A Comprehensive Review on Phytochemistry and Pharmacological Activities of Clinacanthus nutans (Burm.f.) Lindau

Table 2

Phytochemicals (primary and secondary metabolites) that presented in C. nutans.

(a) Phytochemical identification based on column chromatography isolation and spectroscopy structural elucidation

Phytochemical	Plant part	Postharvesting method	Extract/Fraction	Plant origin	Reference
Terpenes-Triterpenoids
Lupeol	Stem^2	Air Dry; Soxhlet^2	Petroleum ether extract^1	Thailand^1,2	[44]^1
	Leaf^3	Oven Dry; Soaking^3	Light petroleum extract^2	Seremban Malaysia^3	[27]^2
			Hexane fraction of methanol extract^3		[45]^3
Betulin	Root	-	-	China	[46]
Terpenes-Phytosterols
β-sitosterol	Stem^2	Air Dry; Soxhlet^2	Petroleum ether extract^1	Thailand^1,2	[44]^1
	Leaf^3	Oven Dry; Soaking^3	Light petroleum extract^2	Seremban Malaysia^3	[27]^2
			Hexane fraction of methanol extract^3		[45]^3
β-Sitosterol-3-O-β glucopyranoside	Stem	Sun Dry; Soaking	Sub-fraction of methanol extract	Vietnam	[47]
β-Sitosterol-3-O-β glucoside	Stem	Sun Dry; Soaking	Sub-fraction of methanol extract	Vietnam	[47]
Stigmasterol	Stem^2	Oven Dry; Soaking^3	Petroleum ether extract^1	Thailand^1,2	[44]^1
	Leaf^3		Light petroleum extract^2	Malaysia^3	[48]^2
			Hexane fraction of methanol extract^3		[45]^3
Stigmasterol-β-D-glucoside	Aerial	Sun Dry; Maceration	Methanol fraction of 96% ethanol extract	Vietnam	[49]
Stigmasteryl-3-O-β-D-glucopyranoside	Leaf	Oven Dry; Soxhlet	Chloroform extract	Thailand	[9]
Phenolics compounds
Shaftoside^1,2,3, vitexin^1,2, isovitexin^1,2, isomollupentin 7-O-β-glucopyranoside^1, orientin^1,2, isoorientin^1,2, gallic acid^2, apigenin 6,8-di-C-α-L-arabinopyranoside^2	Aerial^1,2	Reflux^2	Butanol soluble portion of methanol	Thailand^1	[50]^1
		Oven Dry; Soaking^3	extract^1	Seremban Malaysia^2,3	[33]^2
	Leaf^3	-	30% ethanol extract^2		[45]^3
			Hexane fraction of methanol extract^3
Sulfur-containing glucosides compounds
Clinacoside A, Clinacoside B, Clinacoside C, Cycloclinacoside A1, Cycloclinacoside A2	Aerial	-	Butanol soluble and aqueous soluble portion of methanol extract	Thailand	[51]
Sulfur-containing compounds
Clinamides A^1, Clinamides B^1, Clinamides C^1, Clinamides D^2, Clinamides E^2, 2-cis-entadamide A^1, Entadamide A^1, Entadamide C^1	Aerial^1	Air Dry; Soaking^1	80% Ethanol extract^1	Taiwan^1	[52]^1
	Whole plant^2	Sonication^2	Methanol extract^2	Jelebu, Malaysia^2	[53]^2
Lipids
Myricyl alcohol	-	-	Petroleum ether extract	Thailand	[44]
1,2-O-dilinolenoyl-3-O-β-D-galactopyranosyl-glycerol, 1-O-palmitoyl-2-O-linolenoyl-3-O-(α-D-galactopyranosyl-(→6′)-O-β-D-galacctopyranosyl)-glycerol	Leaf	-	-	Thailand	[54]
Monoacylmonogalactosylglycerol, a mixture of nine cerebrosides	Leaf	-	Ethyl acetate-soluble fraction of 95% ethanol extract	Thailand	[55]
Monogalactosyl diglyceride, digalactosyl diglyceride	Leaf	Soxhlet extraction	Chloroform extract	Thailand	[56]
Chlorophyll a and b derivatives
Purpurin 18 phytyl ester^1,2,4; Phaeophorbide a^1,2,4; 13^2-hydroxy-(13^2-)-chlorophyll b^3,4; 13^2-hydroxy-(13^2-)-chlorophyll b^3,4; 13^2-hydroxy-(13^2-S)-phaeophytin b^1,2,4; 13^2-hydroxy-(13^2-)-phaeophytin b^3,4; 13^2-hydroxy-(13^2-)-phaeophytin a^3,4; 13^2-hydroxy-(13^2-)-phaeophytin a^3,4	Leaf^1,2,3,4	Oven Dry; Soxhlet^1,2,3,4	Chloroform extract^1,2,3,4	Thailand^1,2,3,4	[57]^1; [17]^2; [9]^3; [58]^4
Others
trans-3-methylsulfinyl-2-propenol	Aerial	Air Dry; Soaking	80% Ethanol extract	Taiwan	[52]
3-amino-4,5-dihydroxyfuran-2(3H)-one	Aerial	Sun Dry; Maceration	Methanol fraction of 96% ethanol extract	Vietnam	[49]
polysaccharide–peptide complex	Leaf	Oven Dry	Hot water and 75% ethanol precipitation extract	Seremban Malaysia	[59]

(b) Phytochemical identification based on spectrometry and spectroscopy identification

Phyto-constituents	Plant part	Post-harvesting method	Extract	Plant origin	Analytical tools	Reference
2-ethyl-oxetane, 9,12,15-octadecatrienoic acid, 2,3-dimethylpyridine, 3-deoxyd-mannoic lactone, neophytadiene, phytol, 2,3-dihydrobenzofuran, -hexadecanoic acid	Leaf	Oven dry; Soaking	Abs methanol	Kuala Lumpur Malaysia	GCMS	[19]
-Pentadecanol, eicosane, 1-nonadecene, heptadecane, dibutylphthalate, -Tetracosanol-1, heneicosane, behenic alcohol, 1-heptacosanol, 1,2-Benzenedicarboxylic acid, mono (2-ethylhexyl) ester, nonadecyl heptafluorobutyrate, eicosayl trifluoroacetate, 1,2-benzenedicarcoxylic acid, dinonyl ester, phthalic acid, dodecyl nonylester	Leaf	Oven dry	Chloroform	Selangor Malaysia	GCMS	[32]
Squalene, -tocopherol, vitamin E, Campsterol, stigmasterol, -sitosterol, -amyrin, -amyrin, lupeol, propanoic acid, betulin	Leaf, stem	Combination of air dry and freeze dry; Maceration	Abs methanol, abs ethyl acetate	Sabah Malaysia	GCMS	[29]
Lactic Acid, Glycolic acid, 3-Pyridinol, Glycerol, Phosphonic acid, Catechol, Butanedioic acid, Glyceric acid, Erythrono-1,4-lactone, (Z), Malic acid, Benzaldehyde, 3-methoxy-4-[(trimethylsilyl)oxy]-, O-methyloxime, Cyclooctasiloxane, Levoglucosan, Vanillic Acid, D-Ribo-Hexonic acid, 3-deoxy-2,5,6-tris-O-(trimethylsilyl)-, lactone, D-(-)-Fructofuranose, pentakis(trimethylsilyl) ether (isomer 1), Myristic acid, D-Pinitol, Neophytadiene, D-Fructose, 1,3,4,5,6-pentakis-O-(trimethylsilyl)-, O-methyloxime, Syringic acid, D-Fructose, 1,3,4,5,6-pentakis-O-(trimethylsilyl)-, O-methyloxime, d-Glucose, 2,3,4,5,6-pentakis-O-(trimethylsilyl)-, o-methyloxyme, (1Z)-, Gallic acid, Muco-Inositol, D-Glucose, Heptadecanoic acid, Phytol, 9,12-Octadecadienoic acid (Z,Z)-, Oleic Acid, L-Rhamnose, Cyclononasiloxane, octadecamethyl-, Octadecane-1,2-diol, Ricinoleic acid, Arachidic acid, L-Rhamnose, 1,2-Benzenedicarboxylic acid, mono(1-methylheptyl) ester, (+/−),1-Monopalmitin, Cyclononasiloxane, octadecamethyl-, 1-Monolinolein, Glycerol monostearate, Squalene, β-Gentiobiose, B-tocopherol, γ-tocopherol, α-Tocopherol, Campesterol	Stem	Air dry; Supercritical-soxhlet extraction	-	Seremban Malaysia	GC-QTOF-MS	[28]
Vitamin E, campesterol, stigmasterol, -Sitosterol, -Sitosterol, -amyrin, lupeol, betulin	Root	Freeze dry; Soaking	Methanol	Sabah Malaysia	GCMS	[31]
Oleic acid, squalene, vitamin E, campesterol, stigmasterol, -stosterol, -sitosterol, lup-20(29)-en-3-one, -amyrin, lupeol, lup-20(29)-en-3-ol-acetate, betulin	Root	Freeze dry; Soaking	Ethyl acetate	Sabah Malaysia	GCMS	[31]
Neophytadiene, iron, 7,9-Dodecadien-1-ol, Myristic acid, Palmitic acid, Palmitic acid-methyl ester, Benzenethanol, Phytol, Squalene, Stearic acid-methyl ester, Margaric acid-ethyl ester, Lupeol, Linoleic acid-ethyl ester, Linolenic acid-methyl ester, 2-Butanol, Butanamide, 2-cyclopenten-1-one-2-hydroxy, Glycine, Pentanal, Isoveraldehyde, Dimethyl trisulfide, Thiophene, Succinic acid, Glycolic acid, Oxazolidine, Thiophene, 9-Azabicyclo (6.1.0) non-4-4en-9-amine, 4-Vinyl-2-methoxy-phenol, Phenol,2,6-dimethoxy, 4H-Pyran-4-one,2,3-dihydro-3,5-dihydroxy-6-methyl, Glycerine, 4-Vinylphenol	Aerial	Oven dry; MAE, SFE, Soxhlet	Aqueous ethanol	Kuala Lumpur Malaysia	GCMS	[30]
Isoorientin, orientin, isovitexin, vitexin, schaftoside, 6, 8-apigenin----pyranarabinoside	Aerial	-	30% Ethanol	Seremban Malaysia	HPLC LCMS/MS	[33]
Kaempferol-7-neohesperidoside, Isoschaftoside, Isoorientin, Vitexin, 3′,7-Dimethoxy-3-hydroxyflavone, 2′,6-Dihydroxyflavone, (+)−Catechin, 7-Hydroxyflavone, Gallic acid, Flavanone-7--glycoside	Aerial	Oven dry; MAE, SFE, Soxhlet	86% Ethanol,; 50% Ethanol	KL Malaysia	UPLC-ESI-QTOF/MS	[30]
Schaftoside, Arabinoysl–glucosyl apigenin isomer, Ascorbic acid, Gendarucin A, Gendarucin A isomer, 3, 3-di-O-methylellagic acid, Methyl 2-[cyclohex-2-en-1-yl(hydroxyl) methyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxoprolinate, Methyl 2-[cyclohex-2-en-1-yl(hydroxyl) methyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxoprolinate isomer	Leaf	Air dry; Sonication	70% Ethanol	Seremban Malaysia	UPLC-MS/MS	[4]
Gallic acid, 4-hydroxybenzoic acid, caffeic acid, coumaric acid, ferulic acid, schaftoside, vitexin, orientin, isoorientin, isovitexin, luteolin, apigenin, forsythosides H, forsythosides I, diosmetin glycoside, diosmetin.	Leaf	Oven dry; Soaking	100% Methanol	Kuala Lumpur Malaysia	UHPLC-MS	[19]
Primary metabolites: Fructose, -Glucose, -Glucose, Sucrose, a mixture of cerebrosides, Monoacylmonogalactosylglycerol, Alanine, Glutamate, Glutamine, Proline, Threonine, Tryptophan, Valine, Citric acid, Formic acid, Fumaric acid, Choline, Adenine, Fatty acid, Ascorbic acid; Secondary metabolites: Betulin, Lupeol, Stigmasterol, -sitosterol, Clinacoside A, Clinacoside B, Clinacoside C, Cycloclinacoside A1, Cycloclinacoside A2, Isoorientin, Isovitexin, Orientin, Vitexin, Schaftoside, Gendarucin A, Catechin, Quercetin, Quercetin 3-O-rhamnoside, Quercetin 3-O-arabinofuranoside, Rutin, Chlorogenic acid, Gallic acid	Leaf, Stem	Air dry, Oven dry, Freeze dry; Sonication, Soaking	70% Ethanol	Seremban Malaysia	^1H-NMR	[4]

1, 2, 3, 4: in each phytochemical class, every superscript number attached to a particular phytochemical, plant part, postharvesting method, extract/ fraction, or plant origin indicated that such information is extracted from the reference which has attached with the same superscript number.