Na Zhang , Yang Xu , Dejuan Sun , Yuxia Li , Hua Li , Lixia Chen
{"title":"杜鹃花中的 Chromene meroterpenoids 及其抗炎作用。","authors":"Na Zhang , Yang Xu , Dejuan Sun , Yuxia Li , Hua Li , Lixia Chen","doi":"10.1016/j.phytochem.2024.114200","DOIUrl":null,"url":null,"abstract":"<div><p><em>Rhododendron dauricum</em> L. is a perennial herb belonging to the genus <em>Rhododendron</em>, commonly utilized in formulations for treating coughs and bronchitis, as well as in herbal teas for enhancing immunity and preventing tracheitis. In this study, fifteen previously undescribed chromene meroterpenoids (<strong>1a/1b-4a/4b, 5</strong>–<strong>8, 9b, 10a, 11b</strong>), along with twenty-one known compounds were isolated from the dried twigs and leaves of <em>Rhododendron dauricum</em> L. Of these, (−)-rhodonoid E (<strong>9b</strong>), (+)-confluentin (<strong>10a</strong>), and (−)-rubiginosin D (<strong>11b</strong>) were separated for the first time by chiral HPLC separation. The elucidation of their structures, including absolute configurations, was achieved through a combination of techniques such as NMR, HRESIMS, modified Mosher's method and quantum-chemical calculation of electronic circular dichroism (ECD) spectra. Seven pairs of enantiomers, compounds <strong>1a/1b-4a/4b</strong> and <strong>9a/9b-11a/11b</strong>, were initially obtained in a racemic manner and were further separated by chiral HPLC preparation. The biological assessment of these compounds against NO production was conducted in the LPS-induced RAW264.7 macrophage cells model. Compounds <strong>9a</strong>, <strong>9b</strong>, and <strong>11a</strong> displayed inhibitory rates exceeding 80%, with IC<sub>50</sub> values ranging from 8.69 ± 0.94 to 13.01 ± 1.11 μM. A preliminary examination of the structure-activity relationship (SAR) for these isolates indicated that chromene meroterpenoids with <em>α</em>, <em>β</em>-unsaturated ketone carbonyl and Δ<sup>12(13)</sup> double bond functionalities exhibited enhanced anti-inflammatory properties.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chromene meroterpenoids from Rhododendron dauricum L. and their anti-inflammatory effects\",\"authors\":\"Na Zhang , Yang Xu , Dejuan Sun , Yuxia Li , Hua Li , Lixia Chen\",\"doi\":\"10.1016/j.phytochem.2024.114200\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p><em>Rhododendron dauricum</em> L. is a perennial herb belonging to the genus <em>Rhododendron</em>, commonly utilized in formulations for treating coughs and bronchitis, as well as in herbal teas for enhancing immunity and preventing tracheitis. In this study, fifteen previously undescribed chromene meroterpenoids (<strong>1a/1b-4a/4b, 5</strong>–<strong>8, 9b, 10a, 11b</strong>), along with twenty-one known compounds were isolated from the dried twigs and leaves of <em>Rhododendron dauricum</em> L. Of these, (−)-rhodonoid E (<strong>9b</strong>), (+)-confluentin (<strong>10a</strong>), and (−)-rubiginosin D (<strong>11b</strong>) were separated for the first time by chiral HPLC separation. The elucidation of their structures, including absolute configurations, was achieved through a combination of techniques such as NMR, HRESIMS, modified Mosher's method and quantum-chemical calculation of electronic circular dichroism (ECD) spectra. Seven pairs of enantiomers, compounds <strong>1a/1b-4a/4b</strong> and <strong>9a/9b-11a/11b</strong>, were initially obtained in a racemic manner and were further separated by chiral HPLC preparation. The biological assessment of these compounds against NO production was conducted in the LPS-induced RAW264.7 macrophage cells model. Compounds <strong>9a</strong>, <strong>9b</strong>, and <strong>11a</strong> displayed inhibitory rates exceeding 80%, with IC<sub>50</sub> values ranging from 8.69 ± 0.94 to 13.01 ± 1.11 μM. A preliminary examination of the structure-activity relationship (SAR) for these isolates indicated that chromene meroterpenoids with <em>α</em>, <em>β</em>-unsaturated ketone carbonyl and Δ<sup>12(13)</sup> double bond functionalities exhibited enhanced anti-inflammatory properties.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-06-25\",\"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/S0031942224002371\",\"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/S0031942224002371","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}
Chromene meroterpenoids from Rhododendron dauricum L. and their anti-inflammatory effects
Rhododendron dauricum L. is a perennial herb belonging to the genus Rhododendron, commonly utilized in formulations for treating coughs and bronchitis, as well as in herbal teas for enhancing immunity and preventing tracheitis. In this study, fifteen previously undescribed chromene meroterpenoids (1a/1b-4a/4b, 5–8, 9b, 10a, 11b), along with twenty-one known compounds were isolated from the dried twigs and leaves of Rhododendron dauricum L. Of these, (−)-rhodonoid E (9b), (+)-confluentin (10a), and (−)-rubiginosin D (11b) were separated for the first time by chiral HPLC separation. The elucidation of their structures, including absolute configurations, was achieved through a combination of techniques such as NMR, HRESIMS, modified Mosher's method and quantum-chemical calculation of electronic circular dichroism (ECD) spectra. Seven pairs of enantiomers, compounds 1a/1b-4a/4b and 9a/9b-11a/11b, were initially obtained in a racemic manner and were further separated by chiral HPLC preparation. The biological assessment of these compounds against NO production was conducted in the LPS-induced RAW264.7 macrophage cells model. Compounds 9a, 9b, and 11a displayed inhibitory rates exceeding 80%, with IC50 values ranging from 8.69 ± 0.94 to 13.01 ± 1.11 μM. A preliminary examination of the structure-activity relationship (SAR) for these isolates indicated that chromene meroterpenoids with α, β-unsaturated ketone carbonyl and Δ12(13) double bond functionalities exhibited enhanced anti-inflammatory properties.
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.