# Extraction of Galphimines from Galphimia glauca with Supercritical Carbon Dioxide

^{1}

^{2}

^{*}

## Abstract

**:**

^{−1}.

## 1. Introduction

## 2. Results and Discussion

#### 2.1. Extraction Behavior

_{p}), and volumetric flow rate (Q

_{V}) over the supercritical fluid extraction of Galphimia glauca was evaluated in terms of the extraction yield (e), defined as the ratio between the mass of extract and the mass of solid material fed into the extractor. Experimental conditions were set in a way that a variable was changed in proportional increments, while the others were fixed at a central value. There were four levels for each variable. The extraction yield reached a maximum of 2.22%, although the extraction experiments did not include a static period that would promote better contact between Galphimia glauca and carbon dioxide at the beginning.

_{p}, and Q

_{V}constant, as depicted in Figure 2. This must be attributed to the increase in density that went from 699.75 kg·m

^{−3}(15 MPa) to 892.55 kg·m

^{−3}(33.75 MPa). The latter condition enhanced the solvating power of the supercritical fluid and dissolved more solutes. Besides, the solubility of solutes in supercritical fluids tended to increase with pressure, leading to an increase in e.

_{p}, and Q

_{V}, except for the increment from 313.15 K to 318.15 K. This increment of yield might be attributed to a better dissolution of the solutes because of their vapor pressure increment at a high temperature. This hypothesis could be further tested by measuring the solubility of the extract in supercritical carbon dioxide in order to check the most dominant effect in solubility.

_{V}conditions, the first part of the extraction curves was quite similar.

^{–1}, but e values decreased after this rate. Probably, the low residence time avoided the solute solubilization in the supercritical fluid at the highest flow rate.

#### 2.2. Modeling

_{k}and ̅t had similar values and trends. The external mass transfer coefficients were, on average, one order of magnitude higher than the internal ones. The extraction rate was promoted when the temperature was increased. It could be demonstrated throughout the optimized k

_{f}a parameters, whose values also increased from the lowest to the highest temperature. The transition times tended to be shorter as the temperature was increased, resulting in higher temperatures favoring both yield and extraction rate, as was found by Wagner et al. [42]. The AARD resulted in a maximum of 3.55%.

_{0}) tended to be low when particle size was increased (except for the largest particle size, which might be due to better grinding). In consequence, the experiments performed with the lowest particle size exhibited the highest yield, and hence the solubility dominated the process. On the opposite, kinetics was not so promoted by reducing the particle size because the extraction rate was slow with small particles. This trend was not the one followed by other works that studied the influence of particle size in the kinetics of supercritical fluid extraction [24]. Despite this, a higher particle size did not allow for the extraction of the majority of soluble components, which remained in the cells and were not released by grinding. The best fit correlation was obtained with the model of Sovová in comparison with the model proposed by Papamichail et al. based on the AARD.

^{−1}. The results for this variable are in Table S4. The coefficients k

_{f}a tended to decrease as the volumetric flow rate rose; this behavior was also observed in the supercritical carbon dioxide extraction of betel nut [43]. However, e decreased at the highest Q

_{V}. It could be probably attributed to the high velocity that avoided enough interaction between the supercritical fluid and the solutes, as the mass transfer resistance increased (low coefficients). The low values in e < 5% meant that these proposals were suitable for modeling the supercritical fluid extraction of Galphimia glauca with carbon dioxide at the studied conditions.

#### 2.3. Quantification of Galphimine B

^{−1}, followed by expanded uncertainty with a coverage factor of 2 and relative areas for galphimine B and galphimine E. Content of galphimines in the extract was the content of the global extract, i.e., the mixture of all the extract fractions collected at the time intervals of each experiment.

^{−1}, and the average concentration for all experiments was 19.5 mg·g

^{−1}with a standard deviation of 5.2 mg·g

^{−1}. The effects of pressure, temperature, particle diameter, and solvent flow in the content of galphimines B and E were not as notorious as the variations of yields. This showed that there was uniformity in the concentration of G-B in the extracts, as well as the relative area values of galphimine E, 15.3% with 3.1% of standard deviation.

^{−1}. Then, the amount of the active compound, galphimine B, was found within the limits of concentration of those studies. It is important to remark that the HPLC analysis of the materials extracted with supercritical carbon dioxide showed the presence of galphimines B and E, as well as unknown compounds, whose peaks were not detected in the purified extract used as standard. This could lead to future research about the compounds in supercritical extracts and further tests, as realized by Centro de Investigación Biomédica del Sur from Instituto Mexicano del Seguro Social.

## 3. Materials and Methods

#### 3.1. Material Plant

#### 3.2. Chemicals

#### 3.3. Apparatus and Procedure

#### 3.4. Analyses

^{−1}. From this standard, the unknown composition of galphimine E was also reported as a relative area. A calibration curve with galphimine B was attained using concentrations of 1, 5, 10, 15, 20, 25, 30, 35 μg G-B/mL methanol. Results were adjusted to a linear function: C

_{G-B}= 42.3341AU

_{G-B}– 0.6819, where C

_{G-B}is the concentration of G-B in μg/mL, and AU

_{G-B}is the response area of G-B. In the case of galphimine E, the quantification was limited to as the percentage of the relative area between galphimine E and galphimine B.

#### 3.5. Mathematical Modeling

_{k}, and h

_{k}are defined by the next expressions: G = 1 – x

_{k}/x

_{0}, Z = Nk

_{f}aρ

_{f}/Q(1 – ε)ρ

_{s}, Y = Nk

_{s}ax

_{0}/Q(1 – ε)y

_{r}, Ψ = tQy

_{r}/Nx

_{0}, Ψ

_{k}= G/Z + (1/Y) ln{1 – G [1 – exp(Y)]}, and h

_{k}= (1/Y) ln[1 + {exp[Y(Ψ – G/Z)] – 1}/G]. The above expressions include additional variables, which comprise physical meaning. E is referred to the mass of extracted solute, N denotes the mass of the solid material, x

_{0}corresponds to the initial concentration of solute in the solid phase, x

_{k}represents the interface concentration of solute, t symbolizes the extraction time, Q indicates the mass flow rate of the supercritical fluid, ε expresses the bed porosity, a is the interfacial area, ρ

_{f}represents the supercritical fluid density, ρ

_{s}is referred to the solid density, k

_{f}describes the external mass transfer coefficient, which is optimized together with the interfacial area a as the product k

_{f}a, k

_{s}denotes the internal mass transfer coefficient, and y

_{r}corresponds to the solute solubility in the supercritical fluid as apparent parameter in multicomponent matrixes, which actually is the apparent solubility, as it was not experimentally determined. Apparent solubility was obtained on each experimental condition as the slope of a plot of the cumulative mass of extract versus the mass of CO

_{2}spent per mass of material charged in the extractor.

_{0}denotes the solute solubility in the supercritical fluid similar to y

_{r}from Equation (1), A is a variable that comprises the overall mass transfer coefficient in the fluid phase (k

_{f}a) and is defined as k

_{f}aρ

_{f}/ρ

_{s}(1–ε), and B is quantified by A/(Q̇ + A). Q̇ is expressed as the specific mass flow rate of the supercritical fluid estimated with the Q/N ratio. These additional definitions can state that A is equivalent to the product ZQ̇, as well as ̅x is also equivalent to x

_{k}reported in the equations proposed by Papamichail et al. and Sovová, in that order.

_{0}– ̅x)/[(y

_{0}A(1 – B)]. Moreover, K is the equilibrium constant in Equation (3) that was considered from Perrut et al. [48]:

_{k}as the dimensionless time that is the boundary between the easy and difficult extraction stages. Then, the time of the boundary t

_{k}can be obtained from Ψ

_{k}. A comparable assumption with t

_{k}for the Papamichail et al. model is that ̅t has the equivalent meaning. In the same way, the grinding efficiency G is equivalent to 1 – ̅x/x

_{0}.

_{i}refers to the yield for each experiment. Superscripts exp and calc correspond to the experimental and calculated data points, respectively.

## 4. Conclusions

_{p}, and Q

_{V}on the extracts was studied in a wide range, achieving maximum yield of 2.22% in dry basis. High pressure favored higher yields as the solvent density was superior and allowed the increase of its solvation power and the capacity for dissolving more substances. The values of extraction yields suggested variations in parameters, such as static period previous to dynamic mode, as well as the evaluation of a polar co-solvent, due to the presence of multiple phenolic and high molecular weight compounds. The kinetic curves were represented with good results by the Sovová and Papamichail et al. equations. Successful extraction of galphimine B was attained based on the content of this nor-seco triterpenoid in the extract, whose concentration was comparable with those results via the maceration technique reported previously. The variations of galphimine B content as a function of P, T, d

_{p}, and Q

_{V}was almost negligible; it could probably be associated with the preference of carbon dioxide to dissolve other chemicals among galphimine B and galphimine E.

## Supplementary Materials

_{p}= 326 μm, and Q

_{V}= 3 L·min

^{−1}. Table S2: Modeling results for supercritical fluid extraction of Galphimia glauca at P = 27.50 MPa, d

_{p}= 326 μm, and Q

_{V}= 3 L·min

^{−1}. Table S3: Modeling results for supercritical fluid extraction of Galphimia glauca at P = 27.50 MPa, T = 323.15 K, and Q

_{V}= 3 L·min

^{−1}. Table S4: Modeling results for supercritical fluid extraction of Galphimia glauca at P = 27.50 MPa, T = 323.15 K, and d

_{p}= 326 μm.

## Author Contributions

## Funding

## Acknowledgments

## Conflicts of Interest

## Abbreviations

A | Variable in the model of Papamichail et al. (min^{−1}) |

AU_{G-B} | Response area of galphimine B (absorbance^{2}) |

a | Interfacial area (m^{−1}) |

B | Variable in the model of Papamichail et al. (dimensionless) |

C_{G-B} | Concentration of galphimine B (μg·mL^{−1}) |

d_{p} | Particle size (μm) |

E | Mass of extract (g) |

e | Extraction yield (dimensionless) |

G | Grinding efficiency (dimensionless) |

h | Coordinate in the model of Sovová (dimensionless) |

K | Equilibrium constant in the model of Papamichail et al. (dimensionless) |

k | Mass transfer coefficient (m·min^{−1}) |

N | Mass of solid charged in the extractor (g) |

n | Number of datum |

P | Pressure (MPa) |

Q | Mass flow rate (g·min^{−1}) |

Q_{V} | Volumetric flow rate (L·min^{−1}) |

T | Temperature (K) |

t | Time (min) |

x | Concentration in the solid phase (dimensionless) |

Y | Variable in the model of Sovová (dimensionless) |

y | Concentration in the fluid phase (dimensionless) |

y_{0} | Solubility in the model of Papamichail et al. (g_{extract}·g_{CO2}^{−1}) |

y_{r} | Solubility in the model of Sovová (g_{extract}·g_{CO2}^{−1}) |

Z | Variable in the model of Sovová (dimensionless) |

Greek letters | |

ε | Bed porosity (dimensionless) |

Ψ | Dimensionless time in the model of Sovová (dimensionless) |

ρ | Density (kg·m^{−3}) |

Superscripts | |

̅ | Boundary of extraction periods in the model of Papamichail et al. |

* | Equilibrium condition |

̇ | Specific variable |

calc | Calculated |

exp | Experimental |

Subscripts | |

0 | Initial condition |

f | Fluid phase |

k | Boundary of extraction periods in the model of Sovová. |

s | Solid-phase |

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Sample Availability: Samples of the purified extract of galphimines and the supercritical carbon dioxide extracts of Galphimia glauca are available from the authors. |

**Figure 6.**Schematic diagram of the home-made apparatus. (1) CO

_{2}supply tank; (2) solvent pump; (3) preheater; (4) extractor; (5) thermometer; (6) manometer; (7,8) refrigerated circulating baths; (9) back pressure regulator; (10) U-shaped tubes; (11) wet gas meter; (12) electronic balance.

**Table 1.**Galphimines and yield from supercritical carbon dioxide extraction of Galphimia glauca at temperature = 323.15 K, particle size = 326 μm, and volumetric flow rate = 3 L·min

^{−1}.

P (MPa) | e (%) | Concentration G-B (mg·g extract^{−1}) | Relative area G-B (%) | Relative area G-E (%) |
---|---|---|---|---|

15.00 | 0.70 | 18.1 ± 2.3 | 85.24 | 14.76 |

21.25 | 1.55 | 28.1 ± 8.3 | 88.06 | 11.94 |

27.50 | 1.82 | 21.6 ± 1.5 | 86.11 | 13.89 |

33.75 | 2.22 | 20.3 ± 2.6 | 86.02 | 13.98 |

**Table 2.**Galphimines and yield from supercritical carbon dioxide extraction of Galphimia glauca at pressure = 27.50 MPa, particle size = 326 μm, and volumetric flow rate = 3 L·min

^{–1}.

T (K) | e (%) | Concentration G-B (mg·g Extract^{−1}) | Relative Area G-B (%) | Relative Area G-E (%) |
---|---|---|---|---|

313.15 | 0.92 | 11.5 ± 2.6 | 91.38 | 8.62 |

318.15 | 0.79 | 29.1 ± 2.2 | 84.92 | 15.08 |

323.15 | 1.82 | 21.6 ± 1.5 | 86.11 | 13.89 |

328.15 | 1.96 | 11.7 ± 1.2 | 80.49 | 19.51 |

**Table 3.**Galphimines and yield from supercritical carbon dioxide extraction of Galphimia glauca at pressure = 27.50 MPa, temperature = 323.15 K, and volumetric flow rate = 3 L·min

^{–1}.

d_{p} (μm) | e (%) | Concentration G-B (mg·g Extract^{−1}) | Relative Area G-B (%) | Relative Area G-E (%) |
---|---|---|---|---|

224 | 2.16 | 21.4 ± 2.7 | 79.56 | 20.44 |

326 | 1.82 | 21.6 ± 1.5 | 86.11 | 13.89 |

461 | 1.76 | 17.5 ± 1.8 | 79.54 | 20.46 |

548 | 0.78 | 19.0 ± 2.3 | 84.13 | 15.87 |

**Table 4.**Galphimines and yield from supercritical carbon dioxide extraction of Galphimia glauca at pressure = 27.50 MPa, temperature = 323.15 K, and particle size = 326 μm.

Q_{V} (L·min^{−1}) | e (%) | Concentration G-B (mg·g Extract^{−1}) | Relative Area G-B (%) | Relative Area G-E (%) |
---|---|---|---|---|

1 | 0.91 | 19.5 ± 1.5 | 83.56 | 16.44 |

2 | 1.30 | 19.1 ± 3.1 | 85.79 | 14.21 |

3 | 1.82 | 21.6 ± 1.5 | 86.11 | 13.89 |

4 | 1.40 | 10.4 ± 1.3 | 82.31 | 17.69 |

Average d_{p} (μm) | Apparent Density (kg·m^{−3}) | True Density (kg·m^{−3}) |
---|---|---|

224 | 291 | 1157 |

326 | 266 | 1117 |

461 | 250 | 1091 |

548 | 194 | 994 |

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**MDPI and ACS Style**

Verónico Sánchez, F.J.; Elizalde Solis, O.; Zamilpa, A.; García Morales, R.; Pérez García, M.D.; Jiménez Ferrer, J.E.; Tortoriello, J. Extraction of Galphimines from *Galphimia glauca* with Supercritical Carbon Dioxide. *Molecules* **2020**, *25*, 477.
https://doi.org/10.3390/molecules25030477

**AMA Style**

Verónico Sánchez FJ, Elizalde Solis O, Zamilpa A, García Morales R, Pérez García MD, Jiménez Ferrer JE, Tortoriello J. Extraction of Galphimines from *Galphimia glauca* with Supercritical Carbon Dioxide. *Molecules*. 2020; 25(3):477.
https://doi.org/10.3390/molecules25030477

**Chicago/Turabian Style**

Verónico Sánchez, Francisco Javier, Octavio Elizalde Solis, Alejandro Zamilpa, Ricardo García Morales, Ma. Dolores Pérez García, Jesús E. Jiménez Ferrer, and Jaime Tortoriello. 2020. "Extraction of Galphimines from *Galphimia glauca* with Supercritical Carbon Dioxide" *Molecules* 25, no. 3: 477.
https://doi.org/10.3390/molecules25030477