Amide and phenylpropanoid glycosides from the fruits of Piper longum L. and their anti-inflammatory activity

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2025-03-25 DOI:10.1007/s11418-025-01893-8

Guanghui Gou, Liu Liu, Wenli Bao, Jun Li, Haji Akber Aisa

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Abstract

Ten glycosidic compounds (1–10), including two novel amide glycosides and one new phenylpropanoid glycoside, were isolated from the fruits of Piper longum L. These novel compounds were identified as (E)-N-feruloylpiperidine 4′-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranoside (1), (E)-N-p-coumaroylpiperidine 4′-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranoside (2), and (E)-cinnamyl alcohol 9-O-β-d-glucopyranosyl-(1 → 4)-α-l-rhamnose-(1 → 6)-β-d-glucopyranoside (3) by detailed spectroscopic and spectrometric techniques. Acid hydrolysis was employed to determine the glycosidic linkages, facilitating the structural elucidation of these compounds. The anti-inflammatory activities of all isolated compounds were assessed, and the results demonstrated that compounds 8 and 9 exhibited moderate inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells.

Graphical abstract

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胡椒果实中的酰胺类和苯丙类苷及其抗炎活性。

从辣椒果实中分离到10个糖苷类化合物（1-10），包括2个新的酰胺类糖苷和1个新的苯丙类糖苷。这些新化合物鉴定为(E)- n -阿魏酰基胡椒啶4'- o -β-d-葡萄糖吡喃苷-(1→4)-β-d-葡萄糖吡喃苷(1),(E)- n - n -对香豆基胡椒啶4'- o -β-d-葡萄糖吡喃苷-(1→4)-β-d-葡萄糖吡喃苷(2)，(E)-肉桂醇9-O-β-d-葡萄糖苷-(1→4)-α-l-鼠李糖-(1→6)-β-d-葡萄糖苷(3)。酸水解测定了糖苷键，方便了这些化合物的结构解析。结果表明，化合物8和9对脂多糖（LPS）刺激的RAW264.7细胞一氧化氮（NO）的产生具有中等抑制作用。

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来源期刊

Journal of Natural Medicines 医学-药学

CiteScore

6.90

自引率

3.00%

发文量

审稿时长

1.7 months

期刊介绍： The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers: -chemistry of natural products -biochemistry of medicinal plants -pharmacology of natural products and herbs, including Kampo formulas and traditional herbs -botanical anatomy -cultivation of medicinal plants. The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.