title: Characterization of Neuraminidase Inhibitors in Korean Papaver rhoeas Bee Pollen Contributing to Anti-Influenza Activities In Vitro.
abstract: The active constituents of Korean Papaver rhoeas bee pollen conferring neuraminidase inhibitory activities (H1N1, H3N2, and H5N1) were investigated. Six flavonoids and one alkaloid were isolated and characterized by nuclear magnetic resonance and mass spectrometry data. These included kaempferol-3-sophoroside (1), kaempferol-3-neohesperidoside (2), kaempferol-3-sambubioside (3), kaempferol-3-glucoside (4), quercetin-3-sophoroside (5), luteolin (6), and chelianthifoline (7). All compounds showed neuraminidase inhibitory activities with IC50 values ranging from 10.7 to 151.1 µM. The most potent neuraminidase inhibitor was luteolin, which was the dominant content in the ethyl acetate fraction. All tested compounds displayed noncompetitive inhibition of H3N2 neuraminidase. Furthermore, compounds 1-7 all reduced the severity of virally induced cytopathic effects as determined by the Madin-Darby canine kidney cell-based assay showing antiviral activity with IC50 values ranging from 10.7 to 33.4 µM (zanamivir: 58.3 µM). The active compounds were quantified by high-performance liquid chromatography, and the total amount of compounds 1-7 made up about 0.592 g/100 g bee pollen, contributing a rich resource of a natural antiviral product.
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: In-Kyoung
authors: IK
authors: Lee
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: Byung Soon
authors: BS
authors: Hwang
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: Dae-Won
authors: DW
authors: Kim
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: Ji-Yul
authors: JY
authors: Kim
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: E-Eum
authors: EE
authors: Woo
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: Yoon-Ju
authors: YJ
authors: Lee
authors: Department of Beauty Science, Kwangju Women's University, Sanjeong-dong, Gwangsan-gu, Kwangju, Republic of Korea.
authors: Hwa Jung
authors: HJ
authors: Choi
authors: Division of Biotechnology and Advanced Institute of Environment and Bioscience, Chonbuk National University, Iksan-si, Republic of Korea.
authors: Bong-Sik
authors: BS
authors: Yun
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D001516:Bees; D004285:Dogs; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects; D053124:Influenza A Virus, H5N1 Subtype / Q000187:drug effects; D061985:Madin Darby Canine Kidney Cells / Q000187:drug effects / Q000821:virology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D010207:Papaver / Q000737:chemistry*; D011058:Pollen / Q000737:chemistry*
chemical_list: D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D005419:Flavonoids; D009439:Neuraminidase