Nudifloids O–R, four undescribed diterpenoids from Callicarpa nudiflora with anti-inflammatory activity

IF 3.4 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2025-05-24 DOI:10.1016/j.phytochem.2025.114563

Si-Qi Chen , Ji-Hui Zhang , Xia Tang , Miao-Yu Lai , Xue-Qing Lv , Zhong-Qiu Liu , Li-Xin Duan , Yuan-Yuan Cheng , Guo-Cai Wang , Peng Wu

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Abstract

Four undescribed 3,4-seco-labdane diterpenoid derivatives (nudifloids O–R) along with 12 known terpenoids were isolated from the aerial part of Callicarpa nudiflora Hook. et Arn. Nudifloids O and P (compounds 1 and 2) represent the first examples of 3,4-seco-labdane diterpenoid coupled with 2-methylene-3-butenal likely via the Diels–Alder reaction, forming a rare cyclohexene moiety. The structures including absolute configurations were elucidated using comprehensive spectral data, calculated ¹³C NMR-DP4+ probability analysis, and electronic circular dichroism. Putative biosynthetic pathways for nudifloids O and P were proposed. All isolates were evaluated for their inhibitory activities on NO and IL-1β production in the LPS-stimulated RAW 264.7 macrophage cells. Nudifloids P (compound 2) showed potent inhibitory activities against IL-1β and NO production.

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nudiflids O-R，四种未描述的来自于海葵中具有抗炎活性的二萜类化合物

从海参的地上部分分离得到4个未描述的3,4-二萜衍生物（nudiflora O-R）和12个已知的萜类化合物。在攻击。化合物O和P（化合物1和2）可能是通过Diels-Alder反应与2-亚甲基-3-丁烯偶联的第一个例子，形成罕见的环己烯部分。利用综合光谱数据、计算的13C核磁共振- dp4 +概率分析和电子圆二色性对含绝对构型的结构进行了分析。提出了核蛋白O和P的推定生物合成途径。在lps刺激的RAW 264.7巨噬细胞中，评估了所有分离株对NO和IL-1β产生的抑制活性。Nudifloids P（化合物2）对IL-1β和NO的产生有较强的抑制作用。

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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.