A new approach in extracting active acylphloroglucinol derivatives from Dryopteris wallichiana and Elaphoglossum erinaceum

Published Date

June 2015, Vol.101:222–230, doi:10.1016/j.supflu.2015.03.023

Title 

A new approach in extracting active acylphloroglucinol derivatives from Dryopteris wallichiana and Elaphoglossum erinaceum

• Author 

• Pablo Noé Nuñez ^a
• Alexandre T. do Espirito Santo ^b
• Rodrigo Scopel ^b
• João Gabriel P. Anzolin ^b
• María Luisa Villarreal ^a
• Amélia Teresinha Henriques ^c
• Eduardo Cassel ^b
• Alexandre T. Cardoso Taketa ^a
• Gilsane L. von Poser ^c
• Rubem M.F. Vargas ^b,,

• aCentro de Investigación en Biotecnología, Universidad Autónoma del Estado de Morelos, Cuernavaca, Mexico
• bPGETEMA – Faculdade de Engenharia, PUCRS, CEP 90619-900 Porto Alegre, RS, Brazil
• cPrograma de Pós-Graduação em Ciências Farmacêuticas, UFRGS, CEP 90610-000 Porto Alegre, RS, Brazil

Received 16 December 2014. Revised 27 March 2015. Accepted 28 March 2015. Available online 7 April 2015.

Highlights

• •
  The phloroglucinol derivatives were successfully extracted by SFE CO₂.
• •
  The supercritical fluid extraction produced expressive yields and higher selectivity.
• •
  The mathematical modeling was efficient in the predicting the experimental data.
• •
  The phloroglucinol derivatives were extracted by SFE CO₂ from 90 to 300 bar at 40 °C.
• •
  The presence of phloroglucinol derivatives in both plants was detected by HPLC-PDA.

Abstract

The supercritical carbon dioxide extraction of acylphloroglucinol derivatives from Dryopteris wallichiana and Elaphoglossum erinaceum was investigated and modeled. The plants were submitted to extraction with supercritical fluid at constant temperature (40 °C) and pressures of 90, 120, 150, 200, 250 and 300 bar, successively, as well as to conventional ultrasound assisted extraction using n-hexane. The extracts were dewaxed affording fractions which were analyzed by HPLC-PDA and submitted to Nuclear Magnetic Resonance spectra showing singlets at very low field indicating the presence of compounds with enolizable β-triketones systems. The spectra shed the presence of other signals which characterize acylphloroglucinol derivatives. Mathematical modeling was performed to fit the experimental data obtained at 90 bar. All the extracts of both plants displayed antibacterial activity against Staphylococcus aureus and Escherichia coli. The supercritical fluid extraction of phloroglucinols from both ferns was more selective than the conventional solvent extraction using n-hexane.

Graphical abstract

Keywords

• Dryopteris wallichiana (Spreng.) Hyl.
• Elaphoglossum erinaceum (Fée) T. Moore
• Acylphloroglucinol derivatives
• Chemical analysis
• Supercritical fluid extraction
• Mathematical modeling

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Nomenclature

a

half thickness of slab (m)

c

solubility (g/L)

D

effective diffusion coefficient (m²/s)

e

mass of extract relative to N

k

desorption coefficient (1/s)

k_c

superficial coefficient of mass transfer (m/s)

k_f

mass transfer coefficient in fluid phase (m/s)

k_r

proportionality constant (dimensionless)

k_s

mass transfer coefficient in solid phase (m/s)

L

dimensionless parameter of the model 1

M

mass recovered at time t (g)

M_∞

mass recovered for an infinite time of extraction (g)

steam flow rate (g/s)

N

mass of the solute-free solid phase (g)

n

refers to the end of extraction of easily accessible solute

q

specific amount of solvent (g/g)

mass flow rate of solvent related to N (s⁻¹)

q_m

specific amount of solvent for start of the extraction from the inside of particles

q_n

specific amount of solvent for end of the extraction of easily accessible solute

t

extraction time (s)

u

superficial fluid velocity (m/s)

W

dimensionless parameter of slow-extraction period

w_o

initial mass fraction for the raw material (g/g)

x

molar fraction of liquid phase

x₀

overall initial concentration related to solute-free solid phase (g/g)

x_k

inaccessible oil concentration inside the solid phase particles (g/g)

y

molar fraction of vapor phase

y_r

solubility of the extract in the solvent (g/g)

Z_m

dimensionless parameter of fast extraction period

z_w

dimensionless coordinate of the boundary between fast and slow extraction

ɛ

bed porosity

β

eigenvalue of the one-dimensional diffusion equation

ρ

density of solvent (g/cm³)

ρ_s

density of solid phase (g/cm³)

 Table 1

Table 1.

Fig. 1.

Fig. 2.

 Table 2

Table 2.

 Table 3

Table 3.

Fig. 3.

Fig. 4.

Fig. 5.

Fig. 6.

 Table 4

Table 4.

 Table 5

Table 5.

• ⁎ 
  Corresponding author. Tel.: +55 51 33203653; fax: +55 51 33203625.

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