Three unusual hybrid sorbicillinoids with anti-inflammatory activities from the deep-sea derived fungus Penicillium sp. SCSIO06868

• Published in: Phytochemistry (Oxford) Vol. 202; p. 113311
• Main Authors: Pang, Xiaoyan, Wang, Pei, Liao, Shengrong, Zhou, Xuefeng, Lin, Xiuping, Yang, Bin, Tian, Xinpeng, Wang, Junfeng, Liu, Yonghong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.10.2022; Elsevier
• Subjects: Anti-inflammatory activities; Aspergillaceae; Biochemistry & Molecular Biology; Deep-sea derived fungus; Life Sciences & Biomedicine; Molecular networking; Penicillium sp. SCSIO06868; Plant Sciences; Science & Technology; Sorbicillinoids; Molecular networking; Penicillium sp. SCSIO06868; Aspergillaceae; Deep-sea derived fungus; Sorbicillinoids; Anti-inflammatory activities; ALPHA; DERIVATIVES
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2022.113311

Under the guidance of MS/MS based molecular networking, bisorbicillchaetones A–C, three undescribed hybrid sorbicillinoids, were isolated from cultures of the deep-sea derived fungus Penicillium sp. SCSIO06868. The planar structures and absolute configurations of these compounds were determined by extensive spectroscopic analyses. Bisorbicillchaetones are the first examples of hybrid sorbicillinoids containing a coniochaetone unit. Bisorbicillchaetones A and B exhibited moderate inhibitory effect on NO production in LPS activated RAW264.7 cells with the IC50 values of 80.3 ± 3.6 μM and 38.4 ± 3.3 μM, respectively, without cytotoxicity observed. Three unusual hybrid sorbicillinoids were isolated from the deep-sea derived fungus Penicillium sp. SCSIO06868 with anti-inflammatory activities. [Display omitted] •Three unusual hybrid sorbicillinoids were isolated from a deep-sea derived fungus.•A coniochaetone unit was found in hybrid sorbicillinoids for the first time.•The absolute configurations were elucidated by extensive spectroscopic analyses.•Bisorbicillchaetones A and B exhibited potent anti-inflammatory activities.