The absolute configuration of prunioside A from Spiraea prunifolia and biological activities of related compounds.
The stereochemistry of prunioside A isolated from Spiraea prunifolia was determined by chemical transformations and NMR spectral data analysis. The configurations at C-5 and C-6 were determined to be 5S and 6R by application of the modified Mosher's method, CD analysis, and 13C NMR spectroscopic data analysis of an acetonide derivative. Other compounds related to prunioside A have inhibitory effects on the synthesis of nitric oxide in LPS-stimulated macrophage-like RAW 264.7 cells.
Professional Graduate School of Oriental Medicine, Wonkwang University, Iksan, Chonbuk 570-749, South Korea.
Hyuncheol
H
Oh
Hyungsoo
H
Shin
Gi-Su
GS
Oh
Hyun-Ock
HO
Pae
Kyu-Yun
KY
Chai
Hun-Taeg
HT
Chung
Ho-Sub
HS
Lee
D000818:Animals; D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000096:biosynthesis; D019001:Nitric Oxide Synthase / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II; D031992:Spiraea / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D006027:Glycosides; D013729:Terpenes; C435863:prunioside A; D009569:Nitric Oxide; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse