Longifoliols A–C, three unprecedented isopimarane derivatives from Callicarpa longifolia

IF 2.6 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2026-06-13 DOI:10.1007/s11418-026-02045-2

Le Thi Vien, Ninh Thi Ngoc, Tran Thi Hong Hanh, Nguyen The Cuong, Nguyen Xuan Cuong, Nguyen Hoai Nam, Chau Van Minh

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引用次数: 0

Abstract

One unprecedented isopimarane longifoliol A (1) and two unprecedented C₉-spiro-fused seco-7,8-isopimaranes longifoliols B and C (2 and 3) along with a known phenolic glucoside trichocarpin (4) were obtained from the branches and leaves of Callicarpa longifolia. Their structures were elucidated by extensive analysis of their 1D, 2D NMR and HRESIMS data. The relative configuration was established using spectroscopic experiments as well as conformational analysis, DP4+ calculations, and J-coupling constant predictions (via DU8 and pcnJ methods). The absolute configurations of 1−3 were determined by comparing experimental and calculated ECD spectra and specific optical rotation values. Furthermore, the plausible biosynthetic pathways of 1−3 were proposed. Moreover, all isolates were evaluated for their in vitro nitric oxide (NO) inhibitory activity. Compound 4 revealed moderate activity with IC₅₀ = 67.61 ± 3.23 µM while 1 and 3 exhibited weak inhibitory effect on NO production in LPS-stimulated RAW264.7 cells, with IC₅₀ values of 80.01 ± 3.74 and 82.26 ± 3.45 µM, respectively.

Graphical abstract

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长叶醇A-C，三种前所未有的从长叶黄柏中提取的异糖烷衍生物。

从长叶蝉的枝叶中分离得到了一种前所未有的异吡马烷长叶醇A(1)和两种前所未有的c9 -螺旋融合的seco-7,8-异吡马烷长叶醇B和C(2和3)，以及一种已知的酚类糖苷trichocarpin(4)。通过对它们的1D， 2D NMR和hremsims数据的广泛分析，阐明了它们的结构。通过光谱实验、构象分析、DP4+计算和j -耦合常数预测（通过DU8和pcnJ方法）建立了相对构型。通过比较实验和计算的ECD光谱和比旋光度值，确定了1-3的绝对构型。进一步提出了1-3的生物合成途径。此外，对所有分离株进行了体外一氧化氮（NO）抑制活性评价。化合物4的IC50值为67.61±3.23µM，化合物1和化合物3的IC50值分别为80.01±3.74和82.26±3.45µM，对lps刺激的RAW264.7细胞的NO生成有微弱的抑制作用。

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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.