Structure elucidation of linear triquinane sesquiterpenoids, hirsutuminoids A-Q, from the fungus Stereum hirsutum and their activities. (August 2022)

• Record Type: Journal Article
• Authors: Zhao, Zhen-Zhu; Zhao, Xuan; Si, Ying-Ying; Wang, Zhen-Zhen; Sun, Yan-Jun; Chen, He-Ping; Feng, Wei-Sheng; Liu, Ji-Kai
• Is Part Of: Phytochemistry. Volume 200(2022)
• Publication Date: 2022-08
• Subjects: Stereum hirsutum (Willd.) Pers. -- Stereaceae -- Chemical investigation -- Linear triquinane sesquiterpenoids -- Configuration elucidation -- NO production inhibition; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113227
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Eighteen linear triquinane sesquiterpenoids (LTSs), including seventeen previously undescribed ones (hirsutuminoids A-Q), were isolated from the fermentation of the fungus Stereum hirsutum (Willd.) Pers. The structures and absolute configurations of the isolates were characterized by extensive spectroscopic analysis (1D, 2D NMR, and HRMS data), together with comparing the experimental and calculated data of both electronic circular dichroism and NMR data, as well as X-ray crystallography. Based on the literature survey and efforts on constructing the absolute configurations of these LTSs in this study, one empirical rule about the orientations of substitutions at C-2/C-3/C-7/C-9 was summarized. Anti-inflammatory and cytotoxic bioassays showed that only hirsutuminoid B inhibited the nitric oxide (NO) production in RAW 264.7 macrophages with an IC50 value, 18.9 μM. Graphical abstract: Eighteen linear triquinane sesquiterpenoids (LTSs), established by comprehensive methods, were isolated from Stereum hirsutum . One empirical rule about the orientations of substitutions at C-2/3/7/9 in LTSs was summarized. Hirsutuminoid B showed moderate anti-inflammatory activity. Image 1 Highlights: Hirsutuminoids A-Q, 17 undescribed LTSs, were isolated from S. hirsutum. Their absolute configurations were established by multiple methods. Cytotoxicity and inhibition on NO production of all isolates were evaluated. An empirical rule about the orientations of substitutions at C-2/3/7/9 was summarized.