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Review
. 2012 Aug;10(8):1671-1710.
doi: 10.3390/md10081671. Epub 2012 Aug 10.

Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles

Affiliations
Review

Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles

Vladimir I Kalinin et al. Mar Drugs. 2012 Aug.

Abstract

Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed.

Keywords: activities; biological functions; glycosides; sponges; structures; taxonomic distribution.

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Figures

Chart 1
Chart 1
Structures of sarasinosides.
Chart 2
Chart 2
Erylosides from Erylus formosus.
Chart 3
Chart 3
Erylosides from Erylus lendenfeldi.
Chart 4
Chart 4
Erylosides from Erylus goffrilleri.
Chart 5
Chart 5
Erylosides from Erylus sp.
Chart 6
Chart 6
Sokodosides from Erylus placenta.
Chart 7
Chart 7
Erylosides from Erylus nobilis.
Chart 8
Chart 8
Ulososides from Ulosa sp.
Chart 9
Chart 9
Feroxosides from Ectyoplasia ferox.
Chart 10
Chart 10
Isomalabarican triterpene glycosides from Geodia sp. and Rhabdastrella globostellata.
Chart 11
Chart 11
Pouosides from Lipastrotethya sp.
Chart 12
Chart 12
Sipholenosides from Siphonochalina (=Callispongia) siphonella.
Scheme 1
Scheme 1
Biogenesis of sipholane triterpenoids.
Chart 13
Chart 13
Xestovanin A and secoxestovanin A from Xestospongia (=Neopetrosia) vanilla.
Chart 14
Chart 14
Isoxestovanin A, xestovanins B and C and dehydroxestovanin A from Xestospongia (=Neopetrosia) vanilla.
Chart 15
Chart 15
Epidehydroxestovanin A, dehydroxestovanin C and secodehydroxestovanin A from Xestospongia (=Neopetrosia) vanilla.
Chart 16
Chart 16
Pachastrelloside A and wondosterols A–C from a two sponge association.
Chart 17
Chart 17
Pandarosides from Pandaros acanthifolium.
Chart 18
Chart 18
Acanthifoliosides from Pandaros acanthifolium.
Chart 19
Chart 19
Mycalosides from Mycale laxissima.
Chart 20
Chart 20
Hapaioside andptilosaponosides from Ptilocaulis spiculifer.
Chart 21
Chart 21
Caminosides from Caminus sphaeroconia.
Chart 22
Chart 22
Pachymoside A from Pachymatisma johnstonia and its methyl ether.
Chart 23
Chart 23
Simplexides from Plakortis simplex.
Chart 24
Chart 24
Clathrosides and isoclathrosides from Agelas clathroides.
Chart 25
Chart 25
Clavosolides from Myriastra clavosa.
Chart 26
Chart 26
Latranculinosides from Latrunculia corticata.
Chart 27
Chart 27
Bipolar glycosidlated lipids from Oceanapia (=Rhizochalina) spp.
Chart 28
Chart 28
Erylusamins from Erylus placenta, erulisine and erulisidine from Erylus cf. lendenfeldi.

References

    1. Stonik V.A. Some terpenoid and steroid derivatives from echinoderms and sponges. Pure Appl. Chem. 1986;58:423–436. doi: 10.1351/paC198658030423. - DOI
    1. Stonik V.A., Kalinin V.I., Avilov S.A. Toxins from sea cucumbers (Holothuroids): Chemical structures, properties, taxonomic distribution, biosynthesis and evolution. J. Nat. Toxins. 1999;8:235–248. - PubMed
    1. Moraes G., Northcote P.T., Kalinin V.I., Avilov S.A., Silchenko A.S., Dmitrenok P.S., Stonik V.A., Levin V.S. Structure of the major triterpene glycoside from the sea cucumber Stichopus mollis and evidence to reclassify this species into the new genus Australostichopus. Biochem. Syst. Ecol. 2004;32:637–650. doi: 10.1016/j.bse.2004.02.005. - DOI
    1. Avilov S.A., Kalinin V.I., Smirnov A.V. Use of triterpene glycosides for resolving taxonomic problems in the sea cucumber genus Cucumaria (Holothurioidea, Echinodermata) Biochem. Syst. Ecol. 2004;32:715–733. doi: 10.1016/j.bse.2003.12.008. - DOI
    1. Kalinin V.I., Silchenko A.S., Avilov S.A., Stonik V.A., Smirnov A.V. Sea cucumbers triterpene glycosides, the recent progress in structural elucidation and chemotaxonomy. Phytochem. Rev. 2005;4:221–236. doi: 10.1007/s11101-005-1354-y. - DOI

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