(2R,3R)-3,5,7-Trihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one/Pinobanksin/4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-phenyl-, (2R,3R)-/(2R,3R)-3,5,7-trihydroxy-2-phenyl-2,3-dihydrochromen-4-one
570.6±50.0 °C at 760 mmHg
HS Code Reference
Personal Projective Equipment
For Reference Standard and R&D, Not for Human Use Directly.
provides coniferyl ferulate(CAS#:548-82-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
Propolis is a resinous substance produced by honeybees (Apis mellifera) from the selective collection of exudates and bud secretions from several plants. In previous works, we reported the antiproliferative activity of Sonoran propolis (SP) on cancer cells; in addition we suggested the induction of apoptosis after treatment with SP due to the presence of morphological changes and a characteristic DNA fragmentation pattern. Herein, in this study we demonstrated that the antiproliferative effect of SP is induced through apoptosis in a B-cell lymphoma cancer cell line, M12.C3.F6, by an annexin V-FITC/Propidium iodide double labeling. This apoptotic effect of SP resulted to be mediated by modulations in the loss of mitochondrial membrane potential (ΔΨm) and through activation of caspases signaling pathway (3, 8 and 9). Afterward, in order to characterize the chemical constituents of SP that induce apoptosis in cancer cells, an HPLC-PDA-ESI-MS/MS method followed by a preparative isolation procedure and NMR spectroscopy analysis have been used. Eighteen flavonoids, commonly described in propolis from temperate regions, were characterized. Chrysin, pinocembrin, pinobanksin and its ester derivatives are the main constituents of SP and some of them have never been reported in SP. In addition, two esters of pinobanksin (8 and 13) are described by first time in propolis samples in general. The antiproliferative activity on M12.C3.F6 cells through apoptosis induction was exhibited by pinobanksin (4), pinobanksin-3-O-propanoate (14), pinobanksin-3-O-butyrate (16), pinobanksin-3-O-pentanoate (17), and the already reported galangin (11), chrysin (9) and CAPE. To our knowledge this is the first report of bioactivity of pinobanksin and some of its ester derivatives as apoptosis inducers. Further studies are needed to advance in the understanding of the molecular basis of apoptosis induction by SP and its constituents, as well as the structure-activity relationship of them.
Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.
Chemical characterization; Induction of apoptosis; Pinobanksin ester derivatives; Sonoran propolis
Apoptotic induction by pinobanksin and some of its ester derivatives from Sonoran propolis in a B-cell lymphoma cell line.
Alday E1, Valencia D2, CarreNo AL1, Picerno P3, Piccinelli AL3, Rastrelli L3, Robles-Zepeda R1, Hernandez J4, Velazquez C5.
2015 Dec 5
The effects of the ester group and solvent on the structure and antioxidant activity of pinobanksin were carried out using DFT calculation. First, the properties of the intramolecular hydrogen-bonds in the investigated compounds were studied. Second, the antioxidant capacities of the investigated compounds were analyzed by HAT, SET-PT and SPLET mechanisms from thermodynamic point. The conclusions are: (1) HAT mechanism is most favorable in the gas and CCl4 phases, while SPLET mechanism is more favored in the CH3CN and H2O phases. In the CHCl3 phase, the thermodynamically preferred mechanism is HAT for the 3-OH and 5-OH groups. While, HAT and SPLET mechanisms may run simultaneously for the 7-OH group. (2) Replacing the 3-OH group by ester group with different alkyl chains does not change much of the antioxidant activity of pinobanksin. (3) Besides, the 7-OH group contributes mainly to the antioxidant activities of the investigated compounds.
Copyright © 2017 Elsevier Ltd. All rights reserved.
Density functional theory; Pinobanksin; Pinobanksin-3-O-ester derivatives; Solvent effect; Structure-antioxidant activity relationship
Theoretical studies on the antioxidant activity of pinobanksin and its ester derivatives: Effects of the chain length and solvent.
Zheng YZ1, Deng G2, Chen DF3, Liang Q1, Guo R1, Fu ZM1.
2018 Feb 1
Pinobanksin inhibits peroxidation of low density lipoprotein and it has electron donor properties reducing alpha-tocopherol radicals.
Ondrias K1, Stasko A, Hromadova M, Suchý V, Nagy M.