]

[21]

 158 Terflavin A

T16

T17

T32

L

F

B

[106, 107]

[21]

[137]

 159 Terflavin B

T16

T17

T32

L

L, F

B

[106, 107]

[21, 155]

[137]

 160 3-Methoxy-4-hydroxyphenol-1-O-β-d-(6′-O-galloyl)-glucoside T16 B [41]
 161 3,5-Di-methoxy-4-hydroxyphenol-1-O-β-d-(6′-O-galloyl)-glucoside T16 B [41]
 162 Acutissimin A T16 B [41]
 163 Eugenigrandin A T16 B [41]
 164 Catappanin A T16 B [41]
 165 Castamollinin T40 B [41]
 166 Tergallagin T16 L [106, 107]
 167 Geraniin T16 L [107]
 168 Granatin B T16 L [107]
 169 Gallotannic (tannic acid)

T17,T8

T38

F

L

[113]

[141]

 170 Chebulin T17 F [113, 114]
 171 Terchebin T17 F [113, 119]
 172 Neochebulinic acid

T3

T17

F

F

[154]

[21, 119, 155]

 173 Chebumeinin A T17 F [118]
 174 Chebumeinin B T17 F [118]
 175 Isoterchebulin T32 B [137]
 176 Punicacortein C

T3

T32

T17

F

B

F

[154]

[137]

[159]

 177 Punicacortein D T17 F [159]
 178 4,6-O-Isoterchebuloyl-d-glucose T32 B [137]
 179 Trigalloyl-β-d-glucose T35 L [139]
 180 Tetragalloyl-β-d-glucose T35 L [139]
 181 Pentagalloyl-β-d-glucose T35 L [139]
 182 1,2,3-Tri-O-galloyl-6-O-cinnamoyl-β-d-glucose T17 F [159]
 183 1,2,3,6-Tetra-O-galloyl-4-O-cinnamoyl-β-d-glucose T17 F [159]
 184 1,6-Di-O-galloyl-2-O-cinnamoyl-β-d-glucose T17 F [159]
 185 1,2-Di-O-galloyl-6-O-cinnamoyl-β-d-glucose T17 F [159]
 186 4-O-(2′′, 4′′-di-O-galloyl-α-l-rhamnosyl) ellagic acid T17 F [159]
 187 4-O-(4′′-O-galloyl-α-l-rhamnosyl) ellagic acid T17 F [159]
 188 4-O-(3′′, 4′′-di-O-galloyl-α-l-rhamnosyl) ellagic acid T17 F [159]
 189 1′-O-methyl neochebulanin T17 F [159]
 190 Dimethyl neochebulinate T17 F [159]
 191 Phyllanemblinin E T17 F [159]
 192 1′-O-methyl neochebulinate T17 F [159]
 193 Phyllanemblinin F T17 F [159]
 194 Procyanidin B-1 T16 B [41]
 195 3′-O-galloyl procyanidin B-2 T16 B [41]
Flavonoids (45)
 196 5,7,2′-Tri-O-methylflavanone4′-O-α-l-rhamnosyl-(1 → 4)-β-d-glucoside T1 R [52]
 197 Arjunone T4 B, F [83, 89]
 198 8-Methyl-5,7,2′,4′-tetramethoxy-flavanone 

T1

T39

R

B

[53]

[144]

 199 Naringin

T4

T8

T17

T39

T20

L, S, F

B, F

L, R, F

R, F

B, L, S, R

[23]

[23]

[23]

[23]

[23]

 200 Eriodictyol

T4, T8, T17, T20, T39

T16

B, L, S, R, F

L, S, R, F

[23]

[23]

 201 Hesperitin T24 F [122]
 202 Flavanone T24 F [122]
 203 Arjunolone (6,4-dihydroxy-7-methoxy flavone) T4 SB [64]
 204 Bicalein (5,6,7-trihydroxy flavone) T4 SB [64]
 205 Scutellarein

T4

T8, T17, T20

T16

T39

B, R

B, L, S, R, F

L, F

B, L, R, F

[23]

[23]

[23]

[23]

 206 Luteolin

T4

T8, T20

T17

T16

T39

T24

B, L

L, S

R, L

L

L, S, F

F

[23, 65]

[23]

[23]

[23]

[23]

[122]

 207 Apigenin

T4

T8, T16, T17, T20, T39

B, L, S, R, F

B, L, S, R, F

[23, 66]

[23]

 208 Isoorientin

T11

T4, T8, T17, T16, T20, T39

T35

T36

L

B, L, S, R, F

L

L

[35]

[23]

[139]

[38]

 209 Orientin

T11

T4

T8

T17

T16

T39

T20

T35

T36

L

L, F

B, S

B, L, S, R, F

L, R, F

B, S, F

L, S, F, R

L

L

[35]

[23]

[23]

[23]

[23]

[23]

[23]

[139]

[38]

 210 Isovitexin

T11

T4

T17

T16

T39

T20

T35

T36

L

L, F

L, R, F

L

S, F

L, S, F

L

L

[35]

[23]

[23]

[23, 105]

[23]

[23]

[139]

[38]

 211 Apigenin-6-C-(2″-O-galloyl)-β-d-glucoside T16 L [105]
 212 Apigenin-8-C-(2″-O-galloyl)-β-d-glucoside

T16

T34

L

L

[105]

[35]

 213 Vitexin

T4, T17, T20

T8

T16

T39

T35

T36

B, L, S, R, F

B, L, S, R

L, S, R, F

B, L, S, F

L

L

[23]

[23]

[23]

[23]

[139]

[38]

 214 Amentoflavone

T8

T17

T20

L, S

L, R, F

L

[23]

[23]

[23]

 215 Neosaponarin T36 L [38]
 216 (−)-Epicatechin T4 B [76]
 217 Epicatechin 

T4, T8, T17, T20, T39

T16

T34

B, L, S, R, F

L, S, R, F

SB

[23]

[23]

[35]

 218 Catechin

T34

T11

T4, T8, T16, T17, T20, T39

T44

SB

L

B, L, S, R, F

R

[35]

[35]

[23]

[133]

 219 Catechin–epicatechin T44 R [43]
 220 Catechin–epigallocatechin T44 R [43]
 221 Epigallocatechin T34 SB [35]
 222 (−)-Epicatechin-3-O-gallate T16 B [41]
 223 (−)-Epigallocatechin-3-O-gallate T16 B [41]
 224 Flavanol T24 F [122]
 225 Gallocatechin

T34

T24

SB

F

[35]

[126]

 226 Quercetin

T4

T8

T17

T16

T39

T20

T24

T49

B, L, R

R

S, R, F

L, S, F

L, B

F

F

L

[23]

[23]

[23]

[23]

[23, 142]

[23]

[124]

[124]

 227 Kaempferol

T4

T8

T16, T17

T20, T39

T24

B, L, S, R, F

B, L, S, F

B, L, S, R, F

L, S, R, F

F

[23, 66]

[23]

[23]

[23]

[122]

 228 Kaempferol-3-O-β-d-rutinoside

T4, T8, T17

T16

T39

T20

T36

B, L, S, R, F

L, S, F

L, R, F

L, S, R

L

[23]

[23]

[23]

[23]

[38]

 229 Afzelin (kaempferol 3-O-rhamnoside) T49 L [124]
 230 Rutin

T4, T16

T8

T17, T39

T20

T32

T36

B, L, S, F

L, S

B, L, S, R, F

L, S, F

L

L

[23]

[23]

[23]

[23]

[135, 136]

[38]

 231 Narcissin T32 L [135, 136]
 232 Quercetin-3,4′-di-O-glucoside

T4

T8

T16, T17, T20, T39

B, L, S, F

B, S, F

B, L, S, R, F

[23]

[23]

[23]

 233 Quercetin-7-O-rhamnoside T4 F [80]
 234 2-O-β-glucosyloxy-4,6,2′,4′-tetramethoxychalcone T1 R [53]
 235 Cerasidin T4 F [80]
 236 Genistein

T4

T8, T16, T17, T20, T39

B, L, S, R, F

B, L, S, R, F

[23, 80]

[23]

 237 Cyaniding T4 B [66]
 238 Pelargonidin T4 B [66]
 239 Leucocyanidin T4 B [80]
 240 7-Hydroxy-3′,4-(methylenedioxy)flavan T8 FR [12]
Lignan (27)
 241 Termilignan

T8

T39

FR

B

[12]

[144]

 242 Anolignan B

T8

T44

FR

R

[12]

[43, 151]

 243 Thannilignan T8 FR [12]
 244 Termilignan B T44 R [133]
 245 Ferulic acid dehydrodimer T24 F [125]
 246 (7S,8R,7′R,8′S)-4′-hydroxy-4-methoxy-7,7′-epoxylignan T48 SB [50]
 247 Meso-(rel7S,8R,7′R,8′S)-4,4′-dimethoxy-7,7′-epoxylignan T48 SB [50]
 248 4′-O-cinnamoyl cleomiscosin A T50 R [72]
 249 Diethylstilbestrol monosulphate T24 F [126]
 250 Terminaloside A T19 L [22]
 251 Terminaloside B T19 L [22]
 252 Terminaloside C T19 L [22]
 253 Terminaloside D T19 L [22]
 254 Terminaloside E T19 L [22]
 255 Terminaloside F T19 L [22]
 256 Terminaloside G T19 L [22]
 257 Terminaloside H T19 L [22]
 258 Terminaloside I T19 L [22]
 259 Terminaloside J T19 L [22]
 260 Terminaloside K T19 L [22]
 261 2-Epiterminaloside D T19 L [22]
 262 6-Epiterminaloside K T19 L [22]
 263 Terminaloside L T19 L [121]
 264 Terminaloside M T19 L [121]
 265 Terminaloside N T19 L [121]
 266 Terminaloside O T19 L [121]
 267 Terminaloside P T19 L [121]
Phenols and glycosides (52)
 268 Ellagic acid

T1

T7

T10, TM, TT

T12

T40

T4, T8, T20

T17

T16

T39

T24

T25

T31

T28, T32

T35

T42

T30, T44

T36, T45, T46

T48

T49

B

SB

SB

B

B

B, L, S, R, F

L, SB, R F

SB, L, R, F

B, L, S, R, F, H

F

B, R, Rl

B

H

L, F

R, SB

R

L

SB

L

[55]

[92, 127]

[14]

[100]

[41]

[23, 80, 83, 86]

[3, 9, 21, 23, 111, 119]

[14, 23, 41, 108, 144]

[23, 142]

[123]

[70, 127, 128]

[127, 134]

[128]

[37, 38]

[133]

[133]

[133]

[50]

[124]

 269 Methyl ellagic acid T4 B [90]
 270 3-O-methylellagic acid T33 SB [158]
 271 3,3′-Di-O-methylellagic acid

T28

T39

T48

SB

H,B

SB

[29]

[8, 9, 143, 144]

[50]

 272 3,3′-Di-O-methylellagic acid 4-mono glucoside T39 H [147, 148]
 273 Tetra-O-methyl ellagic acid T39 H [148]
 274 3,3′-Di-O-methylellagic acid 4-O-β-d-glucosyl-(1 → 4)-β-d-glucosyl-(1 → 2)-α-l-arabinoside T1 R [52]
 275 3,4,3′-Tri-O-methylflavellagic acid

T7

T12

T24

T25

T31

T28

T32

T39

B

B

F

L, B, R, Rl

B

SB, H

H, B

H

[126]

[100]

[126]

[26, 70, 127, 128]

[127]

[29, 128]

[128, 138]

[143, 148]

 276 3,3′,4-O-trimethyl-4′-O-β-d-glucosylellagic acid T28 SB [29]
 277 3,3′-Di-O-methyl ellagic acid 4′-O-β-d-xyloside T48 SB [50]
 278 3,4′-Di-O-methylellagic acid 3′-O-β-d-xyloside T48 SB [153]
 279 4′-O-galloy-3,3′-di-O-methylellagic acid 4-O-β-d-xyloside T48 SB [153]
 280 Flavogallonic acid

T7

T40

T31

T12

T36

SB

B

W

R

L

[92]

[41]

[134]

[101]

[38]

 281 Methyl (S)-flavogallonate T36 L [38]
 282 Vanillic acid 4-O-β-d-(6′-O-galloyl) glucoside T32 B [138]
 283 3-O-methylellagic acid 4′-O-α-l-rhamnoside

T4

T34

T33

B

SB

SB

[76]

[35]

[158]

 284 Eschweilenol C (ellagic acid 4-O-α-l-rhamnoside)

T12

T17

B

F

[100]

[164]

 285 3-O-methylellagic acid 4′-O-xyloside T31 R [101]
 286 Brevifolincarboxylic acid T35 L [139]
T17 F [159]
 287 Terflavin D T17 L [21]
 288 Gallic acid

T3

T4, T8, T20, T39

T10, TM, TT

T17

T16

T34

T12

T31

T40

T24

T30

T35

T36

T38

T42

T44

T45, T46

T48

T49

F

B, L, S, R, F

SB

SB, F, R, L

SB, F, R, L

L

B

R, W

B

F

R

L

L

L

R, SB

R

L

SB

L

[154]

[23, 80, 83, 86]

[14]

[14, 21, 23, 118, 119]

[14, 23, 41, 108]

[35]

[100]

[101, 134]

[41]

[123, 125]

[133]

[139]

[38]

[141]

[133]

[133]

[133]

[50]

[124]

289 Phyllemblin (ethyl gallate isomers1 progallin A)

T4

T8

T24

T28

T36

B

F

F

SB

L

[86]

[96, 113]

[126]

[29]

[38]

290 Monogalloyl glucose

T3

T8

T17

T31

F

F

F

R

[154]

[113]

[21]

[101]

 291 Methyl gallate

T14

T8

T32

T36

T48

T49

L

F

L

L

SB

L

[18]

[113]

[135, 136]

[38]

[50]

[124]

 292 Shikimic acid T32 L [135, 136]
 293 5-O-galloyl-(−)-shikimic acid

T3

T17

F

F

[118]

[154, 159]

 294 4-O-galloyl-(−)-shikimic acid T17 F [159]
 295 3,5-Di-O-galloyl-(−)-shikimic acid T3 F [154]
 296 Digallic acid T17 F [159]
 297 Ethyl gallate isomers2 T24 F [126]
 298 Ethyl gallate isomers3 T24 F [126]
 299 Dimethyl gallic acid T35 L [139]
 300 Chebulic acid

T3

T17

T24

T35

F

F

F

L

[154]

[4, 9, 112, 119, 159]

[125, 126]

[139]

 301 6′-O-methyl chebulate T17 F [159]
 302 7′-O-methyl chebulate T17 F [159]
 303 Chebulic acid trimethyl ester T32 L [135, 136]
 304 Terminalin T38 L [39]
 305 Decarboxyellagic acid T3 F [154]
 306 3-O-galloyl-d-glucose T3 F [154]
 307 6-O-galloyl-d-glucose

T3

T17

F

F

[154]

[159]

 308 Vanillic acid

T4, T8, T20, T39

T17

T16

T44

B, L, S, R, F

B

S, R, B, F

R

[23]

[23, 117]

[23]

[43]

 309 Benzoic acid

T44

T24

R

F

[43]

[122]

 310 Hydrocinnamic acid T44 R [43]
 311 Gentisic acid T16 L [108]
 312 Protocatechuic acid T4, T8, T16, T17, T20, T39 B, L, S, R, F [23]
 313 2,3-Di-hydroxyphenyl β-d-glucosiduronic acid T24 F [125]
 314 Quinic acid

T4, T8, T16, T17, T20, T39

T24

B, L, S, R, F

[23]

[125]

 315 p-Coumaric acid

T17

T44

WP

R

[117]

[43]

 316 Caffeic acid

T4, T8

T17

T16

T39

T20

T44

L, S

L, S, R

L

B, L, S, R, F

B

R

[23]

[23]

[23]

[23]

[23]

[43]

 317 Chlorogenic acid

T4

T17

T16, T39

T20

L, S

S, R, F, L

L

B

[23]

[23]

[23]

[23]

 318 Ferulic acid

T4

T8, T17, T20, T39

T16

B, L, S, F

B, L, S, R, F

L, S, R

[23]

[23]

[23]

 319 Sinapic acid

T4, T16, T20, T39

T8

T17

B, L, S, R, F

S, R, F

B, S, R, F

[23]

[23]

[23]

Steroids (8), polyols (9) and esters (6)
 320 β-Sitosterol

T1

T4

T8

T12

T16

T48

T25

T36

T39

T44

B, H

S, F

F

F

B, SB

H

H

SB

B

H, SB, R

[55, 56]

[57, 83]

[96, 113]

[99]

[128]

[128]

[129]

[140]

[147, 148]

[43, 133, 152]

 321 β-Sitosterol-3-acetate T44 SB, R [43]
 322 β-Sitosteryl palmitate

T16

T25, T31

SB, H

L,F

[128]

[128]

 323 Stigmasterol 3-O-β-d-glucoside

T4

T33

F

SB

[80]

[158]

 324 Stigmasterol

T12

T25

T33

T44

B

SB

SB

RB

[99]

[129]

[158]

[133, 152]

 325 Stigma-4-ene-3-one T44 RB [43]
 326 16,17-Dihydroneridienone 3O-β-d-glucosyl-(1 → 6)-O-β-d-galactoside T4 R [59]
 327 Cannogenol 3-O-β-d-galactosyl-(1 → 4)-O-α-l-rhamno-side T8 Se [94]
 328 2-Hexanol T9 L [13]
 329 Octanol T9 L [13]
 330 Methoxycarbonyloxymethyl methylcarbonate T24 F [125]
 331 Ribonolactone T24 F [125]
 332 Apionic acid T24 F [125]
 333 Ascorbic acid T24 F [125]
 334 Gluconolactone T24 F [125]
 335 Glucohepatonic acid-1,4-lactone T24 F [125]
 336 Galacturonic acid T44 R [43]
 337 Geranyl formate T9 L [13]
 338 Citronellyl acetate T9 L [13]
 339 Geranyl acetate T9 L [13]
 340 Geranyl tiglate T9 L [13]
 341 Laxiflorin T31 RB [127]
 342 (1S,5R)-4-oxo-6,8-dioxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid T24 F [125]
Others (26)
 343 Glucuronic acid T24 F [125]
 344 Coumarin T45 L [133]
 345 Eujavonic acid T24 F [125]
 346 Purine T24 F [125]
 347 5-(4-Hydroxy-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (gemfibrozil M1) T24 F [125]
 348 p-Hydroxytiaprofenic acid T24 F [125]
 349 Cis-polyisoprene T32 L [135]
 350 Arachidic acid T17 F [113]
 351 Behenic acid T8, T17 F [113]
 352 Arjunaphthanoloside T4 SB [87]
 353 Resveratrol (3′,4,5′-trihydroxystilbene)

T24

T44

F

R

[126]

[43]

 354 Resveratrol glucoside (piceid)

T24

T44

F

RB

[126]

[152]

 355 Resveratrol-β-d-glucoside T44 RB [152]
 356 Combretastatin T24 F [126]
 357 Combretastatin A1 T24 F [126]
 358 (Z)-Stilbene T44 R [133]
 359 (E)-Stilbene T44 R [133]
 360 3′5′-Dihydroxy-4-(2-hydroxyethoxy) resveratrol-3-O-β-rutinoside T44 R, RB [43, 152]
 361 Resveratrol-3-β-rutinoside glycoside T44 R, RB [43, 152]
 362 1,4-Cineole T9 L [13]
 363 Terpinen-4-ol T9 L [13]
 364 Terminalianone T12 B [98]
 365 Termicalcicolanone A T15 WP [19]
 366 Termicalcicolanone B T15 WP [19]
 367 Mangiferin

T4

T8

T17

T16

T39

T20

B, S, F

B, R, F

B, L, S, R, F

L, R, F

B, L, S, F

L, S, R

[23]

[23]

[23]

[23]

[23]

[23]

 368 Benzoyl-β-d-(4′ → 10″geranilanoxy)-pyranoside T8 F [160]

R root, SB stem bark, B bark, F fruit, S stem, H heartwood, RB root bark, Rl rootlet, Se seed, FR fruit rind, WP whole plant, T1T50 plants from Table 1, TM T. manii, TT T. tomentosa