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- Title
Synthesis of the proposed structure of sibiriaester B and evaluation of its immunomodulatory properties.
- Authors
Sim, Myeonghyeon; Yoon, Jeong Min; Kim, Soobin; Kim, Kwangmi; Han, Young Taek
- Abstract
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.
- Subjects
APRICOT; CAFFEIC acid; T cells; THIOUREA
- Publication
Bulletin of the Korean Chemical Society, 2021, Vol 42, Issue 11, p1430
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.12392