School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China.
School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China.
Bioorg Chem. 2024 Oct;151:107684. doi: 10.1016/j.bioorg.2024.107684. Epub 2024 Jul 30.
Twenty-nine sesquiterpenoids, including pseudoguaiane-type (1-11), eudesmane-type (12-23), and carabrane-type (24-29), have been identified from the plant Carpesium abrotanoides. Of them, compounds 1-4, 12-15, and 24-27, namely carpabrotins A-L, are twelve previously undescribed ones. Compound 3 possessed a pseudoguaiane backbone with a rearrangement modification at C-11, C-12 and C-13, while compound 4 suffered a carbon bond break between the C-4 and C-5 to form a rare 4,5-seco-pseudoguaiane lactone. Compounds 1-3, 5, 13-16 and 25-27 exhibited anti-inflammatory activity by inhibiting NO production in LPS-induced RAW264.7 macrophages with IC values less than 40 μM, while compounds 1, 2, 5, 13, 14, 16, and 25-27 showed significant inhibitory activity comparable to that of dexamethasone. The anti-atopic dermatitis (AD) effects of compounds 5 and 16 were tested according to 2,4-dinitrochlorobenzene (DNCB)-induced AD-like skin lesions in KM mice, and the results revealed that the major products 5 and 16 improved the histological features of AD-like skin lesions and mast cell infiltration in mice. This study suggested that sesquiterpenoids in C. abrotanoides should play a key role in its anti-inflammatory use.
从植物 Carpesium abrotanoides 中鉴定出 29 种倍半萜类化合物，包括伪愈创木烷型（1-11）、大根香叶烷型（12-23）和卡波烷型（24-29）。其中，化合物 1-4、12-15 和 24-27，即 carpabrotins A-L，是 12 种以前未描述过的化合物。化合物 3 具有伪愈创木烷骨架，在 C-11、C-12 和 C-13 处发生重排修饰，而化合物 4 在 C-4 和 C-5 之间发生碳键断裂，形成罕见的 4,5-断链伪愈创木烷内酯。化合物 1-3、5、13-16 和 25-27 通过抑制 LPS 诱导的 RAW264.7 巨噬细胞中 NO 的产生表现出抗炎活性，IC 值小于 40μM，而化合物 1、2、5、13、14、16 和 25-27 表现出与地塞米松相当的显著抑制活性。根据 2,4-二硝基氯苯（DNCB）诱导的 KM 小鼠 AD 样皮肤损伤，测试了化合物 5 和 16 的抗特应性皮炎（AD）作用，结果表明主要产物 5 和 16 改善了 AD 样皮肤损伤和肥大细胞浸润的组织学特征。本研究表明，C. abrotanoides 中的倍半萜类化合物可能在其抗炎作用中发挥关键作用。
