C17-Labdane diterpenoid alkaloids bearing a rare skeleton with anti-inflammatory and anti-oxidant activities from Forsythia suspensa

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-01-01 DOI:10.1016/j.fitote.2024.106345

Jia-Huan Liu , Yue Wang , Sheng-Jun Dai , De-Wu Zhang , Xi-Dian Yue

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Abstract

Two undescribed C₁₇-Labdane diterpenoid alkaloids, named forsylinfenines A and B (1–2), attributable to a rare 4,4,10,13-tetramethyl-1(2),3(4),5(10),6(7)-octahydrobenzo[f]quinolin skeleton, along with three known β-carboline-type alkaloids (3–5), were isolated. The chemical structures including absolute configurations of two undescribed compounds were established by means of integrated spectroscopic techniques and electronic circular dichroism (ECD) calculations. In addition, a plausible biosynthetic pathway for the formation of compounds 1 and 2 was proposed. In vitro, five alkaloids (1–5), especially two undescribed alkaloids with rare skeleton (1–2), exhibited significant anti-inflammatory activities due to inhibiting the release of TNF-α, IL-6, and IL-1β, as well as effective anti-oxidant activities owing to preventing the production of ROS in the LPS-induced RAW264.7 cells.

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连翘中具有抗炎和抗氧化活性的稀有骨架的C17-Labdane二萜生物碱。

分离到两种未描述的C17-Labdane二萜生物碱，命名为forsylinfenines A和B(1-2)，它们属于罕见的4,4,10,13-四甲基-1(2),3(4),5(10),6(7)-八氢苯醌[f]骨架，以及三种已知的β-碳碱型生物碱（3-5）。通过积分光谱技术和电子圆二色性（ECD）计算，确定了两种化合物的化学结构，包括绝对构型。此外，还提出了化合物1和2形成的生物合成途径。在体外实验中，五种生物碱（1-5），特别是两种骨架罕见的生物碱（1-2），由于抑制TNF-α、IL-6和IL-1β的释放而表现出显著的抗炎活性，并且由于阻止lps诱导的RAW264.7细胞产生ROS而表现出有效的抗氧化活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.