Biochemical Systematics and Ecology 96 (2021) 104262
13
Grauso, L., Yegdaneh, A., Sharifi, M., Mangoni, A., Zolfaghari, B., Lanzotti, V., 2019.
Molecular networking-based analysis of cytotoxic saponins from sea cucumber
Holothuria atra. Mar. Drugs 17 (2), 86. https://doi.org/10.3390/md17020086.
Ivanchina, N.V., Kicha, A.A., Malyarenko, T.V., Stonik, V.A., 2017. Recent studies of
polar steroids from starfish: structures, biological activities and biosynthesis. In:
Gomes, R., Rocha-Santos, T., Duarte, A. (Eds.), Advances in Natural Products
Discovery. Nova Sci., New York, NY, USA, pp. 191–224.
Kalinin, V.I., Prokofieva, N.G., Likhatskaya, G.N., Schentsova, E.B., Agafonova, I.G.,
Avilov, S.A., Drozdova, O.A., 1996. Hemolytic activities of triterpene glycosides
from the holothurians order dendrochirotida: some trends in the evolution of this
group of toxins. Toxicon 34, 475–483. https://doi.org/10.1016/0041-0101(95)
00142-5.
Kicha, A.A., Kalinovsky, A.I., Malyarenko, T.V., Ivanchina, N.V., Dmitrenok, P.S.,
Menchinskaya, E.S., Yurchenko, E.A., Pislyagin, E.A., Aminin, D.L., Huong, T.T.T.,
Long, F.Q., Stonik, V.K., 2015. Cyclic steroid glycosides from the starfish Echinaster
luzonicus: structures and immunomodulatory activities. J. Nat. Prod. 78 (6),
1397–1405. https://doi.org/10.1021/acs.jnatprod.5b00332.
Kisha, A.A., Ivanchina, N.V., Kalinovsky, A.I., Dmitrenok, P.S., Stonik, V.A., 2001.
Sulfated steroid compounds from the starfish Aphelasterias japonica of the Kuril
population. 50, 724–727. Russ. Chem. Bull. https://doi.org/10.1023/A:
1011337617808.
Kwon, J.H., B´ elanger, J.M.R., Par´ e, J.R.J., Yaylayan, V.A., 2003. Application of the
microwave-assisted process (MAPTM) to the fast extraction of ginseng saponins.
Food Res. Int. 36, 491–498. https://doi.org/10.1016/S0963-9969(02)00197-7.
Lide, D.R., 2009. CRC Handbook of Chemistry and Physics: a Ready-Reference Book of
Chemical and Physical Data, Edition. CRC Press, London.
Mackie, A.M., Lasker, R., Grant, P.T., 1968. Avoidance reactions of mollusc Buccinum
undatum to saponin-like surface-active substances in extracts of thenstarfish Asterias
rubens and Martasterias glacialis. Comp. Biochem. Physiol. 26, 415–428. https://
doi.org/10.1016/0010-406X(68)90635-X.
Mackie, A.M., Singh, H.T., Owen, J.M., 1977. Studies on the distribution, biosynthesis
and function of steroidal saponins in echinoderms. Comp. Biochem. Physiol. B
Biochem. Mol. Biol. 56, 9–14. https://doi.org/10.1016/0305-0491(77)90214-0.
Malyarenko, T.V., Kicha, A.A., Ivanchina, N.V., Kalinovsky, A.I., Dmitrenok, P.S.,
Stonik, V.A., 2016. Unusual steroid constituents from the tropical starfish leiaster sp.
Nat. Prod. Commun. 11 (9), 1251–1252. https://doi.org/10.1177/
1934578X1601100914.
Malyarenko, O.S., Dyshlovoy, S.A., Kicha, A.A., Ivanchina, N.V., Malyarenko, T.V.,
Carsten, B., Gunhild, V.A., Stonik, V.A., Ermakova, S.P., 2017. The inhibitory
activity of luzonicosides from the starfish Echinaster luzonicus against human
melanoma cells. Mar. Drugs 15 (7), 277. https://doi.org/10.3390/md15070227.
Minale, L., Riccio, R., De Simone, F., Dini, A., Pizza, C., Ramundo, E., 1978. Strafish
saponins I. 3β-HYDROXY-5-α-CHOLESTA-8, 14-DIEN-23-ONE, the major genin from
STARFISH Echinaster sepositus. Tetrahedron Lett. 29, 2609–2612. https://doi.org/
10.1016/S0040-4039(01)94842-7.
Minale, L., Riccio, R., De Simone, F., Dini, A., Pizza, C., 1979. Starfish saponins II. 22, 23epoxysteroids, minor genins from the starfish Echinaster Sepositus. Tetrahedron Lett.
7, 645–648. https://doi.org/10.1016/S0040-4039(01)86026-3.
Minale, L., Riccio, R., Zollo, F., 1993. Steroidal oligoglycosides and polyhydroxysteroids
from echinoderms. In: Herz, W., Kirby, G.W., Moore, R.E., Steglich, W., Tamm, C.
(Eds.), Fortschritte der Chemie organischer Naturstoffe/Progress in the Chemistry of
Organic Natural Products, Fortschritte der Chemie organischer Naturstoffe/Progress
in the Chemistry of Organic Natural Products, vol. 62. Springer, Vienna, pp. 75–308.
https://doi.org/10.1007/978-3-7091-9250-4_2.
Naruse, M., Suetomo, H., Matsubara, T., Sato, T., Yanagawa, H., Hoshi, M.,
Matsumoto, M., 2010. Acrosome reaction-related steroidal saponin, Co-ARIS, from
the starfish induces structural changes in microdomains. Dev. Biol. 347 (1),
147–153. https://doi.org/10.1016/j.ydbio.2010.08.019.
Popov, R.S., Ivanchina, N.V., Kicha, A.A., Malyarenko, T.V., Grebnev, B.B., Stonik, V.A.,
Dmitrenok, V.S., 2019. The distribution of asterosaponins, polyhydroxysteroids and
related glycosides in different body components of the far eastern starfish
lethasterias fusca. Mar. Drugs 17 (9), 523. https://doi.org/10.3390/md17090523.
Riccio, R., De Simone, F., Dini, A., Minale, L., Pizza, C., Senatore, F., Zollo, F., 1981.
Starfish saponins VI-unique .22, 23-epoxysteroids, cyclic glycoside, minor
constituents from Echinaster sepositus. Tetrahedron Lett. 22 (16), 1557–1560.
Riccio, R., Dini, A., Minale, L., Pizza, C., Zollo, F., Sevenet, T., 1982. Starfish saponins
VII. Structure of luzonicoside, a further steroidal cyclic glycoside from the pacific
starfish Echinaster luzonicus. Experientia 38, 68–70. https://doi.org/10.1016/
S0040-4039(01)90377-6.
Riesgo, A., Villamor, A., Becerr, M., 2011. Ultrastructure of the gametogenesis of the
common Mediterranean starfish, Echinaster (Echinaster) sepositus. Invertebr.
Reprod. Dev. 55, 138–151. https://doi.org/10.1080/07924259.2011.558182.
Schoepke, T., Hiller, K., Wray, V., Nimtz, M., 1996. Application of MSMS for the rapid,
comparative analysis of saponin mixtures as exemplified by the deacylated and
partially deacylated triterpenoid saponins of Bellis annua. Planta Med. 62 (4),
336–340. https://doi.org/10.1055/s-2006-957897.
Stonik, V.A., Kalinin, V.I., Avilov, S.A., 1999. Toxins from sea cucumbers (holothuroids):
chemical structures, properties, taxonomic distribution, biosynthesis and evolution.
J. Nat. Toxins 8 (2), 235–248. PMID: 10410334.
Van Dyck, S., Gerbaux, P., Flammang, P., 2009. Elucidation of molecular diversity and
body distribution of saponins in the sea cucumber Holothuria forskali
(Echinodermata) by mass spectrometry. Comp. Biochem. Physiol. B Biochem. Mol.
Biol. 152, 124–134. https://doi.org/10.1016/j.cbpb.2008.10.011.
Van Dyck, S., Gerbaux, P., Flammang, P., 2010a. Qualitative and quantitative saponin
contents in five sea cucumbers from the Indian Ocean. Mar. Drugs 8, 173–189.
https://doi.org/10.3390/md8010173.
Van Dyck, S., Flammang, P., Meriaux, C., Bonnel, D., Salzet, M., Fournier, I.,
Wisztorski, M., 2010b. Localization of secondarymetabolites inmarine invertebrates:
contribution of MALDI MSI for the study of saponins in cuvierian tubules of H.
forskali. PloS One 5 (11), e13923. https://doi.org/10.1371/journal.pone.0013923.
Voogt, P.A., Van Rheenen, J.W.A., 1982. Carbohydrate content and composition of
asterosaponins from different organs of the sea star Asterias rubens: relation to their
haemolytic activity and implications for their biosynthesis. Comp. Biochem. Physiol.
B Biochem. Mol. Biol. 72, 683–688. https://doi.org/10.1016/0305-0491(82)905272.
B. Dahmoune et al.
13
Grauso, L., Yegdaneh, A., Sharifi, M., Mangoni, A., Zolfaghari, B., Lanzotti, V., 2019.
Molecular networking-based analysis of cytotoxic saponins from sea cucumber
Holothuria atra. Mar. Drugs 17 (2), 86. https://doi.org/10.3390/md17020086.
Ivanchina, N.V., Kicha, A.A., Malyarenko, T.V., Stonik, V.A., 2017. Recent studies of
polar steroids from starfish: structures, biological activities and biosynthesis. In:
Gomes, R., Rocha-Santos, T., Duarte, A. (Eds.), Advances in Natural Products
Discovery. Nova Sci., New York, NY, USA, pp. 191–224.
Kalinin, V.I., Prokofieva, N.G., Likhatskaya, G.N., Schentsova, E.B., Agafonova, I.G.,
Avilov, S.A., Drozdova, O.A., 1996. Hemolytic activities of triterpene glycosides
from the holothurians order dendrochirotida: some trends in the evolution of this
group of toxins. Toxicon 34, 475–483. https://doi.org/10.1016/0041-0101(95)
00142-5.
Kicha, A.A., Kalinovsky, A.I., Malyarenko, T.V., Ivanchina, N.V., Dmitrenok, P.S.,
Menchinskaya, E.S., Yurchenko, E.A., Pislyagin, E.A., Aminin, D.L., Huong, T.T.T.,
Long, F.Q., Stonik, V.K., 2015. Cyclic steroid glycosides from the starfish Echinaster
luzonicus: structures and immunomodulatory activities. J. Nat. Prod. 78 (6),
1397–1405. https://doi.org/10.1021/acs.jnatprod.5b00332.
Kisha, A.A., Ivanchina, N.V., Kalinovsky, A.I., Dmitrenok, P.S., Stonik, V.A., 2001.
Sulfated steroid compounds from the starfish Aphelasterias japonica of the Kuril
population. 50, 724–727. Russ. Chem. Bull. https://doi.org/10.1023/A:
1011337617808.
Kwon, J.H., B´ elanger, J.M.R., Par´ e, J.R.J., Yaylayan, V.A., 2003. Application of the
microwave-assisted process (MAPTM) to the fast extraction of ginseng saponins.
Food Res. Int. 36, 491–498. https://doi.org/10.1016/S0963-9969(02)00197-7.
Lide, D.R., 2009. CRC Handbook of Chemistry and Physics: a Ready-Reference Book of
Chemical and Physical Data, Edition. CRC Press, London.
Mackie, A.M., Lasker, R., Grant, P.T., 1968. Avoidance reactions of mollusc Buccinum
undatum to saponin-like surface-active substances in extracts of thenstarfish Asterias
rubens and Martasterias glacialis. Comp. Biochem. Physiol. 26, 415–428. https://
doi.org/10.1016/0010-406X(68)90635-X.
Mackie, A.M., Singh, H.T., Owen, J.M., 1977. Studies on the distribution, biosynthesis
and function of steroidal saponins in echinoderms. Comp. Biochem. Physiol. B
Biochem. Mol. Biol. 56, 9–14. https://doi.org/10.1016/0305-0491(77)90214-0.
Malyarenko, T.V., Kicha, A.A., Ivanchina, N.V., Kalinovsky, A.I., Dmitrenok, P.S.,
Stonik, V.A., 2016. Unusual steroid constituents from the tropical starfish leiaster sp.
Nat. Prod. Commun. 11 (9), 1251–1252. https://doi.org/10.1177/
1934578X1601100914.
Malyarenko, O.S., Dyshlovoy, S.A., Kicha, A.A., Ivanchina, N.V., Malyarenko, T.V.,
Carsten, B., Gunhild, V.A., Stonik, V.A., Ermakova, S.P., 2017. The inhibitory
activity of luzonicosides from the starfish Echinaster luzonicus against human
melanoma cells. Mar. Drugs 15 (7), 277. https://doi.org/10.3390/md15070227.
Minale, L., Riccio, R., De Simone, F., Dini, A., Pizza, C., Ramundo, E., 1978. Strafish
saponins I. 3β-HYDROXY-5-α-CHOLESTA-8, 14-DIEN-23-ONE, the major genin from
STARFISH Echinaster sepositus. Tetrahedron Lett. 29, 2609–2612. https://doi.org/
10.1016/S0040-4039(01)94842-7.
Minale, L., Riccio, R., De Simone, F., Dini, A., Pizza, C., 1979. Starfish saponins II. 22, 23epoxysteroids, minor genins from the starfish Echinaster Sepositus. Tetrahedron Lett.
7, 645–648. https://doi.org/10.1016/S0040-4039(01)86026-3.
Minale, L., Riccio, R., Zollo, F., 1993. Steroidal oligoglycosides and polyhydroxysteroids
from echinoderms. In: Herz, W., Kirby, G.W., Moore, R.E., Steglich, W., Tamm, C.
(Eds.), Fortschritte der Chemie organischer Naturstoffe/Progress in the Chemistry of
Organic Natural Products, Fortschritte der Chemie organischer Naturstoffe/Progress
in the Chemistry of Organic Natural Products, vol. 62. Springer, Vienna, pp. 75–308.
https://doi.org/10.1007/978-3-7091-9250-4_2.
Naruse, M., Suetomo, H., Matsubara, T., Sato, T., Yanagawa, H., Hoshi, M.,
Matsumoto, M., 2010. Acrosome reaction-related steroidal saponin, Co-ARIS, from
the starfish induces structural changes in microdomains. Dev. Biol. 347 (1),
147–153. https://doi.org/10.1016/j.ydbio.2010.08.019.
Popov, R.S., Ivanchina, N.V., Kicha, A.A., Malyarenko, T.V., Grebnev, B.B., Stonik, V.A.,
Dmitrenok, V.S., 2019. The distribution of asterosaponins, polyhydroxysteroids and
related glycosides in different body components of the far eastern starfish
lethasterias fusca. Mar. Drugs 17 (9), 523. https://doi.org/10.3390/md17090523.
Riccio, R., De Simone, F., Dini, A., Minale, L., Pizza, C., Senatore, F., Zollo, F., 1981.
Starfish saponins VI-unique .22, 23-epoxysteroids, cyclic glycoside, minor
constituents from Echinaster sepositus. Tetrahedron Lett. 22 (16), 1557–1560.
Riccio, R., Dini, A., Minale, L., Pizza, C., Zollo, F., Sevenet, T., 1982. Starfish saponins
VII. Structure of luzonicoside, a further steroidal cyclic glycoside from the pacific
starfish Echinaster luzonicus. Experientia 38, 68–70. https://doi.org/10.1016/
S0040-4039(01)90377-6.
Riesgo, A., Villamor, A., Becerr, M., 2011. Ultrastructure of the gametogenesis of the
common Mediterranean starfish, Echinaster (Echinaster) sepositus. Invertebr.
Reprod. Dev. 55, 138–151. https://doi.org/10.1080/07924259.2011.558182.
Schoepke, T., Hiller, K., Wray, V., Nimtz, M., 1996. Application of MSMS for the rapid,
comparative analysis of saponin mixtures as exemplified by the deacylated and
partially deacylated triterpenoid saponins of Bellis annua. Planta Med. 62 (4),
336–340. https://doi.org/10.1055/s-2006-957897.
Stonik, V.A., Kalinin, V.I., Avilov, S.A., 1999. Toxins from sea cucumbers (holothuroids):
chemical structures, properties, taxonomic distribution, biosynthesis and evolution.
J. Nat. Toxins 8 (2), 235–248. PMID: 10410334.
Van Dyck, S., Gerbaux, P., Flammang, P., 2009. Elucidation of molecular diversity and
body distribution of saponins in the sea cucumber Holothuria forskali
(Echinodermata) by mass spectrometry. Comp. Biochem. Physiol. B Biochem. Mol.
Biol. 152, 124–134. https://doi.org/10.1016/j.cbpb.2008.10.011.
Van Dyck, S., Gerbaux, P., Flammang, P., 2010a. Qualitative and quantitative saponin
contents in five sea cucumbers from the Indian Ocean. Mar. Drugs 8, 173–189.
https://doi.org/10.3390/md8010173.
Van Dyck, S., Flammang, P., Meriaux, C., Bonnel, D., Salzet, M., Fournier, I.,
Wisztorski, M., 2010b. Localization of secondarymetabolites inmarine invertebrates:
contribution of MALDI MSI for the study of saponins in cuvierian tubules of H.
forskali. PloS One 5 (11), e13923. https://doi.org/10.1371/journal.pone.0013923.
Voogt, P.A., Van Rheenen, J.W.A., 1982. Carbohydrate content and composition of
asterosaponins from different organs of the sea star Asterias rubens: relation to their
haemolytic activity and implications for their biosynthesis. Comp. Biochem. Physiol.
B Biochem. Mol. Biol. 72, 683–688. https://doi.org/10.1016/0305-0491(82)905272.
B. Dahmoune et al.