[Polyphenolic compounds of the stilbenoid class: classification, representatives, content in plant raw materials, structural features, use in the food industry and pharmacy].

Nowadays, more than 300 representatives of stilbenoids are known - a group of natural, synthetic and semi-synthetic biologic active substances, according to the chemical structure belonging to the group of polyphenolic compounds - phenylpropanoids. Representatives of this group of compounds can be detected in such classes of plants as gymnosperms, angiosperms, bryophytes and pteridophyte. The main food sources are the fruits of grapes, blueberries, blueberries, peanuts, cocoa. The history of their detection is associated with the discovery of the protective functions of plants in response to the action of external stimuli. Further study revealed pronounced antioxidant properties. The mechanism of development of many diseases is associated with the processes of oxidation of free radicals, which can be interrupted by the effect of antioxidants. Possible mechanisms of antioxidant action of stilbenoids and their effect on diseases caused by excessive amounts of free radicals have been studied. Stilbenoids increase the tone and stability of the body to stress factors of the environment, improve the adaptive capacity of the nervous and immune systems, show antitumor, cardio-protective and lipid-lowering activities, inhibit lipid peroxidation. In this regard specialized products, food supplements and drugs containing stilbenoids have been developed. However, representatives of this group of compounds have low consumer properties, are sensitive to environmental factors and have low solubility and absorption. Therefore, solutions of these problems are important when developing new foods and drugs. Nowadays, auxiliary substances (solubilizers) are used, as well as such technological methods as microencapsulation, coacervation, polymerization, and others that can cope with problems of instability, poor solubility, low bioavailability, and unsatisfactory consumer qualities, which improve the effect of stilbenoids on the organism.

Biologically active oligostilbenes from the stems of Vatica mangachapoi and chemotaxonomic significance.

Phytochemical investigation of the stems of Vatica mangachapoi (Dipterocarpaceae) led to the isolation and structural elucidation of twenty-seven oligostilbenes (1-27), including a new natural compound 1. The structure of 1 was elucidated on the basis of spectroscopic analyses including NMR, MS and ECD data, and the known compounds were identified by comparisons with those reported in the literature. The absolute configuration of 1 was first time determined by a combination of NOESY spectrum and quantum chemical computation. Among of isolates were tested for their anti-osteoporosis and anti-HIV-1 activities in vitro by the MTT method. Moreover, the chemotaxonomic significance of these compounds was summarised.

Dihydroresveratrol Type Dihydrostilbenoids: Chemical Diversity, Chemosystematics, and Bioactivity.

BACKGROUND: Dihydrostilbenoids, a diverse class of natural products differing from stilbenoids by the missing double bond in the ethylene chain linking the aromatic moieties, have been reported from fungi, mosses, ferns, and flowering plants. OBJECTIVE: Occurrence, structure, and bioactivity of naturally occurring dihydroresveratrol type dihydrostilbenoids are discussed in this review. METHOD: A Reaxys database search for dihydroresveratrol derivatives with possible substitutions on all atoms, but excluding non-natural products and compounds featuring additional rings involving the ethyl connecting chain, was performed. RESULTS: Structures include simple dihydroresveratrol derivatives, compounds substituted with complex side chains composed of acyl moieties and sugars, and compounds containing polycyclic cores attached to dihydrostilbenoid units. Dihydrostilbenoids have a wide spectrum of bioactivities ranging from expectable antioxidant and anti-inflammatory activities to interesting neuroprotective and anticancer activity. The anticancer activity in particular is very pronounced for some plant-derived dihydrostilbenoids and makes them interesting lead compounds for drug development. Apart from some reports on dihydroresveratrol derivatives as phytoalexins against plant-pathogenic fungi, only very limited information is available on the ecological role of these compounds for the organisms producing them. CONCLUSION: Dihydrostilbenoids are a class of natural products possessing significant biological activities; their scattered but not ubiquitous occurrence throughout the kingdoms of plants and fungi is not easily explained. We are convinced that future studies will identify new sources of dihydrostilbenoids, and we hope that the present review will inspire such studies and will help in directing such efforts to suitable source organisms and towards promising bioactivities.

Classification of stilbenoid compounds by entropy of artificial intelligence.

A set of 66 stilbenoid compounds is classified into a system of periodic properties by using a procedure based on artificial intelligence, information entropy theory. Eight characteristics in hierarchical order are used to classify structurally the stilbenoids. The former five features mark the group or column while the latter three are used to indicate the row or period in the table of periodic classification. Those stilbenoids in the same group are suggested to present similar properties. Furthermore, compounds also in the same period will show maximum resemblance. In this report, the stilbenoids in the table are related to experimental data of bioactivity and antioxidant properties available in the technical literature. It should be noted that stilbenoids with glycoxyl groups esterified with benzoic acid derivatives, in the group g11000 in the extreme right of the periodic table, show the greatest antioxidant activity as confirmed by experiments in the bibliography. Moreover, the second group from the right (g10111) contains E-piceatannol, which antioxidant activity is recognized in the literature. The experiments confirm our results of the periodic classification.