Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production

Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides,...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2008/02/01, Vol.56(2), pp.199-202
Hauptverfasser:	Hong, Seong Su, Lee, Seon A, Han, Xiang Hua, Lee, Min Hee, Hwang, Ji Sang, Park, Jeong Sook, Oh, Ki-Wan, Han, Kun, Lee, Myung Koo, Lee, Heesoon, Kim, Wook, Lee, Dongho, Hwang, Bang Yeon
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Asteraceae Asteraceae - chemistry Cell Line Cell Survival - drug effects Chromatography, High Pressure Liquid Crystallography, X-Ray Lactones - chemistry Lactones - pharmacology Lipopolysaccharides - antagonists & inhibitors Lipopolysaccharides - pharmacology Macrophages - drug effects Macrophages - metabolism melampolide Mice Models, Molecular Nitric Oxide - biosynthesis nitric oxide production inhibitor Plant Extracts - analysis Plant Leaves - chemistry sesquiterpene lactone Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Smallanthus Smallanthus sonchifolius Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Infrared Spectrophotometry, Ultraviolet yacon
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Zusammenfassung:	Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.56.199