Isolation and synthesis of melodamide A, a new anti-inflammatory phenolic amide from the leaves of Melodorum fruticosum.
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.
Department of Pharmacy, China Medical University, Taichung, Taiwan.
Hsiu-Hui
HH
Chan
Tsong-Long
TL
Hwang
Tran Dinh
TD
Thang
Yann-Lii
YL
Leu
Ping-Chung
PC
Kuo
Bui Thi Minh
BT
Nguyet
Do Ngoc
DN
Dai
Tian-Shung
TS
Wu
D000328:Adult; D000577:Amides / Q000737:chemistry; D029061:Annonaceae / Q000737:chemistry*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D002934:Cinnamates / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors; D010636:Phenols / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D013481:Superoxides / Q000037:antagonists & inhibitors; D055815:Young Adult
D000577:Amides; D000894:Anti-Inflammatory Agents, Non-Steroidal; D002934:Cinnamates; D003512:Cyclohexanones; D004791:Enzyme Inhibitors; D010636:Phenols; C585806:melodamide A; D013481:Superoxides; D010196:Pancreatic Elastase