ABSTRACT
Kanjone (1), a bioactive furanoflavone and a potent biomolecule, was first isolated from Pongamia pinnata (L.). Herein, we have developed two approaches to synthesize kanjone as well as its natural analogues 6-methoxyisopongaglabol (2) and 6,3'-dimethoxy-[2â³,3â³:7,8]furanoflavone (3) starting from khellin and 3-hydroxy-4-methoxy-benzaldehyde, respectively.
ABSTRACT
Pongamia pinnata (Linn.) Pierre has anti-inflammatory activity and could significantly decrease serum tumor necrosis factor-α and IL-10 in arthritic rats. Previous research indicated the typical chemical constituent in P. pinnata is furanoflavone. Guided by anti-inflammatory active assay and UPLC-HRESIMS chromatography, 22 compounds were isolated from the ethanol extract of P. pinnata seedpods. One novel furanoflavone, 4'-hydroxypinnatin, was elucidated by HRESIMS, 1D- and 2D-NMR spectra. The 21 known compounds, including 9 furanoflavone, were identified by comparing their NMR data with the previous data in reference. In the known compounds, 5 were isolated for the first time from the species. The anti-inflammatory activities were assayed by assessing LPS-induced NO production in BV-2 cells. 12 compounds can inhibit the production of NO without cytotoxicity at concentration of 50 µM. Among them, compounds 4 can significantly inhibit the production of NO, with the IC50 value of 31.36 µM.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Inflammation/drug therapy , Millettia/chemistry , Plant Extracts/pharmacology , Animals , Anti-Inflammatory Agents/administration & dosage , Anti-Inflammatory Agents/isolation & purification , Cell Line , Chromatography, High Pressure Liquid/methods , Inhibitory Concentration 50 , Lipopolysaccharides/administration & dosage , Magnetic Resonance Spectroscopy , Mice , Microglia/drug effects , Microglia/pathology , Nitric Oxide/metabolism , Plant Extracts/administration & dosage , Plant Extracts/chemistry , SeedsABSTRACT
Chemical investigation of the ethyl acetate extract from the fruits of Derris indica has led to the isolation of a new furanoflavonoid derivative, 4'-hydroxypinnatin (1), and five known compounds. Pinnatin (2) showed strong cytotoxicity against cholangiocarcinoma (KKU-100) and human hepatoma (HepG2) cell lines with IC50 values of 6.0 ± 2.7 and 9.0 ± 4.1 µg/ml, respectively, and showed maximal cell killing effect of about 88-90%. Flavone 5 exhibited the most cytotoxicity against KKU-100 but it showed moderate efficacy (Emax = 50.7%).
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Flavonoids/isolation & purification , Flavonoids/pharmacology , Fruit/chemistry , Millettia/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Cholangiocarcinoma , Drug Screening Assays, Antitumor , Flavonoids/chemistry , Hep G2 Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , ThailandABSTRACT
Object To study the chemical constituents of the dried root of Fordia cauliflora Hemsl which is indigenous to Guangxi and commonly used in traditional medicine of Zhuang and Yao nationalities Methods The constituents were isolated with column chromatography and their structures were elucidated on the basis of physicochemical data and spectral analysis Results The three constituents were isolated and identified as 2 [3 methoxyphenyl] 4H furo[2,3 h] 1 benzoyran 4 one (Ⅲ), 3 methoxy 2 [3 hydroxyphenyl] 4H furo [2, 3 h] 1 benzopyran 4 one (Ⅳ) and pinnatin (Ⅴ) Conclusion The all of them are isolated from this plant for the first time Compound Ⅲ,Ⅳ are new and tentatively named as cauliflorin A and cauliflorin B
