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. 2023 Oct 12;28(20):7060.
doi: 10.3390/molecules28207060.

Exploring the Sequential-Selective Supercritical Fluid Extraction (S3FE) of Flavonoids and Esterified Triterpenoids from Calendula officinalis L. Flowers

Sirine Atwi-Ghaddar  1 , Lydie Zerwette  1 , Emilie Destandau  1 , Eric Lesellier  1
Affiliations

Exploring the Sequential-Selective Supercritical Fluid Extraction (S3FE) of Flavonoids and Esterified Triterpenoids from Calendula officinalis L. Flowers

Sirine Atwi-Ghaddar et al. Molecules. .

Abstract

One of the many advantages of supercritical fluid extraction (SFE) is the possibility of using it in sequential and selective approaches. This is due to the use of a dynamic extraction mode in addition to the possibility of altering the composition of the modifier during the extraction process. In this study, the optimization of Calendula officinalis L. extraction of non-polar and polar compounds was achieved using three-level Box-Behnken designs (BBD). For non-polar compounds, the factors were pressure, temperature, and EtOH percentage. As for the polar compounds, the three variables were temperature, the total modifier percentage, and H2O added in the modifier as an additive. The recovery of selectively rich extracts in triterpendiol esters and narcissin was possible using a sequential two-step SFE. The first step was performed at 80 °C and 15% EtOH, and the second at 40 °C and 30% EtOH:H2O 80:20 v:v with a total of 60 min of extraction. Additionally, the SFE extraction of non-polar compounds was scaled up on a pilot-scale extractor, demonstrating similar results. Finally, the SFE results were compared to ultrasound-assisted extraction (UAE).

Keywords: Box-Behnken design; extraction scale-up; marigold; narcissin.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Response surface heat maps showing the effects of factor variation on the total faradiol esters (faradiol myristate and faradiol palmitate) and peak areas (mAU × min). (a) Interaction between pressure (X1) and temperature (X2), (b) Interaction between temperature (X2) and EtOH percentage (X3).
Figure 2
Figure 2
SFE kinetics of total fardiol esters (faradiol myristate and faradiol palmitate). (a) Variation in EtOH percentage (5 and 15%) at constant pressure (15 MPa) and temperature (80 °C). (b) Variation in pressure (10, 15, and 20 MPa) at a constant temperature of 60 °C and 15% EtOH. (c) Variation in temperature (40, 60, and 80 °C) at a constant pressure (15 MPa) and 15% EtOH.
Figure 3
Figure 3
Schematic representation of the analytical scale extractor (AE) and pilot-scale extractor (PE) used in this study.
Figure 4
Figure 4
Comparison of cumulated peak areas (mAU × min/g) for major faradiol myristate and faradiol palmitate between analytical-scale extraction (AE) and pilot-scale extraction (PE) for CNPE. (a) Extraction kinetics of the total yield of faradiol (b) Variation in the total yield for the function of the solvent-to-feed ratio.
Figure 5
Figure 5
Comparison between supercritical fluid extraction (SFE) and ultrasound-assisted extraction (UAE) for CNPE faradiol esters (myristate and palmitate).
Figure 6
Figure 6
Response surface heat maps showing the effect of this factor’s variation on narcissin yield (mg/g). Variation in the total modifier percentage (X′2) and water percentage (X′3).
Figure 7
Figure 7
SFE kinetics of narcissin (mg/g) from CPE with a variation in temperature 40, 60 and 80 °C constant conditions: 30% EtOH:H2O 80:20 v:v as a modifier, 15 MPa, 3 mL/min.
Figure 8
Figure 8
Comparison between supercritical fluid extraction (SFE) and ultrasound-assisted extraction (UAE) for polar compounds of CPE (total polar molecules represent all polar compounds quantified at 354 nm, including narcissin).
Figure 9
Figure 9
Extraction kinetics of the S3FE of non-polar and polar compounds from Calendula officinalis L. represented in a yield percentage for 60 min of extraction (total polar molecules represent all polar compounds quantified at 354 nm including narcissin).
Figure 10
Figure 10
UHLP/SFC-ELSD analysis of the calendula non-polar extract (CNPE). Peak identification (1) faradiol-3-O-myristate (tr = 19.78 min), (2) fardiol-3-O-palmitate (tr = 23.46 min).
Figure 11
Figure 11
(a) UC-DAD gradient of polar compounds in CNPE. Blue: flow (mL/min), yellow: MeOH + 0.1% MSA (%) and red: pressure (MPa). (b) UC-DAD analysis of polar compounds in CNPE (354 nm)/SFE extract solubilized in MeOH:DCM 1:1 v:v. narcissin (tr = 3.15 min).
Figure 12
Figure 12
UHPLC-DAD analysis of polar extracts (354 nm); narcissin (tr = 1.93 min).
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