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Laboratory of the Chemistry of Marine Natural Products

Head of the Lab     
Natalia V. Ivanchina, Ph.D.
Tel. +7 (423) 231-11-68, ivanchina@piboc.dvo.ru

Founder and first head of the Laboratory     
Valentin A. Stonik 
Academician of Russian Academy of Sciences, Professor, Scientific Director of the Institute
stonik@piboc.dvo.ru

Lab staff
Tatyana N. Makarieva (Major Researcher, Dr.Sci.), Sergey A. Avilov (Leading Researcher, Dr.Sci.), Vladimir I. Kalinin (Leading Researcher, Dr.Sci.), Alla A. Kicha (Leading Researcher, Dr.Sci.), Sergey N. Fedorov (Leading Researcher, Dr.Sci.), Larisa K. Shubina (Senior Researcher, Ph.D.), Ludmila P. Ponomarenko (Senior Researcher, Ph.D.), Timofey V. Malyarenko (Senior Researcher, Ph.D.), Alexandra S. Silchenko (Senior Researcher, Ph.D.), Alla G. Guzii (Senior Researcher, Ph.D.), Elena A. Santalova (Senior Researcher, Ph.D.), Sophya A. Kolesnikova (Senior Researcher, Ph.D.), Irina I. Kapustina (Researcher, Ph.D.), Alexander S. Antonov (Researcher, Ph.D.), Kseniya M. Tabakmaher (Researcher, Ph.D.), Ekaterina K. Kudryashova (Junior Researcher),Vladimir R. Stepanov (Leading Engineer)   

Main research areas
Research in the field of marine bioorganic chemistry (natural compounds). The aim of the research team is to obtain new fundamental knowledge in the field of marine bioorganic chemistry, including on structural diversity, biogenesis and biological functions of new secondary metabolites from marine macroorganisms of the World Ocean. 

We carry out
  • The searching of new biologically active natural compounds, the isolation and structural elucidation of these substances; 
  • Determination of absolute stereochemistry of compounds having asymmetric centers; 
  • The investigation of taxonomical distribution and biosynthetic pathways of some secondary metabolites; 
  • The study of physiological activity of natural products and their molecular mechanisms of action, the use of biologically active substances as models for chemical synthesis of their analogs; 
  • The study of the practical use of marine natural compounds to improve the systematics of marine organisms, in medicine and other areas. Creation of new drugs, biological products and reagents for scientific research on the basis of natural marine compounds. 
Our achievements 
  • The structures and functions of new marine low-molecular bioregulators (natural compounds), their taxonomic distribution, and some properties, including physiological activity, have been studied. The structure of more than 700 new marine natural compounds has been identified and established, which is about 3-4% of all known marine bioregulators. Among them: a large series of glycosides of a holostan series from sea cucumbers (sea cucumbers) and a norlanostan series from sponges; a series of polyhydroxylated steroids, their sulfates and glycosides from starfish, ophiures and sponges; new sterols; alkaloids; polyprenylated hydroquinones and chromenols; aromatic polysulfides; terpenoids and lipids from various marine organisms. 
  • The new classes of natural products were discovered: two-headed sphingolipids, alkaloidosteroids, ergoline and guanidine alkaloids, unusual lipids, penta- and hexanorlanostane glycosides, triterpenic glycosides with a new type of carbocyclic skeleton, etc. 
  • The taxonomic distribution on sea cucumber triterpene glycosides was analyzed and the system of the class Holothurioidea improved. The main evolutionary trends of triterpene glycosides were supposed on the base of its structural-functional relationships. 
  • The digestive function of polyhydroxylated steroids and related substances from starfishes was founded and their biosynthesis from dietary sterols was experimentally established. 
  • The series of tests for the investigation of biological activities of different classes of natural products was established. These provide a focused search of natural compounds with certain properties, such as anticancer or cancer preventive, in particular. The biological activity of variety of new natural products and synthetic substances have been studied, the perspective candidates for possible application in medicine and veterinary selected. 
Awards and prizes received in the team 
  • M.M. Shemyakin Prize of the RAS, 1995 (Academician Stonik V.A., DrSci Makarieva T.N.) 
  • First Prize of the Contest of Fundamental Works of the Far Eastern Branch of the Russian Academy of Sciences in honor of the 275th anniversary of the Russian Academy of Sciences, 1999 (group of authors) 
  • State scientific scholarship for eminent scientists, 2001-2003. (DrSci Makarieva T.N., DrSci Kalinin V.I.) 
  • Soros Professor 1999-2000 (Academician Stonik V.A.) 
  • Soros graduate student in 2000 (PhD student Lyakhova E.G.) 
  • Grants of the Foundation for Assistance to the Development of Domestic Science (D.Sci. Kalinin V.I. 2002-2003, PhD Ivanchina N.V. 2004-2005, PhD student Kolesnikova S.A. 2007 .) 
  • Scholarship of the Scientific Partnership Foundation for 2002-2003 for the work “Synthesis of mimetics of biologically active sulfated polyoxysteroids from sea sponges” (PhD student Santalova EA) 
  • Competition of scientific works of young scientists of the Far East Branch of the Russian Academy of Sciences, 2002, 1st place (Ph.D., Ivanchina N.V.) 
  • 2010 - Academician Stonik V.A. - Honorary Doctor of the Vietnamese Academy of Science and Technology. 
  • 2013 - Academician Stonik V.A. awarded the medal of the Order of Merit for the Fatherland, I degree 
  • Winners of G.B. Elyakov Far Eastern Branch of the Russian Academy of Sciences Prize for work in the field of organic and bioorganic chemistry: 
  • 2007 - PhD Silchenko A.S., 
  • 2009 - PhD Kolesnikova S.A. and PhD Lyakhova E.G., 
  • 2010 - DrSci Makarieva T.N., 
  • 2013 - PhD Dyshlovoi S.A., 
  • 2015 - PhD Malyarenko T.V., 
  • 2018 - DrSci Kicha A.A., DrSci Kalinovsky A.I., PhD Ivanchina N.V. 
International scientific cooperation 
  • Laboratory staff conduct joint research with: 
  • The Bio-Research Center Han-Sung (Busan, South Korea) and the Dong-A University Medical Research Center (Busan, South Korea).
  • Institute of Chemistry of Natural Compounds, Hanoi, Vietnam (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, Hanoi, Viet Nam). 
  • Institute of Marine Biochemistry, Hanoi, Vietnam (Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, Hanoi, Viet Nam). 
  • Korean Ocean Research and Development Institute, Laboratory of Marine Natural Products (Ansan, Seoul, South Korea). 
  • University Hospital Hamburg-Eppendorf (Universitätsklinikum Hamburg-Eppendorf, Germany). 
Selected articles 
1. Dyshlovoy S. A., Menchinskaya E. S., Venz S., Rast S., Amann K., Hauschild J., Otte K., Kalinin V. I., Silchenko A. S., Avilov S. A., Alsdorf W., Madanchi R., Bokemeyer C., Schumacher U., Walther R., Aminin D. L., Fedorov S. N., Shubina L. K., Stonik V. A., Balabanov S., Honecker F., von Amsberg G. The marine triterpene glycoside frondoside A exhibits activity in vitro and in vivo in prostate cancer // Int. J. Cancer. 2016. V. 138, N 10. P. 2450–2465. 
2. Guzii A.G., Makarieva T.N., Denisenko V.A., Dmitrenok P.S., Kuzmich A.S., Dyshlovoy S.A., von Amsberg G., Krasokhin V.B., Stonik V.A. Melonoside A: an ώ-glycosylated fatty acid amide from the Far Eastern marine sponge Melonanchora kobjakovae // Org. Lett. 2016. V. 18, N 14. P. 3478–3481. 
3. Dyshlovoy S.A., Venz S., Hauschild J., Tabakmakher K.M., Otte K., Madanchi R., Walther R., Guzii A.G., Makarieva T.N., Shubina L.K., Fedorov S.N., Stonik V.A., Bokemeyer C., Balabanov S., Honecker F., Amsberg G.V. Anti-migratory activity of marine alkaloid monanchocidin A – proteomics-based discovery and confirmation // Proteomics. 2016. V. 16, N 10. P. 1590–1603. 
4. Dyshlovoy S.A., Tabakmakher K.M., Hauschild J., Shchekaleva R.K., Otte K., Guzii A.G., Makarieva T.N., Kudryashova E.K., Fedorov S.N., Shubina L.K., Bokemeyer C., Honecker F., Stonik V.A., von Amsberg G. Guanidine alkaloids from the marine sponge Monanchora pulchra show cytotoxic properties and prevent EGF-induced neoplastic transformation in vitro // Mar. Drugs. 2016. V. 14, N 7. P. 133 [1–17]. 
5. Dyshlovoy S.A., Otte K., Alsdorf W.H., Hauschild J., Lange T., Venz S., Bauer C.K., Bahring R., Amann K., Mandanchi R., Schumacher U., Schroder-Schwarz J., Makarieva T.N., Guzii A.G., Tabakmakher K.M., Fedorov S.N., Shubina L.K., Kasheverov I.E., Ehmke H., Steuber T., Stonik V.A., Bokemeyer C., Honecker F., von Amsberg G. Marine compound rhizochalinin shows high in vitro and in vivo efficacy in castration resistant prostate cancer // Oncotarget. 2016. V. 7, N 43. P. 69703–69717. 
6. Malyarenko T.V., Kicha A.A., Kalinovsky A.I., Ivanchina N.V., Popov R.S., Pislyagin E.A., Menchinskaya E.S., Padmakuma K.P., Stonik V.A. Four new steroidal glycosides, protolinckiosides A – D, from the starfish Protoreaster linckii // Chem. & Biodiver. 2016. V. 13, N 8. P. 998–1007. 
7. Ponomarenko L.P., Kalinovsky A.I., Berdyshev D.V., Kuzmich A.S., Menchinskaya E.S., Pislyagin E.A., Kim N.Yu., Glazunov V.P., Dmitrenok P.S., Silchenko A.S., Avilov S.A., Gorovoy P.G., Stonik V.A. Chemical constituents of Ligularia alticola Worosch. leaves and their biological activities // Phytochem. Lett. 2016. V. 15. P. 46–52. 
8. Popov R.S., Ivanchina N.V., Kicha A.A., Malyarenko T.V., Dmitrenok P.S., Stonik V.A. LC-ESI MS/MS profiling of polar steroid metabolites of the Far Eastern starfish Patiria (=Asterina) pectinifera // Metabolomics. 2016. V. 12, N 2. P. 21 [1–18]. 
9. Popov R.S., Ivanchina N.V., Kicha A.A., Malyarenko T.V., Grebnev B.B., Dmitrenok P.S., Stonik V.A. LC–MS-based metabolome analysis on steroid metabolites from the starfish Patiria (=Asterina) pectinifera in conditions of active feeding and stresses // Metabolomics. 2016. V. 12, N 6. P. 106 [1–17]. 
10. Silchenko A.S., Kalinovsky A.I., Avilov S.A., Andryjaschenko P.V., Dmitrenok P.S., Kalinin V.I., Chingizova E.A., Minin K.V., Stonik V.A. Structures and biogenesis of fallaxosides D4, D5, D6 and D7, trisulfated non-holostane triterpene glycosides from the sea cucumber Cucumaria fallax // Molecules. 2016. V. 21, N 7. P. 939 [1–12]. 
11. Lyakhova E.G., Kolesnikova S.A., Kalinovsky A.I., Berdyshev D.V., Pislyagin E.A., Kuzmich A.S., Popov R.S., Dmitrenok P.S., Makarieva T.N., Stonik V.A. Lissodendoric acids A and B, manzamine-related alkaloids from the Far Eastern sponge Lissodendoryx florida // Org. Lett. 2017. V. 19, N 19. P. 5320–5323. 
12. Antonov A.S., Kalinovsky A.I., Afiyatullov Sh.Sh., Leshchenko E.V., Dmitrenok P.S., Yurchenko E.A. Kalinin V.I., Stonik V.A. Erylosides F8, V1–V3 amd W–W2 – new triterpene oligoglycosides from the Carribean sponge Erylus goffrilleri // Carbohydrate Res. 2017. V. 449. P. 153–159. 
13. Dyshlovoy S., von Amsberg G., Rast S., Hauschild J., Otte K., Alsdorf W., Madanchi R., Kalinin V.I., Silchenko A.S., Avilov S.A., Dierlamm J., Honecker F., Stonik V.A., Bokemeyer C. Frondoside A induces AIF-associated caspase-independent apoptosis in Burkitt’s lymphoma cells // Leukemia and Lymphoma. 2017. V. 58, N 12. P. 2905–2915. 
14. Dyshlovoy S.A., Madanchi R., Hauschild J., Otte K., Alsdorf W. H., Schumacher U., Kalinin V.I., Silchenko A.S., Avilov S.A., Honecker F., Stonik V.A., Bokemeyer C., von Amsberg G. The marine triterpene glycoside frondoside A induces p53-independent apoptosis and inhibits autophagy in urothelial carcinoma cells // BMC Cancer. 2017. V. 17, N 2. P. 93[1–10]. 
15. Dyshlovoy S.A., Otte K., Venz S., Hauschild J., Junker H., Makarieva T.N., Balabanov S., Alsdorf W.H., Madanchi R., Honecker F., Bokemeyer C., Stonik V.A., von Amsberg G. Proteomic-based investigations on the mode of action of the marine anticancer compound zhizochalinin // Proteomics. 2017. V. 17, N 11. P. 1700048[1–11]. 
16. Kicha A.A., Kalinovsky A.I., Ivanchina N.V., Malyarenko T.V., Dmitrenok P.S., Kuzmich A.S., Sokolova E.V., Stonik V.A. Furostane series asterosaponins and other unusual steroid oligoglycosides from the tropical starfish Pentaceraster regulus // J. Nat. Prod. 2017. V. 80, N 10. P. 2761–2770. 
17. Malyarenko O.S., Dyshlovoy S.A., Kicha A.A., Ivanchina N.V., Malyarenko T.V., Bokemeyer C., von Amsberg G., Stonik V.A., Ermakova S.P. The inhibitory activity of luzonicosides from the starfish Echinaster luzonicus against human melanoma cells // Mar. Drugs. 2017. V. 15, N 7. P. 227[1–11]. 
18. Popov R.S., Ivanchina N.V., Silchenko A.S., Avilov S.A., Kalinin V.I., Dolmatov I.Yu., Stonik V.A., Dmitrenok P.S. Metabolite profiling of triterpene glycosides of the Far Eastern sea cucumber Eupentacta fraudatrix and their distribution in various body components using LC-ESI QTOF-MS // Mar. Drugs. 2017. V. 15, N 10. P. 302[1–17]. 
19. Silchenko A.S., Kalinovsky A.I., Avilov S.A., Dmitrenok P.S., Kalinin V.I., Berdyshev D.V., Chingizova E.A., Andryjaschenko P.V., Minin K.V., Stonik V.A. Fallaxosides B1 and D3, triterpene glycosides with novel skeleton types of aglycones from the sea cucumber Cucumaria fallax // Tetrahedron. 2017. V. 73, N 17. P. 2335-2341. 
20. Dyshlovoy S.A., Otte K., Tabakmakher K.M., Hauschild J., Makarieva T.N., Shubina L.K., Fedorov S.N., Bokemeyer C., Stonik V.A., von Amsberg G. Synthesis and anticancer activity of the derivatives of marine compound rhizochalin in castration resistant prostate cancer // Oncotarget. 2018. V. 9, N 24. P. 16962–16973. 
21. Shubina L.K., Makarieva T.N., Guzii A.G., Denisenko V.A., Popov R.S., Dmitrenok P.S., Stonik V.A. Absolute configuration of the cytotoxic marine alkaloid monanchocidin A // J. Nat. Prod. 2018. V. 81, N 4. P. 1113–1115. 
22. Malyarenko T.V., Malyarenko O.S., Kicha A.A, Ivanchina N.V., Kalinovsky A.I., Dmitrenok P.S., Ermakova S.P., Stonik V.A. In vitro anticancer and proapoptotic activities of steroidal glycosides from the starfish Anthenea aspera // Mar. Drugs. 2018. V. 16, 420. 
23. Kolesnikova S.A., Lyakhova E.G., Kalinovsky A.I., Popov R.S., Yurchenko E.A., Stonik V.A. Oxysterols from a marine sponge Inflatella sp. and their action in 6-hydroxydopamine-induced cell model of Parkinson’s disease // Mar. Drugs. 2018. V. 16, 458.

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