Structural elucidation, total synthesis, and cytotoxic activity of effphenol A

• Published in: Organic & biomolecular chemistry Vol. 18; no. 44; pp. 935 - 938
• Main Authors: Liu, Hongxin, Chen, Shanchong, Zhang, Xiao, Dong, Chunmao, Chen, Yuchan, Liu, Zhaoming, Tan, Haibo, Zhang, Weimin
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 28.11.2020; Royal Society of Chemistry
• Subjects: Biomimetics; Chemistry; Chemistry, Organic; Crystallography; Crystals; Cytotoxicity; Deep sea; Fungi; NMR; Nuclear magnetic resonance; Phenols; Physical Sciences; Science & Technology; Single crystals; Substitutes; Synthesis; Tumor cell lines; X-ray diffraction; DERIVATIVES; NATURAL-PRODUCTS; MEROTERPENOIDS
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d0ob01985b

A highly substituted phenol derivative, effphenol A ( 1 ), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A ( 1 ) toward four human cancer cell lines was assayed. Effphenol A was isolated and elucidated through spectroscopic analysis together with single-crystal X-ray diffraction experiments and further confirmed by the first biomimetic total synthesis.