title: Chemical constituents from Melicope pteleifolia leaves.
abstract: Five acetophenones bearing spiroketal-hexofuranoside rings, one di-C-glycosidic acetophenone and two benzopyrans, along with 16 known compounds were isolated from the leaves of Melicope pteleifolia. Structures of all the isolates were elucidated using extensive spectroscopic methods, including 1D, 2D-NMR and HRESIMS. All the isolates were also evaluated for their neuraminidase inhibitory activities against H1N1, H9N2, wild-type H1N1 and oseltamivir-resistant H1N1 (H274Y mutation) virus strains. Of the isolates, tamarixetin 3-robinobioside was found to exhibit the strongest enzymatic inhibition (IC50 24.93 ± 3.46, 23.19 ± 5.41, 26.67 ± 5.16 and 40.16 ± 4.50 μM, respectively). Selected candidates, kaempferol 3-robinobioside, kaempferol 3-O-β-d-glucopyranosyl (1 → 2)-α-d-xylopyranoside and tamarixetin 3-robinobioside, also showed moderate reductions in H1N1-induced cytopathic effects on MDCK cells.
authors.affiliation: Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 151-742, Republic of Korea.
authors.forename: Ngoc Hieu
authors.initials: NH
authors.lastname: Nguyen
authors.affiliation: Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 151-742, Republic of Korea.
authors.forename: Thi Kim Quy
authors.initials: TK
authors.lastname: Ha
authors.affiliation: International Biological Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon, 305-806, Republic of Korea.
authors.forename: Sangho
authors.initials: S
authors.lastname: Choi
authors.affiliation: International Biological Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon, 305-806, Republic of Korea.
authors.forename: Sangmi
authors.initials: S
authors.lastname: Eum
authors.affiliation: International Biological Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon, 305-806, Republic of Korea.
authors.forename: Chul Ho
authors.initials: CH
authors.lastname: Lee
authors.affiliation: Department of Botany, Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hanoi, 10307, Viet Nam.
authors.forename: Tran The
authors.initials: TT
authors.lastname: Bach
authors.affiliation: Department of Botany, Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hanoi, 10307, Viet Nam.
authors.forename: Vu Tien
authors.initials: VT
authors.lastname: Chinh
authors.affiliation: Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 151-742, Republic of Korea. Electronic address: wkoh1@snu.ac.kr.
authors.forename: Won Keun
authors.initials: WK
authors.lastname: Oh
mesh_terms: D000098:Acetophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004285:Dogs; D005419:Flavonoids / Q000494:pharmacology; D006801:Humans; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects; D007251:Influenza, Human / Q000188:drug therapy; D061985:Madin Darby Canine Kidney Cells; D009439:Neuraminidase / Q000037:antagonists & inhibitors; D053139:Oseltamivir / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D027821:Rutaceae / Q000737:chemistry*
chemical_list: D000098:Acetophenones; D000998:Antiviral Agents; D001578:Benzopyrans; D005419:Flavonoids; C111688:violarvensin; D053139:Oseltamivir; D009439:Neuraminidase; C038699:acetophenone
keywords: H1N1; Melicope pteleifolia; Neuraminidase; Rutaceae; Spiroketal