ETHANOLIC AND HYDROALCOHOLIC EXTRACTS OF <i>PITANGA</i> LEAVES (<i>Eugenia uniflora</i> L.) AND THEIR FRACTIONATION BY SUPERCRITICAL TECHNOLOGY

Garmus, Tábata T.; Kopf, Sarah F. M.; Paula, Julia T.; Aguiar, Ana C.; Duarte, Gustavo H. B.; Eberlin, Marcos N.; Cabral, Fernando A.

doi:10.1590/0104-6632.20190362s20180159

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Thermodynamics • Braz. J. Chem. Eng. 36 (2) • Apr-Jun 2019 • https://doi.org/10.1590/0104-6632.20190362s20180159 copy

ETHANOLIC AND HYDROALCOHOLIC EXTRACTS OF PITANGA LEAVES (Eugenia uniflora L.) AND THEIR FRACTIONATION BY SUPERCRITICAL TECHNOLOGY

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Hydroalcoholic extracts prepared by conventional methods (in stirred vessel at 25 °C and 1 bar) and, hydroalcoholic and supercritical carbon dioxide (scCO₂) extracts prepared in fixed bed extractors (60 ºC and 400 bar) were obtained from pitanga leaves (Eugenia uniflora L.) in order to recover phenolic compounds. Hydroalcoholic and ethanolic extracts obtained in fixed bed were further fractionated in four separators by gradual pressure reduction, using scCO₂ as an antisolvent. All extracts and fractions were characterized in terms of extraction yield and the presence of total phenolics and flavonoids. Solvents were found to significantly influence the extraction yields and composition. Yields increased as a function of polarity, whereas the hydroalcoholic extractions displayed the highest yields and the highest amounts of extracted phenols and flavonoids.

Keywords:
Eugenia uniflora L.; Fractionation; Supercritical extraction; Phenolic compounds

Property	Pitanga (E. uniflora L.)
Volatile and moisture content (VU%)	9.15 ± 0.07%
Moisture (U)	7.30 ± 0.04%
Mean particle diameter (dp)	0.307 mm
Real density (ρ_r)	1.530 ± 0.004 g/cm³
Bed apparent density (ρ_a)	0.421 ± 0.003 g/cm³
Porosity (ԑ)	0.725 ± 0.002

Extraction	Extract*	Yield (%)	Total phenols		Total flavonoids
Extraction	Extract*	Yield (%)	Concentration (mg GAE/g extract)	Yield (mg GAE/ g leaves)	Concentration (mg CE/g extract)	Yield (mg CE/g leaves)
Conventional
This work	HC	25 ± 1	255 ± 40	63 ± 11	40 ± 2	10.0 ± 0.2
[1]**	EC	18 ± 2	151 ± 1	28 ± 3	61 ± 2	11 ± 2
[1]**	AC	27 ± 1	109 ± 1	30 ± 1	20 ± 2	6 ± 1
Fixed Bed
This work	HFB	28 ± 2	265 ± 22	70 ± 6	30 ± 2	7.8 ± 0.6
[1]**	EFB	20 ± 1	164 ± 1	32 ± 2	40 ± 2	8 ± 1
[1]**	AFB	33.3 ± 0.4	152 ± 1	51 ± 1	15 ± 1	5.0 ± 0.4
[1]**	SC	5 ± 1	32.7 ±	1.8 ±	153 ± 4	8 ± 2
[2]***	SC	3.5 ± 0.1	51 ± 7	1.7 ± 0.3	63 ± 1	2.2 ± 0.1
This work	SC	4.6	42 ± 15	2.0 ± 0.7	74 ± 5	3.6 ± 0.2
EFB (Ethanolic) scCO₂ Fractionation	E1	8.7 ± 0.6	264 ± 32	23 ± 2.8	41 ± 3	3.6 ± 0.2
	E2	0.6 ± 0.1	63 ± 6.7	0.35 ± 0.05	51 ± 6	0.28 ± 0.03
	E3	1.6 ± 0.6	25 ± 0.7	0.41 ± 0.01	60 ± 6	0.99 ± 0.09
	E4	1.9 ± 1.6	176 ± 7.2	3.4 ± 0.1	71 ± 17	1.4 ± 0.3
	∑	13 ± 3	M = 212	27.3	M = 48.4	6.2 ± 0.7
HFB (Hydroalcoholic) scCO₂ Fractionation	H1	30.1	231.1	69.6	33.7	10.1
	H2	0.27	26.1	0.07	59.6	0.16
	H3	1.36	46.9	0.63	71.7	0.98
	H4	1.44	16.5	0.24	32.4	0.47
	∑	33.2	212	70.5	35.3	11.7

Compound	m/z experimental	m/z calculated	Molecular formula	Fragments	Error (ppm)	Reference
Myricetin-O-rhamnoside	463.0873	463.0877	C₂₁H₂₀O₁₂	316, 179	-0.77	a,b
Chlorogenic acid	353.0885	353.0890	C₁₆H₁₈O₉	191	-1.42	c
Gallic acid	169.0138	169.0137	C₇H₆O₅	125.0250; 69.0353	0.59	d
Quinic acid	191.0558	191.0555	C₇H₁₂O₆	85.0306	1.57	e
Myricetin-O-hexoside	479.0834	479.0826	C₂₁H₂₀O₁₃	316.0236	1.73	e, f, g, h
Quercetin-O-deoxyhexoside	447.0937	447.0927	C₂₁H₂₀O₁₁	300.0274; 151.0036	2.15	b, f, g
Quercetin glucosyl rhamnoside	609.1465	609.1455	C₂₇H₃₀O₁₆	446.0172; 300.0271	1.61	c
Myricetin-O-pentoside	449.0736	449.0742	C₂₀H₁₈O₁₂	316.0245; 271.0259; 179.0002	-1.34	b
Morin	301.0348	301.0348	C₁₅H₁₀O₇	125.0276; 151.0043	-0.10	f
Uralenneoside	285.0612	285.0610	C₁₂H₁₄O₈	152.0111; 108.0211	0.70	i
3-O-p-Coumaroylquinic acid	337.0921	337.0923	C₁₆H₁₈O₈	191.0566	-0.73	j
5-O-Galloylquinic acid	343.0669	343.0665	C₁₄H₁₆O₁₀	169.00141; 191.0556; 125.0243	1.09	l

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Compound	E1	E2	E3	E4	H1	H2	H3	H4
Myricetin-O-rhamnoside	X	X	X	X	X	X	X	nd
Chlorogenic acid	X	X	X	X	X	X	X	nd
Gallic acid	X	X	X	X	X	X	X	nd
Quinic acid	X	X	X	X	X	X	X	X
Myricetin-O-hexoside	X	X	nd	nd	X	nd	nd	nd
Quercetin-O-deoxyhexoside	X	X	X	X	X	X	X	X
Quercetin glucosyl rhamnoside	X	X	nd	nd	X	nd	nd	nd
Myricetin-O-pentose	X	X	nd	nd	X	X	X	nd
Morin	X	X	X	X	nd	nd	nd	nd
Uralenneoside	X	X	X	X	X	X	X	X
3-O-p-Coumaroylquinic acid	X	X	X	X	X	nd	nd	nd
5-O-Galloylquinic acid	X	X	X	X	X	X	X	nd

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[1] * Corresponding author: Fernando A. Cabral - E-mail: cabral@fea.unicamp.br