MS/MS Molecular Networking Unveils the Chemical Diversity of Biscembranoid Derivatives, Neutrophilic Inflammatory Mediators from the Cultured Soft Coral <i>Sarcophyton trocheliophorum</i>

oleh: Ngoc Bao An Nguyen, Lo-Yun Chen, Po-Jen Chen, Mohamed El-Shazly, Tsong-Long Hwang, Jui-Hsin Su, Chun-Han Su, Pei-Tzu Yen, Bo-Rong Peng, Kuei-Hung Lai

Format: Article
Diterbitkan: MDPI AG 2022-12-01

Deskripsi

Biscembranoids are the distinctive tetraterpenoids owing a 14/6/14 membered tricyclic scaffold that have been mainly discovered in the soft corals, especially the genera <i>Sarcophyton</i>, <i>Lobophytum</i> and <i>Sinularia</i>. Recent findings have demonstrated the great anti-inflammatory potential of biscembranoid analogues in human neutrophils, motivating more chemical and biological explorations targeting these marine-derived natural products. In the current study, the chemical diversity of biscembranoids derived from the cultured-type <i>Sarcophyton trocheliophorum</i> von Marenzeller was illustrated through MS/MS molecular networking (MN) profiling approach. Based on the MN patterns, the prioritization of unknown biscembranoid derivatives was putatively analyzed. As a result, the biscembrane targeting isolation afforded two new metabolites, sarcotrochelides A (<b>1</b>) and B (<b>2</b>), along with six known analogues (<b>3</b>–<b>8</b>). Their structures and relative configurations were determined by spectroscopic methods. In vitro neutrophil inflammatory inhibition was further investigated for all isolates based on reduced superoxide anion (O<sub>2</sub><sup>•−</sup>) generation detections. Compounds <b>5</b>–<b>8</b> showed significant dose-dependently inhibitory effects, suggesting the cruciality of 6,7-dihydrooxepin-2(5H)-one moiety and saturated γ-lactone ring in their reactive oxygen species (ROS)-dependent anti-inflammatory properties.