Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols
1-O-alkylglycerols are a class of natural existing lipids with broad biological activities. However, their use in food or agricultural fields remains to be investigated, especially for their antimicrobial activity. In this work, three 1-O-alkylglycerols, 1-O-octanylglycerol (C8Gly1), 1-O-dodecylglyc...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-11-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844023089983 |
| _version_ | 1827615921152196608 |
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| author | Liangliang Shi Chenyue Jia Jiangtao Feng Weinong Zhang Junbo He |
| author_facet | Liangliang Shi Chenyue Jia Jiangtao Feng Weinong Zhang Junbo He |
| author_sort | Liangliang Shi |
| collection | DOAJ |
| description | 1-O-alkylglycerols are a class of natural existing lipids with broad biological activities. However, their use in food or agricultural fields remains to be investigated, especially for their antimicrobial activity. In this work, three 1-O-alkylglycerols, 1-O-octanylglycerol (C8Gly1), 1-O-dodecylglycerol (C12Gly1), and 1-O-hexadecylglycerol (C16Gly1), were synthesized in the isolated yields of 71.3–89.8 % and characterized by 1H NMR, 13C NMR, FITR, mass spectra, and HPLC-ESLD. The critical micelle concentration (CMC) of 1-O-alkylglycerols was determined to be 1.65 mmol/L (C8Gly1), 0.33 mmol/L (C12Gly1), and 0.23 mmol/L (C16Gly1) using the pyrene method. C12Gly1 and C16Gly1 had similar surface tensions that are lower than C8Gly1. C8Gly1 can form micelles in aqueous solution with excellent nano-dispersed uniformity and stability. Furthermore, C8Gly1 and C12Gly1 not only displayed good antibacterial activity against Staphylococcus aureus, but they also inhibited the growth of Botryosphaeria dothidea, Monilia fructigena, and Phytophthora capsicum at 400 μg/mL. Thus, the C8Gly1 and C12Gly1 can serve as novel antimicrobial agents in food preservation. |
| first_indexed | 2024-03-09T09:17:30Z |
| format | Article |
| id | doaj.art-1d6fe851af2141d79b062b40ba26c0ae |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-03-09T09:17:30Z |
| publishDate | 2023-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-1d6fe851af2141d79b062b40ba26c0ae2023-12-02T07:04:15ZengElsevierHeliyon2405-84402023-11-01911e21790Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerolsLiangliang Shi0Chenyue Jia1Jiangtao Feng2Weinong Zhang3Junbo He4Key Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, ChinaKey Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, ChinaKey Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, China; Hubei Key Laboratory for Processing and Transformation of Agricultural Products, Wuhan Polytechnic University, Wuhan 430023, China; Engineering Research Center of Lipid-based Fine Chemicals of Hubei Province, Wuhan 430023, ChinaKey Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, China; Hubei Key Laboratory for Processing and Transformation of Agricultural Products, Wuhan Polytechnic University, Wuhan 430023, China; Engineering Research Center of Lipid-based Fine Chemicals of Hubei Province, Wuhan 430023, ChinaKey Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, China; Hubei Key Laboratory for Processing and Transformation of Agricultural Products, Wuhan Polytechnic University, Wuhan 430023, China; Engineering Research Center of Lipid-based Fine Chemicals of Hubei Province, Wuhan 430023, China; Corresponding author. Key Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, China.1-O-alkylglycerols are a class of natural existing lipids with broad biological activities. However, their use in food or agricultural fields remains to be investigated, especially for their antimicrobial activity. In this work, three 1-O-alkylglycerols, 1-O-octanylglycerol (C8Gly1), 1-O-dodecylglycerol (C12Gly1), and 1-O-hexadecylglycerol (C16Gly1), were synthesized in the isolated yields of 71.3–89.8 % and characterized by 1H NMR, 13C NMR, FITR, mass spectra, and HPLC-ESLD. The critical micelle concentration (CMC) of 1-O-alkylglycerols was determined to be 1.65 mmol/L (C8Gly1), 0.33 mmol/L (C12Gly1), and 0.23 mmol/L (C16Gly1) using the pyrene method. C12Gly1 and C16Gly1 had similar surface tensions that are lower than C8Gly1. C8Gly1 can form micelles in aqueous solution with excellent nano-dispersed uniformity and stability. Furthermore, C8Gly1 and C12Gly1 not only displayed good antibacterial activity against Staphylococcus aureus, but they also inhibited the growth of Botryosphaeria dothidea, Monilia fructigena, and Phytophthora capsicum at 400 μg/mL. Thus, the C8Gly1 and C12Gly1 can serve as novel antimicrobial agents in food preservation.http://www.sciencedirect.com/science/article/pii/S24058440230899831-O-AlkylglycerolSynthesisSurface propertyAntibacterial activityAntifungal activity |
| spellingShingle | Liangliang Shi Chenyue Jia Jiangtao Feng Weinong Zhang Junbo He Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols Heliyon 1-O-Alkylglycerol Synthesis Surface property Antibacterial activity Antifungal activity |
| title | Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols |
| title_full | Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols |
| title_fullStr | Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols |
| title_full_unstemmed | Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols |
| title_short | Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols |
| title_sort | synthesis characterization antibacterial and antifungal activities of 1 o alkylglycerols |
| topic | 1-O-Alkylglycerol Synthesis Surface property Antibacterial activity Antifungal activity |
| url | http://www.sciencedirect.com/science/article/pii/S2405844023089983 |
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