<br>Pinuseldarone，一种来自松树针叶的 Clerodane 型二萜和植物化学物质，作为调节棕色脂肪生成和生热作用的新型药物,Journal of Natural Products

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Pinuseldarone，一种来自松树针叶的 Clerodane 型二萜和植物化学物质，作为调节棕色脂肪生成和生热作用的新型药物
Journal of Natural Products ( IF 3.3 ) Pub Date : 2023-12-30 , DOI: 10.1021/acs.jnatprod.3c00779
Yeo Rang Cho ₁ , Sanghun Lee ₂ , Hyoju Kim ₂ , Eon Chung Park ₁ , Se Yun Jeong ₁ , Hamed Hamishehkar ₃ , Su Myung Jung ₂ , Ki Hyun Kim ₁

Affiliation

对热松针叶的甲醇提取物进行植物化学研究，分离并鉴定出一种新的克莱丹烷型二萜，松油酮 (pinuseldarone) ( 1 )，以及已知的类黄酮 5,4'-二羟基-3,7,8-三甲氧基- 6-C-甲基黄酮( 2 )，通过HPLC纯化。使用光谱方法（包括 1D 和 2D NMR 以及 HRESIMS）阐明了新化合物1的结构。其绝对构型是通过NOESY分析和计算方法建立的，包括电子圆二色性（ECD）计算和规范原子轨道NMR化学位移计算，然后进行DP4+概率分析。使用源自鼠棕色脂肪组织的培养棕色脂肪细胞模型评估分离化合物的代谢影响。据观察，用二羟基-3,7,8-三甲氧基-6-C-甲基黄酮 ( 2 ) 处理可下调脂肪形成标记物 C/EBPδ 和脂肪酸转运蛋白 CD36，从而导致棕色脂肪细胞分化过程中脂质积累显着减少。然而，pinuseldarone ( 1 ) 处理并不影响棕色脂肪细胞的分化。有趣的是，用松脂酮 (pinuseldarone) 预处理 ( 1 ) 增强了棕色脂肪细胞的药理学刺激，这似乎是通过使棕色脂肪细胞对 β3-肾上腺素受体信号传导的反应敏感来实现的。因此，我们的研究结果表明，从P. eldarica针叶中提取的植物化学物质可能作为调节棕色脂肪组织代谢活性的有价值的化合物，棕色脂肪组织是维持全身代谢稳态的重要组成部分。

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Pinuseldarone, a Clerodane-Type Diterpene from Pinus eldarica Needles and Phytochemicals as Novel Agents for Regulating Brown Adipogenesis and Thermogenesis

Phytochemical investigation of the MeOH extract of Pinus eldarica needles led to the isolation and identification of a new clerodane-type diterpene, pinuseldarone (1), along with a known flavonoid, 5,4′-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone (2), through HPLC purification. The structure of the new compound 1 was elucidated using spectroscopic methods, including 1D and 2D NMR, as well as HRESIMS. Its absolute configuration was established through NOESY analysis and computational methods, including electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4+ probability analysis. The metabolic implications of the isolated compounds were assessed using a cultured brown adipocyte model derived from murine brown adipose tissue. It was observed that treatment with dihydroxy-3,7,8-trimethoxy-6-C-methylflavone (2) downregulates the adipogenic marker C/EBPδ and fatty acid transporter CD36, resulting in a significant reduction in lipid accumulation during brown adipocyte differentiation. However, pinuseldarone (1) treatment did not affect brown adipocyte differentiation. Interestingly, pretreatment with pinuseldarone (1) potentiated the pharmacological stimulation of brown adipocytes, seemingly achieved by sensitizing their response to β3-adrenoreceptor signaling. Therefore, our findings indicate that phytochemicals derived from P. eldarica needles could potentially serve as valuable compounds for adjusting the metabolic activity of brown adipose tissue, a vital component in maintaining whole-body metabolic homeostasis.

更新日期：2023-12-30

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