{"title":"天然烟叶合成辅酶Q10的研究","authors":"Venkata Manikya Kumar Ajjarapu","doi":"10.1016/j.rechem.2025.102279","DOIUrl":null,"url":null,"abstract":"<div><div>The present research work is aimed to develop a methodology for the synthesis of Ubiquinone Q<sub>10</sub> (CoQ<sub>10</sub>) from the natural tobacco leaves (<em>Nicotiana tabacum</em> L). Solanesol (<em>C</em><sub><em>45</em></sub><em>H</em><sub><em>74</em></sub><em>O</em>), a product isolated from the natural tobacco leaves and a valuable source for synthesizing metabolically active quinones and other drugs has been considered as the raw material for the synthesis of Ubiquinone. The characteristics of Ubiquinone as an antioxidant, essential for human life and the critical role of Ubiquinone in slowing down the ageing process and its uses in the treatment of heart diseases, cancer and ulcers are also presented. Bromination of solanesol with PBr<sub>3</sub> results in the formation of solanesyl bromide with an extremely high yield (98 %) and on further treatment with reagents such as ethylacetate followed by the hydrolysis and decarboxylation results in the formation of a ketone with an appreciable yield of 72 % has also been explained. The chemical pathways suggested for the synthesis of decaprenol and isodecaprenol with significant and appreciable yield are also summarized in the research paper. Formation of Ubiquinone has been identified by TLC and further purified by employing a C<sub>18,</sub> 3.9 mm × 150 mm reverse phase column chromatography with methanol and n-hexane (90:10 <em>v</em>/v). Solvent crystallization in alcohol at <img>20<sup>0</sup>C has been carried out and the isolated ubiquinone is analyzed by HPLC for purity and spectroscopic techniques such as UV, <sup>1</sup>H and <sup>13</sup>C NMR, FT- IR, and ESI-MS have been employed for the structural elucidation and the details are discussed at length in the research paper.</div></div>","PeriodicalId":420,"journal":{"name":"Results in Chemistry","volume":"15 ","pages":"Article 102279"},"PeriodicalIF":2.5000,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of ubiquinone Q10 (Co Q10) from natural tobacco leaves\",\"authors\":\"Venkata Manikya Kumar Ajjarapu\",\"doi\":\"10.1016/j.rechem.2025.102279\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The present research work is aimed to develop a methodology for the synthesis of Ubiquinone Q<sub>10</sub> (CoQ<sub>10</sub>) from the natural tobacco leaves (<em>Nicotiana tabacum</em> L). Solanesol (<em>C</em><sub><em>45</em></sub><em>H</em><sub><em>74</em></sub><em>O</em>), a product isolated from the natural tobacco leaves and a valuable source for synthesizing metabolically active quinones and other drugs has been considered as the raw material for the synthesis of Ubiquinone. The characteristics of Ubiquinone as an antioxidant, essential for human life and the critical role of Ubiquinone in slowing down the ageing process and its uses in the treatment of heart diseases, cancer and ulcers are also presented. Bromination of solanesol with PBr<sub>3</sub> results in the formation of solanesyl bromide with an extremely high yield (98 %) and on further treatment with reagents such as ethylacetate followed by the hydrolysis and decarboxylation results in the formation of a ketone with an appreciable yield of 72 % has also been explained. The chemical pathways suggested for the synthesis of decaprenol and isodecaprenol with significant and appreciable yield are also summarized in the research paper. Formation of Ubiquinone has been identified by TLC and further purified by employing a C<sub>18,</sub> 3.9 mm × 150 mm reverse phase column chromatography with methanol and n-hexane (90:10 <em>v</em>/v). Solvent crystallization in alcohol at <img>20<sup>0</sup>C has been carried out and the isolated ubiquinone is analyzed by HPLC for purity and spectroscopic techniques such as UV, <sup>1</sup>H and <sup>13</sup>C NMR, FT- IR, and ESI-MS have been employed for the structural elucidation and the details are discussed at length in the research paper.</div></div>\",\"PeriodicalId\":420,\"journal\":{\"name\":\"Results in Chemistry\",\"volume\":\"15 \",\"pages\":\"Article 102279\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2025-04-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Results in Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2211715625002620\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Results in Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2211715625002620","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
本研究旨在建立一种从天然烟叶(Nicotiana tabacum L)中合成辅酶Q10 (CoQ10)的方法。从天然烟叶中分离得到的产物茄尼醇(C45H74O)是合成代谢活性醌等药物的重要原料,被认为是合成辅酶Q10的原料。本文还介绍了泛醌作为人类生命必需的抗氧化剂的特性,以及泛醌在减缓衰老过程中的关键作用,以及它在治疗心脏病、癌症和溃疡方面的应用。茄尼醇与PBr3的溴化反应生成产率极高(98%)的茄尼基溴化反应,再用乙酸乙酯等试剂进一步处理,然后水解和脱羧,生成产率为72%的酮,这也得到了解释。总结了十正戊烯醇和异十正戊烯醇的化学合成途径。通过薄层色谱鉴定了泛醌的形成,并采用甲醇和正己烷(90:10 v/v)的C18, 3.9 mm × 150 mm反相柱层析进一步纯化。在200℃的酒精溶剂中结晶,用高效液相色谱法对分离得到的泛醌进行纯度分析,并用紫外、1H和13C核磁共振、红外光谱和ESI-MS等光谱技术对其结构进行了解析,并对其进行了详细的讨论。
Synthesis of ubiquinone Q10 (Co Q10) from natural tobacco leaves
The present research work is aimed to develop a methodology for the synthesis of Ubiquinone Q10 (CoQ10) from the natural tobacco leaves (Nicotiana tabacum L). Solanesol (C45H74O), a product isolated from the natural tobacco leaves and a valuable source for synthesizing metabolically active quinones and other drugs has been considered as the raw material for the synthesis of Ubiquinone. The characteristics of Ubiquinone as an antioxidant, essential for human life and the critical role of Ubiquinone in slowing down the ageing process and its uses in the treatment of heart diseases, cancer and ulcers are also presented. Bromination of solanesol with PBr3 results in the formation of solanesyl bromide with an extremely high yield (98 %) and on further treatment with reagents such as ethylacetate followed by the hydrolysis and decarboxylation results in the formation of a ketone with an appreciable yield of 72 % has also been explained. The chemical pathways suggested for the synthesis of decaprenol and isodecaprenol with significant and appreciable yield are also summarized in the research paper. Formation of Ubiquinone has been identified by TLC and further purified by employing a C18, 3.9 mm × 150 mm reverse phase column chromatography with methanol and n-hexane (90:10 v/v). Solvent crystallization in alcohol at 200C has been carried out and the isolated ubiquinone is analyzed by HPLC for purity and spectroscopic techniques such as UV, 1H and 13C NMR, FT- IR, and ESI-MS have been employed for the structural elucidation and the details are discussed at length in the research paper.