. 2023 Jan 31;28(3):1363. doi: 10.3390/molecules28031363

Table 1.

Metabolites identified in aqueous extracts of cauliflower and globe artichoke byproducts. Relative assignments of ¹H and ¹³C NMR signals are reported. L = leaves; S = stalks; F = florets; d = doublet; dd = doublet of doublets; m = multiplet; qd = quartet of doublets; s = singlet; t = triplet.

Metabolite	Assignment	δ ¹H (ppm)	Multiplicity (J_H-H, Hz)	δ ¹³C (ppm)	Globe Artichoke	Cauliflower
	Amino acids
Alanine (Ala)	β-CH₃	1.49 *	d (7.2)	17.2	L, S	L, S, F
Alanine (Ala)	α-CH	3.80		51.5	L, S	L, S, F
Arginine (Arg)	α-CH	3.78		55.1	L	L, S, F
	β-CH₂	1.93		28.6
	γ, γ′-CH₂	1.74; 1.67 *		24.9
	δ-CH₂	3.24		41.5
Asparagine (Asn)	β-CH	2.89	dd (16.9; 7.2)	35.6	L, S	L, S, F
	β′-CH	2.96 *	dd (16.9; 4.5)	35.6
	α-CH	4.01		52.2
Aspartate (Asp)	β-CH	2.71	dd (17.4; 8.1)	37.6	L, S	L, S, F
	β′-CH	2.80 *	dd (17.4; 3.8)	37.6
	α-CH	3.91		53.2
γ-Aminobutyric acid (GABA)	β-CH₂	1.91		24.7	L, S	L, S, F
	α-CH₂	2.30 *	t (7.4)	35.4
	γ-CH₂	3.02	t (7.6)	40.2
Glycine (Gly)	α-CH₂	3.57	s	42.5		L, F
Glutamate (Glu)	β, β′-CH₂	2.13; 2.08	m	28.0	L, S	L, S, F
	γ-CH₂	2.35 *	m	34.4
	α-CH	3.77		55.5
Glutamine (Gln)	β-CH₂	2.15	m	27.3	L, S	L, S, F
	γ-CH₂	2.46 *	m	31.8
	α-CH	3.78		55.2
Histidine (His)	β, β′-CH₂	3.30; 3.24		28.2	L	L, S, F
	α-CH	4.02		55.4
	CH-5	7.18		118.3
	CH-2	8.13 *
Isoleucine (Ile)	δ-CH₃	0.94	t (7.4)	12.1	L, S	L, S, F
	γ-CH₃	1.01 *	d (7.0)	15.7
	γ, γ′-CH₂	1.48; 1.27		25.5
	β-CH	1.98		36.8
	α-CH	3.68		60.5
Leucine (Leu)	δ-CH₃	0.96 *	d (6.2)	22.1	L, S	L, S, F
	δ′-CH₃	0.97 *	d (6.0)	23.0
	β-CH₂	1.73		40.9
	α-CH	3.74		54.4
	γ-CH	1.70		25.2
Lysine (Lys)	α-CH	3.77		55.3	L	L, F
	β-CH₂	1.92		30.9
	γ-CH₂	1.49		22.5
	δ-CH₂	1.74		27.4
	ε-CH₂	3.04 *	t (7.6)	40.0
S-Methyl-L-cysteine-S-oxide (Methiin)	α-CH	4.18	t (6.8)	51.8		L, S, F
	β-CH₂	3.47; 3.28	dd (14.0; 7.2)	54.5
	γ-CH₃	2.84 *	s	39.1
	COOH			173.1
Phenylalanine (Phe)	β, β′-CH₂	3.27; 3.16		37.4	L, S	L, S, F
	α-CH	4.00		56.9
	CH-2,6	7.34	d (7.3)	130.5
	CH-4	7.38	t (7.0)	128.7
	CH-3,5	7.43 *	t (7.3)	130.2
Pyroglutamic acid	β, β’-CH₂	2.04; 2.51		26.3	L	L, F
	γ-CH₂	2.40		30.7
	α-CH	4.18		59.3
Threonine (Thr)	γ-CH₃	1.34 *	d (6.6)	20.5	L, S	L, S, F
	α-CH	3.61		61.4
	β-CH	4.26	qd (6.6; 4.9)	66.9
Tryptophan (Trp)	CH-4	7.73 *	d (7.9)	119.5	L	L, S, F
	CH-7	7.55	d (7.4)	113.0
	CH-6	7.29	t (7.4)	123.2
	CH-5	7.20		120.4
	CH-2	7.34	s	126.2
	α-CH	4.06		55.9
	β, β′-CH₂	3.48; 3.32		27.4
Tyrosine (Tyr)	CH-2,6	7.20	d (8.5)	131.7	L	L, S, F
	CH-3,5	6.91 *	d (8.5)	116.9
	α-CH	3.95		57.1
	β, β′-CH₂	3.19; 3.07		36.5
Valine (Val)	γ-CH₃	1.00	d (7.0)	17.7	L, S	L, S, F
	γ′-CH₃	1.05 *	d (7.0)	19.0
	β-CH	2.28		30.1
	α-CH	3.62		61.3
	Organic acids
Acetic acid (AA)	αCH₃	1.93 *	s	24.4	L, S	L, S, F
Citric acid (CA)	α, γ-CH	2.54 *; 2.68	d (15.5)	46.5	L, S	L, S, F
Formic acid (FA)	HCOO-	8.47 *	s	173.8	L, S	L, S, F
Fumaric acid (FumA)	α, β-HC=CH	6.53 *	s	136.5	L, S	L, S, F
Lactic acid (LA)	β-CH₃	1.33 *	d (6.9)	21.1	S	L
Lactic acid (LA)	α-CH	4.12		69.6	S	L
Malic acid (MA)	β-CH	2.68	dd (15.4; 3.2)	43.6	L, S	L, S, F
	β′-CH	2.39	dd (15.4; 10.0)	43.6
	α-CH	4.30 *	dd (10.0; 3.2)	71.4
Pyruvic acid (PA)	CH₃	2.36	s	30.0		L, F
Quinic acid (QA)	C(OH)COOH			78.1	L, S	L
	2,2′-CH₂	2.04; 1.97		38.5
	6,6′-CH₂	2.08; 1.88 *		41.8
	CH-3	4.16		71.5
	CH-4	3.56		76.3
	CH-5	4.03		68.0
Succinic acid (SA)	α, β-CH₂	2.41 *	s	35.1	L, S	L, S, F
	Carbohydrates, polyols
α-Glucose (α-Glc)	CH-1	5.25 *	d (3.8)	93.1	L, S	L, S, F
	CH-2	3.55		72.4
	CH-3	3.72		73.8
	CH-4	3.42		70.7
	CH-5	3.84		72.5
	CH₂-6	3.84; 3.78		61.6
β-Glucose (β-Glc)	CH-1	4.65 *	d (8.0)	96.9	L, S	L, S, F
	CH-2	3.26		75.2
	CH-3	3.50		76.7
	CH-4	3.42		70.7
	CH-5	3.47		76.9
	CH₂-6	3.90; 3.74		61.7
α-Fructofuranose	CH-3	4.13 *		82.9	L, S	L, S, F
α-Fructofuranose	CH-5	4.07		82.4	L, S	L, S, F
β-Fructofuranose	CH₂-1,1′	3.60; 3.57		63.8	L, S	L, S, F
	CH-3	4.12 *		76.4
	CH-4	4.12 *		75.4
	CH-5	3.83		81.6
	CH₂-6,6′	3.81; 3.68		63.3
β-Fructopyranose	CH₂-1, 1′	3.72; 3.56		64.8	L, S	L, S, F
	CH-3	3.81		68.5
	CH-4	3.90		70.6
	CH-5	4.00		70.2
	CH₂-6,6′	4.03; 3.71		64.4
Sucrose (Suc)	CH-1	5.42 *	d (3.8)	93.2	L, S	L, S, F
	CH-2	3.56		72.0
	CH-3	3.77		73.5
	CH-4	3.48		70.2
	CH-5	3.85		73.4
	CH₂-6	3.82		61.2
	CH₂-1′	3.69		62.4
	C-2	/		104.8
	CH-3′	4.22		77.4
	CH-4′	4.06		75.0
	CH-5′	3.90		82.4
	CH-6′	3.82		63.4
Raffinose	CH-1 (Gal)	5.00 *	d (3.8)	99.4		L, S
Raffinose	CH-1(Glc)	5.44	d (3.8)	93.2		L, S
Inulin	CH-1 (Glc)	5.44 *		93.5	L, S
	CH-3 (Fru)	4.27		77.8
	CH-4 (Fru)	4.10		75.3
chiro-Inositol	CH-1,6	4.05		72.7	L, S
	CH-2,5	3.76		71.4
	CH-3,4	3.59 *		73.8
myo-Inositol	CH-2,5	3.54		72.4	L, S	L, S, F
	CH-1	4.08		73.2
	CH-3,6	3.63		73.5
	CH-4	3.29 *		75.3
scyllo-Inositol	CH-1,2,3,4,5,6	3.36 *	s	74.6	L, S
	Glucosinolates
Glucoiberin	CH-1′ (Gluc)	5.08 *	d (9.8)	82.7		L
	CH-2′	3.47		72.9
	CH-3′	3.58		78.1
	CH-4′	3.47		70.2
	CH-5′	3.60		81.2
	CH₂-6a′,6b′	3.92; 3.73		61.7
	S-CH₃	2.74	s	37.7
	α-CH₂	3.05; 2.99		52.5
	β-CH₂	2.21		20.7
	γ-CH₂	2.95		31.9
	C=N	-		163.6
Glucobrassicin	CH-1′ (Gluc)	4.84		82.4		L
	CH-2′	3.31		72.8
	CH-3′	3.23		77.9
	CH-4′	3.38		69.6
	CH-5′	2.96		80.9
	CH₂-6′	3.59		61.2
	CH₂-1a, 1b	4.28; 4.22		30.4
	CH-2″ (Ind)	7.37		125.2
	CH-4″	7.76 *	d (8.0)	119.5
	CH-5″	7.21		120.8
	CH-6″	7.28		123.2
	CH-7″	7.56		113.1
Glucoraphanin	CH-1′ (Gluc)	5.05	d (9.8)			L
Glucoraphanin	S-CH₃	2.72	s			L
Sinigrin	CH-1′ (Gluc)	5.07	d (9.8)			L
	Miscellaneous
Chlorogenic acid (5-caffeoylquinic acid)	2,2′-CH₂	2.19; 2.02		39.5	L, S
	6,6′-CH₂	2.14; 2.06		38.4
	CH-3	4.26		71.7
	CH-4	3.88		73.9
	CH-5	5.32 *		72.2
	CH-2′	7.18	d (1.6)	116.1
	CH-5′	6.94	d (8.3)	117.5
	CH-6′	7.09	dd (8.3; 1.6)	123.7
	CH-7′	7.60	d (15.9)	147.2
	CH-8′	6.37	d (15.9)	115.6
Neochlorogenic acid (3-caffeoylquinic acid)	2,2′-CH₂	2.21; 2.09			S
	6,6′-CH₂	2.11; 1.93
	CH-3	5.40		74.0
	CH-4	3.76
	CH-5	4.17
	CH-2′	7.23		116.1
	CH-5′	6.97		117.5
	CH-6′	7.14		123.7
	CH-7′	7.66	d (16.0)	147.2
	CH-8′	6.44	d (16.0)	115.6
Glycine betaine	N(CH₃)₃	3.27 *		54.4	L
Glycine betaine	CH₂	3.91		67.3	L
Ethanolamine	CH₂-NH₂	3.15 *		42.2	L	L, S, F
Ethanolamine	CH₂OH	3.83		58.6	L	L, S, F
Choline	N(CH₃)₃	3.21 *	s	54.9	L, S	L, S, F
	CH₂OH	4.06		56.6
	CH₂N	3.52		68.4
Phosphorylcholine	N(CH₃)₃	3.23 *	s	55.0	L, S	L, S, F
	CH₂OPO₃	4.15		62.2
	CH₂N	3.61		67.4
Glycerophosphorylcholine	N(CH₃)₃	3.24 *	s	55.1	L	L, S, F
	CH₂N	3.68		67.0
	CH₂OP	4.33		60.5
	CH₂OP	3.94; 3.89		67.5
	CHOH	3.92		71.6
	CH₂OH	3.67; 3.6		63.1
Trigonelline	CH₃	4.44	s	49.3	L, S	L, F
	CH-6	9.12
	CH-4,2	8.84 *
	CH-3	8.09		128.8
Uridine	CH-6	7.87	d (8.2)	143.0	L, S	L, S, F
	CH-5	5.92 *	d (8.2)	103.4
	CH-1′ (rib)	5.93 *	d (4.6)	90.3
	CH-2′ (rib)	4.36		74.6
	CH-3′ (rib)	4.24		70.5
	CH-4′ (rib)	4.14		85.3

* Asterisks indicate signals used for the integration and quantification of metabolites.