Andrographis paniculata (Burm. f.) Wall. ex Nees: A Review of Ethnobotany, Phytochemistry, and Pharmacology

Table 4

Preclinical pharmacology of isolated phytoconstituents of A. paniculata.

Compound 3D/2D, chemical properties/IUPAC name/part used/extracts/pharmacology
ent-labdane diterpenoids
Chemical properties: C20H30O5; Exact mass: 350.21; Mol. Wt.: 350.45; C, 68.54; H, 8.63; O, 22.83; IUPAC: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one; Part used: , Ae, W,; Extracts: , , , AW^†; Pharmacology: analgesic, antipyretic, antiulcerogenic [78], antiangiogenic [79], antiretroviral [33, 80], antithrombotic [81], anticancer [13, 16, 82–91], antidiabetic [25–27, 92–94], anti-inflammatory [95–100], anti-influenza [101, 102], antileishmaniasis [103], antiproliferative, proapoptotic [104, 105], antiurothelial [106], cardioprotective [107], cholestatic [108], hepatoprotective [40, 41], immunomodulatory [57, 90, 109–114], inhibition of Epstein Barr virus [115], protective activity against alcohol-induced hepatic, radiosensitiser [116], renal toxicity [117]	Chemical properties: C26H40O8; Exact mass: 480.27; Mol. Wt.: 480.59; C, 64.98; H, 8.39; O, 26.63; IUPAC: 4-[2-[(4aS,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one; Part used: , W, , Ae; Exacts: , , AW^†; Pharmacology: antiherpes-simplex virus [33], anti-inflammatory [100, 118, 119], antioxidant [35], antiparasitic [34], chemosensitiser [120], hepatoprotective [9, 43]	Chemical properties: C19H28O5; Exact mass: 336.19; Mol. Wt.: 336.42; C, 67.83; H, 8.39; O, 23.78; IUPAC: 3-(2-((1R,2R,4aR,5S,8aS)-decahydro-2-hydroxy-1-(hydroxymethyl)- 1,4a-dimethyl-6-oxonaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: , W, Ae; Extracts: , , , A; Pharmacology: antibacterial [121, 122], antifungal [123], hepatoprotective [124], immunomodulator [113], platelet activating factor antagonist [110], uterine smooth muscle relaxant [125], vasorelaxant, antihypertensive [126, 127]
Chemical properties: C20H28O4; Exact mass: 332.2; Mol. Wt.: 332.43; C, 72.26; H, 8.49; O, 19.25; IUPAC: 4-[(E)-2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one; Part used: , W, Ae; Extracts: , , , DCM^®; Pharmacology: antidiabetic [128], antifungal [123], antioxidant, hepatoprotective [129], antiretroviral [80], antithrombotic [81], cholestatic [108], cytotoxic [130], vasorelaxant, antihypertensive [126, 127, 131], antiherpes [33], vasorelaxant, antihypertensive [126]	Chemical properties: C19H28O5; Exact mass: 336.19; Mol. Wt.: 336.42; C, 67.83; H, 8.39; O, 23.78; IUPAC: 3-((2S,3aR,5aR,6R,7R,9aR,9bS)-dodecahydro-7-hydroxy-6-(hydroxymethyl)-3a,9a-dimethylnaphtho[2,1-b]furan-2-yl)furan-2(5H)-one; Part used: , Ae, ,; Extracts: , E^#, AW^†; Pharmacology: anti-inflammatory and anticancer [132], antiproliferative [133], cytotoxic [14], differentiation inducer [18], inhibits growth of Bacillus  subtilis [134]	Chemical properties: C27H42O10; Exact mass: 526.28; Mol. Wt.: 526.62; C, 61.58; H, 8.04; O, 30.38; IUPAC: NA; Part used: , W, Ae; Extracts: , , AW^†, PtE^‡, CHL^‡; Pharmacology: hepatoprotective [42]
Chemical properties: C20H30O3; Exact mass: 318.22; Mol. Wt.: 318.45; C, 75.43; H, 9.50; O, 15.07; IUPAC: 3-(2-((1R,4aS,5R)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylenenaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: , Ae; Extracts: ,; Pharmacology: anti-inflammatory [135, 136]	Chemical properties: C20H28O5; Exact mass: 348.19; Mol. Wt.: 348.43; C, 68.94; H, 8.10; O, 22.96; IUPAC: 3-(2-((1R,2R,4aR,5R,8aS)-decahydro-2-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-6-methylenenaphthalen-5-yl)-2-oxoethyl)furan-2(5H)-one; Part used: , Ae; Extracts: M^†, A; Pharmacology: antileishmaniasis [137]	Chemical properties: C20H30O5; Exact mass: 350.21; Mol. Wt.: 350.45; C, 68.54; H, 8.63; O, 22.83; IUPAC: NA; Part uses: Ae, W; Extracts: , AW^†; Pharmacology: cell differentiation inducer [18]
Chemical properties: C21H30O5; Exact mass: 362.21; Mol. Wt.: 362.46; C, 69.59; H, 8.34; O, 22.07; IUPAC: 3-((E)-2-((1R,2R,4aR,5R,8aS)-decahydro- 2-hydroxy-1-(hydroxymethyl)-1,4a- dimethyl-6-methylenenaphthalen-5-yl)vinyl)-5-methoxyfuran-2(5H)-one; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]	Chemical properties: C20H34O3; Exact mass: 322.25; Mol. Wt.: 322.48; C, 74.49; H, 10.63; O, 14.88; IUPAC: (Z)-2-(2-((1R,4aS,5R,8aS)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylenenaphthalen-5-yl)ethyl)but-2-ene-1,4-diol; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]	Chemical properties: C26H40O9; Exact mass: 496.27; Mol. Wt.: 496.59; C, 62.88; H, 8.12; O, 29.00; IUPAC: 3-(2-((1R,2R,4aS,5R)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylene-2-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)naphthalene-5-yl)ethyl)furan-2(5H)-one; Part used: AeP^þ, WP^®; Extracts: M^®, E^þ; Pharmacology: antibacterial [121, 122], antifungal [123]
Chemical properties: C20H30O5; Exact mass: 350.21, Mol. Wt.: 350.45, C, 68.54; H, 8.63; O, 22.83; IUPAC: NA; Part used: AeP; Extracts: , AW^†; Pharmacology: antimicrobial [134]	Chemical properties: C20H30O3; Exact mass: 318.22, Mol. Wt.: 318.45; C, 75.43; H, 9.50; O, 15.07; IUPAC: 3-(2-((1R,4aS,8aS)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylenenaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]	Chemical properties: C28H44O8; Exact mass: 508.3, Mol. Wt.: 508.64; C, 66.12; H, 8.72; O, 25.16; IUPAC: 3-(2-(1-(((2R)-6-(ethoxymethyl)-tetrahydro-3,4,5-trihydroxy-2H-pyran-2-yloxy)methyl)-decahydro-1,4a-dimethyl-; 6-methylenenaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: AeP; Extracts: Pharmacology: cell differentiation inducer [18]
Chemical properties: C20H24O2; Exact mass: 508.3; Mol. Wt.: 508.64; C, 66.12; H, 8.72; O, 25.16; IUPAC: 3-(2-(1-(((2R)-6-(ethoxymethyl)- tetrahydro-3,4,5-trihydroxy-2H-pyran-2-yloxy)methyl)-decahydro-1,4a-dimethyl-6-methylenenaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: AeP; Extracts: E^¬; Pharmacology: cytotoxic [139]	Chemical properties: C20H28O4; Exact mass: 332.2; Mol. Wt.: 332.43; C, 72.26; H, 8.49; O, 19.25; IUPAC: 3-(2-((1R,4aS,5R,8aS)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylene-2-oxonaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]	Chemical properties: C26H40O9; Exact mass: 496.27; Mol. Wt.: 496.59; C, 62.88; H, 8.12; O, 29.00; IUPAC: 3-(2-((1R,2R,4aS,5R,8aS)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylene-2-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)naphthalen-5-yl)ethyl)furan-; 2(5H)-one; Part used: AeP; Extracts: AW^†; Pharmacology: antimicrobial [134]
Chemical properties: C26H40O10; Exact mass: 512.26; Mol. Wt.: 512.59; C, 60.92; H, 7.87; O, 31.21; IUPAC: (S,E)-dihydro-3-(2-((1R,2R,4aS,5R,8aS)-decahydro-1-(hydroxymethyl)-1,4a-dimethyl-6-methylene-2-(tetrahydro-3,4,5-; trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)naphthalen-5-yl)ethylidene)-4-hydroxyfuran-2(3H)-one; Part used: AeP; Extracts: AW^†; Pharmacology: antimicrobial [134]	Chemical properties: C20H32O5; Exact mass: 352.22; Mol. Wt.: 352.47; C, 68.15; H, 9.15; O, 22.70; IUPAC: NA; Part used: AeP; Extracts: AW^†; Pharmacology: antimicrobial [134]	Chemical properties: C20H32O5; Exact mass: 352.22; Mol. Wt.: 352.47; C, 68.15; H, 9.15; O, 22.70; IUPAC: 3-(2-((1R,2R,4aS,5R,8aS)-decahydro-2-hydroxy-1,6-bis(hydroxymethyl)-1,4a-dimethylnaphthalen-5-yl)ethyl)furan-2(5H)-one; Part used: AeP; Extracts: AW^†; Pharmacology: antimicrobial [134]
Chemical properties: C19H28O7; Exact mass: 368.18; Mol. Wt.: 368.42; C, 61.94; H, 7.66; O, 30.40; IUPAC: NA; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]	Chemical properties: C40H56O8; Exact mass: 664.4; Mol. Wt.: 664.87; C, 72.26; H, 8.49; O, 19.25; IUPAC: NA; Part used: AeP; Extracts: Pharmacology: cell differentiation inducer [18], transient receptor potential channel vanilloid-4 (TRPV-4), activator/analgesic, anti-inflammatory [140]	Chemical properties: C21H28O3; Exact mass: 328.2; Mol. Wt.: 328.45; C, 76.79; H, 8.59; O, 14.61; IUPAC: (1R,4aR,5R,8aS)-octahydro-5-((1E)-2-(2,5-dihydro-2-methylenefuran-3-yl)vinyl)-1-(hydroxymethyl)-1,4a-dimethyl-6-methylenenaphthalen-2(1H)-one; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]
Chemical properties: C19H28O6; Exact mass: 352.19; Mol. Wt.: 352.42; C, 64.75; H, 8.01; O, 27.24; IUPAC: 3-(2-((1S,2R,4aS,5S,8aS)-decahydro-1,2,7-trihydroxy-1-(hydroxymethyl)-4a-methyl-6-methylenenaphthalen-5-yl)ethyl)furan-; 2(5H)-one; Part used: AeP; Extracts: E^#; Pharmacology: antiproliferative [138]	Chemical properties: C31H48O12; Exact mass: 612.31; Mol. Wt.: 612.71; C, 60.77; H, 7.90; O, 31.34; IUPAC: NA; Part used: AeP; Extracts: AW^†; Pharmacology: antimicrobial [134]	Echiodinin; Chemical properties: C16H12O5; Mol. Wt.: 285; IUPAC: NA; Part used: in vitro Callu; Extracts: ,; Pharmacology: antibacterial, antioxidant [141]
Flavonoids
Chemical properties: C15H10O4; Exact mass: 254.06; Mol. Wt.: 254.24; C, 70.86; H, 3.96; O, 25.17; IUPAC: 5,7-dihydroxy-2-phenyl-4H-chromen-4-one; Part used: W; Extracts: Pharmacology: antiplatelet aggregator [72]	Chemical properties: C17H14O5; Exact mass: 298.08; Mol. Wt.: 298.29; C, 68.45; H, 4.73; O, 26.82; IUPAC: 5-hydroxy-7,8-dimethoxy-2-phenyl-4H- chromen-4-one; Part used: W; Extracts: , H^¥; Pharmacology: antiplatelet aggregator [72]	Chemical properties: C17H16O5; Exact mass: 300.1; Mol. Wt.: 300.31; C, 67.99; H, 5.37; O, 26.64; IUPAC: (S)-2,3-dihydro-5-hydroxy-6,7-dimethoxy-2-phenylchromen-4-one; Part used: W; Extracts: Pharmacology: antiplatelet aggregator [72]
Chemical properties: C23H25O11; Exact mass: 477.1391; Mol. Wt.: 477.1391; IUPAC: NA; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: C17H16O5; Exact mass: 300.1; Mol. Wt.: 300.31; C, 67.99; H, 5.37; O, 26.64; IUPAC: (S)-2,3-dihydro-5-hydroxy-7,8-dimethoxy-2-phenylchromen-4-one; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: C18H16O6; Exact mass: 328.09; Mol. Wt.: 328.32; C, 65.85; H, 4.91; O, 29.24; IUPAC: 5-hydroxy-7,8-dimethoxy-2-(2-methoxyphenyl)-4H-; chromen-4-one; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]
Chemical properties: NA; IUPAC: NA; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: NA; IUPAC: NA; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: C23H26O10; Exact mass: 462.152597 Mol. Wt.: 462.44654; IUPAC: (2S)-7,8-dimethoxy-2-phenyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]
Chemical properties: C23H24O10; Mol. Wt.: 460.43066, EM: 460.136947; IUPAC: 7,8-dimethoxy-2-phenyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: C15H10O6; Exact mass: 286.047738, Mol. Wt.: 286.2363,; IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: —; IUPAC: —; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]
Chemical properties: —; IUPAC: —; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]	Chemical properties: —; IUPAC: —; Part used: AeP^~; Extracts: E^~; Pharmacology: antiproliferative [142]
Xanthones
Chemical properties: C15H12O6; Exact mass: 288.06; Mol. Wt.: 288.25; C, 62.50; H, 4.20; O, 33.30; IUPAC: 1,2-dihydroxy-6,8-dimethoxy-9H-xanthen-9-one; Part used: R; Extracts: sequential extraction with PtE, M, CHCl3 and water; Pharmacology: antimalarial [143]	Chemical properties: C15H12O6; Exact mass: 288.06; Mol. Wt.: 288.25; C, 62.50; H, 4.20; O, 33.30; IUPAC: 1,8-dihydroxy-2,6-dimethoxy-9H-xanthen-9-one; Part used: R; Extracts: sequential extraction with PtE, M, CHCl3 and water; Pharmacology: antimalarial [143]	Chemical properties: C16H14O6; Exact mass: 302.08; Mol. Wt.: 302.28; C, 63.57; H, 4.67; O, 31.76; IUPAC: 8-hydroxy-1,2,6-trimethoxy-9H-xanthen-9-one; Part used: R; Extracts: sequential extraction with PtE, M, CHCl3 and water; Pharmacology: antimalarial [143]
Xanthones	Quinic acids
Chemical properties: C15H12O6; Exact Mass: 288.06; Mol. Wt.: 288.25; C, 62.50; H, 4.20; O, 33.30; IUPAC: 1,5-dihydroxy-2,7-dimethoxy-9H-xanthen-9-one; Part used: R; Extracts: sequential extraction with PtE, M, CHCl3 and water; Pharmacology: antimalarial [143]	Chemical properties: C26H26O12; Exact mass: 530.14; Mol. Wt.: 530.48; C, 58.87; H, 4.94; O, 36.19; IUPAC: (1S,3R,4R,5R)-3-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)-4-((E)-4-(3,4-dihydroxyphenyl)-2-oxobut-3-enyloxy)-1,5-dihydroxycyclohexanecarboxylic acid; Part used: WP; Extracts: Pharmacology: antiplatelet aggregator [72]

L: leaves, AeP: aerial parts, WP: whole plants, R: roots, M: methanol, E: ethanol, H: hexane, A: acetone, AW: acetone water, PtE: petroleum ether, CHCl₃: chloroform, DCM: dichloromethane, Mol. Wt.: molecular weight.
References: Arifulla et al. 2013 [141]; Chen^* et al. 2006 [144]; Chen^# et al. 2008 [138]; Chen^~ et al. 2014 [142]; Fujit et al. 1984 [145]; Ji^β et al. 2005 [135]; Li et al. 2008 [136]; Matsud et al. 1994 [18]; Pramanic et al. 2006 [146]; Rao^£ et al. 2004 [147]; Reddy^¥ et al. 2003 [148]; Redd et al. 2005 [80]; Seth^‡ et al. 2010 [149]; Shen^† et al. 2006 [134]; Sul et al. 2011 [121]; Sule^® et al. 2012 [123]; Wang^¬ et al. 2009 [139]; W et al. 2008 [72]; Xu^$ et al. 2010 [150]; Zhou^þ et al. 2008 [151]; Zou^ð et al. 2010 [152].