ABSTRACT
Six undescribed C-geranylated flavonoids, including five C-geranylflavanones named as paucatalinones F - J, one C-geranylflavonol named as paucatalinone K, along with seven known geranylated flavanones, were isolated from the fruit peel of Paulownia catalpifolia T. Gong ex D.Y. Hong. Their structures were elucidated distinctly according to their UV, IR, MS, NMR, and CD data. Among them, two compounds were substituted with unusual modified geranyl groups, namely paucatalinone F with an oxygenated cyclogeranyl substituent and paucatalinone H with a terminal pyranoid geranyl substituent. Furthermore, the protective effects on human umbilical vein endothelial cells (HUVECs) injury induced by H2O2 were evaluated, and paucatalinone F showed the most potential activity. The bioactive results suggested that the geranyl substituent may be an important factor for restraining oxidative HUVECs damage and Paulownia C-geranylated flavonoids might have the potential for preventing cardiovascular complications.
Subject(s)
Flavonoids/chemistry , Flavonoids/pharmacology , Lamiales/chemistry , Apoptosis/drug effects , Circular Dichroism , Drug Evaluation, Preclinical/methods , Fruit/chemistry , Human Umbilical Vein Endothelial Cells/drug effects , Humans , Hydrogen Peroxide/toxicity , Magnetic Resonance Spectroscopy , Molecular Structure , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
The fruits of Paulownia catalpifolia Gong Tong are used as a Chinese folk herbal medicine for the treatment of enteritis, tonsillitis, bronchitis, and dysentery, etc. Our previous study has identified new C-geranylated flavanones with obvious anti-proliferative effects in lung cancer A549 cells. In the present study, a new C-geranylated flavone, paucatalinone C (1) and five known C-geranylated flavanones (2-6) were isolated. In addition, a total of 34 C-geranylated flavonoids were detected by HPLC-DAD-ESI-MS/MS coupling techniques from the CH2Cl2 extract of P. catalpifolia. Futhermore, anti-aging effects of isolated compounds were evaluated in vitro with premature senescent 2BS cells induced by H2O2. Phytochemical results indicated that P. catalpifolia was a natural resource of abundant C-geranylated flavonoids. Diplacone (3) and paucatalinone A (5) were the potent anti-aging agents in the premature senescent 2BS cells induced by H2O2 and the C-geranyl substituent may be an important factor because of its lipophilic character.
Subject(s)
Aging/drug effects , Flavonoids/chemistry , Flavonoids/pharmacology , Magnoliopsida/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Cell Line , Chromatography, High Pressure Liquid , Flavonoids/isolation & purification , Fruit/chemistry , Humans , Hydrogen Peroxide/toxicity , Molecular Structure , Plant Extracts/isolation & purification , Tandem Mass SpectrometryABSTRACT
Three new geranylated flavanones, named as paucatalinone A (1), B (2), and isopaucatalinone B (3), were isolated from the fruits of Paulownia catalpifolia Gong Tong (Scrophulariaceae). Their structures were well determined by means of IR, MS, 1D and 2D NMR, and CD techniques. Paucatalinone A (1) is the first sample as a dimeric geranylated flavanone derivative isolated from natural products. Paucatalinone A (1) displayed good antiproliferative effects on human lung cancer cells A549 and resulted in a clear increase of the percentage of cells in G1 phase and a decrease in the percentage of cells in S and G2/M phases in comparison with control cells.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Lung Neoplasms/drug therapy , Scrophulariaceae/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor/drug effects , Drug Screening Assays, Antitumor/methods , Flavanones/chemistry , Flavanones/isolation & purification , Flavanones/pharmacology , Fruit/chemistry , G1 Phase/drug effects , Humans , Lung Neoplasms/pathology , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
OBJECTIVE: To study the chemical constituents of Salsola collina. METHODS: The compounds were isolated by column chromatography, and their structures were identified by physical and chemical properties and spectral data. RESULTS: Seven compounds were isolated and identified as n-lignoceric acid (1), n-dotriacontanic acid (2), beta-sitosterol (3), 5, 2'-dihydroxy-6, 7-methylenedioxy-isoflavone (4), vanillic acid (5), (-)syringaresinol 4,4'-bis-O-beta-D-glucopyranoside (6), salicylic acid (7). CONCLUSION: The compounds of 1, 2, 4, 5 and 6 are isolated from the plant for the first time.
Subject(s)
Fatty Acids/isolation & purification , Isoflavones/isolation & purification , Plants, Medicinal/chemistry , Salsola/chemistry , Vanillic Acid/isolation & purification , Antihypertensive Agents/chemistry , Antihypertensive Agents/isolation & purification , Chromatography, Thin Layer , Disaccharides/chemistry , Disaccharides/isolation & purification , Fatty Acids/chemistry , Isoflavones/chemistry , Molecular Structure , Naphthalenes/chemistry , Naphthalenes/isolation & purification , Plant Components, Aerial/chemistry , Sitosterols/chemistry , Sitosterols/isolation & purification , Vanillic Acid/chemistryABSTRACT
AIM: To study the chemical constituents of Salsola collina Pall.. METHODS: Compounds were isolated by silica gel column chromatography. IR, MS, 1HNMR, 13CNMR, HMQC, HMBC, DEPT were used for the structural identification. RESULTS: Two amide alkaloids were obtained. They were identified as N-transferuloyl-3-methyldopamine (I), (10bS)-1,2,3,5,6, 10b-hexahydropyrrolo [2,1-a]-8,9-dihydroxyisoquinoline-3-one (II). CONCLUSION: Compound I was isolated from this genus for the first time. Compound II is a new compound named salsoline A.