Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci

• DOI: 10.1177/1934578x1200701022
• Publication Date: 2019-03-25T15:23:07Z
• Authors: Wen-Jian Lan; Yang Zhao; Zhong-Liang Xie; Li-Zhen Liang; Wei-Yan Shao; Long-Ping Zhu; De-Po Yang; Xiao-Feng Zhu; Hou-Jin Li
• Keywords: Trichoderma; Spectrometry, Mass, Electrospray Ionization; Antibiotics, Antineoplastic; Magnetic Resonance Spectroscopy; Circular Dichroism; Molecular Conformation; Tetrazolium Salts; Resorcinols; 01 natural sciences; Mass Spectrometry; 0104 chemical sciences; 3. Good health; Starfish; Thiazoles; Cell Line, Tumor; Animals; Humans; Chromans; Drug Screening Assays, Antitumor

Two novel sorbicillinoid analogues, (4' Z)-sorbicillin (1) and (2 S)-2,3-dihydro-7-hydroxy-6-methyl-2-[( E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2 S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[( E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4'/C-5’ double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines.