l‑Phenylalanine Alters the Privileged Secondary Metabolite Production in the Marine-Derived Fungus Trichoderma erinaceum F1‑1

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2020-01, Vol.83 (1), p.79-87
• Main Authors: Guo, Yong-Wei, Gong, Ben-Qiang, Yuan, Jie, Li, Hou-Jin, Mahmud, Taifo, Huang, Yun, Li, Jian-Feng, Yang, De-Po, Lan, Wen-Jian
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Diterpenes - chemistry; Humans; Hypocreales - chemistry; Lactones - chemistry; Magnetic Resonance Spectroscopy - methods; Mass Spectrometry; Melanocytes - chemistry; Melanocytes - drug effects; Molecular Structure; Phenylalanine - chemistry; Polyketides - chemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.9b00710

The effects of a single-amino-acid culture strategy on secondary metabolite production in the marine-derived fungus Trichoderma erinaceum F1-1 were investigated by culturing the fungus in GPY medium supplemented or not supplemented with l-phenylalanine. A suite of secondary metabolites, including seven terpenoids (1–7) and one polyketide (8), among which are four new compounds, harziandione A (1), cyclonerodiols A and B (3, 4), and trichodermaerin A (6), were isolated from the GPY medium without l-phenylanine, whereas 18 aromatic compounds (9–26), including six new compounds, trichoderolides A–F (9, 10, and 14–17), were isolated from the culture grown in the GPY medium with l-phenylalanine. The structures of the new compounds were determined by high-resolution mass spectrometry, NMR spectroscopic analysis, optical rotation calculations, chemical methods, and X-ray crystallography. Compounds 10, 12, 13, and 26 exhibited cytotoxic activities against MDA-MB-435 human melanocyte cancer cells. Compound 26 was cytotoxic to A549 adenocarcinomic human alveolar basal epithelial cells.