{"title":"叶枯素全草中的化学成分及其α-葡萄糖苷酶抑制活性","authors":"","doi":"10.1016/j.phytochem.2024.114290","DOIUrl":null,"url":null,"abstract":"<div><div>From <em>Ceratophyllum demersum</em> growing in Vietnam, twelve compounds were isolated and structurally elucidated, including six previously undescribed compounds, demersones A-D (<strong>1</strong>–<strong>4</strong>), acetylvelutins A and B (<strong>8</strong> and <strong>9</strong>), together with six known compounds, (+)-cyclocolorenone (<strong>5</strong>), 1-hydroxycyclocolorenone (<strong>6</strong>), 10-hydroxycyclocolorenone (<strong>7</strong>), retusin (<strong>10</strong>), betulinic acid (<strong>11</strong>), and lupeol (<strong>12</strong>). The chemical structures and stereochemistry of <strong>1</strong>–<strong>12</strong> were identified through analysis of spectroscopic data (1D and 2D NMR and HRESIMS), ECD data, and DFT calculation. Notably, this is the first time that humulene-type (<strong>1</strong> and <strong>2</strong>), guaiane-type (<strong>3</strong>), and aromadendrane-type (<strong>4</strong>–<strong>7</strong>) sesquiterpenoids have been reported in this genus. Compounds <strong>8</strong> and <strong>9</strong> are the first examples of 8-acetoxyflavones found in nature. Upon evaluation of the alpha-glucosidase of <strong>1</strong>–<strong>3</strong> and <strong>5</strong>–<strong>12</strong>, it was found that <strong>12</strong> exhibited the highest potential with an IC<sub>50</sub> value of 15.4 ± 1.1 μM. The molecular docking of <strong>3</strong> and <strong>8</strong> was further studied.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chemical constituents with their alpha-glucosidase inhibitory activity from the whole plant of Ceratophyllum demersum\",\"authors\":\"\",\"doi\":\"10.1016/j.phytochem.2024.114290\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>From <em>Ceratophyllum demersum</em> growing in Vietnam, twelve compounds were isolated and structurally elucidated, including six previously undescribed compounds, demersones A-D (<strong>1</strong>–<strong>4</strong>), acetylvelutins A and B (<strong>8</strong> and <strong>9</strong>), together with six known compounds, (+)-cyclocolorenone (<strong>5</strong>), 1-hydroxycyclocolorenone (<strong>6</strong>), 10-hydroxycyclocolorenone (<strong>7</strong>), retusin (<strong>10</strong>), betulinic acid (<strong>11</strong>), and lupeol (<strong>12</strong>). The chemical structures and stereochemistry of <strong>1</strong>–<strong>12</strong> were identified through analysis of spectroscopic data (1D and 2D NMR and HRESIMS), ECD data, and DFT calculation. Notably, this is the first time that humulene-type (<strong>1</strong> and <strong>2</strong>), guaiane-type (<strong>3</strong>), and aromadendrane-type (<strong>4</strong>–<strong>7</strong>) sesquiterpenoids have been reported in this genus. Compounds <strong>8</strong> and <strong>9</strong> are the first examples of 8-acetoxyflavones found in nature. Upon evaluation of the alpha-glucosidase of <strong>1</strong>–<strong>3</strong> and <strong>5</strong>–<strong>12</strong>, it was found that <strong>12</strong> exhibited the highest potential with an IC<sub>50</sub> value of 15.4 ± 1.1 μM. The molecular docking of <strong>3</strong> and <strong>8</strong> was further studied.</div></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-09-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942224003273\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224003273","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Chemical constituents with their alpha-glucosidase inhibitory activity from the whole plant of Ceratophyllum demersum
From Ceratophyllum demersum growing in Vietnam, twelve compounds were isolated and structurally elucidated, including six previously undescribed compounds, demersones A-D (1–4), acetylvelutins A and B (8 and 9), together with six known compounds, (+)-cyclocolorenone (5), 1-hydroxycyclocolorenone (6), 10-hydroxycyclocolorenone (7), retusin (10), betulinic acid (11), and lupeol (12). The chemical structures and stereochemistry of 1–12 were identified through analysis of spectroscopic data (1D and 2D NMR and HRESIMS), ECD data, and DFT calculation. Notably, this is the first time that humulene-type (1 and 2), guaiane-type (3), and aromadendrane-type (4–7) sesquiterpenoids have been reported in this genus. Compounds 8 and 9 are the first examples of 8-acetoxyflavones found in nature. Upon evaluation of the alpha-glucosidase of 1–3 and 5–12, it was found that 12 exhibited the highest potential with an IC50 value of 15.4 ± 1.1 μM. The molecular docking of 3 and 8 was further studied.
期刊介绍：
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.
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