ABSTRACT
Trichodermaerin (1), a novel diterpenoid lactone, together with the known compound, harziandione (2) were isolated from the culture broth of the fungus Trichoderma erinaceum associated with the sea star Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. 1 was the Baeyer-Villiger monooxygenase catalyzed oxidation product of 2. Compound 2 did not show cytotoxic activities against various cancer cell lines.
Subject(s)
Diterpenes/isolation & purification , Lactones/isolation & purification , Starfish/microbiology , Trichoderma/chemistry , Animals , Diterpenes/chemistry , Drug Screening Assays, Antitumor , Humans , Lactones/chemistry , MCF-7 Cells , Molecular StructureABSTRACT
Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-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 I 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.
Subject(s)
Antibiotics, Antineoplastic/chemistry , Antibiotics, Antineoplastic/pharmacology , Chromans/chemistry , Chromans/pharmacology , Resorcinols/chemistry , Resorcinols/pharmacology , Starfish/microbiology , Trichoderma/chemistry , Animals , Cell Line, Tumor , Circular Dichroism , Drug Screening Assays, Antitumor , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Conformation , Spectrometry, Mass, Electrospray Ionization , Tetrazolium Salts , ThiazolesABSTRACT
The marine fungus Chondrostereum sp. was collected from a soft coral Sarcophyton tortuosum from the South China Sea. This fungus was cultured in potato dextrose broth medium and the culture broth was extracted with EtOAc. Five new triquinane-type sesquiterpenoids, chondrosterins A-E (1-5), and the known sesquiterpenoid hirsutanol C (6), were isolated. The structures were elucidated mainly on the basis of NMR, MS, and X-ray single-crystal diffraction data. Chondrosterin A (1) showed significant cytotoxic activities against cancer lines A549, CNE2, and LoVo with IC(50) values of 2.45, 4.95, and 5.47 µM, respectively.
