Chemometric optimisation of pressurised liquid extraction for the determination of alliin and S‐allyl‐cysteine in giant garlic ( Allium ampeloprasum L.) by liquid chromatography tandem mass spectrometry

Peterssen‐Fonseca, Darlene; Henríquez‐Aedo, Karem; Carrasco‐Sandoval, Jonathan; Cañumir‐Veas, Juan; Herrero, Miguel; Aranda, Mario

doi:10.1002/pca.3046

Chemometric optimisation of pressurised liquid extraction for the determination of alliin and S‐allyl‐cysteine in giant garlic ( Allium ampeloprasum L.) by liquid chromatography tandem mass spectrometry

Journal Article · Sun Mar 28 04:00:00 EDT 2021 · Phytochemical Analysis

DOI:https://doi.org/10.1002/pca.3046· OSTI ID:1786529

Peterssen‐Fonseca, Darlene ^[1]; ^[1]; Carrasco‐Sandoval, Jonathan ^[1]; Cañumir‐Veas, Juan ^[2]; Herrero, Miguel ^[3]; ^[4]

Laboratorio de Biotecnología y Genética de Alimentos. Departamento de Ciencia y Tecnología de los Alimentos. Facultad de Farmacia Universidad de Concepción Concepción Chile
Laboratorio de Bioprocesos. Departamento de Agroindustrias. Facultad de Ingeniería Agrícola Universidad de Concepción Chillán Chile
Laboratorio de Foodomics Instituto de Investigación en Ciencias de la Alimentación (CIAL, CSIC‐UAM) Madrid Spain
Laboratorio de Investigación en Fármacos y Alimentos, Departamento de Farmacia, Facultad de Química y de Farmacia Pontificia Universidad Católica de Chile Santiago Chile

Abstract Introduction

Giant garlic is a functional food that contains different kinds of bioactive molecules with beneficial effects on chronic noncommunicable diseases like diabetes and cardiovascular conditions. Considering biosynthesis pathways, abundance, and biological activity, alliin and S‐allyl‐cysteine were used as chemical markers of organosulphur compounds present in giant garlic.

Objective

To establish a chemometric optimisation of pressurised liquid extraction for the determination of alliin and S‐allyl‐cysteine in giant garlic by liquid chromatography tandem mass spectrometry (LC–MS/MS).

Methodology

Samples were blanched (ca. 90°C for 10 min) to inactivate alliinase and γ‐glutamyl transpeptidase enzymes and then freeze‐dried. Chemometric optimisation was performed via response surface methodology based on central composite design (CCD). Organosulphur compound yields were determined applying a validated LC–MS/MS method in multiple reaction monitoring (MRM) mode using the following transitions: for alliin m/z 178 → 74 and for S‐allyl‐cysteine m/z 162 → 41.

Results

According to CCD results, under constant conditions of pressure (1500 psi) and time (20 min), the optimal conditions for pressurised liquid extraction of alliin and S‐allyl‐cysteine were 70.75 and 68.97% v/v of ethanol in extraction solvent and 76.45 and 98.88°C as extraction temperature, respectively. Multiple response optimisation for the simultaneous extraction of both organosulphur compounds was established via desirability function. Under these conditions, 2.70 ± 0.27 mg g ⁻¹ dry weight (DW) of alliin and 2.79 ± 0.22 mg g ⁻¹ DW of S‐allyl‐cysteine were extracted.

Conclusions

These results clearly demonstrated that pressurised liquid extraction is an efficient green technique to extract bioactive organosulphur compounds from giant garlic. Extraction yields were significantly ( p < 0.05) higher than those obtained with conventional ultra‐turrax extraction.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

OSTI ID:: 1786529

Journal Information:: Phytochemical Analysis, Journal Name: Phytochemical Analysis Journal Issue: 6 Vol. 32; ISSN 0958-0344

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (32)

Evaluation of phenolic profiles and antioxidant capacity of maqui ( Aristotelia chilensis ) berries and their relationships to drying methods: Evaluation of phenolic profiles and antioxidant capacity of maqui Quispe-Fuentes, Issis; Vega-Gálvez, Antonio; Aranda, Mario Journal of the Science of Food and Agriculture, Vol. 98, Issue 11 https://doi.org/10.1002/jsfa.8938	journal	March 2018
Detection and identification of acetylcholinesterase inhibitors in Annona cherimola Mill. by effect‐directed analysis using thin‐layer chromatography‐bioassay‐mass spectrometry Galarce‐Bustos, Oscar; Pavón, Jessy; Henríquez‐Aedo, Karem Phytochemical Analysis, Vol. 30, Issue 6 https://doi.org/10.1002/pca.2843	journal	June 2019
Variability in S-Alk(en)yl-l-Cysteine Sulfoxides in Garlic within a Seven-Month Period Determined by a Liquid Chromatography – Tandem Mass Spectrometry Method Rektorisova, Michaela; Hrbek, Vojtech; Jiru, Monika Plant Foods for Human Nutrition, Vol. 75, Issue 3 https://doi.org/10.1007/s11130-020-00817-z	journal	May 2020
An LC-MS/MS-SRM Method for Simultaneous Quantification of Four Representative Organosulfur Compounds in Garlic Products Zhu, Qinchang; Kakino, Kenichi; Nogami, Chika Food Analytical Methods, Vol. 9, Issue 12 https://doi.org/10.1007/s12161-016-0535-1	journal	May 2016
Chemometric Optimization of QuEChERS Extraction Method for Polyphenol Determination in Beers by Liquid Chromatography with Ultraviolet Detection Galarce-Bustos, Oscar; Novoa, Lissette; Pavon-Perez, Jessy Food Analytical Methods, Vol. 12, Issue 2 https://doi.org/10.1007/s12161-018-1376-x	journal	October 2018
Pressurized Liquid Extraction of Pigments from Chlamydomonas sp. and Chemical Characterization by HPLC–MS/MS Montero, Lidia; Sedghi, Mahshid; García, Yolanda Journal of Analysis and Testing, Vol. 2, Issue 2 https://doi.org/10.1007/s41664-018-0062-8	journal	April 2018
Statistical designs and response surface techniques for the optimization of chromatographic systems Ferreira, Sergio Luis Costa; Bruns, Roy Edward; da Silva, Erik Galvão Paranhos Journal of Chromatography A, Vol. 1158, Issue 1-2 https://doi.org/10.1016/j.chroma.2007.03.051	journal	July 2007
Green processes for the extraction of bioactives from Rosemary: Chemical and functional characterization via ultra-performance liquid chromatography-tandem mass spectrometry and in-vitro assays Herrero, M.; Plaza, M.; Cifuentes, A. Journal of Chromatography A, Vol. 1217, Issue 16 https://doi.org/10.1016/j.chroma.2009.11.032	journal	April 2010
Comparison of different extraction procedures for the comprehensive characterization of bioactive phenolic compounds in Rosmarinus officinalis by reversed-phase high-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry Borrás Linares, I.; Arráez-Román, D.; Herrero, M. Journal of Chromatography A, Vol. 1218, Issue 42 https://doi.org/10.1016/j.chroma.2011.07.021	journal	October 2011
Enrichment of antioxidant compounds from lemon balm (Melissa officinalis) by pressurized liquid extraction and enzyme-assisted extraction Miron, T. L.; Herrero, M.; Ibáñez, E. Journal of Chromatography A, Vol. 1288 https://doi.org/10.1016/j.chroma.2013.02.075	journal	May 2013
An improved method for a fast screening of α-glucosidase inhibitors in cherimoya fruit (Annona cherimola Mill.) applying effect-directed analysis via high-performance thin-layer chromatography-bioassay-mass spectrometry Galarce-Bustos, Osca; Pavón-Pérez, Jessy; Henríquez-Aedo, Karem Journal of Chromatography A, Vol. 1608 https://doi.org/10.1016/j.chroma.2019.460415	journal	December 2019
Evaluation of garlic ecotypes for allicin and other allyl thiosulphinates Khar, Anil; Banerjee, Kaushik; Jadhav, Manjusha R. Food Chemistry, Vol. 128, Issue 4 https://doi.org/10.1016/j.foodchem.2011.04.004	journal	October 2011
Chemical composition and bioactive compounds of garlic (Allium sativum L.) as affected by pre- and post-harvest conditions: A review Martins, Natália; Petropoulos, Spyridon; Ferreira, Isabel C. F. R. Food Chemistry, Vol. 211 https://doi.org/10.1016/j.foodchem.2016.05.029	journal	November 2016
UPLC/ESI-MS/MS analysis of compositional changes for organosulfur compounds in garlic (Allium sativum L.) during fermentation Kim, Sunyoung; Park, So-Lim; Lee, Sanghee Food Chemistry, Vol. 211 https://doi.org/10.1016/j.foodchem.2016.05.102	journal	November 2016
Profiling of organosulfur compounds and amino acids in garlic from different regions of China Liu, Pingxiang; Weng, Rui; Sheng, Xiaojing Food Chemistry, Vol. 305 https://doi.org/10.1016/j.foodchem.2019.125499	journal	February 2020
Fast and selective method for biogenic amines determination in wines and beers by ultra high-performance liquid chromatography Angulo, María Fernanda; Flores, Mauricio; Aranda, Mario Food Chemistry, Vol. 309 https://doi.org/10.1016/j.foodchem.2019.125689	journal	March 2020
Preliminary evaluation of biogenic amines content in Chilean young varietal wines by HPLC Pineda, Angela; Carrasco, Jonathan; Peña-Farfal, Carlos Food Control, Vol. 23, Issue 1 https://doi.org/10.1016/j.foodcont.2011.07.025	journal	January 2012
The antimicrobial, antioxidant and sensory properties of garlic and its derivatives in Brazilian low-sodium frankfurters along shelf-life Horita, C. N.; Farías-Campomanes, A. M.; Barbosa, T. S. Food Research International, Vol. 84 https://doi.org/10.1016/j.foodres.2016.02.006	journal	June 2016
Stability and extraction of bioactive sulfur compounds from Allium genus processed by traditional and innovative technologies Poojary, Mahesha M.; Putnik, Predrag; Bursać Kovačević, Danijela Journal of Food Composition and Analysis, Vol. 61 https://doi.org/10.1016/j.jfca.2017.04.007	journal	August 2017
Establishing compositional differences between fresh and black garlic by a metabolomics approach based on LC–QTOF MS/MS analysis Molina-Calle, María; de Medina, Verónica Sánchez; Priego-Capote, Feliciano Journal of Food Composition and Analysis, Vol. 62 https://doi.org/10.1016/j.jfca.2017.05.004	journal	September 2017
Techniques for extraction of bioactive compounds from plant materials: A review Azmir, J.; Zaidul, I. S. M.; Rahman, M. M. Journal of Food Engineering, Vol. 117, Issue 4 https://doi.org/10.1016/j.jfoodeng.2013.01.014	journal	August 2013
Is single bulb producing garlic Allium sativum or Allium ampeloprasum? Figliuolo, G.; Di Stefano, D. Scientia Horticulturae, Vol. 114, Issue 4 https://doi.org/10.1016/j.scienta.2007.06.021	journal	November 2007
Comparative studies of nutritional and health-enhancing properties in the “garlic-like” plant Allium ampeloprasum var. ampeloprasum (GHG-L) and A. sativum Najda, Agnieszka; Błaszczyk, Lidia; Winiarczyk, Krystyna Scientia Horticulturae, Vol. 201 https://doi.org/10.1016/j.scienta.2016.01.044	journal	March 2016
Sub- and supercritical fluid extraction of bioactive compounds from plants, food-by-products, seaweeds and microalgae – An update Gallego, Rocío; Bueno, Mónica; Herrero, Miguel TrAC Trends in Analytical Chemistry, Vol. 116 https://doi.org/10.1016/j.trac.2019.04.030	journal	July 2019
Comparative studies of bioactive organosulphur compounds and antioxidant activities in garlic ( Allium sativum L.), elephant garlic ( Allium ampeloprasum L.) and onion ( Allium cepa L.) Kim, Sunyoung; Kim, Dan-Bi; Jin, Wenjie Natural Product Research, Vol. 32, Issue 10 https://doi.org/10.1080/14786419.2017.1323211	journal	May 2017
Characterization of a novel form of fertile great headed garlic (Allium sp.) Hirschegger, P.; Galmarini, C.; Bohanec, B. Plant Breeding, Vol. 125, Issue 6 https://doi.org/10.1111/j.1439-0523.2006.01279.x	journal	December 2006
Thermal kinetics of enzyme inactivation, color changes, and allicin degradation of garlic under blanching treatments Huang, Zhi; Zhou, Quan; Wu, Wei‐Liang Journal of Food Process Engineering, Vol. 42, Issue 3 https://doi.org/10.1111/jfpe.12991	journal	February 2019
Functional foods: traditional use and European legislation Serafini, Mauro; Stanzione, Alessandra; Foddai, Sebastiano International Journal of Food Sciences and Nutrition, Vol. 63, Issue sup1 https://doi.org/10.3109/09637486.2011.637488	journal	November 2011
Garlic Î³-glutamyl transpeptidases that catalyze deglutamylation of biosynthetic intermediate of alliin Yoshimoto, Naoko; Yabe, Ayami; Sugino, Yuka Frontiers in Plant Science, Vol. 5 https://doi.org/10.3389/fpls.2014.00758	journal	January 2015
Chemical Constituents of Three Allium Species from Romania Vlase, Laurian; Parvu, Marcel; Parvu, Elena Molecules, Vol. 18, Issue 1 https://doi.org/10.3390/molecules18010114	journal	December 2012
Allicin: Chemistry and Biological Properties Borlinghaus, Jan; Albrecht, Frank; Gruhlke, Martin Molecules, Vol. 19, Issue 8 https://doi.org/10.3390/molecules190812591	journal	August 2014
Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review El-Saber Batiha, Gaber; Magdy Beshbishy, Amany; G. Wasef, Lamiaa Nutrients, Vol. 12, Issue 3 https://doi.org/10.3390/nu12030872	journal	March 2020

Similar Records

Studies on the antimutagenic activities of garlic extract

Journal Article · Sat Dec 31 23:00:00 EST 1988 · Environmental and Molecular Mutagenesis; (USA) · OSTI ID:7007000

Broccoli seed extract rich in polysaccharides and glucoraphanin ameliorates DSS ‐induced colitis via intestinal barrier protection and gut microbiota modulation in mice

Journal Article · Fri Dec 23 23:00:00 EST 2022 · Journal of the Science of Food and Agriculture · OSTI ID:1906741

Validation of Stage N3 of the Eighth Edition AJCC Staging System for Nasopharyngeal Carcinoma

Journal Article · Thu Jun 18 00:00:00 EDT 2020 · Laryngoscope · OSTI ID:1633844

Chemometric optimisation of pressurised liquid extraction for the determination of alliin and S‐allyl‐cysteine in giant garlic ( Allium ampeloprasum L.) by liquid chromatography tandem mass spectrometry

Citation Formats

References (32)

Similar Records

Related Subjects