title: Regiospecific Prenylation of Hydroxyxanthones by a Plant Flavonoid Prenyltransferase.
abstract: C-Prenylated xanthones are pharmacologically attractive specialized metabolites that are distributed in plants and microorganisms. The prenylation of xanthones often contributes to the structural diversity and biological activities of these compounds. However, efficient regiospecific prenylation of xanthones is still challenging. In this study, the regiospecific prenylation of a number of structurally different hydroxyxanthones (3-10) by MaIDT, a plant flavonoid prenyltransferase with substrate flexibility from Morus alba, is demonstrated. Among the enzymatic products, 2-dimethylallyl-1,3,7-trihydroxyxanthone (3a) effectively attenuated glutamate-induced injury in SK-N-SH neuroblastoma cells. These results suggest a potential approach for the synthesis of bioactive prenylated xanthones by a substrate-relaxed flavonoid prenyltransferase.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Ruishan
authors.initials: R
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Ridao
authors.initials: R
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Jianhua
authors.initials: J
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Kebo
authors.initials: K
authors.lastname: Xie
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Dawei
authors.initials: D
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Peng
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines and ‡Key Laboratory of Biosynthesis of Natural Products of National Health and Family Planning Commission, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, People's Republic of China.
authors.forename: Jungui
authors.initials: J
authors.lastname: Dai
mesh_terms: D004122:Dimethylallyltranstransferase / Q000378:metabolism*; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D031625:Morus / Q000737:chemistry* / Q000201:enzymology; D054876:Prenylation; D013379:Substrate Specificity; D044004:Xanthones / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism
chemical_list: D005419:Flavonoids; D044004:Xanthones; C436833:gentisein; D004122:Dimethylallyltranstransferase