Pub Date : 2022-06-20DOI: 10.20450/mjcce.2022.2491
J. Petreska Stanoeva, Elena Stefova, Marinela Cvetanoska, J. Bogdanov
Pyrrolizidine alkaloids (PAs) are secondary plant metabolites, and their 1,2-unsaturated derivatives, which contain the retronecine, heliotridine, or otonecine type of the necine base, have raised concern due to their ability to form hepatotoxic intermediates and exhibit serious toxic effects. Several hundred individual pyrrolizidine alkaloids and their N-oxides have been identified mostly using liquid chromatography coupled with mass spectrometry, although the number of available reference standards is limited. In this work, characteristic fragment ions and their abundance in the mass spectra of different PAs were used to reveal typical fragmentation patterns for various classes of PAs that can be further employed to distinguish monoesters (retronecine, heliotridine type), open chain diesters and macrocyclic diesters, and corresponding N-oxides. Fragment ions at m/z 120 and 138 were found in all types of PAs with a different relative abundance. Additional observation of fragment ions at m/z 94 and 156 was found to be typical for monoester PAs esterified at position C9 of the necin base, whereas fragment ions at m/z 111 and 172 were characteristic for monoester N-oxides. Fragment ions at m/z 180 and 220 were found to be typical for open chain diesters with esterification at C7 with acetic and angelic acid, respectively, whereas fragment ions at m/z 214 and 254 were characteristic for the respective N-oxides. For the 3ʹ-acetyl PA monoester or open chain diester derivatives, characteristic fragment ions were observed after loss of the acetyl moiety ([M+H]+–60), whereas for macrocyclic diesters and their N-oxides, fragment ions due to the neutral loss of CO were found ([M+H]+–28).
{"title":"Establishing mass spectral fragmentation patterns for characterization of 1,2 -unsaturated pyrrolizidine alkaloids and N-oxides in Boraginaceae species from Macedonia using LC-ESI-MS/MS","authors":"J. Petreska Stanoeva, Elena Stefova, Marinela Cvetanoska, J. Bogdanov","doi":"10.20450/mjcce.2022.2491","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2491","url":null,"abstract":"Pyrrolizidine alkaloids (PAs) are secondary plant metabolites, and their 1,2-unsaturated derivatives, which contain the retronecine, heliotridine, or otonecine type of the necine base, have raised concern due to their ability to form hepatotoxic intermediates and exhibit serious toxic effects. Several hundred individual pyrrolizidine alkaloids and their N-oxides have been identified mostly using liquid chromatography coupled with mass spectrometry, although the number of available reference standards is limited.\u0000In this work, characteristic fragment ions and their abundance in the mass spectra of different PAs were used to reveal typical fragmentation patterns for various classes of PAs that can be further employed to distinguish monoesters (retronecine, heliotridine type), open chain diesters and macrocyclic diesters, and corresponding N-oxides.\u0000Fragment ions at m/z 120 and 138 were found in all types of PAs with a different relative abundance. Additional observation of fragment ions at m/z 94 and 156 was found to be typical for monoester PAs esterified at position C9 of the necin base, whereas fragment ions at m/z 111 and 172 were characteristic for monoester N-oxides. Fragment ions at m/z 180 and 220 were found to be typical for open chain diesters with esterification at C7 with acetic and angelic acid, respectively, whereas fragment ions at m/z 214 and 254 were characteristic for the respective N-oxides. For the 3ʹ-acetyl PA monoester or open chain diester derivatives, characteristic fragment ions were observed after loss of the acetyl moiety ([M+H]+–60), whereas for macrocyclic diesters and their N-oxides, fragment ions due to the neutral loss of CO were found ([M+H]+–28).","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42192915","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-06-12DOI: 10.20450/mjcce.2022.2499
Kristina Mihajlović, V. Divac, M. Kostić, M. Zivanovic, Jelica Grujić, Katarina Virijević
Terpenic alcohols linalool, nerolidol and α-terpineol were subjected to the PhSe-induced cyclization, where corresponding cyclic ethers were obtained. The heterocyclic product derived from α-terpineol is a derivate of the natural product eucalyptol, while linalool cyclization produces precursors of the natural product karahanaenone. All three cyclic ether products have an organoselenium moiety in the side chain, which can represent a significant source of bioactivities. Biological evaluation of obtained products, in vitro cytotoxicity and redox status parameters, was performed on two model systems: HCT-116 – immortalized colon cancer cell line, and MRC-5 – healthy fibroblasts isolated from lung pleura. The results indicate a strong prooxidative character of all compounds on colon cancer HCT-116 and healthy MRC-5 cells in the highest applied concentrations. Selectivity towards cancer cells was not observed, except when nerolidol-derived product was used for longer exposure time. A biological evaluation was conducted to establish the quantitative relationship between enhanced radical species formation and cell viability.
{"title":"Selenium-functionalized cyclic ethers derived from natural terpenic alcohols – biological in vitro profile","authors":"Kristina Mihajlović, V. Divac, M. Kostić, M. Zivanovic, Jelica Grujić, Katarina Virijević","doi":"10.20450/mjcce.2022.2499","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2499","url":null,"abstract":"Terpenic alcohols linalool, nerolidol and α-terpineol were subjected to the PhSe-induced cyclization, where corresponding cyclic ethers were obtained. The heterocyclic product derived from α-terpineol is a derivate of the natural product eucalyptol, while linalool cyclization produces precursors of the natural product karahanaenone. All three cyclic ether products have an organoselenium moiety in the side chain, which can represent a significant source of bioactivities. Biological evaluation of obtained products, in vitro cytotoxicity and redox status parameters, was performed on two model systems: HCT-116 – immortalized colon cancer cell line, and MRC-5 – healthy fibroblasts isolated from lung pleura. The results indicate a strong prooxidative character of all compounds on colon cancer HCT-116 and healthy MRC-5 cells in the highest applied concentrations. Selectivity towards cancer cells was not observed, except when nerolidol-derived product was used for longer exposure time. A biological evaluation was conducted to establish the quantitative relationship between enhanced radical species formation and cell viability.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44474403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-05-30DOI: 10.20450/mjcce.2022.2238
Una-Jovana Vajić, J. Živković, M. Ivanov, D. Jovović, K. Šavikin, B. Bugarski, N. Mihailović-Stanojević
The aim of this study was to optimize the parameters of the extraction of total flavonoids from stinging nettle leaf. Comparison of the effects of different solvents on total flavonoid content showed that, regardless of extraction time, aqueous-methanolic extracts had higher total flavonoid content than aqueous-ethanolic extracts. So, full factorial design and response surface methodology (RSM) were employed to estimate the effects of methanol content (50, 75, and 100 %) and extraction time (30, 60, and 90 minutes) on total flavonoid content and antioxidant capacities of the extracts. RSM analysis showed that methanol content in the solvent influenced significantly total flavonoid content and FRAP (Ferric Reducing Antioxidant Power Assay) antioxidant capacity, while extraction time had no significant effect on either of the responses. Extraction parameters for maximal total flavonoid content were estimated to be 69 % aqueous-methanol and 67 min, and 65 % aqueous-methanol and 83 min for maximal FRAP antioxidant capacity. DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidant capacity was not significantly affected by extraction time or methanol percentage in the solvent.
{"title":"Optimization of the extraction of antioxidants from stinging nettle leaf using response surface methodology","authors":"Una-Jovana Vajić, J. Živković, M. Ivanov, D. Jovović, K. Šavikin, B. Bugarski, N. Mihailović-Stanojević","doi":"10.20450/mjcce.2022.2238","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2238","url":null,"abstract":"The aim of this study was to optimize the parameters of the extraction of total flavonoids from stinging nettle leaf. Comparison of the effects of different solvents on total flavonoid content showed that, regardless of extraction time, aqueous-methanolic extracts had higher total flavonoid content than aqueous-ethanolic extracts. So, full factorial design and response surface methodology (RSM) were employed to estimate the effects of methanol content (50, 75, and 100 %) and extraction time (30, 60, and 90 minutes) on total flavonoid content and antioxidant capacities of the extracts. RSM analysis showed that methanol content in the solvent influenced significantly total flavonoid content and FRAP (Ferric Reducing Antioxidant Power Assay) antioxidant capacity, while extraction time had no significant effect on either of the responses. Extraction parameters for maximal total flavonoid content were estimated to be 69 % aqueous-methanol and 67 min, and 65 % aqueous-methanol and 83 min for maximal FRAP antioxidant capacity. DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidant capacity was not significantly affected by extraction time or methanol percentage in the solvent.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49514165","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-05-27DOI: 10.20450/mjcce.2022.2502
J. Trefil
With the discovery of objects entering the solar system from interstellar environments, the discussion of the possibility of extraterrestrial visitors to Earth has resumed. We examine the question of how long the evidence for such visits could be expected to last on Earth and on the Moon. Using geological estimates and our current knowledge of the lunar regolith, we conclude that evidence for visits to Earth more than 100,000 years ago would not survive to the present. Radiocarbon dating of some organic material (assuming large C-14 abundance) is of the same order of magnitude. Similarly, evidence of visits to the lunar surface would not survive for more than 100 million years.
{"title":"How long would evidence of an extraterrestrial visit survive: an educational exercise","authors":"J. Trefil","doi":"10.20450/mjcce.2022.2502","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2502","url":null,"abstract":"With the discovery of objects entering the solar system from interstellar environments, the discussion of the possibility of extraterrestrial visitors to Earth has resumed. We examine the question of how long the evidence for such visits could be expected to last on Earth and on the Moon. Using geological estimates and our current knowledge of the lunar regolith, we conclude that evidence for visits to Earth more than 100,000 years ago would not survive to the present. Radiocarbon dating of some organic material (assuming large C-14 abundance) is of the same order of magnitude. Similarly, evidence of visits to the lunar surface would not survive for more than 100 million years.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49603829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-05-21DOI: 10.20450/mjcce.2022.2368
V. Petrushevski, Sašo Kalajdžievski
Photographic slides of an aperiodic dodecagonal tiling were used as two-dimensional diffraction gratings to describe and demonstrate the basic properties of dodecagonal quasicrystals. This paper complements our earlier publication on Penrose (decagonal) and Ammann (octagonal) quasicrystals, where we constructed and presented the corresponding diffraction gratings.
{"title":"Dodecagonal quasicrystals: Construction of 2D lattices and demonstrations using laser pointers","authors":"V. Petrushevski, Sašo Kalajdžievski","doi":"10.20450/mjcce.2022.2368","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2368","url":null,"abstract":"Photographic slides of an aperiodic dodecagonal tiling were used as two-dimensional diffraction gratings to describe and demonstrate the basic properties of dodecagonal quasicrystals. This paper complements our earlier publication on Penrose (decagonal) and Ammann (octagonal) quasicrystals, where we constructed and presented the corresponding diffraction gratings.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44402039","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-12-20DOI: 10.20450/mjcce.2021.2445
E. Fidanchevski
The project: Al-rich industrial residues for mineral binders in the ESEE region-RIS ALiCE in the frame of the European Institute of Innovation and Technology, Raw materials (EIT-Raw Materials) co-financed by Horizon 2020/ Europe started on March 2019 and will end on February 2022. The “RIS-ALiCE” consortium consists of partners experienced in the relevant field from seven countries (SIovenia, Bosnia and Hercegovina, North Macedonia, Serbia, Hungary, Austria and France). Slovenian National Building and Civil Engineering Institute, Ljubljana, Slovenia coordinates the project.
该项目：由Horizon 2020/Europe共同资助的欧洲创新与技术研究所（EIT Raw materials）框架下的ESEE地区RIS ALiCE矿物粘合剂的富铝工业残留物于2019年3月开始，将于2022年2月结束。“RIS ALiCE”财团由七个国家（斯洛文尼亚、波斯尼亚和黑塞哥维那、北马其顿、塞尔维亚、匈牙利、奥地利和法国）在相关领域经验丰富的合作伙伴组成。斯洛文尼亚卢布尔雅那国家建筑和土木工程研究所负责协调该项目。
{"title":"RIS ALiCE Project","authors":"E. Fidanchevski","doi":"10.20450/mjcce.2021.2445","DOIUrl":"https://doi.org/10.20450/mjcce.2021.2445","url":null,"abstract":"The project: Al-rich industrial residues for mineral binders in the ESEE region-RIS ALiCE in the frame of the European Institute of Innovation and Technology, Raw materials (EIT-Raw Materials) co-financed by Horizon 2020/ Europe started on March 2019 and will end on February 2022. The “RIS-ALiCE” consortium consists of partners experienced in the relevant field from seven countries (SIovenia, Bosnia and Hercegovina, North Macedonia, Serbia, Hungary, Austria and France). Slovenian National Building and Civil Engineering Institute, Ljubljana, Slovenia coordinates the project.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2021-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42168596","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-12-20DOI: 10.20450/mjcce.2021.2441
M. Lovrić
{"title":"In Memoriam - Šebojka Komorsky-Lovrić","authors":"M. Lovrić","doi":"10.20450/mjcce.2021.2441","DOIUrl":"https://doi.org/10.20450/mjcce.2021.2441","url":null,"abstract":"","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2021-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43749405","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-12-15DOI: 10.20450/mjcce.2021.2424
G. Bogoeva-Gaceva, M. Najdoski, V. Stefov, Suat Ibishi
{"title":"Valorization of carbon nanotubes material obtained from polyethylene waste as adsorbent for dyes from wastewater","authors":"G. Bogoeva-Gaceva, M. Najdoski, V. Stefov, Suat Ibishi","doi":"10.20450/mjcce.2021.2424","DOIUrl":"https://doi.org/10.20450/mjcce.2021.2424","url":null,"abstract":"","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2021-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44991695","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-12-15DOI: 10.20450/mjcce.2021.2429
B. Angjusheva, V. Jovanov, E. Fidanchevski
{"title":"Conversion of coal fly ash glass into glass-ceramics by controlled thermal treatment","authors":"B. Angjusheva, V. Jovanov, E. Fidanchevski","doi":"10.20450/mjcce.2021.2429","DOIUrl":"https://doi.org/10.20450/mjcce.2021.2429","url":null,"abstract":"","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2021-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47348131","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-12-15DOI: 10.20450/mjcce.2021.2430
Elena Lazarevska Todevska, M. Piponski, M. Stefova
{"title":"Development and validation of an analytical method for the determination of related substances in bisoprolol fumarate in dosage forms by HPLC-UV-DAD","authors":"Elena Lazarevska Todevska, M. Piponski, M. Stefova","doi":"10.20450/mjcce.2021.2430","DOIUrl":"https://doi.org/10.20450/mjcce.2021.2430","url":null,"abstract":"","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":"327 1","pages":""},"PeriodicalIF":1.0,"publicationDate":"2021-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67570569","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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