{"title":"Phytocannabinoid-like meroterpenoids from twigs and leaves of Rhododendron spinuliferum","authors":"","doi":"10.1016/j.phytochem.2024.114241","DOIUrl":null,"url":null,"abstract":"<div><p>Six pairs of previously undescribed enantiomeric phytocannabinoid-like meroterpenoids, (±)-spinulinoids A‒F, and two naturally occurring compounds, (+)-rhododaurichromanic acid A and (<em>E</em>)-4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)benzoic acid, together with one known congener, (−)-rhododaurichromanic acid A, were obtained from the twigs and leaves of <em>Rhododendron spinuliferum</em>. Their structures were established by their extensive spectral data (NMR and HRESIMS), ECD calculations, and single-crystal X-ray diffraction data. Spinulinoids A and B are unprecedented phytocannabinoid-like meroterpenoids constructed by the resorcinol moiety and a <em>β</em>-bisabolene unit, whereas spinulinoid C represents a rare adduct of quinone and <em>β</em>-bisabolene with a tricyclic 6/6/6 ring system.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-08","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/S0031942224002784","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
Six pairs of previously undescribed enantiomeric phytocannabinoid-like meroterpenoids, (±)-spinulinoids A‒F, and two naturally occurring compounds, (+)-rhododaurichromanic acid A and (E)-4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)benzoic acid, together with one known congener, (−)-rhododaurichromanic acid A, were obtained from the twigs and leaves of Rhododendron spinuliferum. Their structures were established by their extensive spectral data (NMR and HRESIMS), ECD calculations, and single-crystal X-ray diffraction data. Spinulinoids A and B are unprecedented phytocannabinoid-like meroterpenoids constructed by the resorcinol moiety and a β-bisabolene unit, whereas spinulinoid C represents a rare adduct of quinone and β-bisabolene with a tricyclic 6/6/6 ring system.
从两种已知的同系物(-)-罗汉果二氢色原酸 A 和(E)-4-((3、和(E)-4-((3,7-二甲基辛-2,6-二烯-1-基)氧基)苯甲酸,以及一种已知的同系物(-)-罗汉果罗汉果酸 A,都是从杜鹃花的枝叶中获得的。通过大量的光谱数据(核磁共振和 HRESIMS)、ECD 计算和单晶 X 射线衍射数据,确定了它们的结构。刺桐素 A 和 B 是由间苯二酚分子和一个 β-双大麻烯单元构建而成的前所未有的植物大麻素类 Meroterpenoids,而刺桐素 C 则是一种罕见的醌和β-双大麻烯加合物,具有三环 6/6/6 环系统。
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.