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Archive > Volume 15 Issue 3 > 2023,15(3):457-462. DOI:https://doi.org/10.1016/j.chmed.2023.02.001 Prev Next

白芷中七個新的3,4-二氫呋喃香豆素衍生物

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Seven new 3,4-dihydro-furanocoumarin derivatives from Angelica dahurica

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    摘要:
    目的：研究常用中藥白芷的化學成分。 方法：通過各種色譜手段分離得到化合物，并基于對其1D、2D NMR、HRESI MS、IR和UV光譜數(shù)據(jù)的分析來闡明新化合物的結構，利用計算ECD和衍生化的方法確定新化合物的絕對構型。使用脂多糖激活的RAW 264.7巨噬細胞評估所有化合物對NO產(chǎn)生的抑制活性。 結果：從白芷中分離得到7個新的3,4-二氫呋喃香豆素衍生物（1a/1b，2a/2b，3a/3b，4）和一個已知的化合物呋喃香豆素（5）。新化合物包括三對對映體，（4S, 2′′R）-angelicadin A（1a）/（4R, 2′′S）-angelicadin A（1b）、（4S, 2′′S）-angelicadin A（2a）/（4R, 2′′R）-angelicadin A（2b）、（4S, 2′′S）-secoangelicadin A（3a）/（4R, 2′′R）-secoangelicadin A（3b）和（4R, 2′′R）-secoangelicadin A methyl ester（4）。已知化合物花椒毒酚（5）具有一定程度的抑制NO釋放活性，IC50為32.8 ± 0.8 μmol/L，但所有新化合物在100 μmol/L的濃度下均無抑制活性。 結論：首次從白芷中發(fā)現(xiàn)了3,4-二氫呋喃香豆素，研究結果不僅對了解白芷的化學成分有重要意義，并且進一步豐富了對天然產(chǎn)物的認識。

    Abstract:
    Objective: To study the chemical constituents of the roots of Angelica dahurica, a well-known Chinese herbal medicine named Baizhi in Chinese. Methods: Compounds were separated by various chromatographies, and the structures of the new compounds were elucidated based on the analysis of their spectroscopic and spectrometric data (1D, 2D NMR, HRESI MS, IR, and UV). The absolute configurations of the new compounds were determined by the calculated electronic circular dichroism and chemical derivatization. The inhibitory activities of all isolates against nitric oxide (NO) production were evaluated using lipopolysaccharide-activated RAW 264.7 macrophage cells. Results: Seven new 3,4-dihydro-furanocoumarin derivatives (1a/1b, 2a/2b, 3a/3b, 4) together with a known furanocoumarin (5) were isolated from the roots of A. dahurica. The new compounds included three pairs of enantiomers, (4S, 2′′R)-angelicadin A (1a)/(4R, 2′′S)-angelicadin A (1b), (4S, 2′′S)-angelicadin A (2a)/(4R, 2′′R)-angelicadin A (2b), and (4S, 2′′S)-secoangelicadin A (3a)/(4R, 2′′R)-secoangelicadin A (3b), together with (4R, 2′′R)-secoangelicadin A methyl ester (4). The known xanthotoxol (5) inhibited the NO production with the half-maximal inhibitory concentration (IC50) value of (32.8±0.8) μmol/L, but all the new compounds showed no inhibitory activities at the concentration of 100 μmol/L. Conclusion: This is the first report of the discovery of 3,4-dihydro-furanocoumarins from A. dahurica. The results are not only meaningful for the understanding of the chemical constituents of A. dahurica, but also enrich the reservoir of natural products.

    關鍵詞:
    白芷;抗炎;香豆素;3,4-二氫呋喃香豆素;對映體;(4S, 2′′R)-angelicadin A; (4R, 2′′S)-angelicadin A; (4S, 2′′S)-angelicadin A; (4R, 2′′R)-angelicadin A; (4S, 2′′S)-secoangelicadin A;(4R, 2′′R)-secoangelicadin A; (4R, 2′′R)-secoangelicadin A methyl ester

    Keywords:


    Project Supported:
    This work was financially supported by Beijing Natural Science Foundation (No. 7202125).

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