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Sponges and Steroids

All marine organisms have been proved to be a veritable cornucopia of unusual steroid metabolites, but some believe that marine sponges may provide the most diverse and biogenetically unprecedented array of unconventional steroids in the entire animal kingdom. These steroids are potent inhibitors of histamine release, are anti-inflammatory agents, immunosuppressants, antineoplastic agents, and antiviral agents. However, their full therapeutic potential remains to be delineated. [Pg.553]


Additionally, sulfated sterols have been described from a wide variety of marine organisms, particularly sponges and echinoderms, and several of these steroidal sulfates have exhibited a broad range of activities. Halistanol sulfates are a group of sulfated polyhydroxysteroids from... [Pg.703]

Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Antifouling terpenes and steroids against barnacle larvae from marine sponges, Biofouling, 11, 283, 1997. [Pg.566]

This chapter describes typical sponge metabolites according to the biosynthetic classification, with references to their important roles in drug discovery as well as in marine ecosystems. To avoid duplication, those compounds described in Comprehensive Natural Products Chemistry are not described in detail here. We do not deal with freshwater sponges, from which only lipids and steroids were reported, except for okadaic acid from the Baikalian sponge Lubomirskia baicalensis ... [Pg.329]

The bioactIve secondary metabolites from several marine sources, sponges and tunica-tes (Kobayashl/lshibashi), sea plumes (Katz/Adamczeski) and ascidians (Bowdem) cover a broad range of different chemical structures, terpenoids, unsaturated fatty acids, steroids, alkaloids, cyclic peptides and polysaccharides. [Pg.918]

Bohlin, L., H.P. Gehrken, P.J. Scheuer, and C. Djerassi Minor and Trace Sterols in Marine Invertebrates XVI. 3 -Hydroxymethyl-A- or-5a-gorgostane, a Novel Sponge Sterol. Steroids 35, 295 (1980). [Pg.321]

Stonik, V.A. (1986) Some terpenoids and steroid derivatives from echinoderms and sponges. PureAppl. Chem., 58, 423-436. [Pg.802]

Giner, J.L. and Djerassi, C. (1992b) Minor and trace sterols in marine invertebrates 65. 23-Epidihydrocalysterol a new cyclopropane-containing sponge sterol. Steroids, 57, 258—261. [Pg.1229]

Iwashima, M., Terada, 1., Igudii, K., and Yamori, T. (2002) New biologically active marine sesquiterpenoid and steroid from the Okinawan sponge of the genus Axinyssa. Chem. Pharm. Bull., 50, 1286-1289. [Pg.1236]

Since the theory and medical applications of collagen sponge were described by Chvapil et al. (52-54), they have been used to deliver steroid hormones (55), the anticancer drugs trans-retinoic acid (TRA) (56,57), and 5-fluorouracil (5-FU) (58), and antibiotics (59). [Pg.238]

Steroid chemistry, the glamor area of natural product research in the years following World War II, was replaced by macrolides, alkaloids, and prostanoids. Sterol chemistry again became exciting when an unanticipated rich diversity of marine invertebrate sterols were isolated, notably from sponges. After pioneering research in Italy, the field was reborn in Carl Djerassi s laboratory at Stanford. As a result, we now have a better and more detailed knowledge of sterol biosynthesis than of any other class of marine natural products. The authors of Chapter 1 are Stanford alumni. [Pg.5]

Another example of a nudibranch, which probably modifies dietary metabolites to obtain more effective allomones, is seen in Aldisa cooperi (= A. sanguinea cooperi) [155]. It elaborates two fish antifeedant bile acids (104,105) that are absent in its prey, the sponge Anthoarcuata graceae, where the main steroid is 4-cholesten-3-one (106). Biosynthetic experiments starting from both labelled mevalonic acid and labelled 4-eholesten-3-one would definitely clarify, whether, the two allomones (104-105) are biosynthetized de novo by the mollusc, or if they are derived from a food source. [Pg.114]

There are three classes of cyclic peroxides that were found in marine sponges steroidal peroxides, norsesterterpene and norditerpene peroxides, and polykide peroxides many of them were isolated and their relative and absolute stereochemistry was determined. Most of them (even as crude extracts) show exceptional antimicrobial and antifungal propoperties (cf. Section 8.10.3). For example, the norsesterterpene 1,2-dioxides mycaperoxides A and B 222 and 223 (Scheme 63) showed significant cytotoxicity and in vitro antiviral activity. [Pg.727]

The structure of sokotrasterol sulfate (548), isolated from sponges of the family Halichondriidae was determined by X-ray analysis [453-455]. The steroid, 26-norsokotrasterol sulfate (549), was isolated from the marine sponge Trachyopsis halichondrioides and was identified by NMR spectroscopic analysis [456]. [Pg.700]

An unusual 6a-sterol sulfate (557) was isolated from Dysidea fragilis, from the Venetian lagoon and displayed cytotoxicity against two different tumour cell lines in vitro [460]. Tamosterone sulfates (558-559) are a C14 epimeric pair of polyhydroxylated sterols isolated from a new species of Oceanapia [461]. The Japanese marine sponge Epipolasis sp. contained the steroid polasterol B sulfate (560) along with the known compound halistanol sulfate (532). The structure of compound 560 was determined on the basis of spectroscopic evidence and a chemical conversion [462]. [Pg.702]

An Acanthodendrilla sp. from Japan contained ten steroidal sulfates, acanthosterol sulfates A-J (561-570). Acanthosterol sulfates I (569) and J (570) showed antifungal activity against Saccharomyces cervisiae and its mutants [463]. Clathsterol (571), was isolated from the Red Sea sponge Clathria sp. The structure was established mainly by interpretation of spectral data and a chemical transformation. Clathsterol (571) was active against HIV-1 reverse transcriptase (RT) at a concentration of 10 iM [464]. Toxadocia zumi contains three sterol sulfates (572-574) that are antimicrobial, cytotoxic, ichthyotoxic and larvicidal [465]. [Pg.702]

Polymastiamide A (579), an antimicrobial steroid with an unusual side chain modification involving an amide bond to a non-protein amino acid, was isolated from the Norwegian marine sponge Polymastia boletiformis. The structure of polymastiamide A (579) was elucidated by analysis of spectroscopic data and chemical interconversions [470]. Polymastiamides B-F (580-584), additional amino acid conjugates of steroids, were later isolated from the same sponge [471],... [Pg.704]


See other pages where Sponges and Steroids is mentioned: [Pg.553]    [Pg.555]    [Pg.557]    [Pg.559]    [Pg.561]    [Pg.563]    [Pg.565]    [Pg.567]    [Pg.569]    [Pg.553]    [Pg.555]    [Pg.557]    [Pg.559]    [Pg.561]    [Pg.563]    [Pg.565]    [Pg.567]    [Pg.569]    [Pg.29]    [Pg.59]    [Pg.69]    [Pg.548]    [Pg.1168]    [Pg.46]    [Pg.345]    [Pg.1175]    [Pg.729]    [Pg.3233]    [Pg.646]    [Pg.74]    [Pg.82]    [Pg.10]    [Pg.22]    [Pg.92]    [Pg.71]    [Pg.27]    [Pg.6]    [Pg.74]    [Pg.683]    [Pg.78]    [Pg.176]   


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