Neo-5,10-seco-clerodane diterpenoids from Schnabelia terniflora

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2024-08-15 DOI:10.1016/j.fitote.2024.106190

Yi Chen , Xu-Lan Bai , Ting-Ting Du , Hong-Tao Xu , Yong-Li Wang , Le-Yi Huang , Xu-Dong Mao , Gui-Xin Chou

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Abstract

Three new neo-5,10-seco-clerodane diterpenoids (1–3), four previously undescribed ethoxy/methoxy acetal analogues (4–7), one new etherified labdane diterpenoid (8), and seven known diterpenoids (9–15) were isolated from the whole plant of Schnabelia terniflora. Their structures were established on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction data, calculated electronic circular dichroism (ECD), and Mo₂(OAc)₄-induced circular dichroism. Compounds 2 and 3 represent the first examples of neo-5,10-seco-clerodane diterpenoids containing a 1H-pyrrole-2,5-dione and a pyrrolidine-2,5-dione moiety, respectively. A plausible biosynthetic pathway for 1–3 is proposed. All diterpenoids were evaluated for their cytotoxic activity against non-small-cell lung cancer lines (A549 and H460) and gastric cancer lines (HGC27 and AGS). Among them, 2 and 14 showed moderate cytotoxicity against four cell lines.

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从 Schnabelia terniflora 中提取的新-5,10-seco-clerodane 二萜。

从 Schnabelia terniflora 的全草中分离出了三种新的新-5,10-seco-clerodane 二萜类化合物（1-3）、四种以前未曾描述过的乙氧基/甲氧基乙缩醛类似物（4-7）、一种新的醚化 labdane 二萜类化合物（8）和七种已知的二萜类化合物（9-15）。根据大量的光谱分析、单晶 X 射线衍射数据、电子圆二色性（ECD）计算和 Mo2(OAc)4 诱导的圆二色性，确定了它们的结构。化合物 2 和 3 代表了分别含有 1H-吡咯-2,5-二酮和吡咯烷-2,5-二酮分子的新-5,10-seco-clerodane 二萜化合物的首个实例。提出了 1-3 的合理生物合成途径。评估了所有二萜类化合物对非小细胞肺癌株（A549 和 H460）和胃癌株（HGC27 和 AGS）的细胞毒活性。其中，2 和 14 对四种细胞株具有中等程度的细胞毒性。

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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.