Synthesis of magnolol and honokiol derivatives and their effect against hepatocarcinoma cells

Abstract

The hepatocellular carcinoma is one of the most common malignant tumour with high level of mortality rate due to its rapid progression and high resistance to conventional chemotherapies. Thus, the search for novel therapeutic leads is of global interest. Herein, a small set of derivatives of magnolol 1 and honokiol 2, the main components of Magnolia grandiflora and Magnolia obovata, were evaluated in in vitro assay using tumoral hepatocytes. The pro-drug approach was applied as versatile strategy to the improve bioactivity of the compounds by careful transformation of the hydroxyl groups of magnolol 1 and honokiol 2 in suitable ester derivatives. Compounds 10 and 11 resulted to be more potent than the parental honokiol 2 at concentration down to 1 μM with complete viability of treated fibroblast cells up to concentrations of 80 μM. The combination of a butyrate ester and a bare phenol-OH group in the honokiol structure seemed to play a significant role in the antiproliferative activity identifying an interesting pharmacological clue against hepatocellular carcinoma.

Fibroblast Proliferation and Migration in Wound Healing by Phytochemicals: Evidence for a Novel Synergic Outcome

“…Nevertheless, our results highlight a further use of waste materials to ameliorate regenerative and antioxidant processes. Actually some authors described that extracts from L [61] and C [62] exert a high inhibitory effect on cancer cell proliferation in vitro, without affecting healthy normal cells growing at low concentrations [45], showing a dual and opposite effect depending on the concentration and time of exposure to the plant extracts. At the same time, our waste extracts didn't exhibit any cytotoxic effects on cell proliferation, especially at low concentrations and for prolonged culturing time, both alone (C, L, H) or as pooled waste extracts (CL, CH, LH, CLH).…”

The Cytotoxic Activity of Honokiol‐Triazole Derivatives in Ovarian Cancer Cells

“…Synthesis General Synthetic Procedure for Compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17). Penicillin, streptomycin, and fetal bovine serum (FBS) were obtained from Life Technologies Inc. (Grand Island, NY, USA).…”

“…Honokiol has multiple bioactivities such as antioxidative, 2 antiarrhythmic, 3 anti-inflammatory, 4 antithrombocytic, 5 antiangiogenesis, 6,7 anxiolytic, 8 antiviral, 9 and antitumor activity. 13 Honokiol bisdichloroacetate (Honokiol DCA) and the fluorinated honokiol analog (bis-trifluoromethyl-bis-(4-hydroxy-3-allylphenyl)methane (hexafluoro)) exhibited bioactivity against vemurafenib-resistant melanoma. 13 Honokiol bisdichloroacetate (Honokiol DCA) and the fluorinated honokiol analog (bis-trifluoromethyl-bis-(4-hydroxy-3-allylphenyl)methane (hexafluoro)) exhibited bioactivity against vemurafenib-resistant melanoma.…”

“…Honokiol has multiple bioactivities such as antioxidative, antiarrhythmic, anti‐inflammatory, antithrombocytic, antiangiogenesis, anxiolytic, antiviral, and antitumor activity . Acetyl or butyryl honokiol derivatives inhibited tumoral hepatocytes cells proliferation in the range of 1 ± 80 μM . Honokiol bis‐dichloroacetate (Honokiol DCA) and the fluorinated honokiol analog (bis‐trifluoromethyl‐bis‐(4‐hydroxy‐3‐allylphenyl)methane (hexafluoro)) exhibited bioactivity against vemurafenib‐resistant melanoma …”

Unravelling Cellular Mechanisms of Stem Cell Senescence: An Aid from Natural Bioactive Molecules

“…Natural molecules present in food or plants are largely known for their antioxidant activity, counteracting the formation of free radicals through the inhibition of lipid oxidation [3]. Moreover, these small molecules can be used as an adjuvant treatment beside conventional therapy in cancer, due to their ability to reduce cancer Biology 2020, 9, 57 2 of 8 cell viability without affecting the proliferation of normal healthy cells [4][5][6]. Myrtus communis L. has a large amount of galloyl derivatives, as flavonols, and tannins in its berries, seeds and leaves, exerting important antioxidant and antimutagenic activities [7,8].…”