Table 2.
The chemical constituents isolated from G. littoralis.
| Classes | Compound name | Part of plant | References |
|---|---|---|---|
| Phenylpropanoids | (S)-Phenyllactic acid (1) | Dried roots | [19] |
| (S)-Phenyllactic acid methyl ester (2) | Dried roots | [19] | |
| Caffeic acid (3) | Dried root, dried underground parts | [38, 39] | |
| Chlorogenic acid (4) | Dried root, dried underground parts | [38, 39] | |
| Ferulic acid (5) | Dried root, dried underground parts | [38–40] | |
| 3-Methoxy-4-β-D-glucopyranosyloxypropiophenone (6) | Dried underground parts, dried roots bark | [39, 41] | |
| 4-[β-D-Apiofuranosyl-(1⟶6)-β-D-glucopyranosyloxy]-3-methoxypropiophenone (7) | Dried root, dried underground parts | [39, 42] | |
| 2-Methoxy-4-(1-propionyl) phenyl β-D-glucopyranoside (8) | Fresh root and rhizome | [43] | |
| Syringin (9) | Dried root, dried roots bark | [41, 44] | |
| Glehnilate (10) | Dried underground parts | [45] | |
|
| |||
| Coumarins | Umbelliferone (11) | Dried roots, dried roots and rhizomes | [46–48] |
| Esculetin (12) | Dried root | [49] | |
| Umbelliferone 7-O-β-D-glucopyranoside (13) | Fresh fruit, dried root | [38, 50] | |
| Scopoletin (14) | Dried root and rhizome, dried root, dried underground parts | [38, 39, 46–48, 51, 52] | |
| Scopolin (15) | Dried root | [38, 49] | |
| Scopoletin-apiosyl-glucoside (16) | Dried root | [38] | |
| Osthenol 7-O-β-D-gentibioside (17) | Fresh fruit | [50] | |
| 6-(3,3-Dimethylallyl)-7-hydroxycoumarin (18) | Dried root | [38] | |
| 6-(3,3-Dimethylallyl)-7-hydroxycoumarin-apiosyl-glucoside (19) | Dried root | [38] | |
| 6-(3,3-Dimethylallyl)-7-hydroxycoumarin-diglucoside (20) | Dried root | [38] | |
| 7-O-(3,3-Dimethylallyl) scopoletin (21) | Dried root and rhizome | [52] | |
| (S)-Peucedanol 7-O-β-D-glucopyranoside (22) | Fresh roots and rhizomes | [53] | |
| (S)-Peucedanol 3′-O-β-D-glucopyranoside (23) | Fresh roots and rhizomes | [53] | |
| (R)-Peucedanol 3′-O-β-D-glucopyranoside (24) | Fresh roots and rhizomes | [53] | |
| (S)-7-O-Methylpeucedanol 3′-O-β-D-glucopyranoside (25) | Fresh roots and rhizomes | [53] | |
| (S)-Peucedanol 3′-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (26) | Fresh roots and rhizomes | [53] | |
| (S)-7-O-Methylpeucedanol 3′-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (27) | Fresh roots and rhizomes | [53] | |
| (+)-cis-(3′S,4′S)-Diisobutyrylkhellactone (28) | Whole plants | [54] | |
| 3′-Senecioyl-4′-acetylkhellactone (29) | Whole plants | [54] | |
| 3′-Isovaleryl-4′-acetylkhellactone (30) | Whole plants | [54] | |
| 3′,4′-Disenecioylkhellactone (31) | Whole plants | [54] | |
| 3′-Isovaleryl-4′-senecioylkhellactone (32) | Whole plants | [54] | |
| 3′,4′-Diisobutyrylkhellactone (33) | Whole plants | [54] | |
| Marmesin (34) | Dried root and rhizome | [52] | |
| Rutaretin (35) | Dried root | [38] | |
| Marmesin 4′-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (36) | Fresh roots and rhizomes | [53] | |
| Marmesinin (37) | Fresh and dried roots, dried underground parts, fresh fruit | [39, 50, 53] | |
| Leptophyllin (38) | Dried root | [38] | |
| (3′R)-Hydroxymarmesin 4′-O-β-D-glucopyranoside (39) | Fresh roots and rhizomes, dried roots and rhizomes, fresh fruit | [39, 50, 53] | |
| Oxymarmesinin 5′-O-β-D-glucopyranoside (40) | Fresh fruit | [50] | |
| Leptophyllin-2-glucoside (41) | Dried root | [21] | |
| Oxymarmesin 5′-O-β-D-glucopyranoside (42) | Fresh roots and rhizomes, dried underground parts, fresh fruit | [43, 50] | |
| Psoralen (43) | Dried root, dried underground parts, sliced roots, dried root and rhizome | [38, 39, 51, 52, 55] | |
| Xanthotoxol (44) | Dried root, dried underground parts, dried root and rhizome | [38, 39, 52] | |
| Xanthotoxin (45) | Dried root, sliced roots, dried root and rhizome | [38, 40, 42, 48, 51, 52, 55] | |
| Xanthotoxol 8-O-β-D-glucopyranoside (46) | Fresh fruit | [50] | |
| Xanthotoxol-diglucoside (47) | Dried root | [38] | |
| Xanthotoxol-triglucoside (48) | Dried root | [38] | |
| 8-Methoxy-5-hydroxypsoralen (49) | Dried root | [38] | |
| Bergapten (50) | Dried root, dried root and rhizomes, sliced roots | [38, 40, 47, 48, 51, 52, 55] | |
| 5-Methoxy-8-hydroxypsoralen (51) | Dried root | [38] | |
| Isoimpinellin (52) | Dried root | [38] | |
| 8-Methoxy-5-hydroxypsoralen-glucopyranoside (53) | Dried root | [38] | |
| Bergaptol5-O-β-D-gentiobioside (54) | Dried root, dried underground parts | [39, 56] | |
| Imperatorin (55) | Dried root, sliced roots, dried root, and rhizomes | [38, 42, 51, 52, 55] | |
| 8-(2-Hydroxy-3-methylbut-3-enoxy)-psoralen (56) | Dried root | [38] | |
| 4″-Hydroxyimperatorin (57) | Dried root | [38] | |
| 8-Geranyloxypsoralen (58) | Dried roots and rhizomes, fresh roots and rhizomes | [43, 52] | |
| 4″-Hydroxyrmyperatorin 4″-O-β-D-glucopyranoside (59) | Fresh roots and rhizomes, dried underground parts | [39, 53] | |
| 5″-Hydroxyimperatorin 5″-O-β-D-glucopyranoside (60) | Fresh roots and rhizomes | [53] | |
| Prangenin (61) | Dried root | [38] | |
| 8-(1,1-Dimethylallyl)-5-hydroxypsorolen (62) | Dried root and rhizome | [52] | |
| Alloisoimperatorin (63) | Dried roots and rhizomes | [52] | |
| Byak-angelicol (64) | Dried root | [38] | |
| Byak-angelicin (65) | Dried root | [38] | |
| Phellopterin (66) | Dried root | [38, 57, 58] | |
| Isoimperatorin (67) | Dried root, dried underground parts, sliced roots, dried roots and rhizome | [38, 39, 42, 46, 51, 52, 55, 59] | |
| Cnidilin (68) | Dried root and rhizome, dried root | [38, 40, 52] | |
| Isooxypeucedanin (69) | Dried root | [38] | |
| Pabulenol (70) | Dried root | [38] | |
| Oxypeucedanin hydrate (71) | Dried root | [38] | |
| Oxypeucedanin (72) | Dried root | [38] | |
| 8-[(2E,5E)-7-Hydroxy-3,7-dimethylocta-2,5-dieny-loxy] psoralen (73) | Fresh roots and rhizomes | [43] | |
| Bergaptin (74) | Dried roots and rhizomes | [52] | |
| 8-[(2E)-6-Oxo-3,7-dimethyloct-2-enyloxy] psoralen (75) | Fresh roots and rhizomes | [43] | |
| Demethylsuberosin (76) | Sliced roots | [55] | |
|
| |||
| Lignanoids | (-)-Secoisolariciresinol (77) | Dried underground parts | [39] |
| (-)-Secoisolariciresinol 4-O-β-D-glucopyranoside (78) | Dried root, dried underground parts | [39, 49] | |
| Glehlinoside G (79) | Dried root | [64] | |
| Glehlinoside F (80) | Dried root | [61] | |
| Glehlinoside E (81) | Dried root | [61] | |
| Glehlinoside A (82) | Dried underground parts | [39] | |
| Glehlinoside B (83) | Dried underground parts | [39] | |
| Glehlinoside C (84) | Dried root, dried underground parts | [39, 49] | |
| Citrusin A (85) | Dried underground parts | [39, 62] | |
| Glehlinosides D (86) | Dried root | [63] | |
| Glehlinosides H (87) | Dried root | [64] | |
| 3-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy] propyl-β-D-glucopyranoside (88) | Dried root | [49] | |
| Glehlinosides I (89) | Dried root | [64] | |
| Glehlinoside J (90) | Dried root | [49, 64] | |
| 2,3E-2,3-Dihydro-2-(3′-methoxy-4′-hydroxyphenyl)-3-hydroxymethyl-5-(3″-hydroxypropeyl)-7-O-β-D-glucopyranosyl-1-benzo[b] furan (91) | Dried root | [49] | |
| (7R,8S)-dehydrodiconiferylalcohol-4,9-di-O-β-D-glucopyranoside (92) | Dried root | [56, 60] | |
|
| |||
| Flavonoids | Quercetin (93) | Dried underground parts | [39] |
| Isoquercetin (94) | Dried underground parts | [39] | |
| Rutin (95) | Dried underground parts | [39] | |
|
| |||
| Organic acids and derivatives | Salicylic acid (96) | Dried roots | [19, 40] |
| Vanillic acid (97) | Dried root, dried underground parts | [38–40] | |
| 4-O-β-D-Glucopyranosyl vanillic acid (98) | Dried root | [42] | |
| Vanillic acid 4-O-β-D-glucopyranoside (99) | Dried root | [44] | |
| Protocatechuic acid methyl ester (100) | Dried root | [49] | |
| 1-O-Vanilloyl-β-D-glucose (101) | Dried root | [42] | |
| Vanillic acid 1-O-[β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside] ester (102) | Dried root | [19, 42] | |
| Dibutyl phthalate (103) | Dried roots | [19] | |
| Tetracosanoic acid (104) | Dried roots of three-year-old | [65] | |
| 9-Hydroxystearic acid (105) | Dried roots | [19] | |
| Glehlinosiden (106) | Dried roots bark | [41] | |
| Linoleic acid (107) | Dried root and rhizome | [51] | |
| Nonadecanoic acid (108) | Dried roots of three-year-old | [65] | |
| 1-Linoloyl-3-palmitoylglycerol (109) | Dried roots | [46] | |
|
| |||
| Terpenoids | (−)-Angelicoidenol [(2R,5S)-bornane-2,5-diol] 2-O-β-D-glucopyranoside (110) | Fresh roots and rhizomes | [66] |
| (−)-Angelicoidenol 2-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (111) | Fresh roots and rhizomes | [66] | |
| (2R,6S)-Bornane-2,6-diol 2-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (112) | Fresh roots and rhizomes | [66] | |
| (4R)-p-Menth-1-ene-7,8-diol 8-O-β-D-glucopyranoside (113) | Fresh fruit | [50] | |
| (4R)-p-Menth-1-ene-7,8-diol 8-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (114) | Fresh roots and rhizomes | [66] | |
| trans-p-Menth-2-ene-1,7,8-triol (115) | Fresh fruit | [50] | |
| cis-p-Menth-2-ene-1,7,8-triol (116) | Fresh fruit | [50] | |
| (2R)-Bornane-2,9-diol 2-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (117) | Fresh roots and rhizomes | [66] | |
| (+)-Angelicoidenol [(2S,5R)-bornane-2,5-diol] 2-O-β-D-glucopyranoside (118) | Fresh roots and rhizomes | [66] | |
| trans-p-Menth-2-ene-1α,2β,8-triol (119) | Fresh fruit | [50] | |
| (4S)-p-Menth-1-ene-7,8-diol 8-O-β-D-apiofuranosyl-(1⟶6)-β-D-glucopyranoside (120) | Fresh roots and rhizomes | [66] | |
| (5β,10α)-Lasidiol angelate (121) | Dried root | [47] | |
| Botulin (122) | Dried root | [59] | |
| Lupeol (123) | Dried root | [59] | |
|
| |||
| Polyacetylenes | Falcarindiol (124) | Dried root, sliced roots, dried root, and rhizome | [19, 42, 46, 51, 55, 67] |
| (3R,9Z)-Heptadeca-1,9-dien-4,6-diyn-3-ol (125) | Dried roots | [19] | |
| (8E)-1,8-Heptadecadiene-4,6-diyne-3,10-diol (126) | Dried root, dried root and rhizome | [19, 40, 42, 51, 59] | |
| (3S,9Z)-Heptadeca-1,9-dien-4,6-diyn-3-ol (127) | Dried root, dried root and rhizome | [42, 46, 47, 51, 59] | |
| Ginsenoyne K (128) | Dried root | [42] | |
| (10E)1,10-Heptadecadiene-4,6-diyne-3,8,9-triol (129) | Dried root | [67] | |
| Falcaindiol (130) | Air- dried plant | [68, 69] | |
| Panaxydiol (131) | Air- dried plant | [69] | |
| (9Z)1,9-Heptadecadiene-4,6-diyne-3,8,11-triol (132) | Dried root | [67] | |
|
| |||
| Steroids | β-Sitosterol (133) | Dried roots | [42, 46, 59] |
| Daucosterol (134) | Dried root | [59] | |
| Stigmasterol (135) | Dried roots of three-year-old | [65] | |
| Cerevisterol (136) | Dried roots of three-year-old | [65] | |
|
| |||
| Nitrogen compounds | (3S)-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (137) | Dried roots | [19] |
| (1S,3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (138) | Dried roots | [19] | |
| (1R,3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (139) | Dried roots | [19] | |
| Uridine (140) | Dried underground parts | [39] | |
| Adenosine (141) | Dried root, dried underground parts, fresh fruit | [38, 39, 42, 50] | |
| 9,9a-Dihydro-naphtho [2, 3-c] isoxazol-3(1H)-one (142) | Root | [70] | |
| Arginine (143) | Dried roots | [71] | |
| 5′-Methylthioadenosine (144) | Dried roots | [72] | |
| L-Tryptophan (145) | Dried roots | [72] | |
|
| |||
| Other chemical constituents | Catechol (146) | Dried roots | [19] |
| 4-Hydroxyphenethyl alcohol (147) | Dried roots | [19] | |
| Icariside F2 (148) | Dried root, fresh fruit | [42, 44, 50] | |
| Icariside D (149) | Dried root | [44] | |
| Benzyl β-D-glucopyranoside (150) | Fresh fruit | [50] | |
| Phenethyl β-D-glucopyranoside (151) | Fresh fruit | [50] | |
| 1-β-D-Glucosyloxy-2-(3-methoxy-4-hydroxyphenyl) propane-1,3-diol (152) | Air-dried plant | [68] | |
| 2-Methyl-3-buten-2-ol β-D-apiofuranosyl-(1⟶6)- β-D-glucopyranoside (153) | Fresh root and rhizome | [43] | |
| 2-Methyl-3-buten-2-ol β-D-glucopyranoside (154) | Fresh fruit | [50] | |
| Isopropyl β-D-glucopyranoside (155) | Fresh fruit | [50] | |
| Ethyl β-D-glucopyranoside (156) | Fresh fruit | [50] | |
| Butane-2,3-diol 2-O-β-D-glucopyranoside (157) | Fresh fruit | [50] | |
| Isopropyl β-D-apiofranosyl-(1⟶6)-β-D-glucopyranoside (158) | Fresh fruit | [50] | |
| 3,7-Dimethyloct-3(10)-ene-1,2,6,7-tetrol (159) | Fresh fruit | [50] | |
| (2S,6Z)-3,7-Di-methyloct-3(10)-ene-1,2,6,7-tetrol 1-O-β-D-glucopyranoside (160) | Fresh fruit | [50] | |
| 6-Carboxyethyl-7-methoxy-5-hydroxybenzofuran 5-O-β-D-glucopyranoside (161) | Fresh fruit | [50] | |
| Cnidioside A (162) | Fresh root and rhizome | [43] | |
| Sec-O-glucosylhamaudol (163) | Dried root | [49] | |
| Corchoionoside A (164) | Fresh fruit | [50] | |
| 1,2-Di-O-vanilloyl-β-D-glucopyranoside (165) | Dried roots | [5] | |
| 2-Deoxy-D-ribitol (166) | Fresh fruit | [50] | |
| (3R)-2-Hydroxymethylbutane-1,2,3,4-tetrol (167) | Fresh fruit | [50] | |
| D-Threitol (168) | Fresh fruit | [50] | |
| Erythritol (169) | Fresh fruit | [50] | |
| n-Butyl α-D-fructofuranoside (170) | Dried root | [43] | |
| 5-Methoxyfurfural (171) | Dried roots of three-year-old | [65] | |
| (2E,4E)-Deca-2,4-dienal (172) | Dried roots | [73] | |
| (E)-Oct-2-en-1-ol (173) | Dried roots | [73] | |
| 1,6-Di-O-vanilloyl-β-D-glucopyranoside (174) | Dried roots | [5] | |