Amaryllidaceae alkaloids with nitric oxide inhibitory activity from the leaves of Crinum asiaticum L. var. asiaticum

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Phytochemistry Pub Date : 2025-01-03 DOI:10.1016/j.phytochem.2025.114383

Waraluck Chaichompoo , Pornchai Rojsitthisak , Nassareen Supaweera , Preeyaporn Poldorn , Wachirachai Pabuprapap , Warangkana Chunglok , Yutthana Wongnongwa , Apichart Suksamrarn

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Abstract

Forty-two Amaryllidaceae alkaloids, including eleven previously undescribed alkaloids, crinasiaticines C–M, and three undescribed naturally occurring alkaloids, (+)-dihydroepivittatine, (+)-dihydrovittatine and (+)-dihydrohamayne, were isolated from the leaves of Crinum asiaticum L. var. asiaticum. Their structures and configurations were elucidated using NMR and MS spectroscopic techniques, along with the comparison of experimental electronic circular dichroism spectra to calculated data. The anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide-stimulated RAW264.7 cells was evaluated for most of the isolated alkaloids. Compounds 39, 21, 22, and 35 exhibited considerable NO inhibitory activity, with IC₅₀ values of 2.5–2.6 μM, compared to positive control dexamethasone (IC₅₀ 2.7 μM). However, these compounds demonstrated cytotoxic effects on cells. Compound 15 also possessed the highest selectivity index of 22.5 with minimal cytotoxicity.

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从 Crinum asiaticum L. var. asiaticum 的叶子中提取的具有一氧化氮抑制活性的 Amaryllidaceae 生物碱。

从asiatium L. var. asiatium的叶中分离得到42种Amaryllidaceae生物碱，包括11种未被描述的crinasiaticines C-M和3种未被描述的天然生物碱(+)-二氢维塔碱、(+)-二氢维塔碱和(+)-二氢维塔碱。利用核磁共振和质谱技术分析了它们的结构和构型，并将实验电子圆二色光谱与计算数据进行了比较。大多数分离的生物碱对脂多糖刺激RAW264.7细胞一氧化氮（NO）产生的抗炎活性进行了评价。化合物39、21、22和35与阳性对照地塞米松（IC50为2.7 μM）相比，具有明显的NO抑制活性，IC50值为2.5 ~ 2.6 μM。然而，这些化合物对细胞有细胞毒性作用。化合物15具有最高的选择性指数（22.5）和最小的细胞毒性。

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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.

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