Kaemphenolide: a cyclobutane-bearing phenylpropanoid from Kaempferia galanga L. with nitric oxide inhibitory activity

IF 4.9 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2025-10-02 DOI:10.1007/s13659-025-00547-2

Syarifatul Mufidah, Yusaku Miyamae, Hiroyuki Fuchino, Nobuo Kawahara

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Abstract

An undescribed phenylpropanoid dimer featuring a rare cyclobutane ring was isolated from the rhizomes of Kaempferia galanga L., a medicinal plant traditionally used in Southeast Asia for its anti-inflammatory and therapeutic properties. Kaemphenolide (1), along with five known constituents, was obtained by separations of methanolic extract using chromatography. The presence of a cyclobutane ring within the phenylpropanoid scaffold represents an unusual structural motif among natural products and underscores the chemical uniqueness of this molecule. To evaluate its biological relevance, 1 was tested for its ability to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. The compound exhibited anti-inflammatory activity, with an IC₅₀ value of 23.1 ± 6.40 µM.

Graphical Abstract

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山柰酚内酯：从山柰中提取的含环丁烷的苯丙素，具有抑制一氧化氮的活性。

从东南亚传统药用植物山柰（Kaempferia galanga L.）根茎中分离出一种具有罕见环丁烷环的苯丙二聚体。山柰具有抗炎和治疗特性。Kaemphenolide(1)，连同五个已知的成分，得到分离甲醇提取物使用色谱法。苯基丙烷支架内的环丁烷环的存在代表了天然产物中不寻常的结构基序，并强调了该分子的化学独特性。为了评估其生物学相关性，1测试了其抑制脂多糖（LPS）刺激的RAW264.7巨噬细胞中一氧化氮（NO）产生的能力。化合物具有抗炎活性，IC50值为23.1±6.40µM。

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.