Abstract
The structures of some secondary metabolites and their distribution in the Phylum Echinoder-mata are described. Gangliosides, quinoid pigments and steryl sulfates in echinoderms are widespread, although these compounds are absent or rare in the majority of other marine invertebrates. There are numerous phylogenetic parallelisms dealing with directions of the biosynthesis of low molecular weight natural products between starfishes and sea cucumbers, sea urchins and ophiuroids, sea lilies and starfishes and so on. They indicate a monophyletic origin of all echinoderms. At the same time such metabolites as triterpene glycosides, some gangliosides, Δ 9(11)-sterols, steroid oligoglycosides are linked to separate groups of these animals. Of particular interest among them as chemotaxonomic characters are triterpene glycosides from sea cucumbers, which have been utilized in a meaningful classification of Holothurioidea. The application of these and other secondary metabolites for taxonomic purposes is possible only by considering the cases of biochemical convergence and by invoking Vavilov’s law of homologous series.
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References
Smith PM (1976) The chemotaxonomy of plants. Edward Arnold, London
Laufer H (1962) Macromolecular patterns in development and evolution. In: Leone CA (ed) Taxonomic biochemistry and serology. Ronald, New York, p 171
Harborne JB (1982) Introduction to ecological biochemistry. Academic, London
Scheuer PJ (ed) (1978–1983) Marine natural products chemical and biological perspectives. Academic, New York, vols 1–5
Faulkner DJ (1977) Tetrahedron 33:1421
Hashimoto Y (1979) Marine toxins and other bioactive marine metabolites. Japan Scientific Societies, Tokyo
Krebs HS (1986) Fortschr Chem Org Naturst 35:152
Ubaghs G (1969) General characteristics of the echinoderms. In: Florkin M, Scheer BT (eds) Chemical zoology. Academic, New York, 3:46
Fagerlund UHM (1969) Lipid metabolism. In: Florkin M, Scheer BT (eds) Chemical zoology. Academic, New York, 3:123
Isay SV, Busarova NG (1984) Comp Biochem Physiol 77B:803
Lewis RW (1967) J Fish Res Bd, Canada 24:1101
Dembitsky VM (1987) Bioorg Khim 13:409
Kaneniwa M, Itabashi Y, Endo S, Takagi T (1986) Comp Biochem Physiol 84B:451
Allen WV (1968) J Mar Biol Ass UK 48:521
Takagi T, Kaneniwa M, Itabashi Y (1986) Lipids 21:430
Ackman RG, Hooper SN (1973) Comp Biochem Physiol 46B:153
Takagi T, Eaton CA, Ackman RG (1980) Can J Fish Aquat Sci 37:195
Takagi T, Kaneniwa M, Itabashi Y, Ackman RG (1986) Lipids 21:558
Paradis M, Ackman RG (1977) Lipids 12:170
Debuch H, Seng P (1972) The history of ether-linked lipids through 1960. In: Snyder F (ed) Ether lipids, chemistry and biology. Academic, New York, p 1
Dembitsky VM, Vaskovsky VE (1976) Biol morya 68
Dembitsky VM (1985) J Evol Biochem Physiol 21:70
Dembitsky VM (1980) Bioorg Khim 6:426
Todd D, Rizzi GP (1964) Proc Soc Exp Biol Med 115:218
Karnovsky ML, Rapson WS, Black M (1946) J Soc Chem Ind 65:425
Isay SV, Makarchenko MA, Vaskovsky VE (1976) Comp Biochem Physiol 55B:301
Kostetsky EY, Gerasimenko NI (1984) Biol morya 39
Warren L (1963) Comp Biochem Physiol 10:153
Vaskovsky VE, Kostetsky EY, Svetashev VI, Zhukova IG, Smirnova GB (1970) Comp Biochem Physiol 34:163
Smirnova GP (1985) Gangliosides of invertebrata. In: Torgov IV (ed) Progress in carbohydrate chemistry. Nauka, Moscow, p 126
Kochetkov NK, Zhukova IG, Smirnova GP, Glukhoded IS (1973) Biochem Biophys Acta 326:74
Kochetkov NK, Smirnova GP, Zhukova IG (1970) Dokl Akad Nauk SSSR 193:344
Prokasova NV, Kocharov SL, Sadovskaya VL, Moschensky LD, Bergelson LD, Svesdina ND (1979) Bioorg Khim 5:458
Kochetkov NK, Smirnova GP, Glukhoded IS (1978) Bioorg Khim 4:1093
Hoshi M, Nagai Y (1975) Biochim Biophys Acta 388:152
Shashkov AS, Smirnova GP, Chekareva NV, Dabrovsky J (1986) Bioorg Khim 12:789
Smirnova GP, Chekareva NV, Kochetkov NK (1981) Bioorg Khim 7:123
Smirnova GP, Chekareva NV, Kochetkov NK (1980) Bioorg Khim 6:1667
Zhukova IG, Bogdanovskaya TA, Smirnova GP, Chekareva NV, Kochetkov NK (1973) Dokl Akad Nauk SSSR 208:981
Smirnova GP, Glukhoded IS, Kochetkov NK (1986) Bioorg Khim 12:679
Kochetkov NK, Smirnova GP, Glukhoded IS (1982) Biochim Biophys Acta 712:650
Smirnova GP, Kochetkov NK, Sadovskaya VL (1986) Bioorg Khim 12:1396
Smirnova GP, Kochetkov NK (1980) Biochim Biophys Acta 618:486
Smirnova GP, Kochetkov NK (1985) Bioorg Khim 11:1650
Smirnova GP, Chekareva NV, Kochetkov NK (1986) Bioorg Khim 12:507
Kent RA, Smith IRS, Sutherland MD (1970) Aust J Chem 23:2325
Francesconi KA (1980) Aust J Chem 33:2781
Smith IR, Sutherland MB (1971) Aust J Chem 24:1487
Rideout JA, Smith NM, Sutherland MD (1979) Experientia 35:1273
Rideout JA, Sutherland MD (1981) Aust J Chem 34:2385
Bartolini GL, Erdman TR, Scheuer PJ (1973) Tetrahedron 29:3699
Powell VH, Sutherland MD (1967) Aust J Chem 20:541
Erdman TR, Thomson RH (1972) J Chem Soc Perkin 11291
Rideout JA, Sutherland MD (1985) Aust J Chem 38:793
Blumer M (1951) Microchemie 36–37:1048
Blumer M (1965) Science 149:722
Mayr E (1962) The new systematics. In: Leone CA (ed) Taxonomic biochemistry and serology. Ronald, New York, p 13
Utkina NK, Maximov OB (1977) Khim Prir Soedin 13:636
Utkina NK, Maximov OB (1979) Khim Prir Soedin 15:148
MacMunn CA (1885) Quart J Microscop Sci 25:469
Kuhn R, Wallenfels K (1941) Chem Ber 74:1594
Kuhn R, Wallenfels K (1943) Chem Ber 76:323
Goodwin TW (1969) Pigments in echinodermata. In: Florkin M, Scheer BT (eds) Chemical zoology. Academic, New York, p 135 (Echinodermata, Nematoda and Acanthocephala, vol 3)
Thomson RH (1971) Naturally occurring quinones. Academic, New York, p 257
Fox DL, Hopkins TS (1966) The comparative biochemistry of pigments. In: Boolootian RA (ed) Physiology of echinodermata. Interscience, New York, p 277
Vevers WG (1966) Pigmentation. In: Boolootian RA (ed) Physiology of echinodermata. Interscience, New York, p 267
Chang CWJ (1973) J Chem Educ 50:102
Grossert JS (1972) Chem Soc Revs 1:1
Gough J, Sutherland MD (1964) Tetrahedron Lett 269
Chang CWJ, Moore RE, Scheuer PJ (1964) J Am Chem Soc 86:2959
Chang CWJ, Moore RE, Scheuer PJ (1964) Tetrahedron Lett 3557
Moore RE, Singh H, Scheuer PJ (1966) J Org Chem 31:3645
Moore RE, Singh H, Scheuer PJ (1968) Tetrahedron Lett 4581
Mathieson JW, Thomson RH (1971) J Chem Soc Ser C, p 153
Koltsova EA, Denisenko VA, Maximov OB (1978) Khim Prir Soedin 14:438
Utkina NK, Schedrin AP, Maximov OB (1976) Khim Prir Soedin 12:439
Koltsova EA, Chumak GN, Maximov OB (1977) Khim Prir Soedin 13:202
Binyon J (1972) Physiology of echinoderms. Pergamon, Oxford
Service M, Wardlaw AC (1984) Comp Biochem Physiol 79B:161
Koltsova EA, Boguslavskaya LV, Maximov OB (1981) Intern J Inv Reprod 4:17
Ball EG (1934) Biol Bull 67:327
Asashima M (1971) J Fac Sci Univ Tokyo, IV, 12:299
Koltsova EA, Maximov OB, Utkina NK (1974) Changeability of quinoid pigments of sea urchins. In: Biology of sea molluscs and echinoderms. Materials of Soviet-Japan Symposium, Vladivostok, p 81
Koltsova EA, Maximov OB (1981) Khim Prir Soedin 17:115
Koltsova EA (1983) MSc thesis, Pacific Inst Bioorg Chem, Vladivostok
Singh H, Moore RE, Scheuer PJ (1967) Experientia 23:624
Mukai T (1958) Mem Fac Sci Kyushu Univ Ser C 3:29
Utkina NK (1979) MSc thesis, Pacific Inst Bioorg Chem, Vladivostok
Matsuno T, Fujitani K, Takoda S, Yokota K, Yoshimizu S (1972) Chem Pharm Bull 20:1079
Koltsova EA, Utkina NK, Maximov OB (1975) New data on quinoid pigments of sea urchins from the Sea of Japan. In: Biological resources of Far Eastern seas. Vladivostok, p 147
Kruchkova GA (1974) Development of larval and definite skeletons of sea urchins from the genus Strongylocentrotus. In: Biology of marine molluscs and echinoderms. Materials of Soviet-Japan symposium, Vladivostok, p 92
Utkina NK, Maximov OB (1979) Quinoid pigments and phylogeny of echinoderms. In: Proceedings of 4-th All-union symposium on echinoderms. Tbilisi, p 199
Elyakov GB, Ovodov YuS (1972) Khim Prir Soedin 8:697
Elyakov GB, Stonik VA (1985) Terpenoids of marine organisms, Nauka, Moscow
Burnell DJ, ApSimon JW (1983) Echinoderms saponins. In: Scheuer PJ (ed) Marine natural products. Chemical and biological perspectives. Academic, New York 5–287
Mackie AM, Singh HT, Owen YM (1977) Comp Biochem Physiol 56B:9
Elyakov GB, Stonik VA, Levina EV, Levin VS (1975) Comp Biochem Physiol 52B:321
Anisimov MM, Cirva VY (1980) Pharmazie 35:731
Lucas JS, Hart RJ, Howden MEH, Salather R (1979) J Exp Mar Biol Ecol 40:155
Rio GJ, Stempien ME, Nigrelli RF, Ruggieri GD (1965) Toxicon 3:147
Ikegami S (1976) J Exp Zool 198:359
Aminin DL, Anisimov MM, Mokretsova ND, Strigina LI, Levina EV (1986) Biol Morya 49
Elyakov GB, Stonik VA, Lenina EV, Slanke VP, Levin VS (1973) Comp Biochem Physiol 43B:325
Elyakov GB, Kuznetsova TA, Stonik VA, Albores R (1975) Comp Biochem Physiol 52B:413
Stonik VA (1986) Pure Appl Chem 58:243
Kitagawa I, Nishino T, Matsuno T, Akatsu H, Kyogoku Y (1978) Tetrahedron Lett 19:985
Stonik VA, Chumak AD, Isakov VV, Belogortseva NI, Elyakov GB (1979) Khim Prir Soedin 15:403
Kitagawa I, Inamoto T, Fuchida M, Okada S, Kobayashi M, Nishino T, Kyogoku Y (1980) Chem Pharm Bull 28:1651
Kuznetsova TA, Kalinovskaya NI, Kalinovsky AI, Rovnih NV, Elyakov GB (1982) Khim Prir Soedin 18:482
Kitagawa I, Nishino T, Kobayashi M, Kyogoku Y (1981) Chem Pharm Bull 29:1951
Oleynikova GK, Kuznetsova TA, Ivanova NS, Kalinovsky AI, Rovnih NV, Elyakov GB (1982) Khim Prir Soedin 18:464
Kalinin VI, Stonik VA (1982) Khim Prir Soedin 18:215
Chanley JD, Mezzetti T, Sobotka H (1966) Tetrahedron 22:1857
Tursch B, de Souza Quimaraes IS, Gilbert B, Aplin RT, Duffield AM, Djerassi C (1967) Tetrahedron 23:761
Roller P, Djerassi C, Cloetens R, Tursch B (1969) J Am Chem Soc 91:4918
Kitagawa F, Kobayashi M, Hori M, Kyogoku Y (1981) Chem Pharm Bull 29:282
Sharipov VF, Chumak AD, Stonik VA, Elyakov GB (1981) Khim Prir Soedin 17:181
Stonik VA, Maltsev II, Elyakov GB (1982) Khim Prir Soedin 18:629
Stonik VA, Maltsev II, Kalinovsky AI, Elyakov GB (1982) Khim Prir Soedin 18:200
Kitagawa I, Kobayashi M, Inamoto T, Yasuzawa T, Kyogoku Y, Kido M (1981) Chem Pharm Bull 29:1189
Kitagawa I, Yamanaka H, Kobayashi M, Nishino T, Yosioka I, Sugawara T (1978) Chem Pharm Bull 26:3722
Maltsev II, Stonik VA, Kalinovsky AI, Elyakov GB (1984) Comp Biochem Physiol 78B:421
Afiyatullov ShSh, Stonik VA, Elyakov GB (1983) Khim Prir Soedin 19:654
Avilov SA, Tischenko LYA, Stonik VA (1984) Khim Prir Soedin 20:799
Kalinin VI, Stepanov VR, Stonik VA (1983) Khim Prir Soedin 19:789
Kalinin VI, Kalinovsky AI, Stonik VA (1985) Khim Prir Soedin 21:212
Zurita M Bedoya, Ahond A, Poupat C, Potier P (1986) J Nat Prod 49:809
Habermehl G, Volkwein G (1971) Toxicon 9:319
Kalinovsky AI, Avilov SA, Stepanov VR, Stonik VA (1983) Khim Prir Soedin 19:724
Kalinin VI, Stonik VA (1982) Khim Prir Soedin 18:789
Levin VS, Kalinin VI, Stonik VA (1984) Biol Morya 33
Levin VS, Kalinin VI, Maltsev II, Stonik VA (1985) Biol Morya 3
Levin VS, Kalinin VI, Fedorov SN, Smaily S (1986) Biol Morya 72
Sheikh YM, Djerassi C (1976) J Chem Soc Chem Commun 1057
Vavilov NI (1922) J Genetics 12:47
Minale L, Pizza C, Riccio R, Zollo F (1982) Pure Appl Chem 54:1935
Elyakov GB, Levina EV, Levin VS, Kapustina II (1976) Comp Biochem Physiol 55B:57
Mackie AM, Singh HT, Owen JM (1977) Comp Biochem Physiol 56B:9
Fleming WJ, Salathe R, Wyllie SG, Howden MEH (1976) Comp Biochem Physiol 53B:267
Riccio R, Iorizzi M, Minale L (1986) Bull Soc Chem Belg 95:869
Okano K, Nakamura T, Kamiya Y, Ikegami S (1981) Agric Biol Chem 45:805
Itakura Y, Komori T, Kawasaki T (1983) Liebigs Ann Chem 12:2079
Riccio R, Zollo F, Finamore E, Minale L (1985) J Nat Prod 48:266
D’Auria, Finamore E, Minale L, Pizza C, Riccio R, Zollo F, Pusset M (1984) J Chem Soc Perkin Trans I, 2277
Kitagawa I, Kobayashi M (1978) Chem Pharm Bull 26:1864
Kitagawa I, Kobayashi H, Sugawara T (1978) Chem Pharm Bull 26:1852
Itakura Y, Komori T, Kawasaki T (1983) Liebigs Ann Chem 359
Itakura Y, Komori T, Kawasaki T (1983) Liebigs Ann Chem 56
Riccio R, Dini A, Minale L, Pizza C, Zollo F, Sevenet T (1982) Experientia 38:68
Riccio R, Simone E, Dini A, Minale L, Pizza C, Senatore F, Zollo F (1981) Tetrahedron Lett 22:1557
Riccio R, Pizza C, Squilace-Greco O, Minale L (1985) J Chem Soc Perkin Trans I, 655
Riccio R, Iorizzi M, Squillace-Greco O, Minale L, Debray M, Menon JL (1985) J Nat Prod 48:756
Komori T, Krebs HT, Itakura Y, Higuchi R, Sakamoto R, Taguchi S, Kawasaki T (1983) Liebigs Ann Chem 2092
Minale L, Riccio R, Squillace-Greco O (1985) Comp Biochem Physiol 80B.113
Riccio R, Squillace-Greco O, Minale L (1985) J Nat Prod 48:97
Bruno T, Minale L, Pizza C, Zollo F (1984) J Chem Soc Perkin Trans I, 1875
Komori T, Nanri H, Itakura Y, Sakamoto K, Taguchi S, Higuchi R, Kawasaki T, Higuchi T (1983) Liebigs Ann Chem 37
Neira C, Hoeneisen M, Silva M, Minale L (1985) J Nat Prod 48:848
Riccio R, Minale L, Pizza C, Zollo F, Pusset J (1982) Tetrahedron Lett 23:2899
Kicha AA, Kalinovsky AI, Levina EV, Stonik VA, Elyakov GB (1983) Tetrahedron Lett 24:3893
Kicha AA, Kalinovsky AI, Levina EV, Andrijaschenko PV (1985) Khim Prir Soedin 21:801
Kicha AA, Kalinovsky AI, Andrijaschenko PV, Levina EV (1986) Khim Prir Soedin 21:592
Levina EV, Kalinovsky AI, Andrijaschenko PV, Kicha AA (1987) Khim Prir Soedin 23:246
Zollo F, Finamore E, Minale L, Laurent D, Bargibant G (1986) J Nat Prod 49:919
Minale L, Pizza C, Riccio R, Zollo F (1983) Experientia 39:567
Riccio R, D’Auria MV, lorizzi M, Minale L, Laurent D, Duhet D (1985) Gazz Chim Ital 115:4.5
Minale L, Pizza C, Riccio R, Zollo F, Pusset J, Laboute P (1984) J Nat Prod 47:558
lorizzi M, Minale L, Riccio R, Debray M, Menou JL (1986) J Nat Prod 49:67
Segura de Correa R, Riccio R, Minale L, Duque C (1985) J Nat Prod 48:751
Minale L, Riccio R, Zollo F (1983) Experientia 39:569
Riccio R, Lorizzi M, Squillace-Greco O, Minale L, Laurent D, Barbin Y (1985) Gazz Chim Ital 115:505
Zollo F, Finamore E, Minale L (1985) Gazz Chim Ital 115–303
Minale L, Pizza C, Plomitallo A, Riccio R, Zollo F, Mellon FA (1984) Gazz Chim Ital 114:151
Pizza C, Pezzullo P, Minale L, Breitmaier E, Pusset J, Tirard P (1983) J Chem Res, Synop 76
Pizza C, Minale L, Laurent D, Menou JL (1985) Gazz Chim Ital 115:585
lorizzi M, Minale L, Riccio R, Debray M, Menou JL (1986) J Nat Prod 49:67
Anderson L, Bano S, Bohlin L, Riccio R, Minale L (1985) J Chem Res, Synop 366
Kapustina II, Kalinovsky AI, Polonik SG, Stonik VA (1987) Khim Prir Soedin 23:250
Kicha AA, Kalinovsky AI, Levina EV, Rashkes YaV, Stonik VA (1987) Khim Prir Soedin 21:356
Riccio R, D’Auria MV, Minale L (1986) J Org Chem 51:533
Bergman W (1962) Sterols: Their structure and distribution. In: Florkin M, Mason HS (eds) Comparative biochemistry. Academic, New York 3:103
Gupta KC, Scheuer PJ (1968) Tetrahedron 24:583
Goad LJ (1978) The sterols of marine invertebrates. Composition, biosynthesis and metabolites. In: Scheuer PJ (ed) Marine natural products. Chemical and biological perspectives 2:76
Mackie AM, Singh HT, Fletcher TC (1975) Mar Biol 29:307
Anisimov MM, Aminin DL, Rovin YuG, Lichatskaya GN, Popov AM, Kuznetsova TA, Kalinovskaya NI, Elyakov GB (1983) Dokl Akad Nauk SSSR 270:1985
Kalinovskaya NI, Kalinovsky AI, Kuznetsova TA, Stonik VA, Elyakov GB (1984) Dokl Akad Nauk SSSR 278:630
Findlay JA, Daljeet A, Matsonkas J, Moharir YE (1984) J Nat Prod 47:560
Goad LJ, Garneau F-X, Simard JL, ApSimon JW, Girard M (1986) Comp Biochem Physiol 84B: 189
Ambia K, Goad LJ, Hkycko S, Garneau F-X, Belanger J, ApSimon JW (1987) Comp Biochem Physiol 86B: 191
Goodfellow RM, Goad LJ (1983) Comp Biochem Physiol 76B:575
Kalinovskaya NI, Kuznetsova TA, Popov AM, Antonov AS, Elyakov GB (1983) Comp Biochem Physiol 76B:167
Elyakov GB, Fedorov SN, Chumak AD, Isakov VV, Stonik VA (1982) Comp Biochem Physiol 71 B:325
Riccio R, Minale L, Pagonis S, Pizza C, Zollo F, Pusser J (1982) Tetrahedron 38:3615
Kicha AA, Kalinovsky AI, Levina EV, Stonik VA, Elyakov GB (1983) Bioorg Khim 9:975
Minale L, Pizza C, Zollo F, Riccio R (1982) Tetrahedron Lett 23:1841
Kicha AA, Kalinovsky AI, Levina EV (1984) Khim Prir Soedin 20:738
Minale L, Pizza C, Riccio R, Sorrentino C, Zollo F, Pusset J, Bargibant G (1984) J Nat Prod 47:790
Minale L, Pizza C, Riccio R, Squillace-Greco O, Zollo F, Pusset J, Menou JL (1984) J Nat Prod 47:784
D’Auria MV, Riccio R, Minale L (1985) V-th Intern Symp Mar Nat Prod, Paris, PA-18
Riccio R, D’Auria MV, Minale L (1985) Tetrahedron 24:6041
Bolker HI (1967) Nature 213:905
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Stonik, V.A., Elyakov, G.B. (1988). Secondary Metabolites from Echinoderms as Chemotaxonomic Markers. In: Scheuer, P.J. (eds) Bioorganic Marine Chemistry. Bioorganic Marine Chemistry, vol 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-48346-2_2
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