Vestnik of the Far East Branch of the Russian Academy of SciencesVestnik of the Far East Branch of the Russian Academy of SciencesВестник Дальневосточного отделения Российской академии наук0869-7698The Russian Academy of Sciences68888810.31857/S0869769825010063HHRYRDChemical SciencesХимические наукиResearch ArticleStudies of secondary metabolites from marine sponges in the Laboratory of the Chemistry of Marine Natural Compounds of PIBOC FEB RAS in 2019–2023Исследования вторичных метаболитов из морских губок в лаборатории химии морских природных соединений ТИБОХ ДВО РАН в 2019–2023 годахhttps://orcid.org/0000-0001-7318-8866FedorovSergey N.ФедоровСергей Николаевич
Russian Federation

Doctor of Sciences in Chemistry, Leading Researcher

доктор химических наук, ведущий научный сотрудник

fedorov@piboc.dvo.ruhttps://orcid.org/0000-0002-2446-8543MakarievaTatiana N.МакарьеваТатьяна Николаевна
Russian Federation

Doctor of Sciences in Chemistry, Major Researcher

доктор химических наук, главный научный сотрудник

makarieva@piboc.dvo.ruGuziyAlla G.ГузийАлла Григорьевна
Russian Federation

Candidate of Sciences in Chemistry, Senior Researcher

кандидат химических наук, старший научный сотрудник

gagry@rambler.ruShubinaLarisa K.ШубинаЛариса Кимовна
Russian Federation

Candidate of Sciences in Chemistry, Senior Researcher

кандидат химических наук, старший научный сотрудник

shubina@piboc.dvo.ruTabakmacherKsenia M.ТабакмахерКсения Михайловна
Russian Federation

Candidate of Sciences in Chemistry, Researcher

кандидат химических наук, научный сотрудник

tabakmakher_km@piboc.dvo.ruhttps://orcid.org/0009-0006-8911-6377KudryashovaEkaterina K.КудряшоваЕкатерина Константиновна
Russian Federation

Junior Researcher

младший научный сотрудник

catrinog.81@mail.ruhttps://orcid.org/0000-0001-9503-4833SantalovaElena A.СанталоваЕлена Анатольевна
Russian Federation

Candidate of Sciences in Chemistry, Senior Researcher

кандидат химических наук, старший научный сотрудник

santalova@piboc.dvo.ruhttps://orcid.org/0000-0002-4405-8496KolesnikovaSophia A.КолесниковаСофья Александровна
Russian Federation

Candidate of Sciences in Chemistry, Senior Researcher

кандидат химических наук, старший научный сотрудник

sovin81@inbox.ruhttps://orcid.org/0000-0001-7974-8158KozhushnayaAnastasia B.КожушнаяАнастасия Борисовна
Russian Federation

Junior Researcher

младший научный сотрудник

kozhushnaia.ab@mail.ruhttps://orcid.org/0000-0001-9075-8584IvanchinaNatalia V.ИванчинаНаталья Владимировна
Russian Federation

Candidate of Sciences in Chemistry, Head of Laboratory

кандидат химических наук, заведующая лабораторией

ivanchina@piboc.dvo.ruElyakov Pacific Institute of Bioorganic Chemistry of FEB RASТихоокеанский институт биоорганической химии им. Г.Б. Елякова ДВО РАН04072025169880908202509082025Copyright ©; 2025, Russian Academy of SciencesCopyright ©; 2025, Российская академия наук2025Russian Academy of SciencesРоссийская академия наукhttps://journals.eco-vector.com/0869-7698/article/view/688888

Sea sponges are among the richest sources of biologically active compounds. Among them, terpenoids, alkaloids, polyketides, peptides, steroids, amino acids and other classes of compounds were found. They exhibit a wide range of biological activities such as cytotoxic, antitumor, antibacterial, antifungal, antiviral, anti-inflammatory, antioxidant, enzyme inhibitory and antimalarial. This review covers the structures and biological activities of secondary metabolites isolated from marine sponges in the Laboratory of the Chemistry of Marine Natural Compounds of the Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences and published in 2019–2023.

Морские губки относятся к числу богатейших источников биологически активных веществ. Среди них обнаружены терпеноиды, алкалоиды, поликетиды, пептиды, стероиды, аминокислоты и другие классы соединений. Они демонстрируют широкий спектр биологических активностей, таких как цитотоксическая, противоопухолевая, антибактериальная, противогрибковая, противовирусная, противовоспалительная, антиоксидантная, ферментингибирующая и противомалярийная. Этот обзор охватывает данные о структурах и биологических активностях вторичных метаболитов, выделенных из морских губок в лаборатории химии морских природных соединений ТИБОХ ДВО РАН и опубликованных в 2019–2023 гг.

marine spongessecondary metaboliteschemical structurebiological activityморские губкивторичные метаболитыхимическая структурабиологическая активностьVan Soest R.W.M., Boury-Esnault N., Vacelet J., Dohrmann M., Erpenbeck D., De Voogd N.J., Santodomingo N., Vanhoorne B., Kelly M., Hooper J.N.A. Global diversity of sponges (Porifera). PLoS ONE. 2012;(7):e35105.Van Soest R.W.M., Boury-Esnault N., Vacelet J., Dohrmann M., Erpenbeck D., De Voogd N.J., Santodomingo N., Vanhoorne B., Kelly M., Hooper J.N.A. Global diversity of sponges (Porifera) // PLoS ONE. 2012. Vol. 7. P. e35105.Paul V.J., Puglisi M.P., Ritson-Williams R. Marine chemical ecology. Nat. Prod. Rep. 2006;(23):153–180.Paul V.J., Puglisi M.P., Ritson-Williams R. Marine chemical ecology // Nat. Prod. Rep. 2006. Vol. 23. P. 153–180.Varijakzhan D., Loh J.Y., Yap W.S., Yusoff K., Seboussi R., Lim S.H.E., Lai K.S., Chong C.M. Bioactive compounds from marine sponges: Fundamentals and applications. Mar. Drugs. 2021;(19):246.Varijakzhan D., Loh J.Y., Yap W.S., Yusoff K., Seboussi R., Lim S.H.E., Lai K.S., Chong C.M. Bioactive compounds from marine sponges: Fundamentals and applications // Mar. Drugs. 2021.Vol. 19. P. 246.Li P., Lu H., Zhang Y., Zhang X., Liu L., Wang M., Liu L. The natural products discovered in marine sponge-associated microorganisms: structures, activities, and mining strategy. Front. Mar. Sci. 2023;(10):1191858.Li P., Lu H., Zhang Y., Zhang X., Liu L., Wang M., Liu L. The natural products discovered in marine sponge-associated microorganisms: structures, activities, and mining strategy // Front. Mar. Sci. 2023. Vol. 10. P. 1191858.Carroll A.R., Copp B.R., Davis R.A., Keyzers R.A., Prinsep M.R. Marine natural products. Nat. Prod. Rep. 2024;(41):162–207.Carroll A.R., Copp B.R., Davis R.A., Keyzers R.A., Prinsep M.R. Marine natural products // Nat. Prod. Rep. 2024. Vol. 41. P. 162–207.Hu Y., Chen J., Hu G., Yu J., Zhu X., Lin Y., Chen S., Yuan J. Statistical research on the bioactivity of new marine natural products discovered during the 28 years from 1985 to 2012. Mar. Drugs. 2015;(13):202–221.Hu Y., Chen J., Hu G., Yu J., Zhu X., Lin Y., Chen S., Yuan J. Statistical research on the bioactivity of new marine natural products discovered during the 28 years from 1985 to 2012 // Mar. Drugs. 2015. Vol. 13. P. 202–221.Makar’eva T.N., Guzii A.G., Shubina L.K., Lyakhova E.G., Kolesnikova S.A., Tabakmakher K.M., Kudryashova E.K., Stonik V.A. Poisk i strukturnoe izuchenie novykh bioaktivnykh vtorichnykh metabolitov iz morskikh bespozvonochnykh. Vestnik of the FEB RAS. 2019;(5):48–56. (In Russ.).Макарьева Т.Н., Гузий А.Г., Шубина Л.К., Ляхова Е.Г., Колесникова С.А., Табакмахер К.М., Кудряшова Е.К., Стоник В.А. Поиск и структурное изучение новых биоактивных вторичных метаболитов из морских беспозвоночных // Вестник ДВО РАН. 2019. № 5. С. 48–56.Makarieva T.N., Ogurtsova E.K., Denisenko V.A., Dmitrenok P.S., Tabakmakher K.M., Guzii A.G., Pislyagin E.A., Es′kov A.A., Kozhemyako V.B., Aminin D.L., Wang Y.-M., Stonik V.A. UrupocidinA: a new, inducing iNOS expression bicyclic guanidine alkaloid from the marine sponge Monanchora pulchra. Org. Lett. 2014;(16):4292–4295.Makarieva T.N., Ogurtsova E.K., Denisenko V.A., Dmitrenok P.S., Tabakmakher K.M., Guzii A.G., Pislyagin E.A., Es′kov A.A., Kozhemyako V.B., Aminin D.L., Wang Y.-M., Stonik V.A. Urupocidin A: a new, inducing iNOS expression bicyclic guanidine alkaloid from the marine sponge Monanchora pulchra // Org. Lett. 2014. Vol. 16. P. 4292–4295.Dyshlovoy S.A., Kudryashova E.K., Kaune M., Makarieva T.N., Shubina L.K., Busenbender T., Denisenko V.A., Popov R.S., Hauschild J., Fedorov S.N., Bokemeyer C., Graefen M., Stonik V.A. Urupocidin C: a new marine guanidine alkaloid which selectively kills prostate cancer cells via mitochondria targeting. Sci. Rep. 2020;(10):9764.Dyshlovoy S.A., Kudryashova E.K., Kaune M., Makarieva T.N., Shubina L.K., Busenbender T., Denisenko V.A., Popov R.S., Hauschild J., Fedorov S.N., Bokemeyer C., Graefen M., Stonik V.A. Urupocidin C: a new marine guanidine alkaloid which selectively kills prostate cancer cells via mitochondria targeting // Sci. Rep. 2020. Vol. 10. P. 9764.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;(14):133.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. Vol. 14. P. 133.Dyshlovoy S.A., Shubina L.K., Makarieva T.N., Guzii A.G., Hauschild J., Strewinsky N., Berdyshev D.V., Kudryashova E.K., Menshov A.S., Popov R.S., Dmitrenok P.S., Graefen M., Bokemeyer C., von Amsberg G. New guanidine alkaloids batzelladines O and P from the marine sponge Monanchora pulchra induce apoptosis and autophagy in prostate cancer cells. Mar. Drugs. 2022;(20):738.Dyshlovoy S.A., Shubina L.K., Makarieva T.N., Guzii A.G., Hauschild J., Strewinsky N., Berdyshev D.V., Kudryashova E.K., Menshov A.S., Popov R.S., Dmitrenok P.S., Graefen M., Bokemeyer C., fon Amsberg G. New guanidine alkaloids batzelladines O and P from the marine sponge Monanchora pulchra induce apoptosis and autophagy in prostate cancer cells // Mar. Drugs. 2022. Vol. 20. P. 738.Dyshlovoy S.A., Kaune M., Malte Kriegs M., Hauschild J., Busenbender T., Shubina L.K., Makarieva T.N., Bokemeyer C., Graefen M., Stonik V.A., von Amsberg G. Marine alkaloid monanchoxymycalin C induces prostate cancer cell death via specific activation of JNK1/2 kinase. Sci. Rep. 2020;(10):13178.Dyshlovoy S.A., Kaune M., Malte Kriegs M., Hauschild J., Busenbender T., Shubina L.K., Makarieva T.N., Bokemeyer C., Graefen M., Stonik V.A., von Amsberg G. Marine alkaloid monanchoxymycalin C induces prostate cancer cell death via specific activation of JNK1/2 kinase // Sci. Rep. 2020. Vol. 10. P. 13178.Makarieva T.N., Ivanchina N.V., Dmitrenok P.S., Guzii A., Stonik V.A., Dalisay D.S., Molinski T.F. Oceanalin B, a hybrid α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp. Mar. Drugs. 2021;(19):635.Makarieva T.N., Ivanchina N.V., Dmitrenok P.S., Guzii A., Stonik V.A., Dalisay D.S., Molinski T.F. Oceanalin B, a hybrid α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp. // Mar. Drugs. 2021. Vol. 19. P. 635.Makarieva T.N., Denisenko V.A., Dmitrenok P.S., Guzii A.G., Santalova E.A., Stonik V.A., MacMillan J.B., Molinski T.F. Oceanalin A, a hybrid α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp. Org. Lett. 2005;(7):2897–2900.Makarieva T.N., Denisenko V.A., Dmitrenok P.S., Guzii A.G., Santalova E.A., Stonik V.A., MacMillan J.B., Molinski T.F. Oceanalin A, a hybrid α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp. // Org. Lett. 2005. Vol. 7. P. 2897–2900.Guzii A.G., Makarieva T.N., Fedorov S.N., Menshov A.S., Denisenko V.A., Popov R.S., Yurchenko E.A., Menchinskaya E.S., Grebnev B.B., Iarotsckaia V.V., Kim N.Yu., Stonik V.A. Toporosides A and B, cyclopentenyl-containing ω-glycosylated fatty acid amides, and toporosides C and D from the northwestern pacific marine sponge Stelodoryx toporoki. J. Nat. Prod. 2022;(85):1186−1191.Guzii A.G., Makarieva T.N., Fedorov S.N., Menshov A.S., Denisenko V.A., Popov R.S., Yurchenko E.A., Menchinskaya E.S., Grebnev B.B., Iarotsckaia V.V., Kim N.Yu., Stonik V.A. Toporosides A and B, cyclopentenyl-containing ω-glycosylated fatty acid amides, and toporosides C and D from the northwestern pacific marine sponge Stelodoryx toporoki // J. Nat. Prod. 2022. Vol. 85. P. 1186−1191.Einarsdottir E., Liu H.B., Freysdottir J., Gotfredsen C.H., Omarsdottir S. Immunomodulatory N-acyl dopamine glycosides from the Icelandic marine sponge Myxilla incrustans collected at a hydrothermal Vent Site. Planta Med. 2016;(82):903–909.Einarsdottir E., Liu H.B., Freysdottir J., Gotfredsen C.H., Omarsdottir S. Immunomodulatory N-acyl dopamine glycosides from the Icelandic marine sponge Myxilla incrustans collected at a hydrothermal Vent Site // Planta Med. 2016. Vol. 82. P. 903–909.Kudryashova E.K., Makarieva T.N., Shubina L.K., Guzii A.G., Popov R.S., Menshov A.S., Berdyshev D.V., Pislyagin E.A., Menchinskaya E.S., Grebnev B.B., Stonik V.A. Assimiloside A, a glycolipid with immunomodulatory activity from the Northwestern Pacific marine sponge Hymeniacidon assimilis. J. Nat. Prod. 2023;(86):2073–2078.Kudryashova E.K., Makarieva T.N., Shubina L.K., Guzii A.G., Popov R.S., Menshov A.S., Berdyshev D.V., Pislyagin E.A., Menchinskaya E.S., Grebnev B.B., Stonik V.A. Assimiloside A, a glycolipid with immunomodulatory activity from the Northwestern Pacific marine sponge Hymeniacidon assimilis // J. Nat. Prod. 2023. Vol. 86. P. 2073–2078.Fan B.Y., Lu Y., Yang M., Li J.L., Chen G.T. Evolvulins I and II, resin glycosides with a trihydroxy aglycone unit from Evolvulus alsinoides. Org. Lett. 2019;(21):6548–6551.Fan B.Y., Lu Y., Yang M., Li J.L., Chen G.T. Evolvulins I and II, resin glycosides with a trihydroxy aglycone unit from Evolvulus alsinoides // Org. Lett. 2019. Vol. 21. P. 6548–6551.Yin F., Hu L., Lou F., Pan R. Dammarane-type glycosides from Gynostemma pentaphyllum. J. Nat. Prod. 2004;(67):942–952.Yin F., Hu L., Lou F., Pan R. Dammarane-type glycosides from Gynostemma pentaphyllum // J. Nat. Prod. 2004. Vol. 67. P. 942–952.Dyshlovoy S.A., Fedorov S.N., Svetashev V.I., Makarieva T.N., Kalinovsky A.I., Moiseenko O.P., Krasokhin V.B., Shubina L.K., Guzii A.G., von Amsberg G., Stonik V.A. 1-O-Alkylglycerol ethers from the marine sponge Guitarra abbotti and their cytotoxic activity. Mar. Drugs. 2022;(20):409.Dyshlovoy S.A., Fedorov S.N., Svetashev V.I., Makarieva T.N., Kalinovsky A.I., Moiseenko O.P., Krasokhin V.B., Shubina L.K., Guzii A.G., von Amsberg G., Stonik V.A. 1-O-Alkylglycerol ethers from the marine sponge Guitarra abbotti and their cytotoxic activity // Mar. Drugs. 2022. Vol. 20. P. 409.Santalova Е.А., Denisenko V.А., Dmitrenok P.S. Structural analysis of oxidized cerebrosides from the extract of deep-sea sponge Aulosaccus sp.: Occurrence of amide-linked allylically oxygenated fatty acids. Molecules. 2020;(25):6047.Santalova Е.А., Denisenko V.А., Dmitrenok P.S. Structural analysis of oxidized cerebrosides from the extract of deep-sea sponge Aulosaccus sp.: Occurrence of amide-linked allylically oxygenated fatty acids // Molecules. 2020. Vol. 25. P. 6047.Santalova Е.А., Kuzmich A.S., Chingizova E.A., Menchinskaya E.S., Pislyagin E.A., Dmitrenok P.S. Phytoceramides from the marine sponge Monanchora clathrata: structural analysis and cytoprotective effects. Biomolecules. 2023;(13):677.Santalova Е.А., Kuzmich A.S., Chingizova E.A., Menchinskaya E.S., Pislyagin E.A., Dmitrenok P.S. Phytoceramides from the marine sponge Monanchora clathrata: structural analysis and cytoprotective effects // Biomolecules. 2023. Vol. 13. P. 677.Dyshlovoy S.A., Hauschild J., Venz S., Krisp C., Kolbe K., Zapf S., Heinemann S., Fita K.D., Shubina L.K., Makarieva T.N., Guzii A.G., Rohlfing T., Kaune M., Busenbender T., Mair T., Moritz M., Poverennaya E.V., Schlüter H., Serdyuk V., Stonik V.A., Dierlamm J., Bokemeyer C., Mohme M., Westphal M., Lamszus K., von Amsberg G., Maire C.L. Rhizochalinin exhibits anticancer activity and synergizes with EGFR inhibitors in glioblastoma in vitro models. Mol. Pharm. 2023;(20):4994–5005.Dyshlovoy S.A., Hauschild J., Venz S., Krisp C., Kolbe K., Zapf S., Heinemann S., Fita K.D., Shubina L.K., Makarieva T.N., Guzii A.G., Rohlfing T., Kaune M., Busenbender T., Mair T., Moritz M., Poverennaya E.V., Schlüter H., Serdyuk V., Stonik V.A., Dierlamm J., Bokemeyer C., Mohme M., Westphal M., Lamszus K., von Amsberg G., Maire C.L. Rhizochalinin exhibits anticancer activity and synergizes with EGFR inhibitors in glioblastoma in vitro models // Mol. Pharm. 2023. Vol. 20. P. 4994–5005.Makarieva T., Denisenko V., Stonik V., Milgrom Y.M., Rashkes Y.V. Rhizochalin, a novel secondary metabolite of mixed biosynthesis from the sponge Rhizochalina incrustata. Tetrahedron Lett. 1989;(30):6581−6584.Makarieva T., Denisenko V., Stonik V., Milgrom Y.M., Rashkes Y.V. Rhizochalin, a novel secondary metabolite of mixed biosynthesis from the sponge Rhizochalina incrustata // Tetrahedron Lett. 1989. Vol. 30. P. 6581−6584.Tabakmakher K.M., Makarieva T.N., Denisenko V.A., Popov R.S., Dmitrenok P.S., Dyshlovoy S.A., Grebnev B.B., Bokemeyer C., von Amsberg G., Cuong N.X. New trisulfated steroids from the Vietnamese marine sponge Halichondria vansoesti and their PSA expression and glucose uptake inhibitory activities. Mar. Drugs. 2019;(17):E445.Tabakmakher K.M., Makarieva T.N., Denisenko V.A., Popov R.S., Dmitrenok P.S., Dyshlovoy S.A., Grebnev B.B., Bokemeyer C., von Amsberg G., Cuong N.X. New trisulfated steroids from the Vietnamese marine sponge Halichondria vansoesti and their PSA expression and glucose uptake inhibitory activities // Mar. Drugs. 2019. Vol. 17. P. E445.Guzii A.G., Makarieva T.N., Denisenko V.A., Dmitrenok P.S., Burtseva Y.V., Krasokhin V.B., Stonik V.A. Topsentiasterol sulfates with novel iodinated and chlorinated side chains from the marine sponge Topsentia sp. Tetrahedron Lett. 2008;(49):7191–7193.Guzii A.G., Makarieva T.N., Denisenko V.A., Dmitrenok P.S., Burtseva Y.V., Krasokhin V.B., Stonik V.A. Topsentiasterol sulfates with novel iodinated and chlorinated side chains from the marine sponge Topsentia sp. // Tetrahedron Lett. 2008. Vol. 49. P. 7191–7193.Fusetani N., Takahashi M., Matsunaga S. Topsentiasterol sulfates, antimicrobial sterolsulfates possessing novel side chains, from a marine sponge, Topsentia sp. Tetrahedron. 1994;(50):7765–7770.Fusetani N., Takahashi M., Matsunaga S. Topsentiasterol sulfates, antimicrobial sterol sulfates possessing novel side chains, from a marine sponge, Topsentia sp. // Tetrahedron. 1994. Vol. 50. P. 7765–7770.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;(9):16962–16973.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 cast ration resistant prostate cancer // Oncotarget. 2018. Vol. 9. P. 16962–16973.Antonarakis E.S., Lu C., Wang H., Luber B., Nakazawa M., Roeser J.C., Chen Y., Mohammad T.A., Chen Y., Fedor H.L., Lotan T.L., Zheng Q., De Marzo A.M., Isaacs J.T., Isaacs W.B., Nadal R., Paller C.J., Denmeade S.R., Carducci M.A., Eisenberger M.A., Luo J. AR-V7 and resistance to enzalutamide and abiraterone in prostate cancer. New Engl. J. Med. 2014;(371):1028–1038.Antonarakis E.S., Lu C., Wang H., Luber B., Nakazawa M., Roeser J.C., Chen Y., Mohammad T.A., Chen Y., Fedor H.L., Lotan T.L., Zheng Q., De Marzo A.M., Isaacs J.T., Isaacs W.B., Nadal R., Paller C.J., Denmeade S.R., Carducci M.A., Eisenberger M.A., Luo J. AR-V7 and resistance to enzalutamide and abiraterone in prostate cancer // New Engl. J. Med. 2014. Vol. 371. P. 1028–1038.Shubina L.K., Makarieva T.N., Denisenko V.A., Popov R.S., Dyshlovoy S.A., Grebnev B.B., Dmitrenok P.S., von Amsberg G., Stonik V.A. Gracilosulfates A–G, monosulfated polyoxygenated steroids from the marine sponge Haliclona gracilis. Mar. Drugs. 2020;(18):454.Shubina L.K., Makarieva T.N., Denisenko V.A., Popov R.S., Dyshlovoy S.A., Grebnev B.B., Dmitrenok P.S., von Amsberg G., Stonik V.A. Gracilosulfates A–G, monosulfated polyoxygenated steroids from the marine sponge Haliclona gracilis // Mar. Drugs. 2020. Vol. 18. P. 454.Santalova E.A., Denisenko V.A. Steroids from a Far-Eastern glass sponge Aulosaccus sp. Nat. Prod. Commun. 2019;(14):1–8.Santalova E.A., Denisenko V.A. Steroids from a Far-Eastern glass sponge Aulosaccus sp. // Nat. Prod. Commun. 2019. Vol. 14. P. 1–8.Stonik V.A., Kolesnikova S.A. Malabaricane and isomalabaricane triterpenoids, including their glycoconjugated forms. Mar. Drugs. 2021;(19):327.Stonik V.A., Kolesnikova S.A. Malabaricane and isomalabaricane triterpenoids, including their glycoconjugated forms // Mar. Drugs. 2021. Vol. 19. P. 327.Cárdenas P., Gamage J., Hettiarachchi C.M., Gunasekera S. Good practices in sponge natural product studies: Revising vouchers with isomalabaricane triterpenes. Mar. Drugs. 2022;(20):190.Cárdenas P., Gamage J., Hettiarachchi C.M., Gunasekera S. Good practices in sponge natural product studies: Revising vouchers with isomalabaricane triterpenes // Mar. Drugs. 2022. Vol. 20. P. 190.Kolesnikova S.A., Lyakhova E.G., Kalinovsky A.I., Berdyshev D.V., Pislyagin E.A., Popov R.S., Grebnev B.B., Makarieva T.N., Minh C.V., Stonik V.A. Cyclobutastellettolides A and B, C19 norterpenoids from a Stelletta sp. marine sponge. J. Nat. Prod. 2019;(82):3196−3200.Kolesnikova S.A., Lyakhova E.G., Kalinovsky A.I., Berdyshev D.V., Pislyagin E.A., Popov R.S., Grebnev B.B., Makarieva T.N., Minh C.V., Stonik V.A. Cyclobutastellettolides A and B, C19 norterpenoids from a Stelletta sp. marine sponge // J. Nat. Prod. 2019. Vol. 82. P. 3196−3200.Tang S., Pei Y., Fu H., Deng Z., Li J., Proksch P., Lin W. Jaspolides A–F, six new isomalabricane-type terpenoids from the sponge Jaspis sp. Chem. Pharm. Bull. 2006;(54):4–8.Tang S., Pei Y., Fu H., Deng Z., Li J., Proksch P., Lin W. Jaspolides A–F, six new isomalabricane-type terpenoids from the sponge Jaspis sp. // Chem. Pharm. Bull. 2006. Vol. 54. P. 4–8.Li J., Xu B., Cui J., Deng Z., de Voogd N.J., Proksch P., Lin W. Globostelletins A–I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata. Bioorg. Med. Chem. 2010;(18):4639–4647.Li J., Xu B., Cui J., Deng Z., de Voogd N.J., Proksch P., Lin W. Globostelletins A–I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata // Bioorg. Med. Chem. 2010. Vol. 18. P. 4639–4647.Li J., Zhu H., Ren J., Deng Z., de Voogd N.J., Proksch P., Lin W. Globostelletins J–S, isomalabaricanes with unusual cyclopentane sidechains from the marine sponge Rhabdastrella globostellata. Tetrahedron. 2012;(68):559–565.Li J., Zhu H., Ren J., Deng Z., de Voogd N.J., Proksch P., Lin W. Globostelletins J–S, isomalabaricanes with unusual cyclopentane sidechains from the marine sponge Rhabdastrella globostellata // Tetrahedron. 2012.Vol. 68. P. 559–565.Kolesnikova S.A., Lyakhova E.G., Kozhushnaya A.B., Kalinovsky A.I., Berdyshev D.V., Popov R.S., Stonik V.A. New isomalabaricane-derived metabolites from a Stelletta sp. marine sponge. Molecules. 2021;(26):678.Kolesnikova S.A., Lyakhova E.G., Kozhushnaya A.B., Kalinovsky A.I., Berdyshev D.V., Popov R.S., Stonik V.A. New isomalabaricane-derived metabolites from a Stelletta sp. marine sponge // Molecules. 2021. Vol. 26. P. 678.Kozhushnaya A.B., Kolesnikova S.A., Yurchenko E.A., Lyakhova E.G., Menshov A.S., Kalinovsky A.I., Popov R.S., Dmitrenok P.S., Ivanchina N.V. Rhabdastrellosides A and B: two new isomalabaricane glycosides from the marine sponge Rhabdastrella globostellata, and their cytotoxic and cytoprotective effects. Mar. Drugs. 2023;(21):554.Kozhushnaya A.B., Kolesnikova S.A., Yurchenko E.A., Lyakhova E.G., Menshov A.S., Kalinovsky A.I., Popov R.S., Dmitrenok P.S., Ivanchina N.V. Rhabdastrellosides A and B: two new isomalabaricane glycosides from the marine sponge Rhabdastrella globostellata, and their cytotoxic and cytoprotective effects // Mar. Drugs. 2023. Vol. 21. P. 554.Ivanchina N.V., Kalinin V.I. Triterpene and steroid glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities. Molecules. 2023;(28):2503.Ivanchina N.V., Kalinin V.I. Triterpene and steroid glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities // Molecules. 2023. Vol. 28. P. 2503.Tabudravu J.N., Jaspars M. Stelliferin riboside, a triterpene monosaccharide isolated from the Fijian sponge Geodia globostellifera. J. Nat. Prod. 2001;(64):813–815.Tabudravu J.N., Jaspars M. Stelliferin riboside, a triterpene monosaccharide isolated from the Fijian sponge Geodia globostellifera // J. Nat. Prod. 2001. Vol. 64. P. 813–815.Fouad M., Edrada R.A., Ebel R., Wray V., Muller W.E.G., Lin W.H., Proksch P. Cytotoxic isomalabaricane triterpenoids from the marine sponge Rhabdastrella globostellata. J. Nat. Prod. 2006;(69):211–218.Fouad M., Edrada R.A., Ebel R., Wray V., Muller W.E.G., Lin W.H., Proksch P. Cytotoxic isomalabaricane triterpenoids from the marine sponge Rhabdastrella globostellata // J. Nat. Prod. 2006. Vol. 69. P. 211–218.Clement J.A., Li M., Hecht S.M., Kingston D.I. Bioactive isomalabaricane triterpenoids from Rhabdastrella globostellata that stabilize the binding of DNA polymerase β to DNA. J. Nat. Prod. 2006;(69):373–376.Clement J.A., Li M., Hecht S.M., Kingston D.I. Bioactive isomalabaricane triterpenoids from Rhabdastrella globostellata that stabilize the binding of DNA polymerase β to DNA // J. Nat. Prod. 2006. Vol. 69. P. 373–376.Dyshlovoy S.A., Shubina L.K., Makarieva T.N., Hauschild J., Strewinsky N., Guzii A.G., Menshov A.S., Popov R.S., Grebnev B.B., Busenbender T., Oh-Hohenhorst S.J., Maurer T., Tilki D., Graefen M., Bokemeyer C., Stonik V.A., von Amsberg G. New diterpenes from the marine sponge Spongionella sp. overcome drug resistance in prostate cancer by inhibition of P-glycoprotein. Sci. Rep. 2022;(12):13570.Dyshlovoy S.A., Shubina L.K., Makarieva T.N., Hauschild J., Strewinsky N., Guzii A.G., Menshov A.S., Popov R.S., Grebnev B.B., Busenbender T., Oh-Hohenhorst S.J., Maurer T., Tilki D., Graefen M., Bokemeyer C., Stonik V.A., von Amsberg G. New diterpenes from the marine sponge Spongionella sp. overcome drug resistance in prostate cancer by inhibition of P-glycoprotein // Sci. Rep. 2022. Vol. 12. P. 13570.