A series of meroterpenoids with highly oxygenated skeletons from the endophytic fungus Penicillium sp. and their anti-inflammatory activities

IF 3.4 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Phytochemistry Pub Date : 2025-03-28 DOI:10.1016/j.phytochem.2025.114493

Tu-Xiang Mo , Liu-Xia Lv , Xi-Shan Huang, Jia-Tong Zhou, Qian Wu, Xian-Hua He, Li-Qi Liang, Wei-Feng Xu, Jun Li, Rui-Yun Yang

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Abstract

Four undescribed meroterpenoids, peniclactone D (1) and penichrodrimanins A−C (5−7), along with five known analogues (2−4, 8, and 9), were isolated from the fungus Penicillium sp. GDGJ-285. Their structures and absolute configurations were established on the basis of spectroscopic analyses and single-crystal X-ray diffraction. Compound 1 represents a highly oxygenated 6/5/6/5/5/5 polycyclic ring system, and 7 is a chrodrimanin-type meroterpenoid with a rare ether linkage between rings A and B via C-3 and C-9. Compound 5 exhibited notable inhibitory effect on nitric oxide (NO) production in LPS-induced RAW 264.7 cells, with the IC₅₀ value of 18.50 ± 1.26 μM compared to dexamethasone (33.61 ± 4.45 μM). The further investigation indicated that 5 could suppress LPS-induced TNF-α, IL-1β, and iNOS expression via inhibition of NF-κB signaling pathway.

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来自内生真菌青霉菌的一系列高氧骨架的萜类化合物及其抗炎活性

从真菌Penicillium sp. GDGJ-285中分离到四种未描述的甲萜类化合物，即青内酯D(1)和penichrodrimanins A−C(5−7)，以及五种已知的类似物（2−4、8和9）。通过光谱分析和单晶x射线衍射确定了它们的结构和绝对构型。化合物1为高氧化的6/5/6/5/5多环体系，化合物7为染色质蛋白型萜类化合物，环a和环B之间通过C-3和C-9有罕见的醚连接。化合物5对lps诱导的RAW 264.7细胞产生一氧化氮（NO）有显著的抑制作用，IC50值为18.50±1.26 μM，而地塞米松的IC50值为33.61±4.45 μM。进一步研究表明，5可通过抑制NF-κB信号通路抑制lps诱导的TNF-α、IL-1β和iNOS的表达。

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.