TY  - JOUR
AU  - Aničić, Neda
AU  - Matekalo, Dragana
AU  - Skorić, Marijana
AU  - Gašić, Uroš M.
AU  - Nestorović Živković, Jasmina
AU  - Dmitrović, Slavica
AU  - Božunović, Jelena
AU  - Milutinović, Milica
AU  - Petrović, Luka
AU  - Dimitrijević, Milena
AU  - Anđelković, Boban D.
AU  - Mišić, Danijela
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6454
AB  - Iridoids, a class of atypical monoterpenes, exhibit exceptional diversity within the Nepeta genus (subfam. Nepetoidae, fam. Lamiaceae).The majority of these plants produce iridoids of the unique stereochemistry, with nepetalactones (NLs) predominating; however, a few Nepeta species lack these compounds. By comparatively analyzing metabolomics, transcriptomics, gene co-expression, and phylogenetic data of the iridoid-producing N. rtanjensis Diklić & Milojević and iridoid-lacking N. nervosa Royle & Bentham, we presumed that one of the factors responsible for the absence of these compounds in N. nervosa is iridoid synthase (ISY). Two orthologues of ISY were mined from leaves transcriptome of N. rtanjensis (NrPRISE1 and NrPRISE2), while in N. nervosa only one (NnPRISE) was identified, and it was phylogenetically closer to the representatives of the Family 1 isoforms, designated as P5βRs. Organ-specific and MeJA-elicited profiling of iridoid content and co-expression analysis of IBG candidates, highlighted NrPRISE2 and NnPRISE as promising candidates for ISY orthologues, and their function was confirmed using in vitro assays with recombinant proteins, after heterologous expression of recombinant proteins in E. coli and their His-tag affinity purification. NrPRISE2 demonstrated ISY activity both in vitro and likely in planta, which was supported by the 3D modeling and molecular docking analysis, thus reclassification of NrPRISE2 to NrISY is accordingly recommended. NnPRISE also displays in vitro ISY-like activity, while its role under in vivo conditions was not here unambiguously confirmed. Most probably under in vivo conditions the NnPRISE lacks substrates to act upon, as a result of the loss of function of some of the upstream enzymes of the iridoid pathway. Our ongoing work is conducted towards re-establishing the biosynthesis of iridoids in N. nervosa.
PB  - Frontiers Media
T2  - Frontiers in Plant Science
T1  - Functional iridoid synthases from iridoid producing and non-producing Nepeta species (subfam. Nepetoidae, fam. Lamiaceae)
VL  - 14
DO  - 10.3389/fpls.2023.1211453
ER  - 

@article{
author = "Aničić, Neda and Matekalo, Dragana and Skorić, Marijana and Gašić, Uroš M. and Nestorović Živković, Jasmina and Dmitrović, Slavica and Božunović, Jelena and Milutinović, Milica and Petrović, Luka and Dimitrijević, Milena and Anđelković, Boban D. and Mišić, Danijela",
year = "2024",
abstract = "Iridoids, a class of atypical monoterpenes, exhibit exceptional diversity within the Nepeta genus (subfam. Nepetoidae, fam. Lamiaceae).The majority of these plants produce iridoids of the unique stereochemistry, with nepetalactones (NLs) predominating; however, a few Nepeta species lack these compounds. By comparatively analyzing metabolomics, transcriptomics, gene co-expression, and phylogenetic data of the iridoid-producing N. rtanjensis Diklić & Milojević and iridoid-lacking N. nervosa Royle & Bentham, we presumed that one of the factors responsible for the absence of these compounds in N. nervosa is iridoid synthase (ISY). Two orthologues of ISY were mined from leaves transcriptome of N. rtanjensis (NrPRISE1 and NrPRISE2), while in N. nervosa only one (NnPRISE) was identified, and it was phylogenetically closer to the representatives of the Family 1 isoforms, designated as P5βRs. Organ-specific and MeJA-elicited profiling of iridoid content and co-expression analysis of IBG candidates, highlighted NrPRISE2 and NnPRISE as promising candidates for ISY orthologues, and their function was confirmed using in vitro assays with recombinant proteins, after heterologous expression of recombinant proteins in E. coli and their His-tag affinity purification. NrPRISE2 demonstrated ISY activity both in vitro and likely in planta, which was supported by the 3D modeling and molecular docking analysis, thus reclassification of NrPRISE2 to NrISY is accordingly recommended. NnPRISE also displays in vitro ISY-like activity, while its role under in vivo conditions was not here unambiguously confirmed. Most probably under in vivo conditions the NnPRISE lacks substrates to act upon, as a result of the loss of function of some of the upstream enzymes of the iridoid pathway. Our ongoing work is conducted towards re-establishing the biosynthesis of iridoids in N. nervosa.",
publisher = "Frontiers Media",
journal = "Frontiers in Plant Science",
title = "Functional iridoid synthases from iridoid producing and non-producing Nepeta species (subfam. Nepetoidae, fam. Lamiaceae)",
volume = "14",
doi = "10.3389/fpls.2023.1211453"
}

Aničić, N., Matekalo, D., Skorić, M., Gašić, U. M., Nestorović Živković, J., Dmitrović, S., Božunović, J., Milutinović, M., Petrović, L., Dimitrijević, M., Anđelković, B. D.,& Mišić, D.. (2024). Functional iridoid synthases from iridoid producing and non-producing Nepeta species (subfam. Nepetoidae, fam. Lamiaceae). in Frontiers in Plant Science
Frontiers Media., 14.
https://doi.org/10.3389/fpls.2023.1211453

Aničić N, Matekalo D, Skorić M, Gašić UM, Nestorović Živković J, Dmitrović S, Božunović J, Milutinović M, Petrović L, Dimitrijević M, Anđelković BD, Mišić D. Functional iridoid synthases from iridoid producing and non-producing Nepeta species (subfam. Nepetoidae, fam. Lamiaceae). in Frontiers in Plant Science. 2024;14.
doi:10.3389/fpls.2023.1211453 .

Aničić, Neda, Matekalo, Dragana, Skorić, Marijana, Gašić, Uroš M., Nestorović Živković, Jasmina, Dmitrović, Slavica, Božunović, Jelena, Milutinović, Milica, Petrović, Luka, Dimitrijević, Milena, Anđelković, Boban D., Mišić, Danijela, "Functional iridoid synthases from iridoid producing and non-producing Nepeta species (subfam. Nepetoidae, fam. Lamiaceae)" in Frontiers in Plant Science, 14 (2024),
https://doi.org/10.3389/fpls.2023.1211453 . .

TY  - JOUR
AU  - Božunović, Jelena
AU  - Živković, Suzana
AU  - Gašić, Uroš M.
AU  - Glamočlija, Jasmina
AU  - Ćirić, Ana D.
AU  - Matekalo, Dragana
AU  - Šiler, Branislav
AU  - Soković, Marina
AU  - Tešić, Živoslav Lj.
AU  - Mišić, Danijela
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2579
AB  - The present study was principally aimed at ascertaining the differences in metabolomics profiles and biological activities between non-hydrolyzed (ME) and hydrolyzed methanol extract (HME) of Centaurium erythraea Rafn. UHPLC-MS/MS Orbitrap analysis showed that the enzymatic hydrolysis of the extract caused changes in beta-Dglycoside/aglycone ratio of both flavonoid and secoiridoid compounds. UHPLC/DAD/ + HESI - qqqMS characterization and/or quantification of secoiridoid glucosides (SGs) and their aglycones in both ME and HME revealed gentiopicral and erythrocentaurin as the major aglycones, the same metabolic products which appear after the hydrolysis of pure swertiamarin, the dominant secoiridoid glucoside of C. erythraea. SGs played an antioxidant role only in ABTS assay, whilst the remarkable antioxidant potential of C. erythraea methanol extract is ascribed chiefly to phenolics detected in it. Interestingly, antioxidant activities of swertiamarin and sweroside recorded in ABTS assay increased after the compounds have been hydrolyzed, which highlighted their possible antioxidant role during ingestion. Strong antimicrobial activities of ME and HME against a vast array of pathogens, which exceed the effects of the reference antibiotics and antimycotics, largely depended on the amount of secoiridoids in either of the glycosylation forms. Extracts and pure secoiridoids were especially effective against most of the tested Penicillium species. On the other hand, P. funiculosum has evolved an efficient mechanism of detoxification of sub-lethal concentrations of secoiridoid glucosides, involving their biotransformation and complete digestion. The presented findings will contribute to clarify the fate and role of the SGs after C. erythraea ingestion within in vivo systems, and to further promote this remarkable plant as a food preservation additive with significant health benefits.
PB  - Elsevier Science Bv, Amsterdam
T2  - Industrial Crops and Products
T1  - In vitro and in vivo transformations of Centaurium erythraea secoiridoid glucosides alternate their antioxidant and antimicrobial capacity
VL  - 111
SP  - 705
EP  - 721
DO  - 10.1016/j.indcrop.2017.11.040
ER  - 

@article{
author = "Božunović, Jelena and Živković, Suzana and Gašić, Uroš M. and Glamočlija, Jasmina and Ćirić, Ana D. and Matekalo, Dragana and Šiler, Branislav and Soković, Marina and Tešić, Živoslav Lj. and Mišić, Danijela",
year = "2018",
abstract = "The present study was principally aimed at ascertaining the differences in metabolomics profiles and biological activities between non-hydrolyzed (ME) and hydrolyzed methanol extract (HME) of Centaurium erythraea Rafn. UHPLC-MS/MS Orbitrap analysis showed that the enzymatic hydrolysis of the extract caused changes in beta-Dglycoside/aglycone ratio of both flavonoid and secoiridoid compounds. UHPLC/DAD/ + HESI - qqqMS characterization and/or quantification of secoiridoid glucosides (SGs) and their aglycones in both ME and HME revealed gentiopicral and erythrocentaurin as the major aglycones, the same metabolic products which appear after the hydrolysis of pure swertiamarin, the dominant secoiridoid glucoside of C. erythraea. SGs played an antioxidant role only in ABTS assay, whilst the remarkable antioxidant potential of C. erythraea methanol extract is ascribed chiefly to phenolics detected in it. Interestingly, antioxidant activities of swertiamarin and sweroside recorded in ABTS assay increased after the compounds have been hydrolyzed, which highlighted their possible antioxidant role during ingestion. Strong antimicrobial activities of ME and HME against a vast array of pathogens, which exceed the effects of the reference antibiotics and antimycotics, largely depended on the amount of secoiridoids in either of the glycosylation forms. Extracts and pure secoiridoids were especially effective against most of the tested Penicillium species. On the other hand, P. funiculosum has evolved an efficient mechanism of detoxification of sub-lethal concentrations of secoiridoid glucosides, involving their biotransformation and complete digestion. The presented findings will contribute to clarify the fate and role of the SGs after C. erythraea ingestion within in vivo systems, and to further promote this remarkable plant as a food preservation additive with significant health benefits.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Industrial Crops and Products",
title = "In vitro and in vivo transformations of Centaurium erythraea secoiridoid glucosides alternate their antioxidant and antimicrobial capacity",
volume = "111",
pages = "705-721",
doi = "10.1016/j.indcrop.2017.11.040"
}

Božunović, J., Živković, S., Gašić, U. M., Glamočlija, J., Ćirić, A. D., Matekalo, D., Šiler, B., Soković, M., Tešić, Ž. Lj.,& Mišić, D.. (2018). In vitro and in vivo transformations of Centaurium erythraea secoiridoid glucosides alternate their antioxidant and antimicrobial capacity. in Industrial Crops and Products
Elsevier Science Bv, Amsterdam., 111, 705-721.
https://doi.org/10.1016/j.indcrop.2017.11.040

Božunović J, Živković S, Gašić UM, Glamočlija J, Ćirić AD, Matekalo D, Šiler B, Soković M, Tešić ŽL, Mišić D. In vitro and in vivo transformations of Centaurium erythraea secoiridoid glucosides alternate their antioxidant and antimicrobial capacity. in Industrial Crops and Products. 2018;111:705-721.
doi:10.1016/j.indcrop.2017.11.040 .

Božunović, Jelena, Živković, Suzana, Gašić, Uroš M., Glamočlija, Jasmina, Ćirić, Ana D., Matekalo, Dragana, Šiler, Branislav, Soković, Marina, Tešić, Živoslav Lj., Mišić, Danijela, "In vitro and in vivo transformations of Centaurium erythraea secoiridoid glucosides alternate their antioxidant and antimicrobial capacity" in Industrial Crops and Products, 111 (2018):705-721,
https://doi.org/10.1016/j.indcrop.2017.11.040 . .

TY  - DATA
AU  - Božunović, Jelena
AU  - Živković, Suzana
AU  - Gašić, Uroš M.
AU  - Glamočlija, Jasmina
AU  - Ćirić, Ana D.
AU  - Matekalo, Dragana
AU  - Šiler, Branislav
AU  - Soković, Marina
AU  - Tešić, Živoslav Lj.
AU  - Mišić, Danijela
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3208
PB  - Elsevier Science Bv, Amsterdam
T2  - Industrial Crops and Products
T1  - Supplementary material for the article: Božunović, J.; Živković, S.; Gašić, U.; Glamočlija, J.; Ćirić, A.; Matekalo, D.; Šiler, B.; Soković, M.; Tešić, Ž.; Mišić, D. In Vitro and in Vivo Transformations of Centaurium Erythraea Secoiridoid Glucosides Alternate Their Antioxidant and Antimicrobial Capacity. Industrial Crops and Products 2018, 111, 705–721. https://doi.org/10.1016/j.indcrop.2017.11.040
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3208
ER  - 

@misc{
author = "Božunović, Jelena and Živković, Suzana and Gašić, Uroš M. and Glamočlija, Jasmina and Ćirić, Ana D. and Matekalo, Dragana and Šiler, Branislav and Soković, Marina and Tešić, Živoslav Lj. and Mišić, Danijela",
year = "2018",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Industrial Crops and Products",
title = "Supplementary material for the article: Božunović, J.; Živković, S.; Gašić, U.; Glamočlija, J.; Ćirić, A.; Matekalo, D.; Šiler, B.; Soković, M.; Tešić, Ž.; Mišić, D. In Vitro and in Vivo Transformations of Centaurium Erythraea Secoiridoid Glucosides Alternate Their Antioxidant and Antimicrobial Capacity. Industrial Crops and Products 2018, 111, 705–721. https://doi.org/10.1016/j.indcrop.2017.11.040",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3208"
}

Božunović, J., Živković, S., Gašić, U. M., Glamočlija, J., Ćirić, A. D., Matekalo, D., Šiler, B., Soković, M., Tešić, Ž. Lj.,& Mišić, D.. (2018). Supplementary material for the article: Božunović, J.; Živković, S.; Gašić, U.; Glamočlija, J.; Ćirić, A.; Matekalo, D.; Šiler, B.; Soković, M.; Tešić, Ž.; Mišić, D. In Vitro and in Vivo Transformations of Centaurium Erythraea Secoiridoid Glucosides Alternate Their Antioxidant and Antimicrobial Capacity. Industrial Crops and Products 2018, 111, 705–721. https://doi.org/10.1016/j.indcrop.2017.11.040. in Industrial Crops and Products
Elsevier Science Bv, Amsterdam..
https://hdl.handle.net/21.15107/rcub_cherry_3208

Božunović J, Živković S, Gašić UM, Glamočlija J, Ćirić AD, Matekalo D, Šiler B, Soković M, Tešić ŽL, Mišić D. Supplementary material for the article: Božunović, J.; Živković, S.; Gašić, U.; Glamočlija, J.; Ćirić, A.; Matekalo, D.; Šiler, B.; Soković, M.; Tešić, Ž.; Mišić, D. In Vitro and in Vivo Transformations of Centaurium Erythraea Secoiridoid Glucosides Alternate Their Antioxidant and Antimicrobial Capacity. Industrial Crops and Products 2018, 111, 705–721. https://doi.org/10.1016/j.indcrop.2017.11.040. in Industrial Crops and Products. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3208 .

Božunović, Jelena, Živković, Suzana, Gašić, Uroš M., Glamočlija, Jasmina, Ćirić, Ana D., Matekalo, Dragana, Šiler, Branislav, Soković, Marina, Tešić, Živoslav Lj., Mišić, Danijela, "Supplementary material for the article: Božunović, J.; Živković, S.; Gašić, U.; Glamočlija, J.; Ćirić, A.; Matekalo, D.; Šiler, B.; Soković, M.; Tešić, Ž.; Mišić, D. In Vitro and in Vivo Transformations of Centaurium Erythraea Secoiridoid Glucosides Alternate Their Antioxidant and Antimicrobial Capacity. Industrial Crops and Products 2018, 111, 705–721. https://doi.org/10.1016/j.indcrop.2017.11.040" in Industrial Crops and Products (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3208 .