Triterpene and Steroid Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities

Abstract

The article is a comprehensive review concerning tetracyclic triterpene and steroid glycosides from sponges (Porifera, Demospongiae). The extensive oxidative transformations of the aglycone and the use of various monosaccharide residues, with up to six possible, are responsible for the significant structural diversity observed in sponge saponins. The saponins are specific for different genera and species but their taxonomic distribution seems to be mosaic in different orders of Demospongiae. Many of the glycosides are membranolytics and possess cytotoxic activity that may be a cause of their anti-predatory activities. All these data reveal the independent origin and parallel evolution of the glycosides in different taxa of the sponges. The information concerning chemical structures, biological activities, biological role, and taxonomic distribution of the sponge glycosides is discussed.

Additional Sarasinosides from the Marine Sponge Melophlus sarasinorum Collected from the Bismarck Sea

“…This is the first assessment of cytotoxicity and antimicrobial activity of sarasinoside C 1 and sarasinosides with equivalent aglycone units to 3 and 4 , as sarasinosides H 2 and I 2 were not previously evaluated . The lack of activity for 3 and 4 is in agreement with the hypothesis that sarasinosides with Δ 8(9) unsaturation or a Δ 7(8),9(11) diene system show increased activity in comparison to Δ 8(14) unsaturation and highly oxygenated aglycone systems . Previous evaluations of sarasinosides for biological activity have reported cytotoxicity against K562 leukemia and A549 lung carcinoma cell lines (LC 50 values between 7.4 and >100 μM).…”

“…19 The lack of activity for 3 and 4 is in agreement with the hypothesis that sarasinosides with Δ 8 (9) unsaturation or a Δ 7(8),9 (11) diene system show increased activity in comparison to Δ 8 (14) unsaturation and highly oxygenated aglycone systems. 24 Previous evaluations of sarasinosides for biological activity have reported cytotoxicity against K562 leukemia and A549 lung carcinoma cell lines (LC 50 values between 7.4 and >100 μM). However, according to the current reference standards, they are considered inactive.…”

Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application

“…From these sponges, approximately 60 different steroids were isolated, with A-norsteroids (17)(18)(19)(20)(21)(22)(23)(24)(25)(26) among them. Notably, extracts from Agelas mauritiana and Darwinella australiensis have displayed hemolytic activities [33][34][35][36].…”

“…The compound 24-ethyl-3hydroxymethyl-A-norcholestane (31) was detected in Acanthella aurantiaca, Axinella verrucosa, and Homaxinella trachys [38,40]. A-Norcholistane-3-methanol (28) was found in Axinella verrucosa and Hymeniacidon aldis [41][42][43][44], and (3β,5α,22E,24R)-3-Hydroxymethyl-24-methyl-A-norcholest-22-ene (36) was isolated from these same sponges [41][42][43][44].…”

“…Researchers from the University of California focused on the Gulf of Mexico sponge Teichaxinella morchella, discovering that its extracts contained exclusively 3-hydroxymethyl-A-nor-sterols (32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43). The exclusive presence of A-norsterols, with no normal sterols, indicates that these compounds might be biotransformation products of dietary precursors or result from bacteria transforming common sterols into A-norsterols [41,42,45].…”