Traditional Uses, Bioactive Compounds, and Pharmacological Investigations of Calendula arvensis L.: A Comprehensive Review

Table 2

Chemical compounds of C. arvensis.

Countries	Parts	Extracts/EOs	Compounds groups	Compounds	References
Italy	Aerial parts	Methanolic extract	Saponins	3-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid-28-O- β-D-glucopyranoside, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyluronic acid) oleanolic acid-28-O- β-D-glucopyranoside, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyluronic acid) oleanolic acid	[84]
Italy	Aerial parts	Methanolic extract	Saponins	4-O-(β-D-fucopyranosyl)-4-alloaromadendrole, and three derivatives of arvensoside B	[84]
Tunisia	Aerial parts	Methanolic extract	Saponins	Arvensoside A and arvensoside B	[85]
Tunisia	Aerial parts	Ethanolic extract	Saponins	Calenduloside D, calenduloside C, arvensoside B, and arvensoside A	[86]
Italy	Aerial parts	Chloroform extract	Saponins	3-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid-28-O- β-D-glucopyranoside, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyluronic acid) oleanolic acid-28-O- β-D-glucopyranoside, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyluronic acid) oleanolic acid, 4-O-(β-D-fucopyranosyl)-4-alloaromadendrole, 4-O-(β -D-fucopyranosyl)-4-alloaromadendrol-2″-methylpropanoyl esters, 4-O-(β -D-fucopyranosyl)-4-alloaromadendrol -2″-methyl-2″-butenoyl esters	[87]
Italy	Aerial parts	Methanol- diethyl ether-petroleum ether (1 : 1 : 1)	Sesquiterpeneglycosides	3α,7β-dihydroxy-5β,6β-epoxyeudesm-4(15)-ene-11-(O-β-D-fucopyranoside-2′,4′ -diangelate-3′-acetate), 7β-Hydroxy-3β-acetoxy-5β,6β-epoxyeudesm-5(15)-ene-11-(O-β-D-ficopyranoside-2′,4′-diangelate-3′-acetate), 3α,7β-Dihydroxy-5β,6β-epoxyeudesm-4(15)-ene-11-(O-β-D-fucopyranoside-2′,4′-diangelate-3′-isobutyrate), 3α,7β-dihydroxy -5β, 6β-epoxyeudesm-4(15)-ene-11-(O-β-D-fucopyranoside-2′, 4′-diangelate-3′-methylbutyrate), and 3α,7β-dihydroxy-15-acetoxyeudesm-4(5)-ene-11-(O-β-D-fucopyranoside-2′,4′-diangelate-3′-acetate)	[12]
Morocco	Flowers	Aqueous extract	Phenolic and flavonoid contents	Total phenolic contents: 47.89 ± 2.34 mg GAE/g DW; Total flavonoid contents: 74.93 ± 1.50 mg RE/g DW	[47]
		Hexanolic extract		Total phenolic contents: n.d; Total flavonoid contents: n.d
		Methanolic extract		Total phenolic contents: 50.26 ± 0.18 mg GAE/g DW; Total flavonoid contents: 174.93 ± 5.21 mg RE/g DW
Saudi Arabia	Flowers	Ethyl acetate extract	Fatty acids	Stearic acid, oleic acid, linoleic acid, linolenic acid, palmitic acid, and palmitoleic acid	[10]
			Phenolic and flavonoid contents	Total phenolic contents: 354 μg/mL; Total flavonoid contents: 270 μg/mL
Pakistan	Leaves	Methanolic/chloroform extract	Phenolic and flavonoid contents	Terpenoids, tannins, saponins, and alkaloids; Total phenolic contents: 25 ± 2.0 mg GAE/g DW; Total flavonoid contents: 8.0 ± 2.3 mg QE/g DW	[38]
		Aqueous extract	Phenolic and flavonoid contents	Total phenolic contents: 24.6 ± 3.5 mg GAE/g DW; Total flavonoid contents: 10.2 ± 2.5 mg QE/g DW
Malta	Aerial parts	Petroleum ether extract	Phytochemical screening	Flavonoids	[48]
		Chloroform extract		Alkaloids, proteins, and terpenoids
		Ethanolic extract		Alkaloids, flavonoids, and proteins
		Aqueous-ethanolic extract (1 : 1)		Flavonoids, proteins, and terpenoids
		Distilled water		n.d
Algeria	Aerial parts	Essential oil	Terpenoids	γ-terpinene, limonene, p-cymene, 2-pentylfurane, myrcene, β-pinene, sabinene, α-pinene, α-thujene, and (Z)-hex-3-en-1-ol, (E)-sabinene hydrate, nonanal, terpinen-4-ol, 7-β-silphiperfol-5-ene, α-longipinene, α-copaene, (E)-β-caryophyllene, β-acoradiene, (E)-β-farnesene, α-himachalene, allooromadendrene, γ-muurolene, γ-curcumene, germacrene D, zingiberene, bicyclogermacrene, (E,E)-α-farnesene, γ-cadinene, β-curcumene, β-sesquiphellandrene, (E)-α-bisabolene, epi-globulol, globulol, guaiol, viridiflorol, zingiberenol 1 and 2, eremoligenol, τ-cardinol, τ-muurolol, α-cadinol, (Z,Z)-farnesol, α-bisabolol, (E,Z)-farnesol, heptadecane, α-oxo-bisabolene, nonadecane, eicosane, heneicosane, (E)-phytol, tricosane, tetracosane, and pentacosane	[88]
		Hydrosol extract	Terpenoids	Terpinen-4-ol, globulol, guaiol, zingiberenol 1, zingiberenol 2, eremoligenol, τ-cardinol, τ-muurolol, α-cadinol, α-bisabolol, (E,Z)-farnesol, and α-oxo-bisabolene	[88]
Italy	Aerial parts	Steam distillation extract	Aldehydes, esters, sulfur compounds, alkyl pyrazines, ketones, lactones, and terpenoid compounds	Ethyl butyrate, 2-methyl-3-furanthiol, methional, 1-octen-3-one, ethyl hexanoate, 2-6-Dimethyl-3 ethyl pyrazine, (E)-2-nonenal, (E,E)-2,4-octadienal, 5-methyl-2-furanaldehyde, citronellol, phenethylacetate, α-terpineol, lactone-like, and δ-decalactone	[11]
Italy	Aerial parts	Methanolicextract	Saponins	3-O-(β-D-galactopyranosyl-(1⟶3)-β-D-Glucopyranosyl) oleanolic acid-28-O- β-D-Glucopyranoside, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyluronic acid) oleanolic acid-28-O-β-D-glucopyranoside, 3β-O-[β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyluronic acid) oleanolic acid, 3-O-{β-D-ga1actopyranosyl-(1⟶3)(β-D-glucopyranosyl-(1⟶4))-β-D-glucopyranosyl}oleanolic acid; (28⟶1)-β-D-glucopyranosyl ester, 3-O-{β-D-ga1actopyranosyl-(1⟶3)(β-D-glucopyranosyl-(1⟶4))-β-D-glucopyranosyl}oleanolic acid	[87]
France	Aerial parts	Hydro-ethanolic extract (60%)	Saponins	3-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid-28-O- β-D-glucopyranoside, 3β-O-(β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid, and 3-O-(β-D-glucopyranosyl-(1⟶2)-β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid-28-O- β-D-glucopyranoside, 3-O-(β-D-glucopyranosyl-(1⟶2)- β-D-galactopyranosyl-(1⟶3)-β-D-glucopyranosyl) oleanolic acid	[89]
Turkey	Flower parts	Methanolic extract	Phenolic and flavonoid contents	Total phenoliccontents: 118.18 ± 10.29 mg GAE/g extract; Total flavonoid contents: 74.14 ± 3.09 mg QE/g extract	[49]
Portugal	Aerial parts	Hexane extract	Carboxylic acids and derivatives	Stearic acid, α-linolenic acid, linoleic acid, palmitic acid, quinic acid, citric acid, and tetracosanoic acid	[90]
			Carbohydrates	L-threonic acid, D-(−)-tagatofuranose, D-(−)-fructofuranose, D-(−)-fructopyranose, D-(−)-psicopyranose, D-(+)-mannopyranose, D-(+)-galactopyranose, β-D-glucopyranose, D-gluconic acid, galactaric acid, sucrose, and cellobiose
			Terpenoids	Neophytadiene, phytol, α-bisabolol, 8,14-cedranoxide, stigmasterol, stigmast-5-ene, amyrin, lup-20(29)-en-28-al, and 3-oxo-ursan-28-oic acid
			Alcohols, alkanes, amino acids, and pyrrolizidine Alkaloids	Myo-inositol, 1H-benzocyclohepten-9-ol, 1-hexacosanol, untriacontane, 4-aminobutanoic acid, and an isomer of platynecine derivative
Portugal	Aerial parts	Methanolic extract	Phenolic compounds	Isomeric form hydroxy ferulic acid hexoside, 5-O-caffeoylquinic acid, 4-O-caffeoylquinc acid, caffeic acid, sinapic acid hexoside, sinapic acid, hexoside derivative, caffeoylshikimic acid, 3,4-O-dicaffeoylquinic acid, 5-O-feruloylquinic acid, quercetin hydrate, apigenin-8-C-pentose-6-chexose or apigenin-8-chexose-6-C- pentose, quercetin dihexoside, quercetin-3-O-rutinoside, quercetin-3-oneohesperidoside, quercetin-3-omalonylhexoside, isorhamnetin-3-O-hexoside, quercetin acetyl hexoside, quercetin hexoside I, apigenin-O-hexosylpentosyl, protocatechuic acidpentoside, quinic acid with an aldonic residue, ligstroside hexoside, calendasaponin A, and calenduloside G isomer	[42]
			Alcohols, aldehydes, aliphatic hydrocarbons, esters, and ketones	(Z)-3-Hexen-1-ol, hexanal, (E)-2-hexenal, decanal, nonanal, dodecane, ethyl hexanoate, ethyl octanoate, and thymol methyl ether
Portugal	Flower parts	Fresh petals	Alcohols, aldehydes, aliphatic hydrocarbons, esters, ketones, sesquiterpenes, and terpenes	Aromadendrene, (E)-α-bergamotene, α-caryophyllene, α-gurjunene, β-cubebene, β-copaene, β-bourbonene, α-copaene, α-ylangene, α-cubebene, and δ-elemene, β-caryophyllene, γ-muurolene, alloromadendrene, germacrene D, α-muurolene, δ-cadinene, α-cadinene, α-calacorene, epi-α-cadinol, α-thujene, styrene, limonene, α-terpinene, α-phellandrene, β-myrecene, sabinene, and α-pinene, (E)-β-ocimene, (Z)-sabinene hydrate, p-cymenene, linalool, δ-terpinene, β-thujone, perillene, alloocimene, neo-allo-ocimene, 3-thujen-2-one, terpin-4-ol, terpinolene, estragole, (Z)-cadina-1(6),4-diene, and (E)-cadina-1,4-diene	[91]
		Water: acetone (6 : 4; v/v) extract	Monomeric anthocyanins, total flavonoids, and hydrolysabletannins contents	Total flavonoids: 0.35 ± 0.10 mg QE/g DW; hydrolyzable tannins: 3.7 ± 1.8 mg TAE/g DW; Total monomericanthocyanins: 0.07 ± 0.01 mg Cy 3-glu/gDW
Serbia	Flower parts	Methanolic extract	Phenolic and flavonoid contents	Total phenolic contents: 15.12 ± 0.40 mg CAE/g DW; Total flavonoid contents: 5.31 ± 0.36 mg RE/g DW	[92]
		Water extract	Phenolic and flavonoid contents	Total phenolic contents: 14.49 ± 0.38 mg CAE/g DW; Total flavonoid contents: 5.26 ± 0.36 mg RE/g DW
Turkey	Aerial parts	Butanolic extract from methanolic extract (liq-liq)	Saponins	Arvensoside C, arvensoside A, arvensoside B, glycoside C, and calenduloside D	[93]
		Ethyl acetate extract from methanolic extract (liq-liq)	Flavonol glycosides	Quercetin 3-O-β-D-galactopyranoside, quercetin 3-O-β-D-glucopyranoside, and isorhamnetin 3-O-β-D-glucopyranoside
Portugal	Stems and leaves	Chloroform extract	Phytosterols	β-sitosterol	[94]
France	Aerial parts	Essential oil	Terpenoids	(Z)-Hex-3-en-1-ol, α-thujene, α-pinene, sabinene, p-cymene, myrcene, β-pinene, β-phellandrene, limonene, p-cymenene, linalool, terpinolene, cis-Sabinene hydrate, 4-methyl acetophenone, terpinen-4-ol, dill ether, cis-piperitol, decanal, α-terpinen-7-al, p-menth-1-en-9-ol, α-cubebene, (E,E)-2,4-decadienal, geranyl acetate, α-copaene, iso-ledene, aromadendrene, trans-a-bergamotene, (E)-β-caryophyllene, α-gurjunene, β-cubebene, β-bourbonene, cis-muurola-3,5-dienev α-humulene, allo-aromadendrene, carota-5,8-diene, γ-muurolene, α-curcumene, γ-humulene, germacrene-D, trans-muurola-4(14),5-diene, eremophila-1(10),7-diene, 4-epi-cubebol, bicyclogermacrene, ledene, valencene, α-muurolene, β-bisabolene, γ-cadinene, cubebol, calamenene (cis and/or trans), presilphiperfolane-9a-ol, δ-cadinene, zonarene, cadina-1,4-diene, α-calacorene, α-cadinene, α-agarofurane, (E)-nerolidol, β-calacorene, cis-sesquisabinene hydrate, palustrol, spathulenol, germacrene D-4-ol, caryophyllene oxide, gleenol, globulol, cubeban-11-ol, germacradien-11-ol, β-oplopenone, guaiol, ledol, zingiberenol, α-cadinol, τ-cadinol, τ-muurolol, cubenol, cadin-4-en-7-ol, 1-epi-cubenol, 10-epi-γ-eudesmol, 1,10-di-epi-cubenol, (Z,Z)-farnesol, α-bisabolol, (E,Z)-farnesol, cedryl methyl ketone, and (E)-phytol	[7]
France	—	—	Monodesmosidesaponins	Arvensoside B and arvensoside D	[95]
Turkey	Aerial parts	Essential oil	Terpenoids	α-pinene, α-cubebene, α-longifolene, α-copaene, α-gurjenene, β-cubebene, β-caryophyllene, epi-zonarene, α-caryophyllene, ledene, bicyclosesquiphallendrene, germacrene D, α-muurolene, δ-cadinene, β-sesquiphallendrene, cadina-1,4-diene, calamenene, epi-cubebol, neophytodieneisomer, palustrol, cubebol, ledol, cubenol, 1-epi-cubenol, 1,10-di-epi-cubenol, β-oplopenene, viridiflorol, sesquisabinene hydrate, hexahydrofarnesyl acetone, spathulenol, zingiberenol, τ-cadinol, δ-cadinol, α-bisabolol, α-cadinol, and phytol	[96]
Jordan	Aerial parts	Aqueous extract	Phenolic content	Total phenolic contents: 16.8 ± 0.7 mg GAE/g DW	[97]
		Methanolic extract		Total phenolic contents: 12.3 ± 0.4 mg GAE/g DW
France	—	—	Saponins	Arvensoside B and arvensoside D	[43]
Turkey	Fresh plant	Essential oil	Terpenoids, hydrocarbons, and other compounds	α-thujene, γ-terpinene, (Z)-β-ocimene, p-mentha-1(7),8-diene, limonene, α-phellandrene, myrcene, β-pinene, sabinene, α-pinene, p-cymenene, neo-allo-ocimene, terpinen-4-ol, anethofuran, α-terpinen-7-al, 7-epi-silphiperfol-5-ene, iso-ledene, α-gurjunene, β-elemene, β-bourbonene, α-copaene, E-caryophyllene, β-gurjunene, germacrene D, α-guaiene, (E)-β-farnesene, α-humulene, β-selinene, viridiflorene, α-selinene, 2-norpinene, δ-amorphene, α-cuprenene, α-muurolol, epi-α-muurolol, α-acerenol, (Z)-sesquilavandulol, viridiflorol, α-agorofuran, ledol, E-phytol, (Z)-α-santalol, 2E-3,7,11,15-tetramethyl-2-hexadecen-1-ol, Z-Jasmone, hexahydrofarnesyl acetone, eicosane, heneicosane, docosane, tricosane, tetracosane, pentacosane, benzaldehyde, nonanal, methyl salicylate, decanal, and ethyl linoleoate	[41]

n.d.:not detected; mg Cy 3-glu/g DW: mg cyanidin-3-glucoside/g DW; mg QE/g DW: mg of quercetin equivalent/g DW; mg TAE/g DW: mg of tannic acid equivalent/g DW; mg GAE/g DW: mg gallic acid equivalent/g DW; mg RE/g DW: rutin equivalent; mg QE/g DW: quercetin equivalent/g DW; mg CAE/g DW: chlorogenic acid equivalents/g DW.