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Pinobanksin

$1,120

  • Brand : BIOFRON

  • Catalogue Number : BD-P0945

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 548-82-3

  • Formula : C15H12O5

  • Molecular Weight : 272.25

  • PUBCHEM ID : 73202

  • Volume : 25mg

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Catalogue Number

BD-P0945

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

272.25

Appearance

Cryst.

Botanical Source

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC=C(C=C1)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O

Synonyms

(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

IUPAC Name

(2R,3R)-3,5,7-trihydroxy-2-phenyl-2,3-dihydrochromen-4-one

Applications

Density

1.5±0.1 g/cm3

Solubility

Methanol

Flash Point

222.0±23.6 °C

Boiling Point

570.6±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C15H12O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,14-17,19H/t14-,15+/m0/s1

InChl Key

SUYJZKRQHBQNCA-LSDHHAIUSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

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

No Technical Documents Available For This Product.

PMID

26367700

Abstract

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.

KEYWORDS

Chemical characterization; Induction of apoptosis; Pinobanksin ester derivatives; Sonoran propolis

Title

Apoptotic induction by pinobanksin and some of its ester derivatives from Sonoran propolis in a B-cell lymphoma cell line.

Author

Alday E1, Valencia D2, CarreNo AL1, Picerno P3, Piccinelli AL3, Rastrelli L3, Robles-Zepeda R1, Hernandez J4, Velazquez C5.

Publish date

2015 Dec 5

PMID

28946279

Abstract

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.

KEYWORDS

Density functional theory; Pinobanksin; Pinobanksin-3-O-ester derivatives; Solvent effect; Structure-antioxidant activity relationship

Title

Theoretical studies on the antioxidant activity of pinobanksin and its ester derivatives: Effects of the chain length and solvent.

Author

Zheng YZ1, Deng G2, Chen DF3, Liang Q1, Guo R1, Fu ZM1.

Publish date

2018 Feb 1

PMID

9266597

Title

Pinobanksin inhibits peroxidation of low density lipoprotein and it has electron donor properties reducing alpha-tocopherol radicals.

Author

Ondrias K1, Stasko A, Hromadova M, Suchý V, Nagy M.

Publish date

1997 Jul