Sesquiterpene lactones from Seriphidium transiliense and their anti-inflammation activity

IF 2.6 3区 医学 Q3 CHEMISTRY, MEDICINAL Fitoterapia Pub Date : 2025-03-01 Epub Date: 2024-12-19 DOI:10.1016/j.fitote.2024.106349
Fangsheng Wang , Huizhen Wen , Liu Liu , Jun Li , Fei He , Haji Akber Aisa , Xuelei Xin
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Abstract

Six undescribed sesquiterpene lactones (16) and fifteen known compounds (721) were isolated from Seriphidium transiliense. The chemical structures were determined by extensive NMR spectroscopic data, HRESIMS, ECD and X-ray diffraction. Among the known compounds, twelve known compounds were isolated for the first time from this plant, including taurine (9), 11-epitaurin (10), α-santonin (11), artesin (13), 11-epiartesin (14), 1α-hydroxy-3β-acetoxyeudesm-4-en-6β, 7α, 11βH-12, 6-olide (15), 1α-hydroxy-3β-acetoxyeudesm-4-en-6β, 7α, 11αH-12, 6-olide (16), artegallin (17), 8α-hydroxytaurin (18), 8α-acetoxytaurine (19), methyl-4α-hydroxy-11(13)-eudesmen-12-oatesaniculamoid D (20), and saniculamoid D (21). The absolute configuration of 2 was determined by X-ray. The X-ray crystal structures of 15 and 16 were reported for the first time. At a concentration of 20 μM, all compounds (121) showed significant inhibition of NO production in LPS- stimulated BV2 cells. Among them, compounds 3 and 4 inhibited NO release with IC50 values of 19.30 and 22.05 μM, respectively. Based on the present results, these compounds may be potential anti-inflammatory agents.

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绢蝇倍半萜内酯及其抗炎活性。
从绢蝇中分离得到6个未描述的倍半萜内酯(1-6)和15个已知的化合物(7-21)。化学结构是通过广泛的核磁共振光谱数据,hresms, ECD和x射线衍射确定的。其中,首次从该植物中分离得到12个已知化合物,分别为牛磺酸(9)、11-表黄素(10)、α-山芦苷(11)、青蒿素(13)、11-表黄素(14)、1α-羟基-3β-乙酰氧基yeudesm-4-en-6β、7α、11α -h -12、6-烯内酯(15)、1α-羟基-3β-乙酰氧基yeudesm-4-en-6β、7α、11α -h -12、6-烯内酯(16)、青蒿素(17)、8α-羟基牛磺酸(18)、8α-乙酰氧基牛磺酸(19)、甲基-4α-羟基-11(13)、8α-乙酰氧基牛磺酸(19)、甲基-4α-羟基-11(18)、8α-乙酰氧基牛磺酸-12-燕麦酰胺D(20)、saniculamoid D(21)。用x射线测定了2的绝对构型。其中15和16的x射线晶体结构为首次报道。在20 μM的浓度下,所有化合物(1-21)均能显著抑制LPS刺激的BV2细胞NO的产生。其中化合物3和4抑制NO释放的IC50值分别为19.30和22.05 μM。基于目前的结果,这些化合物可能是潜在的抗炎剂。
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来源期刊
Fitoterapia
Fitoterapia 医学-药学
CiteScore
5.80
自引率
2.90%
发文量
198
审稿时长
1.5 months
期刊介绍: Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.
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