<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE root>
<article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:ali="http://www.niso.org/schemas/ali/1.0/" article-type="review-article" dtd-version="1.2" xml:lang="en"><front><journal-meta><journal-id journal-id-type="publisher-id">Vestnik of the Far East Branch of the Russian Academy of Sciences</journal-id><journal-title-group><journal-title xml:lang="en">Vestnik of the Far East Branch of the Russian Academy of Sciences</journal-title><trans-title-group xml:lang="ru"><trans-title>Вестник Дальневосточного отделения Российской академии наук</trans-title></trans-title-group></journal-title-group><issn publication-format="print">0869-7698</issn><publisher><publisher-name xml:lang="en">The Russian Academy of Sciences</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="publisher-id">676052</article-id><article-id pub-id-type="doi">10.31857/S0869769824030049</article-id><article-id pub-id-type="edn">ISNKLF</article-id><article-categories><subj-group subj-group-type="toc-heading" xml:lang="en"><subject>Chemical Sciences. Bioorganic chemistry</subject></subj-group><subj-group subj-group-type="toc-heading" xml:lang="ru"><subject>Химические науки. Биоорганическая химия</subject></subj-group><subj-group subj-group-type="article-type"><subject>Review Article</subject></subj-group></article-categories><title-group><article-title xml:lang="en">Structural studies on sea cucumber triterpene glycosides and sterols in G.B. Elyakov Pacific Institute of Bioorganic Chemistry of FEB RAS. The recent achievements</article-title><trans-title-group xml:lang="ru"><trans-title>Исследование структур тритерпеновых гликозидов и стеринов из голотурий в Тихоокеанском институте биоорганической химии им. Г.Б. Елякова ДВО РАН. Последние достижения</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Kalinin</surname><given-names>Vladimir I.</given-names></name><name xml:lang="ru"><surname>Калинин</surname><given-names>Владимир Иванович</given-names></name></name-alternatives><address><country country="RU">Russian Federation</country></address><bio xml:lang="en"><p>Doctor of Sciences in Biology, Leading Researcher</p></bio><bio xml:lang="ru"><p>доктор биологических наук, ведущий научный сотрудник</p></bio><email>kalininv@piboc.dvo.ru</email><xref ref-type="aff" rid="aff1"/></contrib><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Avilov</surname><given-names>Sergey A.</given-names></name><name xml:lang="ru"><surname>Авилов</surname><given-names>Сергей Анатольевич</given-names></name></name-alternatives><address><country country="RU">Russian Federation</country></address><bio xml:lang="en"><p>Doctor of Sciences in Chemistry, Leading Researcher</p></bio><bio xml:lang="ru"><p>доктор химических наук, ведущий научный сотрудник</p></bio><email>avilov-1957@mail.ru</email><xref ref-type="aff" rid="aff1"/></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-9367-1158</contrib-id><name-alternatives><name xml:lang="en"><surname>Silchenko</surname><given-names>Alexandra S.</given-names></name><name xml:lang="ru"><surname>Сильченко</surname><given-names>Александра Сергеевна</given-names></name></name-alternatives><address><country country="RU">Russian Federation</country></address><bio xml:lang="en"><p>Doctor of Sciences in Chemistry, Leading Researcher</p></bio><bio xml:lang="ru"><p>доктор химических наук, ведущий научный сотрудник</p></bio><email>sialexandra@mail.ru</email><xref ref-type="aff" rid="aff1"/></contrib><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Kapustina</surname><given-names>Irina I.</given-names></name><name xml:lang="ru"><surname>Капустина</surname><given-names>Ирина Ивановна</given-names></name></name-alternatives><address><country country="RU">Russian Federation</country></address><bio xml:lang="en"><p>Candidate of Science in Chemistry, Researcher</p></bio><bio xml:lang="ru"><p>кандидат химических наук, научный сотрудник</p></bio><email>ikapust@rambler.ru</email><xref ref-type="aff" rid="aff1"/></contrib><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Ponomarenko</surname><given-names>Ludmila P.</given-names></name><name xml:lang="ru"><surname>Пономаренко</surname><given-names>Людмила Петровна</given-names></name></name-alternatives><address><country country="RU">Russian Federation</country></address><bio xml:lang="en"><p>Candidate of Science in Chemistry, Senior Researcher</p></bio><bio xml:lang="ru"><p>кандидат химических наук, старший научный сотрудник</p></bio><email>ponjmarenko@inbox.ru</email><xref ref-type="aff" rid="aff1"/></contrib></contrib-group><aff-alternatives id="aff1"><aff><institution xml:lang="en">G.B. Elyakov Pacific Institute of Bioorganic Chemistry, FEB RAS</institution></aff><aff><institution xml:lang="ru">Тихоокеанский институт биоорганической химии им. Г.Б. Елякова ДВО РАН</institution></aff></aff-alternatives><pub-date date-type="pub" iso-8601-date="2024-06-15" publication-format="electronic"><day>15</day><month>06</month><year>2024</year></pub-date><issue>3</issue><issue-title xml:lang="ru"/><fpage>69</fpage><lpage>89</lpage><history><date date-type="received" iso-8601-date="2025-02-28"><day>28</day><month>02</month><year>2025</year></date></history><permissions><copyright-statement xml:lang="en">Copyright ©; 2024, Russian Academy of Sciences</copyright-statement><copyright-statement xml:lang="ru">Copyright ©; 2024, Российская академия наук</copyright-statement><copyright-year>2024</copyright-year><copyright-holder xml:lang="en">Russian Academy of Sciences</copyright-holder><copyright-holder xml:lang="ru">Российская академия наук</copyright-holder></permissions><self-uri xlink:href="https://journals.eco-vector.com/0869-7698/article/view/676052">https://journals.eco-vector.com/0869-7698/article/view/676052</self-uri><abstract xml:lang="en"><p>The article briefly discusses main achievements in the investigation of structures of sea cucumber triterpene glycosides and sterols in G.B. Elyakov Pacific Institute of Bioorganic Chemistry of FEB RAS in the period from 2019 by now, including isolation and structural elucidation of more than 80 new triterpene glycosides from Pacific Ocean sea cucumbers while several of<bold> </bold>them possess unique structural features.</p></abstract><trans-abstract xml:lang="ru"><p>Кратко обсуждаются основные достижения в исследовании строения тритерпеновых гликозидов и стеринов голотурий в Тихоокеанском институте биоорганической химии им. Г.Б. Елякова ДВО РАН в период с 2019 г. по настоящее время, главным из которых является выделение и установление структуры более 80 новых тритерпеновых гликозидов из тихоокеанских голотурий, причем ряд из них обладает уникальными структурными чертами.</p></trans-abstract><kwd-group xml:lang="en"><kwd>sea cucumbers</kwd><kwd>triterpene glycosides</kwd><kwd>sterols</kwd></kwd-group><kwd-group xml:lang="ru"><kwd>слова: голотурии</kwd><kwd>тритерпеновые гликозиды</kwd><kwd>стерины</kwd></kwd-group></article-meta></front><body></body><back><ref-list><ref id="B1"><label>1.</label><citation-alternatives><mixed-citation xml:lang="en">Kalinin V. I., Aminin D. L., Avilov S. A., Silchenko A. S., Stonik V. A. Triterpene glycosides from sea cucumbers (Holothurioidae, Echinodermata), biological activities and functions. In: Studies in Natural Product Chemistry (Bioactive Natural Products). Atta-ur-Rahman (ed.). The Netherlands: Elsevier Science Publisher; 2008. Vol. 35. P. 135–196.</mixed-citation><mixed-citation xml:lang="ru">Kalinin V. I., Aminin D. L., Avilov S. A., Silchenko A. S., Stonik V. A. Triterpene glycosides from sea cucumbers (Holothurioidae, Echinodermata), biological activities and functions // Studies in Natural Product Chemistry (Bioactive Natural Products) / ed. Atta-ur-Rahman. The Netherlands: Elsevier Science Publisher, 2008. Vol. 35. P. 135–196.</mixed-citation></citation-alternatives></ref><ref id="B2"><label>2.</label><citation-alternatives><mixed-citation xml:lang="en">Aminin D. L., Pislyagin E. A., Menchinskaya E. S., Silchenko A. S., Avilov S. A., Kalinin V. I. Immunomodulatory and anticancer activity of sea cucumber triterpene glycosides. In: Studies in Natural Products Chemistry. Atta-ur-Rahman (ed.). The Netherlands: Elsevier Science B. V.; 2014. Vol. 41. P. 75–94.</mixed-citation><mixed-citation xml:lang="ru">Aminin D. L., Pislyagin E. A., Menchinskaya E. S., Silchenko A. S., Avilov S. A., Kalinin V. I. Immunomodulatory and anticancer activity of sea cucumber triterpene glycosides // Studies in Natural Products Chemistry / ed. Atta-ur-Rahman. The Netherlands: Elsevier Science B. V., 2014. Vol. 41. P. 75–94.</mixed-citation></citation-alternatives></ref><ref id="B3"><label>3.</label><citation-alternatives><mixed-citation xml:lang="en">Aminin D. L., Menchinskaya E. S., Pisliagin E. A., Silchenko A. S., Avilov S. A., Kalinin V. I. Anticancer activity of sea cucumber triterpene glycosides. Mar. Drugs. 2015;13:1202–1223.</mixed-citation><mixed-citation xml:lang="ru">Aminin D. L., Menchinskaya E. S., Pisliagin E. A., Silchenko A. S., Avilov S. A., Kalinin V. I. Anticancer activity of sea cucumber triterpene glycosides // Mar. Drugs. 2015. Vol. 13. P. 1202–1223.</mixed-citation></citation-alternatives></ref><ref id="B4"><label>4.</label><citation-alternatives><mixed-citation xml:lang="en">Kalinin V. I., Avilov S. A., Silchenko A. S., Stonik V. A. Triterpene glycosides of sea cucumbers (Holothuroidea, Echinodermata) as taxonomic markers. Nat. Prod. Commun. 2015;10(1):21–26.</mixed-citation><mixed-citation xml:lang="ru">Kalinin V. I., Avilov S. A., Silchenko A. S., Stonik V. A. Triterpene glycosides of sea cucumbers (Holothuroidea, Echinodermata) as taxonomic markers // Nat. Prod. Commun. 2015. Vol. 10, N1. P. 21–26.</mixed-citation></citation-alternatives></ref><ref id="B5"><label>5.</label><citation-alternatives><mixed-citation xml:lang="en">Kalinin V. I., Silchenko A. S., Avilov S. A. Triterpenovye glikozidy goloturij. Taksonomicheskoe znachenie i ekologicheskaya rol = [Triterpene glycosides of sea cucumbers. Taxonomic significance and ekological role]. Izvestia Rossijskoj Akademii Nauk. Ser. Biologicheskaya. 2016;(6):616–624. (In Russ.).</mixed-citation><mixed-citation xml:lang="ru">Калинин В. И., Сильченко А. С., Авилов С. А. Тритерпеновые гликозиды голотурий. Таксономическое значение и экологическая роль // Известия РАН. Серия биологическая. 2016. № 6. С. 616–624.</mixed-citation></citation-alternatives></ref><ref id="B6"><label>6.</label><citation-alternatives><mixed-citation xml:lang="en">Kalinin V. I., Avilov S. A., Silchenko A. S. Issledovanie struktury triterpenovych glycozidov goloturij w Tikhookeanskom Institute Bioorganicheskoj Khimii im. G. B. Elyakova DVO RAN = [The studies of structures of sea cucumber triterpene glycosides in G. B. Elyakov Pacific Institute of Bioorganic Chemistry of the FEB RAS]. Vestnik of the FEB RAS. 2019;(5):40–46. (In Russ.).</mixed-citation><mixed-citation xml:lang="ru">Калинин В. И., Авилов С. А., Сильченко А. С. Исследование структуры тритерпеновых гликозидов голотурий в Тихоокеанском институте биоорганической химии им. Г. Б. Елякова ДВО РАН // Вестн. ДВО РАН. 2019. № 5. С. 40–46.</mixed-citation></citation-alternatives></ref><ref id="B7"><label>7.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Avilov S. A., Kalinovsky A. I., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S. Psolusosides C1, C2, and D1, novel triterpene hexaosides from the sea cucumber Psolus fabricii (Psolidae, Dendrochirotida). Nat. Prod. Commun. 2018;13:1623–1628.</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Avilov S. A., Kalinovsky A. I., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S. Psolusosides C1, C2, and D1, novel triterpene hexaosides from the sea cucumber Psolus fabricii (Psolidae, Dendrochirotida) // Nat. Prod. Commun. 2018. Vol. 13. P. 1623–1628.</mixed-citation></citation-alternatives></ref><ref id="B8"><label>8.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Avilov S. A., Kalinovsky A. I., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S., Popov R. S., Chingizova E. A., Kasakin M. F. Psolusosides C3 and D2–D5, five novel triterpene hexaosides from the sea cucumber Psolus fabricii (Psolidae, Dendrochirotida): chemical structures and bioactivities. Nat. Prod. Commun. 2019:1–12. DOI: 10.1177/1934578X19861253.</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Avilov S. A., Kalinovsky A. I., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S., Popov R. S., Chingizova E. A., Kasakin M. F. Psolusosides C3 and D2–D5, five novel triterpene hexaosides from the sea cucumber Psolus fabricii (Psolidae, Dendrochirotida): chemical structures and bioactivities // Nat. Prod. Commun. 2019. P. 1–12. DOI: 10.1177/1934578X19861253.</mixed-citation></citation-alternatives></ref><ref id="B9"><label>9.</label><citation-alternatives><mixed-citation xml:lang="en">Le H., Vien L. T., Hanh T. T.H., Thanh N. V., Cuong N. X., Nam N. H., Thung D. C., Ivanchina N. V., Thao D. T., Dmitrenok P. S., Kicha A. A., Kiem P. V., Minh C. V. Triterpene glycosides from the Vietnamese sea cucumber Holothuria edulis. Nat. Prod. Res. 2020;34:1061–1067.</mixed-citation><mixed-citation xml:lang="ru">Le H., Vien L. T., Hanh T. T.H., Thanh N. V., Cuong N. X., Nam N. H., Thung D. C., Ivanchina N. V., Thao D. T., Dmitrenok P. S., Kicha A. A., Kiem P. V., Minh C. V. Triterpene glycosides from the Vietnamese sea cucumber Holothuria edulis // Nat. Prod. Res. 2020. Vol. 34. P. 1061–1067.</mixed-citation></citation-alternatives></ref><ref id="B10"><label>10.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S., Popov R. S., Chingizova E. A., Ermakova S. P., Malyarenko O. S. Structures and bioactivities of six new triterpene glycosides, psolusosides E, F, G, H, H1, and I and the corrected structure of psolusoside B from the sea cucumber Psolus fabricii. Mar. Drugs. 2019;17. 358 [1–24].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S., Popov R. S., Chingizova E. A., Ermakova S. P., Malyarenko O. S. Structures and bioactivities of six new triterpene glycosides, psolusosides E, F, G, H, H1, and I and the corrected structure of psolusoside B from the sea cucumber Psolus fabricii // Mar. Drugs. 2019. Vol. 17. 358 [1–24].</mixed-citation></citation-alternatives></ref><ref id="B11"><label>11.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S., Popov R. S., Chingizova E. A. Structures and bioactivities of psolusosides B1, B2, J, K, L, M, N, O, P and Q from the sea cucumber Psolus fabricii. The first finding of tetrasulfated marine low molecular weight metabolites. Mar. Drugs. 2019;17. 631 [1–24].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Kalinin V. I., Andrijaschenko P. V., Dmitrenok P. S., Popov R. S., Chingizova E. A. Structures and bioactivities of psolusosides B1, B2, J, K, L, M, N, O, P and Q from the sea cucumber Psolus fabricii. The first finding of tetrasulfated marine low molecular weight metabolites // Mar. Drugs. 2019. Vol. 17. 631 [1–24].</mixed-citation></citation-alternatives></ref><ref id="B12"><label>12.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Ermakova S. P., Malyarenko O. S., Dautov S. Sh., Kalinin V. I. Structures and bioactivities of quadrangularisosides A, A1, B, B1, B2, C, C1, D, D1–D4, and E from the sea cucumber Colochirus quadrangularis: the first discovery of the glycosides, sulfated by C-4 of the terminal 3-O-methylglucose residue. Synergetic effect on colony formation of tumor HT-29 cells of these glycosides with radioactive irradiation. Mar. Drugs. 2020;18. 394 [1–35].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Ermakova S. P., Malyarenko O. S., Dautov S. Sh., Kalinin V. I. Structures and bioactivities of quadrangularisosides A, A1, B, B1, B2, C, C1, D, D1–D4, and E from the sea cucumber Colochirus quadrangularis: the first discovery of the glycosides, sulfated by C-4 of the terminal 3-O-methylglucose residue. Synergetic effect on colony formation of tumor HT-29 cells of these glycosides with radioactive irradiation // Mar. Drugs. 2020. Vol. 18. 394 [1–35].</mixed-citation></citation-alternatives></ref><ref id="B13"><label>13.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andryjaschenko P. V., Dmitrenok P. S., Kalinin V. I., Yurchenko E. V., Dolmatov I. Y. Colochirosides B1, B2, B3 and C, novel sulfated triterpene glycosides from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Nat. Prod. Commun. 2015;10:1687–1694.</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andryjaschenko P. V., Dmitrenok P. S., Kalinin V. I., Yurchenko E. V., Dolmatov I. Y. Colochirosides B1, B2, B3 and C, novel sulfated triterpene glycosides from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida) // Nat. Prod. Commun. 2015. Vol. 10. P. 1687–1694.</mixed-citation></citation-alternatives></ref><ref id="B14"><label>14.</label><citation-alternatives><mixed-citation xml:lang="en">Rodriguez J., Riguera R. Lefevreosides: four novel triterpenoid glycosides from the sea cucumber Cucumaria lefevrei. J. Chem. Res. (M). 1989:2620–2636.</mixed-citation><mixed-citation xml:lang="ru">Rodriguez J., Riguera R. Lefevreosides: four novel triterpenoid glycosides from the sea cucumber Cucumaria lefevrei // J. Chem. Res. (M). 1989. P. 2620–2636.</mixed-citation></citation-alternatives></ref><ref id="B15"><label>15.</label><citation-alternatives><mixed-citation xml:lang="en">Zurita M. B., Ahond A., Poupat C., Potier P. Invertebres marins du lagon Neo-Caledonien, VII. Etude structurale d’un nouveau saponoside sulfate extrait de l’holothurie Neothyonidium magnum. J. Nat. Prod. 1986;49:809–813.</mixed-citation><mixed-citation xml:lang="ru">Zurita M. B., Ahond A., Poupat C., Potier P. Invertebres marins du lagon Neo-Caledonien, VII. Etude structurale d’un nouveau saponoside sulfate extrait de l’holothurie Neothyonidium magnum // J. Nat. Prod. 1986. Vol. 49. P. 809–813.</mixed-citation></citation-alternatives></ref><ref id="B16"><label>16.</label><citation-alternatives><mixed-citation xml:lang="en">Chludil H. D., Muniain C. C., Seldes A. M., Maier M. S. Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoidema spectabilis. J. Nat. Prod. 2002;65:860–865.</mixed-citation><mixed-citation xml:lang="ru">Chludil H. D., Muniain C. C., Seldes A. M., Maier M. S. Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoidema spectabilis // J. Nat. Prod. 2002. Vol. 65. P. 860–865.</mixed-citation></citation-alternatives></ref><ref id="B17"><label>17.</label><citation-alternatives><mixed-citation xml:lang="en">Yi Y.-H., Xu Q.-Z., Li L., Zhang S.-L., Wu H.-M., Ding J., Tong Y. G., Tan W.-F., Li M.-H., Tian F., Wu J.-H., Liaw C.-C., Bastow K. F., Lee K.-H. Philinopsides A and B, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis. Helv. Chim. Acta. 2006;89:54–63.</mixed-citation><mixed-citation xml:lang="ru">Yi Y.-H., Xu Q.-Z., Li L., Zhang S.-L., Wu H.-M., Ding J., Tong Y. G., Tan W.-F., Li M.-H., Tian F., Wu J.-H., Liaw C.-C., Bastow K. F., Lee K.-H. Philinopsides A and B, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis // Helv. Chim. Acta. 2006. Vol. 89. P. 54–63.</mixed-citation></citation-alternatives></ref><ref id="B18"><label>18.</label><citation-alternatives><mixed-citation xml:lang="en">Zhang S.-L., Li L., Yi Y.-H., Sun P. Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis. Nat. Prod. Res. 2006;20:399–407.</mixed-citation><mixed-citation xml:lang="ru">Zhang S.-L., Li L., Yi Y.-H., Sun P. Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis // Nat. Prod. Res. 2006. Vol. 20. P. 399–407.</mixed-citation></citation-alternatives></ref><ref id="B19"><label>19.</label><citation-alternatives><mixed-citation xml:lang="en">Kalinovskii A. I., Avilov S. A., Stepanov V. R., Stonik V. A. Glycosides of marine invertebrates. XXIII. Kurilogenin – a new genin from the glycosides of the holothurian Duasmodactyla kurilensis. Chem. Nat. Compds. 1983;19:688–691.</mixed-citation><mixed-citation xml:lang="ru">Kalinovskii A. I., Avilov S. A., Stepanov V. R., Stonik V. A. Glycosides of marine invertebrates. XXIII. Kurilogenin – a new genin from the glycosides of the holothurian Duasmodactyla kurilensis // Chem. Nat. Compds. 1983. Vol. 19. P. 688–691.</mixed-citation></citation-alternatives></ref><ref id="B20"><label>20.</label><citation-alternatives><mixed-citation xml:lang="en">Avilov S. A., Kalinovskii A. I. New triterpene aglycone from the holothurian Duasmodactyla kurilensis. Chem. Nat. Compds. 1989;25:309–311.</mixed-citation><mixed-citation xml:lang="ru">Avilov S. A., Kalinovskii A. I. New triterpene aglycone from the holothurian Duasmodactyla kurilensis // Chem. Nat. Compds. 1989. Vol. 25. P. 309–311.</mixed-citation></citation-alternatives></ref><ref id="B21"><label>21.</label><citation-alternatives><mixed-citation xml:lang="en">Avilov S. A., Kalinovskii A. I., Stonik V. A. Two new triterpene glycosides from the holothurian Duasmodactyla kurilensis. Chem. Nat. Compds. 1991;27:188–192.</mixed-citation><mixed-citation xml:lang="ru">Avilov S. A., Kalinovskii A. I., Stonik V. A. Two new triterpene glycosides from the holothurian Duasmodactyla kurilensis // Chem. Nat. Compds. 1991. Vol. 27. P. 188–192.</mixed-citation></citation-alternatives></ref><ref id="B22"><label>22.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Kalinin V. I. Kurilosides A1, A2, C1, D, E and F – triterpene glycosides from the Far Eastern sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): structures with unusual non-holostane aglycones and cytotoxicities. Mar. Drugs. 2020;18. 551 [1–21].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Kalinin V. I. Kurilosides A1, A2, C1, D, E and F – triterpene glycosides from the Far Eastern sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): structures with unusual non-holostane aglycones and cytotoxicities // Mar. Drugs. 2020. Vol. 18. 551 [1–21].</mixed-citation></citation-alternatives></ref><ref id="B23"><label>23.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Kalinin V. I. Triterpene glycosides from the Far Eastern sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): the structures, cytotoxicities, and biogenesis of kurilosides A3, D1, G, H, I, I1, J, K, and K1. Mar. Drugs. 2021;19. 187 [1–25].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Kalinin V. I. Triterpene glycosides from the Far Eastern sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): the structures, cytotoxicities, and biogenesis of kurilosides A3, D1, G, H, I, I1, J, K, and K1 // Mar. Drugs. 2021. Vol. 19. 187 [1–25].</mixed-citation></citation-alternatives></ref><ref id="B24"><label>24.</label><citation-alternatives><mixed-citation xml:lang="en">Kalinin V. I., Avilov S. A., Kalinina E. Y., Korolkova O. G., Kalinovsky A. I., Stonik V. A., Riguera R., Jimenez C. Structure of eximisoside A, a novel triterpene glycoside from the Far-Eastern sea cucumber Psolus eximius. J. Nat. Prod. 1997;60:817–819.</mixed-citation><mixed-citation xml:lang="ru">Kalinin V. I., Avilov S. A., Kalinina E. Y., Korolkova O. G., Kalinovsky A. I., Stonik V. A., Riguera R., Jimenez C. Structure of eximisoside A, a novel triterpene glycoside from the Far-Eastern sea cucumber Psolus eximius // J. Nat. Prod. 1997. Vol. 60. P. 817–819.</mixed-citation></citation-alternatives></ref><ref id="B25"><label>25.</label><citation-alternatives><mixed-citation xml:lang="en">Murray A. P., Muniain C., Seldes A. M., Maier M. Patagonicoside A: a novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus. Tetrahedron. 2001;57:9563–9568.</mixed-citation><mixed-citation xml:lang="ru">Murray A. P., Muniain C., Seldes A. M., Maier M. Patagonicoside A: a novel antifungal disulfated triterpene glycoside from the sea cucumber Psolus patagonicus // Tetrahedron. 2001. Vol. 57. P. 9563–9568.</mixed-citation></citation-alternatives></ref><ref id="B26"><label>26.</label><citation-alternatives><mixed-citation xml:lang="en">Careaga V. P., Muniain C., Maier M. S. Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus. Chem. Biodivers. 2011;8:467–475.</mixed-citation><mixed-citation xml:lang="ru">Careaga V. P., Muniain C., Maier M. S. Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus // Chem. Biodivers. 2011. Vol. 8. P. 467–475.</mixed-citation></citation-alternatives></ref><ref id="B27"><label>27.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Kalinin V. I. Unusual structures and cytotoxicities of chitonoidosides A, A1, B, C, D, and E, six triterpene glycosides from the Far Eastern sea cucumber Psolus chitonoides. Mar. Drugs. 2021;19. 449 [1–18].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Dmitrenok P. S., Chingizova E. A., Kalinin V. I. Unusual structures and cytotoxicities of chitonoidosides A, A1, B, C, D, and E, six triterpene glycosides from the Far Eastern sea cucumber Psolus chitonoides // Mar. Drugs. 2021. Vol. 19. 449 [1–18].</mixed-citation></citation-alternatives></ref><ref id="B28"><label>28.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Kalinin V. I., Dmitrenok P. S. Triterpene glycosides from the Far Eastern sea cucumber Psolus chitonoides: chemical structures and cytotoxicities of chitonoidosides E1, F, G, and H. Mar. Drugs. 2021;19(12). 696 [1–17].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Kalinin V. I., Dmitrenok P. S. Triterpene glycosides from the Far Eastern sea cucumber Psolus chitonoides: chemical structures and cytotoxicities of chitonoidosides E1, F, G, and H // Mar. Drugs. 2021. Vol. 19, N12. 696 [1–17].</mixed-citation></citation-alternatives></ref><ref id="B29"><label>29.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Dmitrenok P. S., Kalinovsky A. I., Rasin A. B., Kalinin V. I. Structures and biologic activity of chitonoidosides I, J, K, K1 and L – triterpene di-, tri- and tetrasulfated hexaosides from the sea cucumber Psolus chitonoides. Mar. Drugs. 2022;20(6). 369 [1-21].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Dmitrenok P. S., Kalinovsky A. I., Rasin A. B., Kalinin V. I. Structures and biologic activity of chitonoidosides I, J, K, K1 and L – triterpene di-, tri- and tetrasulfated hexaosides from the sea cucumber Psolus chitonoides // Mar. Drugs. 2022. Vol. 20, N6. 369 [1–21].</mixed-citation></citation-alternatives></ref><ref id="B30"><label>30.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Avilov S. A., Andrijaschenko P. V., Popov, R.S., Chingizova E. A., Grebnev B. B., Rasin A. B., Kalinin V. I. The isolation, structure elucidation and bioactivity study of chilensosides A, A1, B, C, and D, holostane triterpene di-, tri-and tetrasulfated pentaosides from the sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). Molecules. 2022;27. 7655 [1–18].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Grebnev B. B., Rasin A. B., Kalinin V. I. The isolation, structure elucidation and bioactivity study of chilensosides A, A1, B, C, and D, holostane triterpene di-, tri-and tetrasulfated pentaosides from the sea cucumber Paracaudina chilensis (Caudinidae, Molpadida) // Molecules. 2022. Vol. 27. 7655 [1–18].</mixed-citation></citation-alternatives></ref><ref id="B31"><label>31.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Grebnev B. B., Rasin A. B., Kalinin V. I. Chilensosides E, F, and G – new tetrasulfated triterpene glycosides from the sea cucumber Paracaudina chilensis (Caudinidae, Molpadida): structures, activity, and biogenesis. Mar. Drugs. 2023;21(2). 114 [1–14].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Avilov S. A., Andrijaschenko P. V., Popov R. S., Chingizova E. A., Grebnev B. B., Rasin A. B., Kalinin V. I. Chilensosides E, F, and G – new tetrasulfated triterpene glycosides from the sea cucumber Paracaudina chilensis (Caudinidae, Molpadida): structures, activity, and biogenesis // Mar. Drugs. 2023. Vol. 21, N2. 114 [1–14].</mixed-citation></citation-alternatives></ref><ref id="B32"><label>32.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Popov R. S., Dmitrenok P. S., Chingizova E. A., Menchinskaya E. S., Panina E G., Stepanov V. G., Kalinin V. I., Stonik V. A. Djakonoviosides A, A1, A2, B1–B4 – triterpene monosulfated tetra- and pentaosides from the sea cucumber Cucumaria djakonovi: the first finding of a hemiketal fragment in the aglycones; activity against human breast cancer cell lines. Int. J. Mol. Scis. 2023;24. 11128 [1–24].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Popov R. S., Dmitrenok P. S., Chingizova E. A., Menchinskaya E. S., Panina E. G. Stepanov V. G., Kalinin V. I., Stonik V. A. Djakonoviosides A, A1, A2, B1–B4 – triterpene monosulfated tetra- and pentaosides from the sea cucumber Cucumaria djakonovi: the first finding of a hemiketal fragment in the aglycones; activity against human breast cancer cell lines // Int. J. Mol. Sci. 2023. Vol. 24. 11128 [1–24].</mixed-citation></citation-alternatives></ref><ref id="B33"><label>33.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Popov R. S., Chingizova E. A., Menchinskaya E. S., Zelepuga E. A., Panina E. G., Stepanov V. G., Kalinin V. I., Dmitrenok P. S. Sulfated triterpene glycosides from the Far Eastern sea cucumber Cucumaria djakonovi: djakonoviosides C1, D1, E1, and F1; cytotoxicity against human breast cancer cell lines; quantitative structure – activity relationships. Mar. Drugs. 2023;21. 602 [1–29].</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Kalinovsky A. I., Avilov S. A., Popov R. S., Chingizova E. A., Menchinskaya E. S., Zelepuga E. A., Panina E. G., Stepanov V. G., Kalinin V. I., Dmitrenok P. S. Sulfated triterpene glycosides from the Far Eastern sea cucumber Cucumaria djakonovi: djakonoviosides C1, D1, E1, and F1; cytotoxicity against human breast cancer cell lines; quantitative structure – activity relationships // Mar. Drugs. 2023. Vol. 21. 602 [1–29].</mixed-citation></citation-alternatives></ref><ref id="B34"><label>34.</label><citation-alternatives><mixed-citation xml:lang="en">Silchenko A. S., Avilov S. A., Kalinovsky A. I., Dmitrenok P. S., Kalinin V. I., Morre J., Deinzer M. L., Woodward C., Collin P. D. Glycosides from the North Atlantic sea cucumber Cucumaria frondosa V – Structures of five new minor trisulfated triterpene oligoglycosides, frondosides A7-1, A7-3, A7-4, and isofrondoside C. Can. J. Chem. 2007;85:626–636.</mixed-citation><mixed-citation xml:lang="ru">Silchenko A. S., Avilov S. A., Kalinovsky A. I., Dmitrenok P. S., Kalinin V. I., Morre J., Deinzer M. L., Woodward C., Collin P. D. Glycosides from the North Atlantic sea cucumber Cucumaria frondosa V – Structures of five new minor trisulfated triterpene oligoglycosides, frondosides A7-1, A7-3, A7-4, and isofrondoside C // Can. J. Chem. 2007. Vol. 85, N. 9. P. 626–636.</mixed-citation></citation-alternatives></ref><ref id="B35"><label>35.</label><citation-alternatives><mixed-citation xml:lang="en">Avilov S. A., Kalinin V. I., Smirnov A. V. Use of triterpene glycosides for resolving taxonomic problems in the sea cucumber genus Cucumaria (Holothorioidea, Echinodermata). Biochem. System. Ecol. 2004;32:715–733.</mixed-citation><mixed-citation xml:lang="ru">Avilov S. A., Kalinin V. I., Smirnov A. V. Use of triterpene glycosides for resolving taxonomic problems in the sea cucumber genus Cucumaria (Holothorioidea, Echinodermata) // Biochem. System. Ecol. 2004. Vol. 32. P. 715–733.</mixed-citation></citation-alternatives></ref><ref id="B36"><label>36.</label><citation-alternatives><mixed-citation xml:lang="en">Ponomarenko L. P., Kapustina I. I., Dautov S. S., Dautova T. N., Stonik V. A. Free sterol composition of deep-sea holothurian Orphnurgus cf. glaber. Nat. Prod. Commun. 2022;17(12):1–6. DOI: 10.1177/1934578X221142791.</mixed-citation><mixed-citation xml:lang="ru">Ponomarenko L. P., Kapustina I. I., Dautov S. S., Dautova T. N., Stonik V. A. Free sterol composition of deep-sea holothurian Orphnurgus cf. glaber // Nat. Prod. Commun. 2022. Vol. 17, N12. P. 1–6. DOI: 10.1177/1934578X221142791.</mixed-citation></citation-alternatives></ref><ref id="B37"><label>37.</label><citation-alternatives><mixed-citation xml:lang="en">Sheikh Y. M., Djerassi C. Biosynthesis of sterols in the sea cucumber Stichopus californicus. Tetrahedron Letters. 1977;36:3111–3114.</mixed-citation><mixed-citation xml:lang="ru">Sheikh Y. M., Djerassi C. Biosynthesis of sterols in the sea cucumber Stichopus californicus // Tetrahedron Letters. 1977. Vol. 36. P. 3111–3114.</mixed-citation></citation-alternatives></ref><ref id="B38"><label>38.</label><citation-alternatives><mixed-citation xml:lang="en">Cordeiro M. L., Djerassi C. Biosynthetic studies of marine lipids. 25. Biosynthesis of Δ9(11)- and Δ7-sterols and saponins in sea cucumbers. J. Org. Chem. 1990;55(9):2806–2813.</mixed-citation><mixed-citation xml:lang="ru">Cordeiro M. L., Djerassi C. Biosynthetic studies of marine lipids. 25. Biosynthesis of Δ9(11)- and Δ7-sterols and saponins in sea cucumbers // J. Org. Chem. 1990. Vol 55, N9. P. 2806–2813.</mixed-citation></citation-alternatives></ref></ref-list></back></article>
