TY  - JOUR
AU  - Ivanović, Stefan
AU  - Mandrone, Manuela
AU  - Simić, Katarina
AU  - Ristić, Mirjana
AU  - Todosijević, Marina
AU  - Mandić, Boris
AU  - Gođevac, Dejan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4908
AB  - Oregano is one of the most used culinary herb and it is often adult­erated with cheaper plants. In this study, GC–MS was used for identification and quan­tification of metabolites from 104 samples of oregano (Origanum vul­gare and O. onites) adulterated with olive (Olea europaea), venetian sumac (Cotinus coggy­gria) and myrtle (Myrtus communis) leaves, at five different concentration levels. The metabolomics profiles obtained after the two-step derivatization, involving methoxyamination and silanization, were subjected to multivariate data analysis to reveal markers of adulteration and to build the reg­ression models on the basis of the oregano-to-adulterants mixing ratio. Ortho­gonal partial least squares enabled detection of oregano adulterations with olive, Venetian sumac and myrtle leaves. Sorbitol levels distinguished oregano samples adulterated with olive leaves, while shikimic and quinic acids were recognized as discrimination factor for adulteration of oregano with venetian sumac. Fructose and quinic acid levels correlated with oregano adulteration with myrtle. Orthogonal partial least squares discriminant analysis enabled dis­crimination of O. vulgare and O. onites samples, where catechollactate was found to be discriminating metabolite.
AB  - Оригано је једна од најчешће коришћених кулинарских биљака и често се криво- твори јефтинијим биљкама. У овој студији, гаснa хроматографијa–масенa спектро- метријa коришћена је за идентификацију и квантификацију метаболита из 104 узорка оригана (Origanum vulgare и O. onites) кривотвореног маслином (Olea europea), венеци- јанским сумаком (Cotinus coggygria) и миртом (Myrtus communis), у пет различитих концентрација. Метаболомички профили добијени након двостепене дериватизације, која укључује метоксиаминовање и силанизацију, подвргнути су мултиваријантној ана- лизи података како би се открили маркери кривотворења и направили регресиони модели на основу односа мешања оригана и биљака за кривотворење. Ортогонална дели- мична анализа најмањих квадрата је омогућила детекцију кривотворења оригана лишћем маслине, венецијанског сумака и мирте. Садржај сорбитола разликовао је узорке оригана кривотворених лишћем маслине, док су шикиминска и кининска кисе- лина препознате као фактор разликовања за кривотворење оригана венецијанским сумаком. Садржај фруктозе и кининске киселине у корелацији су са кривотворењем оригана миртом. Ортогонална делимична анализа најмањих квадрата – дискриминантна анализа је омогућила разликовање узорака O. vulgare и O. onites, при чему је одређено да је катехоллактат метаболит који разликује ове две биљне врсте.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - GC-MS-based metabolomics for the detection of adulteration in oregano samples
T1  - Метаболомика заснована на гасној хроматографији–масеној спектрометрији за детекцију кривотворења узорака оригана.
IS  - 12
SP  - 1195
EP  - 1203
DO  - 10.2298/JSC210809089I
ER  - 

@article{
author = "Ivanović, Stefan and Mandrone, Manuela and Simić, Katarina and Ristić, Mirjana and Todosijević, Marina and Mandić, Boris and Gođevac, Dejan",
year = "2021",
abstract = "Oregano is one of the most used culinary herb and it is often adult­erated with cheaper plants. In this study, GC–MS was used for identification and quan­tification of metabolites from 104 samples of oregano (Origanum vul­gare and O. onites) adulterated with olive (Olea europaea), venetian sumac (Cotinus coggy­gria) and myrtle (Myrtus communis) leaves, at five different concentration levels. The metabolomics profiles obtained after the two-step derivatization, involving methoxyamination and silanization, were subjected to multivariate data analysis to reveal markers of adulteration and to build the reg­ression models on the basis of the oregano-to-adulterants mixing ratio. Ortho­gonal partial least squares enabled detection of oregano adulterations with olive, Venetian sumac and myrtle leaves. Sorbitol levels distinguished oregano samples adulterated with olive leaves, while shikimic and quinic acids were recognized as discrimination factor for adulteration of oregano with venetian sumac. Fructose and quinic acid levels correlated with oregano adulteration with myrtle. Orthogonal partial least squares discriminant analysis enabled dis­crimination of O. vulgare and O. onites samples, where catechollactate was found to be discriminating metabolite., Оригано је једна од најчешће коришћених кулинарских биљака и често се криво- твори јефтинијим биљкама. У овој студији, гаснa хроматографијa–масенa спектро- метријa коришћена је за идентификацију и квантификацију метаболита из 104 узорка оригана (Origanum vulgare и O. onites) кривотвореног маслином (Olea europea), венеци- јанским сумаком (Cotinus coggygria) и миртом (Myrtus communis), у пет различитих концентрација. Метаболомички профили добијени након двостепене дериватизације, која укључује метоксиаминовање и силанизацију, подвргнути су мултиваријантној ана- лизи података како би се открили маркери кривотворења и направили регресиони модели на основу односа мешања оригана и биљака за кривотворење. Ортогонална дели- мична анализа најмањих квадрата је омогућила детекцију кривотворења оригана лишћем маслине, венецијанског сумака и мирте. Садржај сорбитола разликовао је узорке оригана кривотворених лишћем маслине, док су шикиминска и кининска кисе- лина препознате као фактор разликовања за кривотворење оригана венецијанским сумаком. Садржај фруктозе и кининске киселине у корелацији су са кривотворењем оригана миртом. Ортогонална делимична анализа најмањих квадрата – дискриминантна анализа је омогућила разликовање узорака O. vulgare и O. onites, при чему је одређено да је катехоллактат метаболит који разликује ове две биљне врсте.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "GC-MS-based metabolomics for the detection of adulteration in oregano samples, Метаболомика заснована на гасној хроматографији–масеној спектрометрији за детекцију кривотворења узорака оригана.",
number = "12",
pages = "1195-1203",
doi = "10.2298/JSC210809089I"
}

Ivanović, S., Mandrone, M., Simić, K., Ristić, M., Todosijević, M., Mandić, B.,& Gođevac, D.. (2021). GC-MS-based metabolomics for the detection of adulteration in oregano samples. in Journal of the Serbian Chemical Society
Serbian Chemical Society.(12), 1195-1203.
https://doi.org/10.2298/JSC210809089I

Ivanović S, Mandrone M, Simić K, Ristić M, Todosijević M, Mandić B, Gođevac D. GC-MS-based metabolomics for the detection of adulteration in oregano samples. in Journal of the Serbian Chemical Society. 2021;(12):1195-1203.
doi:10.2298/JSC210809089I .

Ivanović, Stefan, Mandrone, Manuela, Simić, Katarina, Ristić, Mirjana, Todosijević, Marina, Mandić, Boris, Gođevac, Dejan, "GC-MS-based metabolomics for the detection of adulteration in oregano samples" in Journal of the Serbian Chemical Society, no. 12 (2021):1195-1203,
https://doi.org/10.2298/JSC210809089I . .

TY  - JOUR
AU  - Mandrone, Manuela
AU  - Marincich, Lorenzo
AU  - Chiocchio, Ilaria
AU  - Petroli, Alessandra
AU  - Gođevac, Dejan
AU  - Maresca, Immacolata
AU  - Poli, Ferruccio
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4577
AB  - In this work 1H NMR metabolomics has been employed for quality control of oregano samples. NMR data and morphological analysis (MA) were combined by PCA, obtaining a model able to individuate non-marketable samples, and to distinguish between the two marketable oregano species (Origanum vulgare and O. onites) on the basis of their metabolomic profile. Through this approach distinctive biomarkers of the two species were found, namely apigenin and p-cymene for O. onites, and salvianolic acid B for O. vulgare. Furthermore, the percentage of the samples’ impurity (evaluated by MA) and the metabolomic profiles were correlated by OPLS models, which showed that, in addition to the species-specific biomarkers, thymol and rosmarinic acid (common to both marketable species) strongly correlate to oregano degree of purity. Cistus was one of the most frequent contaminants, thus, a further OPLS model, able to detect the degree of cistus contamination in oregano samples, was also built.
PB  - Elsevier
T2  - Food Control
T1  - NMR-based metabolomics for frauds detection and quality control of oregano samples
VL  - 127
SP  - 108141
DO  - 10.1016/j.foodcont.2021.108141
ER  - 

@article{
author = "Mandrone, Manuela and Marincich, Lorenzo and Chiocchio, Ilaria and Petroli, Alessandra and Gođevac, Dejan and Maresca, Immacolata and Poli, Ferruccio",
year = "2021",
abstract = "In this work 1H NMR metabolomics has been employed for quality control of oregano samples. NMR data and morphological analysis (MA) were combined by PCA, obtaining a model able to individuate non-marketable samples, and to distinguish between the two marketable oregano species (Origanum vulgare and O. onites) on the basis of their metabolomic profile. Through this approach distinctive biomarkers of the two species were found, namely apigenin and p-cymene for O. onites, and salvianolic acid B for O. vulgare. Furthermore, the percentage of the samples’ impurity (evaluated by MA) and the metabolomic profiles were correlated by OPLS models, which showed that, in addition to the species-specific biomarkers, thymol and rosmarinic acid (common to both marketable species) strongly correlate to oregano degree of purity. Cistus was one of the most frequent contaminants, thus, a further OPLS model, able to detect the degree of cistus contamination in oregano samples, was also built.",
publisher = "Elsevier",
journal = "Food Control",
title = "NMR-based metabolomics for frauds detection and quality control of oregano samples",
volume = "127",
pages = "108141",
doi = "10.1016/j.foodcont.2021.108141"
}

Mandrone, M., Marincich, L., Chiocchio, I., Petroli, A., Gođevac, D., Maresca, I.,& Poli, F.. (2021). NMR-based metabolomics for frauds detection and quality control of oregano samples. in Food Control
Elsevier., 127, 108141.
https://doi.org/10.1016/j.foodcont.2021.108141

Mandrone M, Marincich L, Chiocchio I, Petroli A, Gođevac D, Maresca I, Poli F. NMR-based metabolomics for frauds detection and quality control of oregano samples. in Food Control. 2021;127:108141.
doi:10.1016/j.foodcont.2021.108141 .

Mandrone, Manuela, Marincich, Lorenzo, Chiocchio, Ilaria, Petroli, Alessandra, Gođevac, Dejan, Maresca, Immacolata, Poli, Ferruccio, "NMR-based metabolomics for frauds detection and quality control of oregano samples" in Food Control, 127 (2021):108141,
https://doi.org/10.1016/j.foodcont.2021.108141 . .

TY  - JOUR
AU  - Mandrone, Manuela
AU  - Marincich, Lorenzo
AU  - Chiocchio, Ilaria
AU  - Petroli, Alessandra
AU  - Gođevac, Dejan
AU  - Maresca, Immacolata
AU  - Poli, Ferruccio
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4550
AB  - In this work 1H NMR metabolomics has been employed for quality control of oregano samples. NMR data and morphological analysis (MA) were combined by PCA, obtaining a model able to individuate non-marketable samples, and to distinguish between the two marketable oregano species (Origanum vulgare and O. onites) on the basis of their metabolomic profile. Through this approach distinctive biomarkers of the two species were found, namely apigenin and p-cymene for O. onites, and salvianolic acid B for O. vulgare. Furthermore, the percentage of the samples’ impurity (evaluated by MA) and the metabolomic profiles were correlated by OPLS models, which showed that, in addition to the species-specific biomarkers, thymol and rosmarinic acid (common to both marketable species) strongly correlate to oregano degree of purity. Cistus was one of the most frequent contaminants, thus, a further OPLS model, able to detect the degree of cistus contamination in oregano samples, was also built.
PB  - Elsevier
T2  - Food Control
T1  - NMR-based metabolomics for frauds detection and quality control of oregano samples
VL  - 127
SP  - 108141
DO  - 10.1016/j.foodcont.2021.108141
ER  - 

@article{
author = "Mandrone, Manuela and Marincich, Lorenzo and Chiocchio, Ilaria and Petroli, Alessandra and Gođevac, Dejan and Maresca, Immacolata and Poli, Ferruccio",
year = "2021",
abstract = "In this work 1H NMR metabolomics has been employed for quality control of oregano samples. NMR data and morphological analysis (MA) were combined by PCA, obtaining a model able to individuate non-marketable samples, and to distinguish between the two marketable oregano species (Origanum vulgare and O. onites) on the basis of their metabolomic profile. Through this approach distinctive biomarkers of the two species were found, namely apigenin and p-cymene for O. onites, and salvianolic acid B for O. vulgare. Furthermore, the percentage of the samples’ impurity (evaluated by MA) and the metabolomic profiles were correlated by OPLS models, which showed that, in addition to the species-specific biomarkers, thymol and rosmarinic acid (common to both marketable species) strongly correlate to oregano degree of purity. Cistus was one of the most frequent contaminants, thus, a further OPLS model, able to detect the degree of cistus contamination in oregano samples, was also built.",
publisher = "Elsevier",
journal = "Food Control",
title = "NMR-based metabolomics for frauds detection and quality control of oregano samples",
volume = "127",
pages = "108141",
doi = "10.1016/j.foodcont.2021.108141"
}

Mandrone, M., Marincich, L., Chiocchio, I., Petroli, A., Gođevac, D., Maresca, I.,& Poli, F.. (2021). NMR-based metabolomics for frauds detection and quality control of oregano samples. in Food Control
Elsevier., 127, 108141.
https://doi.org/10.1016/j.foodcont.2021.108141

Mandrone M, Marincich L, Chiocchio I, Petroli A, Gođevac D, Maresca I, Poli F. NMR-based metabolomics for frauds detection and quality control of oregano samples. in Food Control. 2021;127:108141.
doi:10.1016/j.foodcont.2021.108141 .

Mandrone, Manuela, Marincich, Lorenzo, Chiocchio, Ilaria, Petroli, Alessandra, Gođevac, Dejan, Maresca, Immacolata, Poli, Ferruccio, "NMR-based metabolomics for frauds detection and quality control of oregano samples" in Food Control, 127 (2021):108141,
https://doi.org/10.1016/j.foodcont.2021.108141 . .

TY  - DATA
AU  - Mandrone, Manuela
AU  - Marincich, Lorenzo
AU  - Chiocchio, Ilaria
AU  - Petroli, Alessandra
AU  - Gođevac, Dejan
AU  - Maresca, Immacolata
AU  - Poli, Ferruccio
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4551
AB  - Table S1. Summary of NMR experiments performed in order to elucidate the structure of salvianolic acid B. Sample was solubilized in CD3OD. Fig. S1 1H NMR spectrum obtained for apigenin (in fraction 114) solubilized in CD3OD. Fig. S2. 1H NMR spectrum obtained for rosmarinic acid (found in EtOAc fraction from Oregano vulgare) solubilized in CD3OD. Fig. S3 1H NMR spectrum obtained for thymol, and p-cymene (found in CHCl3 fraction from Oregano onites) solubilized in CD3OD. Fig. S4 1H NMR spectrum of salvianolic acid B solubilized in CD3OD. Fig. S5 NMR COSY spectrum of salvianolic acid B solubilized in CD3OD. Fig. S6 NMR HSQC spectrum of salvianolic acid B solubilized in CD3OD. Fig. S7 NMR HMBC spectrum of salvianolic acid B solubilized in CD3OD. Fig. S8 NMR J-res spectrum of salvianolic acid B solubilized in CD3OD. Fig. S9 A) S-plot from OPLS-DA model showing the most important spectral bins for the discrimination between the two commercial species of oregano. B) Result of the permutation test of the OPLS-DA model. C) Loading column plot from OPLS-DA model. Fig. S10 Main biomarkers found in this work. Fig. S11. PCA score scatter plot where unknown species (green dots) are distinguished from marketable oregano and placed as outliers by the model. Fig. S12 Extended regions of observed vs predicted plots from OPLS models (y = % of total impurity) of A) Origanum vulgare B) Origanum onites. Fig. S13 Graphic obtained by permutation test of the OPLS model built using as y variable the % of cistus contamination. Fig. S14 J-res spectra of Oregano contaminated with cistus (A) and pure oregano (B). The contaminated sample presents a singlet at δ 3.57.
PB  - Elsevier
T2  - Food Control
T1  - Supporting Material for: "NMR-based metabolomics for frauds detection and quality control of oregano samples"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4551
ER  - 

@misc{
author = "Mandrone, Manuela and Marincich, Lorenzo and Chiocchio, Ilaria and Petroli, Alessandra and Gođevac, Dejan and Maresca, Immacolata and Poli, Ferruccio",
year = "2021",
abstract = "Table S1. Summary of NMR experiments performed in order to elucidate the structure of salvianolic acid B. Sample was solubilized in CD3OD. Fig. S1 1H NMR spectrum obtained for apigenin (in fraction 114) solubilized in CD3OD. Fig. S2. 1H NMR spectrum obtained for rosmarinic acid (found in EtOAc fraction from Oregano vulgare) solubilized in CD3OD. Fig. S3 1H NMR spectrum obtained for thymol, and p-cymene (found in CHCl3 fraction from Oregano onites) solubilized in CD3OD. Fig. S4 1H NMR spectrum of salvianolic acid B solubilized in CD3OD. Fig. S5 NMR COSY spectrum of salvianolic acid B solubilized in CD3OD. Fig. S6 NMR HSQC spectrum of salvianolic acid B solubilized in CD3OD. Fig. S7 NMR HMBC spectrum of salvianolic acid B solubilized in CD3OD. Fig. S8 NMR J-res spectrum of salvianolic acid B solubilized in CD3OD. Fig. S9 A) S-plot from OPLS-DA model showing the most important spectral bins for the discrimination between the two commercial species of oregano. B) Result of the permutation test of the OPLS-DA model. C) Loading column plot from OPLS-DA model. Fig. S10 Main biomarkers found in this work. Fig. S11. PCA score scatter plot where unknown species (green dots) are distinguished from marketable oregano and placed as outliers by the model. Fig. S12 Extended regions of observed vs predicted plots from OPLS models (y = % of total impurity) of A) Origanum vulgare B) Origanum onites. Fig. S13 Graphic obtained by permutation test of the OPLS model built using as y variable the % of cistus contamination. Fig. S14 J-res spectra of Oregano contaminated with cistus (A) and pure oregano (B). The contaminated sample presents a singlet at δ 3.57.",
publisher = "Elsevier",
journal = "Food Control",
title = "Supporting Material for: "NMR-based metabolomics for frauds detection and quality control of oregano samples"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4551"
}

Mandrone, M., Marincich, L., Chiocchio, I., Petroli, A., Gođevac, D., Maresca, I.,& Poli, F.. (2021). Supporting Material for: "NMR-based metabolomics for frauds detection and quality control of oregano samples". in Food Control
Elsevier..
https://hdl.handle.net/21.15107/rcub_cer_4551

Mandrone M, Marincich L, Chiocchio I, Petroli A, Gođevac D, Maresca I, Poli F. Supporting Material for: "NMR-based metabolomics for frauds detection and quality control of oregano samples". in Food Control. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4551 .

Mandrone, Manuela, Marincich, Lorenzo, Chiocchio, Ilaria, Petroli, Alessandra, Gođevac, Dejan, Maresca, Immacolata, Poli, Ferruccio, "Supporting Material for: "NMR-based metabolomics for frauds detection and quality control of oregano samples"" in Food Control (2021),
https://hdl.handle.net/21.15107/rcub_cer_4551 .