{"title":"藤黄属植物和怒江藤黄属植物中的色酮和双黄酮类化合物及其抗炎活性。","authors":"Xiaojie Fan, Jiaxin Guo, Dongyan Feng, Dahong Li, Huiming Hua","doi":"10.1016/j.phytochem.2024.114166","DOIUrl":null,"url":null,"abstract":"<div><p>Plants of the <em>Garcinia</em> genus were rich in structurally diverse and naturally bioactive components, while limited studies have been reported for <em>Garcinia pedunculata</em> Roxb. and <em>G. nujiangensis</em> C. Y. Wu & Y. H. Li. Four previously undescribed compounds including three chromones, garpedunchromones A-C (<strong>1</strong>–<strong>3</strong>), and one biflavonoid, nujiangbiflavone A (<strong>14</strong>), along with fifteen known analogs (<strong>4</strong>–<strong>13</strong>, <strong>15</strong>–<strong>19</strong>) were isolated from <em>G. pedunculata</em> and <em>G. nujiangensis</em>. The structures of the isolated compounds were determined based on their HRESIMS data, extensive NMR spectroscopic analyses, and ECD calculations. The chromone derivatives were isolated from <em>Garcinia</em> for the first time. Compound <strong>14</strong> was a rare biflavonoid with C-3─C-6″ linkage. The biological evaluation of these isolates against NO production was conducted in the LPS-induced RAW 264.7 cells, resulting in the identification of a series of potent NO inhibitors, of which garpedunchromone B (<strong>2</strong>) was the most active with an IC<sub>50</sub> value of 18.11 ± 0.96 μM. In the network pharmacology studies, the potential targets of compounds and inflammation were obtained from PharmMapper and GeneCards database. GO and KEGG enrichment analysis revealed that the overlapped targets were closely related to the major pathogenic processes linked to inflammation. Garpedunchromone B and proteins binding sites were being predicted.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chromones and biflavonoids from Garcinia pedunculata and Garcinia nujiangensis and their anti-inflammatory activity\",\"authors\":\"Xiaojie Fan, Jiaxin Guo, Dongyan Feng, Dahong Li, Huiming Hua\",\"doi\":\"10.1016/j.phytochem.2024.114166\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Plants of the <em>Garcinia</em> genus were rich in structurally diverse and naturally bioactive components, while limited studies have been reported for <em>Garcinia pedunculata</em> Roxb. and <em>G. nujiangensis</em> C. Y. Wu & Y. H. Li. Four previously undescribed compounds including three chromones, garpedunchromones A-C (<strong>1</strong>–<strong>3</strong>), and one biflavonoid, nujiangbiflavone A (<strong>14</strong>), along with fifteen known analogs (<strong>4</strong>–<strong>13</strong>, <strong>15</strong>–<strong>19</strong>) were isolated from <em>G. pedunculata</em> and <em>G. nujiangensis</em>. The structures of the isolated compounds were determined based on their HRESIMS data, extensive NMR spectroscopic analyses, and ECD calculations. The chromone derivatives were isolated from <em>Garcinia</em> for the first time. Compound <strong>14</strong> was a rare biflavonoid with C-3─C-6″ linkage. The biological evaluation of these isolates against NO production was conducted in the LPS-induced RAW 264.7 cells, resulting in the identification of a series of potent NO inhibitors, of which garpedunchromone B (<strong>2</strong>) was the most active with an IC<sub>50</sub> value of 18.11 ± 0.96 μM. In the network pharmacology studies, the potential targets of compounds and inflammation were obtained from PharmMapper and GeneCards database. GO and KEGG enrichment analysis revealed that the overlapped targets were closely related to the major pathogenic processes linked to inflammation. Garpedunchromone B and proteins binding sites were being predicted.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-05-27\",\"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/S0031942224002036\",\"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/S0031942224002036","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}
引用次数: 0
摘要
藤黄属植物富含结构多样的天然生物活性成分,而对Garcinia pedunculata Roxb.和G. nujiangensis C. Y. Wu & Y. H. Li的研究报道有限。从 G. pedunculata 和 G. nujiangensis 中分离出了 4 个以前未曾描述过的化合物,包括 3 个色酮类化合物 garpedunchromones A-C (1-3)和 1 个双黄酮类化合物 nujiangbiflavonone A (14),以及 15 个已知的类似物 (4-13,15-19)。根据 HRESIMS 数据、大量 NMR 光谱分析和 ECD 计算确定了分离化合物的结构。首次从藤黄属植物中分离出了铬酮衍生物。化合物 14 是一种罕见的具有 C-3─C-6" 连接的双黄酮类化合物。在 LPS 诱导的 RAW 264.7 细胞中对这些分离物进行了抑制 NO 生成的生物学评价,结果发现了一系列强效的 NO 抑制剂,其中加苯醌 B(2)的活性最高,IC50 值为 18.11 ± 0.96 μM。在网络药理学研究中,化合物和炎症的潜在靶点来自 PharmMapper 和 GeneCards 数据库。GO和KEGG富集分析表明,重叠的靶点与炎症的主要致病过程密切相关。预测了 Garpedunchromone B 与蛋白质的结合位点。
Chromones and biflavonoids from Garcinia pedunculata and Garcinia nujiangensis and their anti-inflammatory activity
Plants of the Garcinia genus were rich in structurally diverse and naturally bioactive components, while limited studies have been reported for Garcinia pedunculata Roxb. and G. nujiangensis C. Y. Wu & Y. H. Li. Four previously undescribed compounds including three chromones, garpedunchromones A-C (1–3), and one biflavonoid, nujiangbiflavone A (14), along with fifteen known analogs (4–13, 15–19) were isolated from G. pedunculata and G. nujiangensis. The structures of the isolated compounds were determined based on their HRESIMS data, extensive NMR spectroscopic analyses, and ECD calculations. The chromone derivatives were isolated from Garcinia for the first time. Compound 14 was a rare biflavonoid with C-3─C-6″ linkage. The biological evaluation of these isolates against NO production was conducted in the LPS-induced RAW 264.7 cells, resulting in the identification of a series of potent NO inhibitors, of which garpedunchromone B (2) was the most active with an IC50 value of 18.11 ± 0.96 μM. In the network pharmacology studies, the potential targets of compounds and inflammation were obtained from PharmMapper and GeneCards database. GO and KEGG enrichment analysis revealed that the overlapped targets were closely related to the major pathogenic processes linked to inflammation. Garpedunchromone B and proteins binding sites were being predicted.
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.