The Synthesis Of Phosphorous Derivatives Of Daidzein, Solanesol And ESI Investigation Of Non-covalent Complexes Between Phosphorylated Daidzein Derivatives And Protein

Daidzein (7, 4'-dihydroxyisoflavone) is one of the most abundant isoflavonoids, found in legumes, especially soybeans. It has comprehensive pharmacological activities, including preventing of cardiovascular disease, lessening the symptoms of the menopause and protecting against osteoporosis. Due to its structural similarity to estradiol, more attention has been paid to its phytoestrogen activities in the past few years. In the work described in the dissertation, the recent studies on pharmacological action, extraction and isolation, pharmaceutical and structural modifications of daidzein were introduced in chapter one.Extensively pharmaceutical values in clinic of daidzein have made it common interests as mentioned in many published papers. Lots of efforts have been made to synthesized daidzein derivatives with better activities in recent years. Structural modification is one of the most important aspects in terms of increasing its water-solubility, lowering its toxicity and improving its biological assimilation. The studies on phosphorous modifications of daidzein and non-covalent interaction with protein were shown in this dissertation. The relating works included:1. Seven novel daidzein phosphorous derivatives were synthesized. The structures of all compounds were determined by ESI-MS, IR and NMR. Especially 2D NMR spectra of some compounds were assigned in details.2. ESI experiment shows that phosphorylated daidzein derivatives could interact with the protein lysozyme, insulin and cytochrome C. Even though different parameters were tried, no corresponding non-covalent protein-daidzein complexes were detected. The experiment suggests that the phosphorylated daidzein derivatives could form non-covalent complexes with protein more easily than the unphosphorylated daidzein. Different phosphorylated daidzein derivatives could tolerance different high orifice voltage. The relative stability of the non-covalent complexes was closely associated with the length of the hydrophobic chain.Solanesol, a long-chain terpenoid alcohol, mainly existing in tobacco leaves, is the starting material for many high-value biochemicals, including Vitamin K analogues and co-enzyme Q₁₀, which is useful in the treatment of heart diseases, cancers and ulcers. The recent studies on character, extraction and isolation, pharmaceutical and structural modifications of solanesol were reviewed. In the work described in this paper, three solanesyl phosphonates were synthesized using standard Arbuzov-Michaelis reaction, and their structures were elucidated by ESI-MS, NMR.