Chemical constituents of the culture broth of Dentipellis fragilis and their anti-inflammatory activities

Dae-Won Ki; Chae-Won Kim; Dae-Cheol Choi; Gun-Woo Oh; Thi-Phuong Doan; Ji-Yul Kim; Won-Keun Oh; In-Kyoung Lee; Bong-Sik Yun

doi:10.1016/j.phytochem.2023.113828

Chemical constituents of the culture broth of Dentipellis fragilis and their anti-inflammatory activities

Phytochemistry. 2023 Oct:214:113828. doi: 10.1016/j.phytochem.2023.113828. Epub 2023 Aug 16.

Authors

Dae-Won Ki¹, Chae-Won Kim², Dae-Cheol Choi², Gun-Woo Oh³, Thi-Phuong Doan⁴, Ji-Yul Kim³, Won-Keun Oh⁴, In-Kyoung Lee², Bong-Sik Yun⁵

Affiliations

¹ Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University, Gobong-ro 79, Iksan, 54596, South Korea. Electronic address: dwki0916@gmail.com.
² Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University, Gobong-ro 79, Iksan, 54596, South Korea.
³ National Marine Biodiversity Institute of Korea, Seocheon, Republic of Korea.
⁴ Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 08826, Republic of Korea.
⁵ Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University, Gobong-ro 79, Iksan, 54596, South Korea. Electronic address: bsyun@jbnu.ac.kr.

PMID: 37595773
DOI: 10.1016/j.phytochem.2023.113828

Abstract

Seven undescribed compounds, dentipellinones A‒D (1, 2, 5, and 6), dentipellinol (3), methoxyerinaceolactone B (4), and erinaceolactomer A (7), were isolated from the culture broth of Dentipellis fragilis. Chemical structures of these isolated compounds were determined by analyses of 1D and 2D-NMR and MS data in comparison with data reported in the literature. Absolute configurations of 1‒7 were also determined by Electronic Circular Dichroism calculations. The isolated compounds were evaluated for their anti-inflammatory effects on NO production and pro-inflammatory cytokines levels in LPS-stimulated RAW264.7 cells. Compounds 5 and 7 were evaluated for their anti-inflammatory effects on NO production and pro-inflammatory cytokine levels in LPS-stimulated RAW264.7 cells. They exhibited inhibitory effects on LPS-induced NO production in a dose-dependent manner, and significantly reduced the levels of inflammatory-related cytokines such as IL-1β and IL-6. TNF-α was not involved in the anti-inflammatory effects of these compounds. Finally, compounds 5 and 7 showed significant anti-inflammatory effects.

Keywords: Anti-inflammatory; Chiral HPLC; Dentipellinol; Dentipellinones; Dentipellis fragilis; Erinaceolactomer; Hericiaceae; Iso-benzofuranones; Methoxyerinaceolactone.