Table 1.
Chemical constituents of Andrographis paniculata: ent-labdane diterpenoids, flavonoids, and other substances.
| Chemical Substances | Parts * | References |
|---|---|---|
| (13R,14R) 3,13,14,19-tetrahydroxy-ent-labda-8(17),11-dien-16,16-olide | LV | [39] |
| 12-epi-14-deoxy-12-methoxyandrographolide | AP AP AP |
[21] [40] 13] |
| 12-hydroxyandrographolide | AP | [40] |
| 13,14,15,16-tetranor-ent-labda-8(17)-ene-3,12,19-triol | AP | [41] |
| 14-deoxy-11-hydroxyandrographolide | AP | [42] |
| 14-deoxy 11,12-didehydroandrographolide | WP LV AP LV AP AP LV AP AP AP LV AP AP |
[43] [44] [41] [45] [46] [21] [13] [47] [48] [40] [49] [42] [50] |
| 14-deoxy-11,12-didehydroandrographiside | AP AP LV AP AP |
[21] [41] [13] [51] [42] |
| 14-deoxy-11,12-dihydroandrographiside | AP | [40] |
| 14-deoxy-11,12-dihydroandrographolide | LV, ST LV WP WP |
[37] [52] [53] [34] |
| 14-deoxy-11,14-didehydroandrographolide | AP | [54] |
| 14-deoxy-11-hydroxyandrographiside | AP | [42] |
| 14-deoxy-11-hydroandrographolide | LV | [37] |
| 14-deoxy-11-hydroxyandrographolide | AP AP WP AP |
[21] [13] [53] [40] |
| 14-deoxy-11-hydroxy-ent-labda-8(17),12-diene-16,15-olide | LV | [37] |
| 14-deoxy-11-oxoandrographolide | WP LV AP AP AP |
[43] [45] [46] [40] [42] |
| 14-deoxy-12-hydroxyandrographolide | AP AP LV AP |
[21] [13] [52] [40] |
| 14-deoxy-12-methoxyandrographolide | LV AP AP AP WP |
[45] [21] [13] [40] [34] |
| 14-deoxy-14,15-didehydroandrographolide | AP | [54] |
| 14-deoxy-15-isopropylidene-11,12 didehydroandrographolide | LV WP AP |
[13] [53] [47] |
| 14-deoxy-15-methoxyandrographolide | AP | [55] |
| 14-deoxy-17-hydroxyandrographolide | AP | [40] |
| 14-deoxy-8,17-epoxy-andrographolide | AP | [42] |
| 14-deoxyandrographiside | LV AP AP LV |
[37] [46] [42] [39] |
| 14-deoxyandrographolide | CL WP AP LV AP AP LV LV LV WP AP AP AP WP LV |
[56] [43] [41] [45] [46] [21] [13] [44] [52] [53] [48] [40] [42] [34] [39] |
| 14-deoxyandrographolide-19-β-glucoside | N/A | [57] |
| 14-deoxyandrographoside | N/A | [57] |
| 14-epi-andrographolide | AP LV |
[21] [13] |
| 15-methoxy-3,19-dihydroxy-8(17)11,13-ent-labda-trien-16,15-olide | AP | [58] |
| 15-spiro diterpenoids dimer bisandrographolide G | AP | [59] |
| 19-[(β-d-glucopyranosyl)oxy]-19-oxo-ent-labda-8(17),13-dien-16,15-olide | AP | [41] |
| 19-hydroxy-3-oxo-ent-labda-8(17),11,13-trien-16,15-olide | AP | [41] |
| 19-hydroxy-ent-labda-8(17),13-dien-15,16-olide | AP | [41] |
| 19-nor andrographolide A-C | AP | [60] |
| 19-O-β-d-glucopyranosyl-ent-labda-8(17),13-dien-15,16,19-triol | AP | [51] |
| 19-O-[β-d-apiofuranosyl-β-d-glucopyranosyl]-3,14-dideoxyandrographolide | AP | [50] |
| 19-O-[β-d-apiofuranosyl(1→2)-β-d-glucopyranoyl]-3,14-dideoxyandrographolide | AP | [40] |
| 19-O-β-d-glucopyranosyl-ent-labda-8(17),13-dien-15,16,19-triol | AP AP |
[42] [50] |
| 19-O-[β-d-apiofuranosyl(1→2)-β-d-glucopyranoyl]-3,14-dideoxyandrographolide | AP | [40] |
| 21-nor-3,19-isopropylidine-14-deoxy-ent-labda-8(17),13-diene-16,15-olide | LV | [52] |
| 3-O-β-d-glucopyranosylandrographolide | AP | [40] |
| 3,13,14,19-tetrahydroxy-ent-labda-8(17),11-dien-16,15-olide | LV | [39] |
| 3,14-deoxy-17β-hydroxy andrographolide | AP | [42] |
| 3,14-dideoxyandrographolide | AP AP |
[41] [46] |
| 3,15,19-trihydroxy-ent-labda-8(17),13-dien-16-oic acid | AP | [41] |
| 3,18,19-trihydroxy-ent-labda-8(17),13-dien-16,15-olide | AP LV |
[41] [37] |
| 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid | AP LV |
[41] [37] |
| 3,19-dihydroxy-15-methoxy-ent-labda-8(17),11,13-trien-16,15-olide | AP | [41] |
| 3,19-dihydroxy-ent-labda-8(17),12-dien-16,15-olide | AP AP |
[42] [41] |
| 3,19-isopropylidene-14-deoxy-ent-labda-8(17),13-diene-16,15-olide | LV | [39] |
| 3-deoxy-andrographoside | AP | [55] |
| 3-O-β-d-glcopyranosyl 14,19-dideoxyandrographolide | AP | [40] |
| 3-O-β-d-glucopyranosylandrographolide | AP | [40] |
| 3-O-β-d-glucosyl-14-deoxy-11,12-didehydroandrographiside | AP | [61] |
| 3-O-β-d-glucosyl-14-deoxyandrographiside | AP | [62] |
| 3-oxo-14-deoxy-11,12-didehydroandrographolide | AP | [58] |
| 3-oxo-14-deoxyandrographolide | AP | [58] |
| 3-O-β-d-glucopyranosyl-14,19-dideoxyandrographolide | AP | [40] |
| 3-O-β-d-glucopyranosylandrographolide | AP | [42] |
| 3-O-β-d-glucosyl-14-deoxy-11,12-didehydroandrographiside | AP | [62] |
| 3-O-β-d-glucosyl-14-deoxyandrographiside | AP | [62] |
| 5-hydroxy-7,20,60-trimethoxyflavone | RT | [13] |
| 6ʹ-acetylneoandrographolide | AP AP |
[21] [42] |
| 8,17-epoxy-14-deoxyandrographolide | AP | [40] |
| 8-methylandrographolide | LV | [39] |
| 8α-methoxyl-14-deoxy-17β-hydroxyandrographolide | AP | [63] |
| Andrograpanin | CL LV LV LV LV AP AP RT |
[56] [45] [64] [65] [44] [48] [40] [66] |
| Andrographane | LV | [13] |
| Andrographatoside | AP | [40] |
| Andrographic acid | N/A | [67] |
| Andrographidine A | RT N/A RT AP |
[68] [67] [66] [35] |
| Andrographidine B | RT RT |
[68] [66] |
| Andrographidine C | RT RT AP |
[68] [66] [35] |
| Andrographidine D | RT | [68] |
| Andrographidine E | RT | [68] |
| Andrographidine F | RT | [68] |
| Andrographidoids A–E | RT | [69] |
| Andrographiside | AP AP AP AP AP AP AP |
[41] [46] [21] [51] [40] [42] [50] |
| Andrographolactone | LV, ST AP |
[37] [70] |
| Andrographolide | N/A LV LV CL N/A AP AP AP AP AP WP LV WP AP AP AP LV LV AP WP LV RT |
[18] [45] [52] [56] [71] [41] [54] [72] [46] [21] [13] [44] [53] [47] [48] [40] [49] [73] [42] [34] [39] [50] |
| Andrographone | LV | [13] |
| Andrographoside | N/A WP LV |
[57] [53] [39] |
| Andropaniculoside A | WP | [34] |
| Andropaniculosin A | WP | [34] |
| Andropanioside A–B | AP | [51] |
| Andropanolide | LV LV AP |
[45] [44] [51] |
| Andropanoside | AP | [40] |
| Bisandrographolide A | AP | [21] |
| Bisandrographolide B | AP AP |
[21] [40] |
| Bisandrographolide C | AP AP |
[21] [40] |
| Bisandrographolide D | AP | [21] |
| Bisandrographolide ether | AP | [48] |
| Dehydroandrographolide | AP | [50] |
| Deoxyandrographiside | AP AP WP AP |
[21] [41] [34] [50] |
| Deoxyandrographolide | LV | [73] |
| Deoxyandrographolide-19β-d-glucoside | LV | [73] |
| Dihydroxyl dimethyl 19-[(β-d-glucopyranosyl)oxy]-19-oxo-ent-labda-8(17),13-dien-16,15-olide | LV, ST | [37] |
| ent-labda-8(17),13-dien-15,16,19-triol | AP | [41] |
| Isoandrographiside | AP | [42] |
| Isoandrographolide | AP AP LV AP AP AP WP |
[54] [21] [44] [47] [40] [42] [34] |
| Methyl methoxy 14-deoxyandrographiside | LV, ST | [37] |
| Methyl methoxy andrographolide | LV, ST | [37] |
| Methyl methoxy neoandrographolide | LV, ST | [37] |
| Neoandrographolide | CL AP LV LV AP AP AP AP AP AP LV LV AP AP LV AP WP LV RT |
[56] [74] [37] [45] [54] [72] [46] [21] [13] [51] [44] [52] [47] [40] [49] [42] [34] [39] [50] |
| Panicolin | RT | [13] |
| Paniculide A | CL | [75] |
| Paniculide B | CL | [75] |
| Paniculide C | CL | [75] |
| Propyl neoandrographolide dimer | LV | [37] |
| Tetraacetate neoandrographolide | LV | [49] |
| Wightiolide | RT AP |
[66] [42] |
| Flavonoids | ||
| onysilin | WP | [34] |
| 5-hydroxy-7,8-dimethoxyflavanone | AP | [44] |
| (2S)-5,2ʹ-dihydroxy-7,8-dimethoxyflavanone | AP | [54] |
| (2S)-7,8-dimethoxy-5β-d-glucopyranosyloxyflavanone | AP | [54] |
| 2ʹ,5-dihydroxy-7,8-dimethoxyflavone-2ʹ-O-β-d-glucopyranoside | AP | [54] |
| 2ʹ-hydroxy-2,4ʹ6ʹ-trimethoxychalone | ST | [37] |
| 2ʹ-hydroxy-8,7,8-trimethoxyflavone | RT | [66] |
| 5,2ʹ,6ʹ-trihydroxy-7-methoxyflavone 2ʹ-O-β-d-glucopyranoside | RT | [66] |
| 5,2ʹ-dihydroxy-7,8-dimethoxyflavone 2ʹ-O-β-d-glucopyranoside | RT | [66] |
| 5,2ʹ-dihydroxy-7,8-dimethoxyflavone | RT CL |
[66] [76] |
| 5,4ʹ-dihydroxy-7,8,2ʹ,3ʹ-tetramethoxyflavone | RT AP |
[66] [35] |
| 5,4ʹ-dihydroxy-7-methoxy-8-O-β-d-glucopyranosyloxyflavone | AP | [77] |
| 5,4ʹ-dihydroxy-7-methoxyflavone-8-yl-β-d-glucopyranoside | AP | [78] |
| 5,4ʹ-dihydroxy-7-methoxyflavone-6-yl-β-d-glucopyranoside | AP | [78] |
| 5,4ʹ-dihydroxy-7-O-β-d-glucopyranosyloxyflavone | AP | [77] |
| 5,4ʹ-dihydroxy-7-O-β-d-pyranoglycuronatebutylester | AP | [77] |
| 5,5ʹ-dihydroxy-7,8,2ʹ-trimethoxyflavone | RT | [66] |
| 5,6,4ʹ-trihydroxy-7-methoxyflavone-6-O-β-d-glucoside | AP | [54] |
| 5,7,2ʹ,3ʹ-tetramethoxyflavanone | WP | [53] |
| 5,7,2ʹ,3ʹ-tetramethoxyflavone | RT | [47] |
| 5,7,8,2ʹ-tetramethoxyflavone | WP RT |
[53] [66] |
| 5,7,8-trimethoxydihydroflavone | AP | [77] |
| 5-hydroxy 7,8,2ʹ,3ʹ-tetramethoxyflavone | RT WP RT |
[13] [53] [66] |
| 5-hydroxy-2ʹ,7,8-trimethoxyflavone | AP | [54] |
| 5-hydroxy-3,7,8,2ʹ-tetramethoxyflavone | RT | [79] |
| 5-hydroxy-7,2ʹ,3ʹ-trimethoxyflavone | WP | [53] |
| 5-hydroxy-7,2ʹ,6ʹ-trimethoxyflavone | WP RT |
[53] [78] |
| 5-hydroxy-7,8,2ʹ,3ʹ,4ʹ-pentamethoxyflavone | RT | [66] |
| 5-hydroxy-7,8,2ʹ,3ʹ-tetramethoxyflavone | RT | [66] |
| 5-hydroxy-7,8,2ʹ,5ʹ-tetramethoxy (2R)-flavone-5-O-β-d-glucopyranoside | N/A | [67] |
| 5-hydroxy-7,8,2ʹ,5ʹ-tetramethoxyflavone | AP AP RT, ST WP RT WP |
[35] [54] [80] [53] [66] [34] |
| 5-hydroxy-7,8,2ʹ,6ʹ-tetramethoxyflavone | RT | [66] |
| 5-hydroxy-7,8,2ʹ,3ʹ-tetramethoxyflavone | AP | [35] |
| 5-hydroxy-7,8,2ʹ-trimethoxyflavone | CL RT, ST RT |
[76] [80] [66] |
| 5-hydroxy-7,8-dimethoxy (2R)-flavanone-5-O-β-d-glucopyranoside | N/A | [67] |
| 5-hydroxy-7,8-dimethoxyflavanone | AP RT RT |
[54] [79] [66] |
| 5-hydroxy-7,8-dimethoxyflavone | AP RT CL RT, ST AP RT |
[54] [81] [82] [80] [44] [66] |
| 7,8,2ʹ,5ʹ-tetramethoxy-5-O-β-d-glucopyranosyloxyflavone | AP | [77] |
| 7,8-dimethoxy-2ʹ-hydroxy-5-O-β-d-glucopyranosyloxyflavone | AP | [77] |
| 7,8-dimethoxy-5 β-d-glucopyranosyloxyflavone | AP | [54] |
| 7-O-methylwogonin 5-O-glucoside | WP RT |
[53] [78] |
| 7-O-methyldihydrowogonin | LV, ST AP WP RT |
[37] [77] [53] [78] |
| 7-O-methylwogonin | LV, ST WP AP WP RT |
[37] [34] [77] [53] [78] |
| Andrographidine A | RT | [68] |
| Andropaniculoside A | WP | [34] |
| Andropaniculosin A | WP | [34] |
| Apigenin | WP AP |
[34] [77] |
| Apigenin-7-O-β-d-methylglucuronide | WP | [34] |
| Apigenin-7-O-glucoronide | LV | [37] |
| Cosmosiin | WP | [34] |
| Dihydroneobaicalein | RT | [66] |
| Dihydroskullcapflavone I | ST WP |
[37] [53] |
| Diosmetin-7-glycoside | LV | [37] |
| Isoswertisin | WP | [34] |
| Luteolin | AP | [35] |
| Luteolin-7-O-glucoronide | LV | [37] |
| Quercetin | WP | [34] |
| Scutellarin-6-O-β-d-glucoside-7-methyl ether | WP | [34] |
| Skullcapflavone I 2ʹ-O-glucoside | WP RT |
[53] [78] |
| Skullcapflavone I 2ʹ-methyl ether | WP RT |
[53] [78] |
| Skullcapflavone I | WP | [34] |
| Skullcapflavone-2ʹ-methoxyether | AP | [77] |
| Other Chemical Constituents | ||
| 1,2-dihydroxy-6,8-dimethoxyxanthone | RT | [83] |
| 1,8-dihydroxy-3,7-dimethoxyxanthone | RT | [83] |
| 3,4-dicaffeoylquinic acid | WP | [34] |
| 3,7,8-trimethoxy-1-hydroxyxanthone | RT | [83] |
| 4,8-dihydroxy-2,7-dimethoxyxanthone | RT | [83] |
| 4-hydroxy-2-methoxycinnamaldehyde | RT | [66] |
| α-sitosterol | RT | [13] |
| β-sitosterol | WP RT |
[53] [66] |
| β-daucosterol | RT | [66] |
| Caffeoylquinic acid | ST | [37] |
| Caffeic acid | WP | [53] |
| Caffeic glycoside | LV | [37] |
| Chloragenic glycoside | LV WP |
[37] [53] |
| Cinnamic acid | LV WP |
[52] [53] |
| Coumaroylquinic acid | LV | [37] |
| Dihydroxyl glucosyl cyclohexane | LV, ST | [37] |
| Ferulic acid | WP LV |
[53] [52] |
| Feruloylquinic acid | LV | [37] |
| Methyl-3,4-dicaffeoylquinate | WP | [34] |
| Oleanolic acid | RT | [66] |
| Quinic acid | LV, ST | [37] |
| Stigmasterol | LV | [49] |
| Trans-cinnamic acid | RT | [66] |
* AP: aerial parts, CL: callus, LV: leaves, RT: roots, ST: stems, WP: whole plants.