Characterization of a bioactive meroterpenoid isolated from the marine-derived fungus Talaromyces sp

• Published in: Applied microbiology and biotechnology 2022-04, Vol.106 (8), p.2927-2935
• Main Authors: Hong, Xuan, Guan, Xiaoqing, Lai, Qiliang, Yu, Dehua, Chen, Zhongwei, Fu, Xiaoteng, Zhang, Beibei, Chen, Changkun, Shao, Zongze, Xia, Jinmei, Qin, Jiang-Jiang, Wang, Weiyi
• Format: Article
• Language: English
• Subjects: Absolute configuration; Analysis; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Anticancer properties; Antitumor activity; Apoptosis; Biological activity; Biomedical and Life Sciences; Biotechnological Products and Process Engineering; Biotechnology; Cancer; Configurations; Diffraction; E coli; Escherichia coli; Fungi; Gastric cancer; Humans; Identification and classification; Isomers; Life Sciences; Mass spectrometry; Methods; Microbial Genetics and Genomics; Microbiology; Molecular Structure; NMR; Nuclear magnetic resonance; Planar structures; Polyketides; Properties; Quantum chemistry; Separation (Technology); Staphylococcus aureus; Stomach Neoplasms; Structure; Talaromyces; Talaromyces - chemistry; Terpenoids; X-ray diffraction; X-rays
• ISSN: 0175-7598; 1432-0614
• DOI: 10.1007/s00253-022-11914-1

A new meroterpenoid, taladrimanin A ( 1 ), was isolated from a marine-derived fungus Talaromyces sp. HM6-1–1, together with eleven biogenetically related compounds ( 2–12 ). A plausible biosynthetic pathway for the meroterpenoids ( 1–4 ) was proposed. The planar structure of 1 was assigned by HRESIMS and NMR. Its relative configuration was established by quantum chemical NMR calculation of two possible isomers and analyzed by DP4 + method. Finally, X-ray diffraction unambiguously confirmed the relative configuration and revealed the absolute configuration of compound 1 . 2–12 were assigned by comparing their NMR data with those reported in the literature. 1 was the first drimane-type meroterpenoid with a C10 polyketide unit bearing an 8 R -configuration. In the bioactive assay, 1 exhibited antitumor activity against gastric cancer cells MGC803 and MKN28; it also inhibited the colony formation and induced apoptosis in MGC803 cells both in a concentration-dependent manner. Additionally, 1 displayed selective antibacterial activity against Staphylococcus aureus 6538P, and low activities towards strains of Vibrio parahaemolyticus and Escherichia coli in this study. Key points • Twelve compounds were obtained from Talaromyces sp., including four meroterpenoids, one of which was new. • The new compound taladrimanin A ( 1 ) inhibits the growth of gastric cancer cells MGC803 and MKN28 as well as the pathogenic bacteria Staphylococcus aureus 6538P. • The biosynthetic pathway of the meroterpenoids was proposed.