{"title":"Alkaloids from Anacyclus pyrethrum","authors":"","doi":"10.1016/j.phytochem.2024.114255","DOIUrl":null,"url":null,"abstract":"<div><p>Twelve undescribed alkaloids, including eight pyrrolo[3,2-<em>g</em>]isoquinoline alkaloids (+)/(−)-anacyquinoline A (<strong>1a</strong>/<strong>1b</strong>), (±)-anacyquinoline B (<strong>2</strong>), (+)/(−)-anacyquinoline C (<strong>3a</strong>/<strong>3b</strong>), (±)-anacyquinoline D (<strong>4</strong>), (±)-anacyquinoline E (<strong>5</strong>), and (±)-anacyquinoline F (<strong>6</strong>), together with four pyrrolo[2,3-<em>g</em>]quinoline alkaloids (+)/(−)-anacyquinoline G (<strong>7a</strong>/<strong>7b</strong>), (±)-anacyquinoline H (<strong>8</strong>), and (±)-anacyquinoline I (<strong>9</strong>), were isolated from the roots of <em>Anacyclus pyrethrum</em> (L.) DC. Their structures were determined via spectroscopic analyses (UV, IR, NMR), HRESIMS, quantum chemical calculations of ECD, DP4+ analysis, and single-crystal X-ray diffraction analysis (Cu Kα). Furthermore, in bioassay, (+)/(−)-anacyquinoline G (<strong>7a</strong>/<strong>7b</strong>) and (±)-anacyquinoline H (<strong>8</strong>) showed inhibition on nitric oxide production in lipopolysaccharide -induced RAW 264.7 cells with IC<sub>50</sub> values of 41.4, 44.1, and 31.4 μM, respectively, indicating their potential anti-inflammatory bioactivity.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-30","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/S0031942224002929","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
Abstract
Twelve undescribed alkaloids, including eight pyrrolo[3,2-g]isoquinoline alkaloids (+)/(−)-anacyquinoline A (1a/1b), (±)-anacyquinoline B (2), (+)/(−)-anacyquinoline C (3a/3b), (±)-anacyquinoline D (4), (±)-anacyquinoline E (5), and (±)-anacyquinoline F (6), together with four pyrrolo[2,3-g]quinoline alkaloids (+)/(−)-anacyquinoline G (7a/7b), (±)-anacyquinoline H (8), and (±)-anacyquinoline I (9), were isolated from the roots of Anacyclus pyrethrum (L.) DC. Their structures were determined via spectroscopic analyses (UV, IR, NMR), HRESIMS, quantum chemical calculations of ECD, DP4+ analysis, and single-crystal X-ray diffraction analysis (Cu Kα). Furthermore, in bioassay, (+)/(−)-anacyquinoline G (7a/7b) and (±)-anacyquinoline H (8) showed inhibition on nitric oxide production in lipopolysaccharide -induced RAW 264.7 cells with IC50 values of 41.4, 44.1, and 31.4 μM, respectively, indicating their potential anti-inflammatory bioactivity.
12 种未描述的生物碱，包括 8 种吡咯并[3,2-g]异喹啉生物碱 (+)/(-)-anacyquinoline A (1a/1b)、(±)-anacyquinoline B (2)、(+)/(-)-anacyquinoline C (3a/3b)、(±)-anacyquinoline D (4)、(±)-anacyquinoline E (5)、和 (±)-anacyquinoline F (6)，以及四种吡咯并[2,3-g]喹啉生物碱 (+)/(-)-anacyquinoline G (7a/7b)、(±)-anacyquinoline H (8) 和 (±)-anacyquinoline I (9)。DC.通过光谱分析（紫外、红外、核磁共振）、HRESIMS、ECD 量子化学计算、DP4+ 分析和单晶 X 射线衍射分析（Cu Kα）确定了它们的结构。此外，在生物测定中，(+)/(-)-金并喹啉 G（7a/7b）和(±)-金并喹啉 H（8）对脂多糖诱导的 RAW 264.7 细胞产生的一氧化氮具有抑制作用，IC50 值分别为 41.4、44.1 和 31.4 μM，表明它们具有潜在的抗炎生物活性。
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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