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Alkaloids and Coumarins with Adiponectin-Secretion-Promoting Activities from the Leaves of Orixa japonicaopen access
- Authors
- Nhoek, Piseth; Ahn, Sungjin; Pel, Pisey; Kim, Young-Mi; Huh, Jungmoo; Kim, Hyun Woo; Noh, Minsoo; Chin, Young-Won
- Issue Date
- Jan-2023
- Publisher
- American Chemical Society
- Keywords
- Acetylsalicylic Acid; Adiponectin; Auraptene; Bergapten; Glibenclamide; Isopimpinellin; Methoxsalen; Pentosalen; Pioglitazone; Psoralen; Resveratrol; Adiponectin; Alkaloids; Coumarins; Ppar Gamma; 2',3' Acetyl 3',3' Dimethyl 8 Methoxy 6,7 Dihydropyrano[3,2 G]coumarin; 3 (3',3' Dimethylallyl) 4,8 Dimethoxy N Methylquinolin 2 One; 4,8 Dimethoxy 3 (3' Methyl 2' Oxobutyl) 2 Quinolone; 5 Hydroxy 1 Methyl 2 Phenyl 4 Quinolone; 5 Hydroxy 6 Methoxy 1 Methyl 2 (4 Methoxyphenyl) 4 Quinolone; 5 Methoxy 1 Methyl 2 (4 Hydroxyphenyl) 4 Quinolone; 6,8 Dimethoxy 7 (6' Peroxy 3',7' Dimethyl 2',7' Octadienyloxy)coumarin; 7 ( 7' Methoxy 3',7' Dimethylocta 2',5' Dienyloxy)coumarin; 7 (6' Hydroxy 3',7' Dimethyl 2',7' Octadienyloxy)coumarin; 7 (7' Peroxy 3',7' Dimethylocta 2',5' Dienyloxy) 6,8 Dimethoxycoumarin; 7 Geranyloxy 6 Methoxycoumarin; 7 Hydroxy 4,8 Dimethoxy 3 (3 Methylbut 2 Enyl) N Methyl 2 Quinolone; 7 Hydroxy 4,8 Dimethoxy 3 (3' Methyl But 2' Enyl) 2 Quinolone; 8alpha Acetoxyelemol; 8alpha,11 Elemodiol; Acetylsalicylic Acid; Adiponectin; Alkaloid; Altissimacoumarin D; Auraptene; Bergapten; Coumarin Derivative; Glibenclamide; Isogosferol; Isopimpinellin; Methoxsalen; N Methylatanine; N Methylflindersine; Oplopanone; Orijanone; Orixalone B; Pentosalen; Peroxisome Proliferator Activated Receptor Gamma; Peroxisome Proliferator Activated Receptor Gamma Agonist; Pioglitazone; Psoralen; Quinoline Derivative; Resveratrol; Unclassified Drug; Article; Binding Assay; Bone Marrow Mesenchymal Stem Cell; Controlled Study; Drug Mechanism; Drug Screening; Drug Structure; Ec50; Electronic Circular Dichroism; Human; Human Cell; Molecular Model; Nonhuman; Nuclear Magnetic Resonance Spectroscopy; Orixa Japonica; Plant Leaf; Rutaceae; Structure Analysis; Chemical Structure; Chemistry; Adiponectin; Alkaloids; Coumarins; Humans; Molecular Structure; Plant Leaves; Ppar Gamma
- Citation
- Journal of Natural Products, v.86, no.1, pp 138 - 148
- Pages
- 11
- Indexed
- SCIE
SCOPUS
- Journal Title
- Journal of Natural Products
- Volume
- 86
- Number
- 1
- Start Page
- 138
- End Page
- 148
- ISSN
- 0163-3864
1520-6025
- Abstract
- Fractionation of a methanol extract of Orixa japonica leaves led to the identification of five new quinoline alkaloids (1, 2, 4, 8, and 9), three new coumarins (15, 17, and 19), and 20 known compounds. The structures were determined by analysis of 1D and 2D NMR spectroscopic data. The absolute configuration of 19 was proposed by electronic circular dichroism calculation. Among the compounds tested in the phenotypic screening to measure adiponectin secretion in human bone marrow mesenchymal stem cells, metabolites 4 and 12 stimulated adiponectin secretions with EC50 values of 13.8 and 25.8 mu M, respectively. Further PPARy binding assay and molecular modeling suggested that compounds 4 and 12 are selective PPARy agonists.
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Related Researcher
- Kim, Hyun Woo
- College of Pharmacy (Department of Pharmacy)