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(Synonyms: 短叶松素,3,5,7-Trihydroxyflavanone) 目录号 : GC20019

Pinobanksin 在 B 细胞淋巴瘤细胞系中具有凋亡诱导作用。

Pinobanksin Chemical Structure

Cas No.:548-82-3

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1mg
¥1,147.00
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5mg
¥3,010.00
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Chemical Properties

Cas No. 548-82-3 SDF Download SDF
别名 短叶松素,3,5,7-Trihydroxyflavanone
分子式 C15H12O5 分子量 272.257
溶解度 储存条件 2-8°C
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1 mg 5 mg 10 mg
1 mM 3.673 mL 18.365 mL 36.73 mL
5 mM 0.7346 mL 3.673 mL 7.346 mL
10 mM 0.3673 mL 1.8365 mL 3.673 mL
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Research Update

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

Chem Biol Interact 2015 Dec 5;242:35-44.PMID:26367700DOI:10.1016/j.cbi.2015.09.013.

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.

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

Food Chem 2018 Feb 1;240:323-329.PMID:28946279DOI:10.1016/j.foodchem.2017.07.133.

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.

Polish and New Zealand Propolis as Sources of Antioxidant Compounds Inhibit Glioblastoma (T98G, LN-18) Cell Lines and Astrocytoma Cells Derived from Patient

Antioxidants (Basel) 2022 Jun 29;11(7):1305.PMID:35883797DOI:10.3390/antiox11071305.

Gliomas, including glioblastoma multiforme and astrocytoma, are common brain cancers in adults. Propolis is a natural product containing many active ingredients. The aim of this study was to compare the chemical composition, total phenolic content and concentration of toxic elements as well as the anticancer potential of Polish (PPE) and New Zealand (Manuka-MPE) propolis extracts on diffuse astrocytoma derived from patient (DASC) and glioblastoma (T98G, LN-18) cell lines. The antioxidants such as flavonoids and chalcones (pinocembrin, Pinobanksin, Pinobanksin 3-acetate and chrysin) were the main components in both types of propolis. The content of arsenic (As) and lead (Pb) in MPE was higher than PPE. The anti-proliferative study showed strong activity of PPE and MPE propolis on DASC, T98G, and LN-18 cells by apoptosis induction, cell cycle arrest and attenuated migration. These findings suggest that despite their different geographic origins, Polish and New Zealand propolis are sources of antioxidant compounds and show similar activity and a promising anti-glioma potential in in vitro study. However, further in vivo studies are required in order to assess therapeutic potential of propolis.

The Profile of Polyphenolic Compounds, Contents of Total Phenolics and Flavonoids, and Antioxidant and Antimicrobial Properties of Bee Products

Molecules 2022 Feb 15;27(4):1301.PMID:35209088DOI:10.3390/molecules27041301.

This study aimed to characterize bee products (bee bread, bee pollen, beeswax, and multiflorous honey) with the profile of phenolic compounds, total phenolic (TPC) and flavonoid (TFC) contents, and antioxidant and microbiological properties. The TP and TF contents could be ordered as follows: bee pollen > bee bread > beeswax > honey. The UPLC-PDA-MS/MS analysis allowed identifying 20 polyphenols. Sinapic acid dominated in bee pollen, gallic acid in the bee bread and honey, while Pinobanksin was the major compound of beeswax. The data showed that bee pollen and bee bread had a stronger antioxidant potential than honey and beeswax. Moreover, the antibacterial activity of the bee products was studied using 14 bacterial strains. Bee bread's and bee pollen's antimicrobial activity was higher towards Gram-negative strains. In comparison, honey was more potent in inhibiting Gram-positive bacteria. Our study indicates that bee products may represent valuable sources of bioactive compounds offering functional properties.

European propolis is highly active against trypanosomatids including Crithidia fasciculata

Sci Rep 2019 Aug 6;9(1):11364.PMID:31388043DOI:10.1038/s41598-019-47840-y.

Extracts of 35 samples of European propolis were tested against wild type and resistant strains of the protozoal pathogens Trypanosoma brucei, Trypanosoma congolense and Leishmania mexicana. The extracts were also tested against Crithidia fasciculata a close relative of Crithidia mellificae, a parasite of bees. Crithidia, Trypanosoma and Leishmania are all members of the order Kinetoplastida. High levels of activity were obtained for all the samples with the levels of activity varying across the sample set. The highest levels of activity were found against L. mexicana. The propolis samples were profiled by using liquid chromatography with high resolution mass spectrometry (LC-MS) and principal components analysis (PCA) of the data obtained indicated there was a wide variation in the composition of the propolis samples. Orthogonal partial least squares (OPLS) associated a butyrate ester of Pinobanksin with high activity against T. brucei whereas in the case of T. congolense high activity was associated with methyl ethers of chrysin and Pinobanksin. In the case of C. fasciculata highest activity was associated with methyl ethers of galangin and Pinobanksin. OPLS modelling of the activities against L. mexicana using the mass spectrometry produced a less successful model suggesting a wider range of active components.