A new flavanone glycoside from the dried immature fruits of Poncirus trifoliata.
A new flavanone glycoside, (2R)-5-hydroxy-4'-methoxyflavanone-7-O-{beta-glucopyranosyl-(1-->2)-beta-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E(2) (PGE(2)) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.
Han
Ah-Reum
AR
College of Pharmacy and Center for Cell Signaling and Drug Discovery Research, Ewha Womans University, Seoul, Korea.
Kim
Jong-Bin
JB
Lee
Jun
J
Nam
Joo-Won
JW
Lee
Ik-Soo
IS
Shim
Chang-Koo
CK
Lee
Kyung-Tae
KT
Seo
Eun-Kyoung
EK
D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D015232:Dinoprostone / Q000096:biosynthesis; D044950:Flavanones / Q000737:chemistry* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015850:Interleukin-6 / Q000096:biosynthesis; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000633:toxicity; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D032104:Poncirus / Q000737:chemistry*; D011448:Prostaglandin Antagonists / Q000494:pharmacology; D012333:RNA, Messenger / Q000096:biosynthesis; D020133:Reverse Transcriptase Polymerase Chain Reaction; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013778:Tetrazolium Salts; D013844:Thiazoles; D000093242:Interleukin-6 Inhibitors
D015232:Dinoprostone; D044950:Flavanones; D006027:Glycosides; D015850:Interleukin-6; D008070:Lipopolysaccharides; D011448:Prostaglandin Antagonists; D012333:RNA, Messenger; D013778:Tetrazolium Salts; D013844:Thiazoles; D000093242:Interleukin-6 Inhibitors; C522680:(2R)-5-hydroxy-4'-methoxyflavanone-7-O-(beta-glucopyranosyl-(1-2)-beta-glucopyranoside); C022616:thiazolyl blue