Laboratory of Natural Quinonoid Chemistry

Founded by Oleg†Maksimov in 1963 as the Laboratory of Chemistry of Humic Acids. It has had its current name since 1974.

Head of laboratory
Sergey A. Fedoreev, D.Sc.,

Lab staff
Natalya Mischenko (Leading researcher, Ph.D.), Natalya Utkina (Senior researcher, Ph.D.), Natalia Pokhilo (Senior researcher, Ph.D.), Daria Tarbeeva (Researcher, Ph.D.), Elena Vasilyeva (Researcher, Ph.D.), Valentina Belova (Engineer)

Main research areas
The laboratory studies the chemical composition and biological activity of polyphenolic metabolites of Far Eastern plants of the legume family (Fabaceae): Lespedeza bicolor and Amur maakia (Lespedeza bicolor and Maackia amurensis).
A number of prenylated polyphenols were isolated from the stem and root bark of L. bicolor: the well-known pterocarpen lespedesol A2, five new pterocarpans (6aR,11aR)-6a,11a-dihydrolespedesol A2, dihydrolespedesol A2, (6aR, 11aR)-8-O-methyl-6a,11a-dihydrolespedesol A2, (6aR, 11aR, 3'R)-6a,11a-dihydrolespedesol A3, (6aR,11aR,3'S)-6a,11a -dihydrolespedesol A3, a new stilbenoid bicoloketone containing a 1,2-dicarbonyl fragment in the molecule, a prenylated dimeric flavonoid containing pterocarpan and aribenzofuran fragments in its structure (lespebicolin A), as well as flavanones: eriodictyol, 7-O-β-D-glucopyranoside eriodictyol and 7-O-I-D-glucopyranoside naringenin. The structures of all isolated compounds were established by mass spectrometry, NMR and CD spectroscopy. It has been established for the first time that the cytotoxic effect of the new pterocarpan (6aR,11aR)-2-isoprenyl-6a,11a-dihydrolespedesol A2 in relation to five types of human tumor cells: triple-negative breast cancer (HTB-19), esophageal cancer (Kyse-30 ), liver cancer (HEPG-2), prostate cancer (PC-3 and 22Rv1), and three normal cell lines: ocular pigment epithelium (RPE-1), human embryonic kidney cells (HEK-293), fibroblasts (MRC-9 ) is comparable to the effect of the well-known anticancer drug cisplatin.
It was shown that prenylated pterocarpans significantly caused DNA fragmentation in PC-3 prostate cancer cells, which is one of the most important signs of apoptosis.
Under the action of lespedesol A2, (6aR,11aR)-6a,11a-dihydrolespedesol A2 and (6aR,11aR)-2-isoprenyl-6a,11a-dihydrolespedesol A2 on PC-3 cells, a significant number of cells accumulated in S and G2/M phases . These polyphenols have shown the ability to inhibit mRNA expression of the human cyclin-dependent kinases CDK1, CDK2, CDK4 and CDK5. Pterocarpanes (6aR,11aR)-8-O-methyl-6a,11a-dihydrolespedesol A2, (6aR,11aR,3'R)-6a,11a-dihydrolespedesol A3, (6aR,11aR,3'S)-6a,11a-dihydrolespedesol A3 and stilbenoid bicoloketone stopped the cell cycle in the G1 phase.

Two new prenylated flavanones, isomaakiaflavanone A, isomaakiaflavanone B, and a new prenylated stilbene maakiastilbene, as well as five known flavanones, have been isolated from the bark of the Amur maakia roots. The cytotoxicity of the isolated compounds was determined on two human tumor cell lines HeLa and SK-MEL-5 using the MTS method. The compounds maakiaflavanone, maakiaflavanone B and 5-hydroxysophoranone showed the highest cytotoxic activity among the tested compounds. In addition to polyphenols from plants of the Fabaceae family, five known isoflavonoids, one flavonoid, four hydroxybenzoic acids, and a novel 7-O-I-D-glucopyranoside 5,7-dihydroxy-6,2 have been isolated and identified from the roots of the Iris pseudacorus plant (family Iridaceae). '-dimethoxyisoflavone. The content of polyphenols in the stems and roots of this plant was determined and their influence on the growth of colonies of human intestinal carcinoma HT-19 cells was studied. It was shown that trans-3-hydroxy-5,7-dimethoxyflavanone had a pronounced inhibitory activity on the formation of cell colonies at a concentration of 25 μM.
In addition, the chemical composition of the alkaloids of callus cultures obtained from the leaves of Stephania glabra (ROXB.) Miers was studied. (Menispermaceae). According to high-resolution chromatography-mass spectrometry, methanol extracts from cell cultures contained eleven alkaloids: magnoflorin, menisperin, roemerin, palmatin, corydalmin, N-methylcorydalmine, columbamine, tetrahydropalmatine, iatroricin and tetrandrin, as well as stefarin. Quantitative analysis showed that the content of the valuable alkaloid stefarin in calluses reached 0.9% of the mass of dry cells. The growth parameters and productivity of the obtained cell culture remained at a stable level for a long period of time (3 years).

For structural analogues of echinochrome isolated from Far Eastern sea urchins, which differ in nature and position of substituents in the molecule, the structure-function dependence was studied.
Together with Korean colleagues from the Center for Cardiovascular and Metabolic Diseases of Inyo University from Busan (Republic of Korea), the antioxidant effect of echinochrome and its analogs in relation to AC16 human cardiomyocyte cells in the presence of the initiator of oxidative stress hydrogen peroxide, anti-inflammatory, cardioprotective and antidiabetic properties were studied. The most effective antioxidants that reduce the production of free radicals in cardiomyocytes up to 1.5 times were binaphthoquinone, echinamines A and B, spinochromes D and E. We have shown that the most common quinoid pigment in sea urchins, echinochrome A, reduces intraocular inflammation and has antistress properties. , affects the biogenesis of mitochondria in cardiomyocytes and preserves their functions when exposed to cardiotoxic drugs. Echinochrome A inhibits the enzyme acetylcholinesterase, which opens up prospects for its use in the treatment of neurodegenerative diseases, such as Alzheimer's disease. Echinochrome A increases exercise tolerance, increases the energy potential of skeletal and cardiac muscles, which may be of interest for adaptive and sports medicine. Together with scientists from the Institute of Epidemiology and Microbiology. P.G. Somov (Vladivostok) for the first time studied the antiviral properties of echinochrome A and its composition with other antioxidants against encephalitis and herpes viruses.