Synthesis of the proposed structure of sibiriaester B and evaluation of its immunomodulatory properties,Bulletin of the Korean Chemical Society

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Synthesis of the proposed structure of sibiriaester B and evaluation of its immunomodulatory properties
Bulletin of the Korean Chemical Society ( IF 2.3 ) Pub Date : 2021-09-14 , DOI: 10.1002/bkcs.12392
Myeonghyeon Sim ₁ , Jeong Min Yoon ₂ , Soobin Kim ₁ , Kwangmi Kim ₂ , Young Taek Han ₁

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Herein, we report a concise synthesis of the proposed structure of sibiriaester B, a novel antioxidant phenyl caffeate derivative isolated from the leaves of Armeniaca sibirica. Proposed sibiriaester B was obtained via simple esterification between the known TBS-protected caffeic acid and the commercially available methyl 4-hydroxybenzoate, and subsequent deprotection. However, the NMR spectral data of the synthesized sibiriaester B were not consistent with those in previous reports. The structure of the synthesized sibiriaester B was confirmed using combined 2D-NMR analysis, including COSY, HSQC, and HMBC. The synthesized sibiriaester B was observed to exhibit more potent immunomodulatory activity in murine epidermal T cells than p-hydroxyphenyl caffeate, an immunomodulatory natural caffeate derivative, as treatment with sibiriaester B significantly reduced the production of interleukin 13 by murine epidermal T cells at lower concentrations than p-hydroxyphenyl caffeate.

中文翻译：

Sibiriaester B 拟议结构的合成及其免疫调节特性的评价

在此，我们报告了 sibiriaester B 的拟议结构的简明合成，这是一种从Armeniaca sibirica叶子中分离的新型抗氧化苯基咖啡酸酯衍生物。通过已知的 TBS 保护的咖啡酸和市售的 4-羟基苯甲酸甲酯之间的简单酯化和随后的脱保护，获得了建议的 sibiriaester B。然而，合成的西伯利亚酯 B 的 NMR 光谱数据与之前的报道不一致。合成的 sibiriaester B 的结构使用联合 2D-NMR 分析确认，包括 COSY、HSQC 和 HMBC。观察到合成的西伯利亚酯 B 在鼠表皮 T 细胞中表现出比p更有效的免疫调节活性-羟基苯基咖啡酸酯是一种免疫调节性天然咖啡酸酯衍生物，因为用西伯利亚酯 B 处理显着降低了小鼠表皮 T 细胞产生的白细胞介素 13，其浓度低于对羟基苯基咖啡酸酯。

更新日期：2021-11-22

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