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5,7--羟基奥蓬酮的结构修饰与绝对构型及.根茎中倍半萜的抗骨质疏松活性

Structure revision and absolute configuration of 5,7--hydroxyoplopanone and anti-osteoporotic activities of sesquiterpenoids from the rhizomes of .

机构信息

Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, Hue City, Vietnam.

Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh City, Ho Chi Minh, Vietnam.

出版信息

Nat Prod Res. 2024 Jul;38(14):2453-2462. doi: 10.1080/14786419.2023.2180505. Epub 2023 Feb 20.

Abstract

Five sesquiterpenoids including 2-hydroxyoplopanone , oplopanone (), 1,4,6-trihydroxy-eudesmane (), 1,4,7-trihydroxy-eudesmane () and bullatantriol () were isolated from . The structure of the previously reported compound, 5,7--2-hydroxyoplopanone (), has been revised to by the spectroscopic evidences (1D-/2D-NMR, IR, UV and HRESIMS) and by comparison between experimental and theoretical NMR data using DP4+ protocol. Furthermore, the absolute configuration of was unambiguously assigned by ECD experiments. Compounds and displayed a potent ability to stimulate osteogenic differentiation of MC3T3-E1 cells at 4 µg/mL (by 123.74% and 131.07%, respectively) and 20 µg/mL (by 112.45% and 126.41%, respectively) whilst and did not show any activities. At 20 µg/mL, and significantly promoted the mineralization of MC3T3-E1 cells with values of 112.95% and 116.37%, respectively, whereas and were inactive. The results indicated that could be an excellent component for anti-osteoporosis studies from the rhizomes of .

摘要

从根茎中分离得到 5 种倍半萜类化合物,包括 2-羟基莪术酮、莪术酮()、1,4,6-三羟基-桉烷()、1,4,7-三羟基-桉烷()和大根香叶二醇()。先前报道的化合物 5,7--2-羟基莪术酮()的结构通过光谱证据(1D-/2D-NMR、IR、UV 和 HRESIMS)以及使用 DP4+ 方案通过实验和理论 NMR 数据之间的比较进行了修订,修订为 。此外,通过 ECD 实验明确确定了 的绝对构型。化合物 和 在 4μg/mL(分别为 123.74%和 131.07%)和 20μg/mL(分别为 112.45%和 126.41%)时显示出强烈的刺激 MC3T3-E1 细胞成骨分化的能力,而 和 则没有显示出任何活性。在 20μg/mL 时, 和 显著促进了 MC3T3-E1 细胞的矿化,值分别为 112.95%和 116.37%,而 和 则没有活性。结果表明,从根茎中分离得到的 可能是抗骨质疏松研究的优秀成分。

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