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Asperjinone 和 Asperimide C 的全合成及抗炎活性。

Total Synthesis and Anti-inflammatory Activity of Asperjinone and Asperimide C.

机构信息

Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90110, Thailand.

Office of Research Administration, Chiang Mai University, Chiang Mai 50200, Thailand.

出版信息

J Nat Prod. 2024 Aug 23;87(8):2045-2054. doi: 10.1021/acs.jnatprod.4c00557. Epub 2024 Aug 7.

DOI:10.1021/acs.jnatprod.4c00557
PMID:39110498
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11348413/
Abstract

Total syntheses of two γ-butenolide natural products, asperjinone () and asperimide C () in both racemic and chiral forms have been accomplished utilizing Basavaiah's one-pot Friedel-Crafts/maleic anhydride formation protocol as a key strategy. Our syntheses verified the revised structure of proposed by Williams et al. and the structure and absolute configuration of reported by the Li group. This work also discloses the unprecedented anti-inflammatory activity of . Synthetic exhibited significant anti-inflammatory activity in renal proximal tubular epithelial cells (RPTEC) by suppression of gene expression of pro-inflammatory cytokines TNF-α, IL-1β and IL-6 under LPS-induced renal inflammation condition and was superior to ()-, -, , and a positive drug control, indomethacin. Moreover, compound inhibited downstream signaling of inflammation by significantly reducing iNOS and COX-2 gene expression and total NO production. The anti-inflammatory activity of asperjinone () renders it a potential and promising candidate for developing novel anti-inflammatory agents against inflammation worsening acute kidney injury.

摘要

已经完成了两种γ-丁烯内酯天然产物asperjinone（）和asperimide C（）的全合成，以 Basavaiah 的一锅 Friedel-Crafts/马来酸酐形成方案为关键策略，同时实现了外消旋和手性形式。我们的合成验证了 Williams 等人提出的结构修订和 Li 小组报道的结构和绝对构型。这项工作还揭示了的前所未有的抗炎活性。合成的在 LPS 诱导的肾炎症条件下通过抑制促炎细胞因子 TNF-α、IL-1β 和 IL-6 的基因表达，在肾近端管状上皮细胞（RPTEC）中表现出显著的抗炎活性，优于（）-、（）-、（）-和阳性药物对照，吲哚美辛。此外，化合物通过显著降低 iNOS 和 COX-2 基因表达和总 NO 产生来抑制炎症的下游信号。Asperjinone（）的抗炎活性使其成为开发新型抗炎药物以对抗炎症加重急性肾损伤的潜在有前途的候选药物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/fa9fcacb64e3/np4c00557_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/2da6e9b29fb1/np4c00557_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/be92804310ed/np4c00557_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/cbf29b9ba9de/np4c00557_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/65777d541f22/np4c00557_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/44c662033c09/np4c00557_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/7424e35f00e0/np4c00557_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/affe7078a44a/np4c00557_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/bb2fbe85b0d3/np4c00557_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/fa9fcacb64e3/np4c00557_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/2da6e9b29fb1/np4c00557_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/be92804310ed/np4c00557_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/cbf29b9ba9de/np4c00557_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/65777d541f22/np4c00557_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/44c662033c09/np4c00557_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/7424e35f00e0/np4c00557_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/affe7078a44a/np4c00557_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/bb2fbe85b0d3/np4c00557_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a41b/11348413/fa9fcacb64e3/np4c00557_0005.jpg

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本文引用的文献

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