Table 6.

Other compounds identified in C. medica L.

Compounds	Formula	Structure	* Extraction Method	Method Analyses	Part of the Plant	Abundance	References
Alkaloids
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid	C12H12N2O2		IX	EI–MS, HR–EI–MS	fresh fruit	-	[43]
Acridine derivatives
Medicacridone	C20H21NO4		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Citracridone-I	C20H19NO5		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
citracridone-III	C19H17NO5		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
5-hydroxynoracronycine 3	C19H17NO4		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Xanthones
Medicaxanthone	C51H75O8		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Lichenxanthone	C15H12O6		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Glycol
2,3-Butanediol	C4H10O2		X	GC–MS	exocarp, mesocarp	23.7%	[54]
Furan derivatives
Furfural	C5H4O2		X	GC–MS	exocarp, mesocarp	3.9%	[54]
2(3H)-Furanone, 5-methyl	C8H12O2		X	GC–MS	exocarp, mesocarp	0.9%	[54]
5- 5-Hydroxymethylfurfural	C6H6O3		X	GC–MS	exocarp, mesocarp	1.9%	[54]
Hydrocarbons
1,3-Cyclopentadiene	C5H6		XIII	GC–MS	fresh fructus	1.75–2.36%	[45]
Benzene	C6H6		XI	GC–MS	fructus	1.67%	[58]
Eicosane	C20H42		I	GC–MS	flavedo	0.10%	[50]
Nonacosane	C29H60		I	GC–MS	flavedo	0.10%	[50]
Mono or polyunsaturated aldehyde
Undecanal	C11H22O		V, VI, VII	GC–MS	flavedo	0.1–0.2%	[48]
			II, III, IV	HRGC–MS	flavedo	0.03–0.06%	[49]
Dodecanal	C12H24O		II, III, IV	HRGC–MS	flavedo	0.02–0.03%	[49]
			V, VI, VII	GC–MS	flavedo	0.1%	[48]
9,17-octadecadienal	C18H32O		I	GC–MS	flavedo	9.29%	[50]
16-Octadecenal	C18H34O		I	GC–MS	flavedo	0.10%	[50]
Nonanal	C9H18O		II, III, IV	HRGC–MS	flavedo	0.04–0.07%	[49]
Tetradecanal	C14H28O		V, VI, VII	GC–MS	flavedo	0.1%	[48]
Pentadecanal	C15H30O		V, VI, VII	GC–MS	flavedo	0.1%	[48]
Phenylpropanoids
Coniferin	C16H22O8		IX	EI–MS, HR–EI–MS	fresh fruit	-	[43]
Syringin	C17H24O9		IX	EI–MS, HR–EI-MS	fresh fruit	-	[43]
Phytosterols
Lupeol	C26H32O7		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Stigmasterol	C29H48O		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Ꞵ-Sitosterol	C29H50O		VIII	ESI–HR, EI–MS, HMQC, HMBC	bark	-	[37]
Fatty acids and their esters
Lauric acid	C12H24O2		I	GC–MS	flavedo	0.11%	[50]
Myristic acid	C14H28O2		I	GC–MS	flavedo	0.23%	[50]
Palmitic acid	C16H32O2		I	GC–MS	flavedo	5.17%	[50]
Hexadecanal	C16H32O		XIII	GC–MS	mesocarp	1.6%	[54]
			V, VI, VII	GC–MS	flavedo	0.1%	[48]
Pentadecanoic acid methyl ester	C16H32O2		I	GC–MS	flavedo	0.22%	[50]
Palmitoleic acid	C17H32O2		I	GC–MS	flavedo	0.19%	[50]
Heptadecanoic acid	C17H34O2		I	GC–MS	flavedo	0.20%	[50]
Stearic acid	C18H36O2		I	GC–MS	flavedo	0.18%	[50]
16-Octadecenal	C18H34O		I	GC–MS	flavedo	0.10%	[50]
Linoleic acid, methyl ester	C19H34O2		I	GC–MS	flavedo	0.19%	[50]
Linolenic acid, methyl ester	C19H32O2		I	GC–MS	flavedo	0.41%0.30%	[50]
Stearic acid, methyl ester	C19H38O2		I	GC–MS	flavedo	0.30%	[50]
Benzoates
Methyl vanillate methyl ester	C9H10O4		IX	EI–MS, HR–EI–MS	fresh fruit	-	[43]
Methyl benzoate	C8H8O2		IX	EI–MS, HR–EI–MS	fresh fruit	-	[43]
Methyl paraben	C8H8O3		IX	EI–MS, HR–EI–MS	fresh fruit	-	[43]

* Extraction method. I: Maceration of peel with n-hexane at room temperature; II: aspiration of the oil from the utricles present on the peel by means of a syringe with a thin needle; III: the rinds of the fruit were squeezed to cause the breaking of the utricles in order to release the oil, which was collected by extraction with hexane; IV: manual abrasion of the rind by means of a stainless steel grater, followed by manual pressing and centrifugation of the water–oil emulsion; V: hydro-distillation; VI: soxhlet apparatus using pentane and ethanol as solvents; VII: SCF–CO2; VIII: maceration in MeOH; IX: MeOH under reflux; X: maceration and UAE in MeOH; XI: distillation using a Clevenger-type apparatus; XII: steam-based hydro-distillation; XIII: exocarp and mesocarp were pulverized in liquid nitrogen with a chilled mortar and pestle, and then weighed and placed in MeOH. The mixtures were sonicated.