ent-Kaurane diterpenoids from Isodon henryi and their anti-inflammatory activities

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2024-08-17 DOI:10.1016/j.phytochem.2024.114247

{"title":"ent-Kaurane diterpenoids from Isodon henryi and their anti-inflammatory activities","authors":"","doi":"10.1016/j.phytochem.2024.114247","DOIUrl":null,"url":null,"abstract":"<div>Phytochemical investigation of the 70% ethanol extract of Isodon henryi Kudô afforded fifteen ent-kaurane diterpenoids, including nine previously undescribed compounds, named isohenolides C–K (1–9). Compounds 1–6 featured an unusual 6,7;8,15-diseco-7,20-olide ent-kaurane diterpenoid scaffold, in which 1 also possessed an 11,15-lactone ring while 2–6 all contained a free α-methylene-γ-carboxylic acid. Compound 6 was also a rare 6,8-cyclo-7,20-olide ent-kauranoid. Their structures were elucidated primarily by HRESIMS, 1D and 2D NMR spectroscopy, electronic circular dichroism and X-ray diffraction (Cu Kα) methods. Additionally, most compounds were also screened for anti-inflammatory actions against lipopolysaccharide-induced RAW 264.7 cells, and compounds 9 and 13 exhibited stronger nitric oxide inhibition, with IC50 values of 15.99 ± 0.75 and 18.19 ± 0.42 μM, respectively.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-17","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/S003194222400284X","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

Phytochemical investigation of the 70% ethanol extract of Isodon henryi Kudô afforded fifteen ent-kaurane diterpenoids, including nine previously undescribed compounds, named isohenolides C–K (1–9). Compounds 1–6 featured an unusual 6,7;8,15-diseco-7,20-olide ent-kaurane diterpenoid scaffold, in which 1 also possessed an 11,15-lactone ring while 2–6 all contained a free α-methylene-γ-carboxylic acid. Compound 6 was also a rare 6,8-cyclo-7,20-olide ent-kauranoid. Their structures were elucidated primarily by HRESIMS, 1D and 2D NMR spectroscopy, electronic circular dichroism and X-ray diffraction (Cu Kα) methods. Additionally, most compounds were also screened for anti-inflammatory actions against lipopolysaccharide-induced RAW 264.7 cells, and compounds 9 and 13 exhibited stronger nitric oxide inhibition, with IC₅₀ values of 15.99 ± 0.75 and 18.19 ± 0.42 μM, respectively.

Abstract Image

查看原文本刊更多论文

Isodon henryi 中的ent-Kaurane 二萜及其抗炎活性。

通过对 Isodon henryi Kudô 的 70% 乙醇提取物进行植物化学研究，发现了十五种ent-kaurane 二萜类化合物，其中包括九种以前未曾描述过的化合物，命名为异henolides C-K（1-9）。化合物 1-6 具有不寻常的 6,7;8,15-二癸-7,20-内酯ent-kaurane 二萜支架，其中 1 还具有一个 11,15 内酯环，而 2-6 均含有一个游离的 α-亚甲基-γ-羧酸。化合物 6 也是一种罕见的 6,8-Cyclo-7,20-olide ent-kauranoid。这些化合物的结构主要是通过 HRESIMS、一维和二维核磁共振光谱、电子圆二色性和 X 射线衍射（Cu Kα）方法阐明的。此外，还筛选了大多数化合物对脂多糖诱导的 RAW 264.7 细胞的抗炎作用，其中化合物 9 和 13 表现出更强的一氧化氮抑制作用，IC50 值分别为 15.99 ± 0.75 和 18.19 ± 0.42 μM。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

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.