Sponges, natural products from

Scheme 20 Lobophorolide (72) from the brown alga Lobophora variegata, and structurally similar natural products from cyanobacteria and the sponge Theonella swinhoei...

Preservation of natural products from the animals is more difficult. Zoos remain living stores of animals that, like the civet cat and the amphibians, give unusual metabolites. Aquaria might serve the same scope for marine invertebrates. However, many productive species, such as the sponges and the anthozoans, do not survive long in aquaria. 

Baby, J. and Sujatha, S. (2010). Pharmacologically important natural products from marine sponges. J. Nat. Prod. 4, 5-12. 

Pomponi, S. A., Willoughby, R., Kaighn, M. E., and Wright, A. E., Development of techniques for in vitro production of bioactive natural products from marine sponges, in Invertebrate Cell Culture Novel Directions and Biotechnology Applications, Maramorosch, K. and Mitsuhashi, J., Eds., Academic Press, New York, 1997. 

Cytosine arabinoside (69), a synthetic analog of the C-nucleosides spongouridine (70) and spongothymidine (71) from the sea sponge Cryptotheca cripta, was the first and, so far, the only marine-derived compound used routinely as an anticancer agent (110). However, a number of chemically diverse natural products from marine sources have been progressed to clinical trials. The three most advanced compounds are in phase II trials ecteinascidin-743 (72), a tetrahydroisoquino-... 

Several isoquinolinequinones are natural products. From a bright-blue marine sponge of Reniera sp., renierone (260) was isolated as the major antimicrobial antimetabolite (79TL4163). Later, related quinones were isolated... 

ABSTRACT Marine invertebrates such as ascidians, sponges and others are a prolific source of bioactive secondary metabolites. We have isolated a variety of marine natural products from the Okinawan marine invertebrates by using the sea urchin egg assay. Our recent work, the isolation, structure determination and activities of chlorinated macrolides, sesterterpenic acids, a bromotyrosine derivative, acetogenin derived endoperoxides, diterpene alkaloids, sesquiterpene quinones and spiro-sesquiterpenes, is presented in this article. The syntheses of these metabolites are also described. 

A similar refinement of the synthetic route was developed in the approach to niphate-sine C 357 (R=Me) and norniphatesine C 357 (R=H) [125], sponge natural product alkaloids with cytotoxic activity. These compounds were readily prepared from the advanced intermediate 356 that was generated by a cross-coupling reaction using 152. 

Kobayashi, J., Kondo, K., Ishibashi, M., Walchli, M. R., and Nakamura, T. (1993). Theone-zolide A A novel polyketide natural product from the Okinawan marine sponge Theonella sp. J. Am. Chem. Soc. 115, 6661-6665. 

Manoallde. C2jH3603, Mr 416.56, amorphous solid, as 25-acetate mp. 117 -119 °C. A sesterterpenoid marine natural product from the sponge Luffariella variabilis, the name is derived from the Manoa valley, Oahu, Ha-... 

Proksch P, Putz A, Qrtlepp S, Kjer J, Bayer M. Bioactive natural products from marine sponges and fungal endophytes. Phytochem Rev 2010 9(4) 475-89, SI. 

McCarthy, RJ, T.P. Pitts, G.P Gunawardana, et al., 1992. Antifungal activity of meridine, a natural product from the marine sponge Corticium sp. J. Nat. Prod., 55 1664-1668. 

FIGURE 16.13 Summary of the absorption capacity for diesel oil measured from CNT sponges, natural products (cotton, loofah), polymeric sponges (polyurethane, polyester) and activated carbon. The maximum weight gain for oils by previously reported nanowire membranes (Q=20) [104] is included for comparison. 

Brauers, G., Ebel, R., Edrada, R.-A, Wray, V., Berg, A., Grafe, U and Proksch, P. (2001) Hortein, a new natural product from the fungus Hortaea wemeckii associated with the sponge Aplysina aerophoba. J. Nat. Prod., 64, 651-652. 

Sharma, G. and Magdoflf-Fairdiild, B. (1977) Natural products from sponges. 7. The constitution of weakly basic guanidine compoimds, dibromophakellin and monobromophakellin. J. Org. Chem., 42, 4118 124. 

Barrow, R.A. and Capon, R.J. (1992) Sulfolane as a natural product from the sponge/tunicate composite, Batzella sp./Lissodinum sp. /. Nat Prod., 55,1330-1331. 

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