Isolation and synthesis of melodamide A, a new anti-inflammatory phenolic amide from the leaves of Melodorum fruticosum

• Published in: Planta medica Vol. 79; no. 3-4; p. 288
• Main Authors: Chan, Hsiu-Hui, Hwang, Tsong-Long, Thang, Tran Dinh, Leu, Yann-Lii, Kuo, Ping-Chung, Nguyet, Bui Thi Minh, Dai, Do Ngoc, Wu, Tian-Shung
• Format: Journal Article
• Language: English
• Published: Germany 01.03.2013
• Subjects: Adult; Amides - chemistry; Annonaceae - chemistry; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Chemistry Techniques, Synthetic; Cinnamates - chemical synthesis; Cinnamates - isolation & purification; Cinnamates - pharmacology; Crystallography, X-Ray; Cyclohexanones - chemical synthesis; Cyclohexanones - isolation & purification; Cyclohexanones - pharmacology; Enzyme Inhibitors - pharmacology; Humans; Inhibitory Concentration 50; Magnetic Resonance Spectroscopy; Molecular Structure; Neutrophils - drug effects; Neutrophils - enzymology; Pancreatic Elastase - antagonists & inhibitors; Phenols - chemistry; Plant Leaves - chemistry; Superoxides - antagonists & inhibitors; Young Adult
• ISSN: 1439-0221
• DOI: 10.1055/s-0032-1328131

Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 µM. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.