Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea

• Published in: Bioorganic & medicinal chemistry letters 2012-07, Vol.22 (13), p.4368-4372
• Main Authors: Li, Cui, La, Ming-Ping, Tang, Hua, Pan, Wei-Hua, Sun, Peng, Krohn, Karsten, Yi, Yang-Hua, Li, Ling, Zhang, Wen
• Format: Article
• Language: English
• Subjects: Absolute configuration; Animals; Anthozoa - chemistry; Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; anti-infective properties; Apoptosis - drug effects; bacteria; bioassays; Biological activity; Biological and medical sciences; Briarane diterpenoids; Cell Line, Tumor; chemistry; China; Dichotella gemmacea; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; diterpenoids; doxorubicin; Escherichia coli; Escherichia coli - drug effects; fungi; Fungi - drug effects; General pharmacology; Gorgonian; growth retardation; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - isolation & purification; Heterocyclic Compounds, 4 or More Rings - pharmacology; Humans; Magnetic Resonance Spectroscopy; Medical sciences; Molecular Conformation; Mycosphaerella graminicola; Oceans and Seas; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; spectroscopy; Structure elucidation; Ustilago violacea
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2012.05.001

Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogues from the South China Sea gorgonian Dichotella gemmacea. Compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity. Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici.