Table 4.

Bioactive compounds identified from Brassica seed/derivative extracts and essential oil using different analytical techniques (%).

Chemical Composition	Species	Subspecies/var	Sample Analyzed	Extracting Solvent	Separation and Detection Methods	Bioactive Compounds	Reference
Polyphenols	B. nigra		Seeds		UHPLC–MS/MS	4-hydroxybenzoic acid, caffeic acid, p-coumaric acid, ferulic acid, sinapic acid, and procatechuic acid	[119]
	B. oleracea	var. acephala	Oil		GC-FID, MS, HPLC-DAD, HPLC–MS, HPLC fluorescence	11 polyphenols, 5 flavonoids, and 6 hydroxycinnamic acids	[35]
		var. costata	Seeds	H2O	Reverse-phase HPLC-DAD–MS/MS-ESI and HPLC-DAD	13 phenolic compounds: 2 sinapoylgentiobiose isomers (sinapoylgentiobiose (0.03% (w/w)) and sinapoylgentiobiose isomer (0.03% (w/w))), 3 sinapoylglucose isomers (1-sinapoylglucose isomer (0.04% (w/w)), 1-sinapoylglucose isomer (0.04% (w/w)), and 1-sinapoylglucose (0.07% (w/w))), kaempferol-3 (sinapoyl) sophorotrioside-7-glucoside, sinapoylcholine, kaempferol-3,7-diglucoside-4’-(sinapoyl) glucoside, 3 disinapoylgentiobiose isomers (1,2-disinapoylgentiobiose isomer (0.02% (w/w)), 1,2-disinapoylgentiobiose isomer (0.04% (w/w)), and 1,2-disinapoylgentiobiose (0.10% (w/w))), 1,2,2’-trisinapoylgentiobiose, and 1,2-disinapoylglucose	[103]
	B. rapa L.	RCN	Seed meal	70% methanol	LC–MS	Polyphenols: flavonol and hydroxycinnamic derivatives: K−3−O-(methoxycaffeoyl) sophotrioside−7−O-glc, K−3−O-sophotrioside−7−O-glc, Q−3−O-(coumaroyl) sophoroside −7−O-glc, K−3−O-(sinapoyl) sophotrioside−7−O-glc, I−3−O-(cumaroyl) sophotrioside−7−O-sophoroside, I-3,7−O-di-glc, I−3−O-glc−7−O-sophoroside, caffeoyl derivative, K−3−O-sophoroside, Q−3−O-sophoroside, K−3−O-(feruloyl) sophoroside, Q−3−O-glc, 1,2-disinapoylgentiobioside, 1-sinapoyl-2-feruloylgentiobioside, K−3−O-glc, and I−3−O-glc	[51]
	B. juncea		Seeds		UHPLC–MS/MS	4-hydroxybenzoic acid, syringic acid, p-coumaric acid, ferulic acid, sinapic acid (0.02% (w/w), procatechuic acid, and kaempferol	[119]
				30% etthanol	LC–MS/MS	Caffeic acid, p-coumaric acid, epigallocatechin gallate, myricetin, apigenin, quercetin-3-O-(caffeoyl)-glucoside, and quercetin	[120]
	B. napus	spring oilseed rape (Napus cv. Drakkar)	Seeds	Hexane–80% aq. methanol	Combination of high-field NMR spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI)	15 constituents: glucose, kaempferol glycoside esters, gentiobiose,, sinapine (sinapoylcholine), and sinapoylmalate; 1 of the glucose esters (1,6-di-O-sinapoylglucose), 2 kaempferol conjugates [4’-(6-O-sinapoylglucoside)-3,7-di-O-glucoside and 3-O-sophoroside-7-O-(2-O-sinapoylglucoside)], and 2 gentiobiose esters (1-O-caffeoylgentiobiose, and 1,2,6’-tri-O-sinapoylgentiobiose)are new plant products	[121]
		winter type: Aviso (00), CMB1039 (00), Doublol (00), JetNeuf (0þ) and PR3984 (00)	Seed coat	Methanol/acetone/water/TFA mixture (40:32:28:0.05 v/v/v/v)	LC–ESI-MSn	13 different flavonoids: (−)-epicatechin, 7 flavonols (quercetin-3-O-glucoside, quercetin-dihexoside, kaempferol-sinapoyl-trihexoside, isorhamnetin-3-O-glucoside, isorhamnetin-dihexoside, isorhamnetin-hexoside-sulfate, and isorhamnetin-sinapoyl-trihexoside), and 5 procyanidins	[90]
		Canola	Seeds	80% methanol	Sephadex LH-20 chromatography	Free phenolic compound: trans-sinapic acid (19.34% (w/w)); sinapic acid derivatives: 1-O-β-D-glucopyranosyl sinapate and 1,2-di-O- sinapoyl-β-D-glucose	[82]
		cv.Yang 6	Seeds	80% methanol	HPLC-PDA–ESI(−)-MSn/HRMS	Detection of 91 flavonoids and hydroxycinnamic acid derivatives: 6 flavanols and their oligomers, 39 kaempferol derivatives, 5 quercetin derivatives, 11 isorhamnetin derivatives, and 30 hydroxycinnamic acid derivatives	[89]
	B. alba		Seeds		UHPLC–MS/MS	4-hydroxybenzoic acid, apigenin, p-coumaric acid, ferulic acid, and sinapic acid (0.12% (w/w))	[119]
Glucosinolates	B. oleracea	italica (broccoli)	Seed isothiocyanates (ITCs)	Ethyl acetate	GC–MS	3-BITC (3-butenyl isothiocyanate) (13.85% (w/w)) and sulforaphane (4.98% (w/w))	[96]
		Alboglabra (Chinese kale)				3-BITC (7.76% (w/w))
		italica (broccoli)	Seeds	H2O	HPLC	Aliphatic glucosinolates: sinigrin (0–1.94% (w/w)), progoitrin (0–5.51% (w/w)), glucoraphanin (0.12–6.18% (w/w)), gluconapin (0–0.7% (w/w)), glucoerucin, glucoiberin, and glucoiberverin. Indolic glucosinolates: glucobrassicin (0–0.17% (w/w)), and 4-hydroxy-glucobrassicin (0–0.33% (w/w))	[122]
		italica cv. Legacy	Seeds	Dichloromethane (DCM)	HPLC	Sulforaphane (0.36% (w/w))	[36]
	B. rapa L.	Rapa L	Seeds	DCM	GC–MS	Phenylethylbrassinin and 3-phenylpropionitrile	[123]
		RCN	Seed meal	70% methanol	LC–MS	(R)-2-Hydroxy-3-butenyl (progoitrin), 4-methylsulfinylbutyl (glucoraphanin), 3-butenyl (gluconapin), 4-hydroxy-3-indolylmethyl (4-hydroxyglucobrassicin), 4-pentenyl (glucobrassicanapin), 3-indolylmethyl (glucobrassicin), and N-methoxy-3-indolylmethy (neoglucobrassicin)	[51]
	B. juncea		Seeds	5% ethyl alcohol		Allyl isothiocyanate (0.48% (w/w))	[41]
		raya	Oil	Ethyl acetate	GC/GC–MS	GSLs hydrolytic products in ethyl acetate oil: allyl isothiocyanate (23% (w/w)), 2-phethyl isothiocyanate (~20% (w/w)), 3-butenyl isothiocyanate (18% (w/w)), 3-(methylthio) propyl isothiocyanate, allyl thiocyanate, and 1-isothiocyanato-3-methyl butane	[97]
				DCM	GC/GC–MS	GSLs hydrolytic products: phenethyl isothiocyanate (15.15% (w/w)), 4-pentenyl isothiocyanate (12.548% (w/w)), sec-butyl isothiocyanate, allyl isothiocyanate, and isothiocyanic acid
		Coss and Czern	Seeds	Methanol	13C-NMR, 1H-NMR	3 native glucosinolates isolated: p-hydroxybenzyl glucosinolates, newly described in B. juncea seeds, and 2 new compounds 9-(methyl-sulfonyl) nonyl and 8-(methylsulfonyl) octyl glucosinolates	[118]
			Seeds	Double-distilled water (ddH2O)	HPLC	4 aliphatic GLSs: sinigrin, progoitrin, gluconapin, and glucoiberin, 4 indolic GLSs: glucobrassicin, neoglucobrassicin, 4-methoxyglucobrassicin and 4-hydroxy glucobrassicin, and one aromatic GLS: gluconasturtiin; sinigrin is the predominant GLS with 90% of total GLSs, followed by gluconapin	[114]
			Seeds	DCM	GC	Glucosinolates breakdown products (GBPs): 5 ITCs: [2-propenyl isothiocyanate, 3-butenyl isothiocyanate, 5-vinyl-1,3-oxazolidine-2-thione, 3-methyl sulfinylpropyl isothiocyanate, and 2-phenylethyl isothiocyanate], 2 CNs: [3-butenenitrile and 4-pentenenitrile], and 3 EPNs: [3,4-epithiobutanenitrile, 4,5-epithiopentanenitrile, and 3-hydroxy-4,5-epithiopentanenitrile]; 2-propenyl isothiocyanate is the predominant individual GBP with 51–98% of total GBPs, followed by 3-butenenitrile, 3,4-epithiobutanenitrile, 3,4-epithiobutanenitrile, and 3-butenyl isothiocyanate.
	B. hirta	Sinapis alba	Seeds	5% ethyl alcohol		Allyl isothiocyanate (0.15% (w/w))	[41]
	B. campestris		Isothiocyanates (ITCs)	Ethyl acetate	GC–MS	3-BITC (3-butenyl isothiocyanate) contained (7.76% (w/w))	[96]
Carotenoids	B. oleracea	var. acephala	Seed oil		GC-FID, MS, HPLC-DAD, HPLC–MS, HPLC fluorescence	13 carotenoids, with all-elutein as the main component	[35]
Amino acids	B. oleracea	italica cv. Legacy	Seeds	Hydrochloric acid	HPLC	Glutamic acid (7.28% (w/w)), asparagine (5.18% (w/w)), serine + histidine (3.42% (w/w)), proline (2.33% (w/w)), threonine (1.88% (w/w)), leucine (1.37% (w/w)), valine (1.03% (w/w)), tyrosine (0.95% (w/w)), phenylalanine (0.87% (w/w)), isoleucine (0.8% (w/w)), glycine (0.74% (w/w)), methionine (0.42% (w/w)), arginine (0.39% (w/w)), and alanine (0.23% (w/w))	[36]
Fatty acids	B. nigra		Cold-press oil		GC–MS	Methyl erucate (38.23% (w/w)), 8,11,14-docosatrienoic acid, methyl ester (23.72% (w/w)), 11-eicosenoic acid, methyl ester (15.82% (w/w)), and methyl linoleate (10.13% (w/w))	[78]
	B. hirta		Cold-press oil		GC–MS	Methyl linoleate (68.19% (w/w)), methyl oleate (15.79% (w/w)), and hexadecanoic acid, methyl ester (10.51% (w/w))
	B. juncea	raya	Oil	Ethyl acetate and DCM	GC/GC–MS	Octadecenoic acid (5.67–23.3% (w/w)), hexaicenoic acid (4.98–20% (w/w)), butanedioic acid (1.6–16% (w/w)), and nonanedioic acid (4.73% (w/w))	[97]
Organic acids	B. oleracea	var. costata	Seeds	H2O	HPLC-UV	7 organic acids: aconitic (0.02% (w/w)), citric (0.47% (w/w)), ascorbic (0.86% (w/w)), malic + quinic (0.31% (w/w)), shikimic, and fumaric acids	[103]
Sterols	B. juncea		Seeds		HPLC, GC, 1H-NMR	Sterol, 22-dehydrocampesterol [(24S)24-methylcholesta-5, E-22-dien-3β-ol], newly discovered in higher plants	[124]
Essential oil	B. hirta	Sinapis alba	Essential oil	H2O	GC–MS and GC-FID	2-methylbutyronitrile, 3-pentenenitrile, hexanal, furfural, 2-furanmethanol, cyclopropyl isothiocyanate, allyl isothiocyanate, isobutyl isothiocyanate, 3-butenyl isothiocyanate, benzene acetaldehyde, 3-methylbutyl isothiocyanate, 3-(methylthio) propyl cyanide, 2-phenylethyl cyanide, and 2-phenethyl isothiocyanate	[105]
			Cold-press oil		GC–MS	Cyclopropanenonanoic acid, 2-[(2-butylcyclopropyl) methyl] -, methyl ester (48.7% (w/w)), and hexadecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester (42. 08% (w/w))	[78]
	B. oleracea	var. botrytis (L.), Romanesco group	Seed/volatile oil	DCM	GC and GC–MS	Natalino variety: 43 compounds (99.7% (w/w)), contained 10 cyanides (88.1% (w/w)), 10 isothiocyanates (8.8% (w/w)), and 8 aldehydes (1.3% (w/w)) Campid oglio variety: 41 compounds (99.6% (w/w)) contained 10 cyanides (92.3% (w/w)), 10 isothiocyanates (6.2% (w/w)), and 6 aldehydes (0.4% (w/w)) Navona variety: 32 compounds (99.5% (w/w)) contained 9 cyanides (91.0% (w/w)), 6 isothiocyanates (7.5% (w/w)), and 6 aldehydes (0.6% (w/w)) Cyanides: 2-methylpropyl cyanide, but-3-enyl cyanide, 3-methylbutyl cyanide, n-pentyl cyanide, 4-methylpentyl cyanide, n-hexyl cyanide, 3-(methylthio) propyl cyanide, benzyl cyanide, 4-(methylthio) butyl cyanide, and 2-phenylethyl cyanide. Isothiocyanates: allyl thiocyanate, allyl isothiocyanate, 2-methylpropyl isothiocyanate, but-3-enyl isothiocyanate, 3-methylbutyl isothiocyanate, 4-methylpentyl isothiocyanate, 3-(methylthio)propyl isothiocyanate, benzyl isothiocyanate, 4-(methylthio) butyl isothiocyanate, 2-phenylethyl isothiocyanate, and 5-(methylthio) pentyl isothiocyanate Aldehydes: hexanal, furfural; 3-(methylthio) propanal, phenylacetaldehyde, nonanal, non-2(E)-enal, deca-2(E),4(E)-dienal, and syringaldehyde The predominant compounds were cyanides: 4-(methylthio) butyl cyanide (61.3%, 66.3%, and 79.6% (w/w), respectively), 3-(methylthio) propyl cyanide (21.7%, 21.6%, and 10.7% (w/w)), and isothiocyanates: 4-(methylthio) butyl isothiocyanate (5.3%, 4.0%, and 6.7% (w/w)) for the three oils	[125]
	B. tournefortii	Gouan	Volatile oil	diethyl ether	GC–MS	14 compounds (76.1% (w/w)): propane, 1-isothiocyanato-3-(methylthio) (24.39% (w/w)), 2-propenal, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl), ionone (1.7% (w/w)), aromadendrene (6.69% (w/w)), 2-pentadecanone,6,10,14-trimethyl, elimicin (1.864% (w/w)), 8,11-octadecanoic acid, methyl ester, α –bisabolol, 1-hexadecanol, hexadecanoic acid, di-2-propenyltetrasulfide (19.803%), n-heneicosane, 12-octadecanoic acid, and n-octadecanoic acid	[126]