Discodermia calyx

Discodermia calyx, Lithistida, Porif/lab tool as an okadaic acid-like tumor promoter... 

Three sulfated ceramides, calyceramides A-C (626-628) were isolated as inhibitors of neuraminidase from the marine sponge Discodermia calyx. Their structures were determined by spectroscopic and chemical methods [497],... 

Following the first report of tumor promotion by okadaic acid, additional tumor promoters of the okadaic acid activity class have been identified, e.g., microcystin [513,514], and calyculin derivatives, Fig. (63) reported in marine sponges such as Discodermia calyx [515] and Theonella swinhoei [516] as potent inhibitors of tumor cell proliferation. A two-sponge association, Poecillastra sp. and Jaspis sp., yielded cytotoxic toxins which exhibited selective activity against several tumoral cell lines [517],... 

The Japanese sponge Discodermia calyx has yielded the new calyculin, calyculin J (1669) (1631). The highly toxic (ichthyotoxicity, hemolytic activity) prymnesin-1 (1670) and -2 (1671), possessing unprecedented structural complexity, were characterized from the red tide alga Prymnesium parvum (1632-1634). 

Matsunaga S, Wakimoto T, Fusetani N (1997) Isolation of Four New Calyculins from the Marine Sponge Discodermia calyx. J Org Chem 62 2640... 

Calycnlin A (38) is an extraordinary metabolite composed of C28 fatty acid and two y-amino acids isolated from the sponge Discodermia calyx. It is not only highly antifnngal and antitnmor bnt also a potent cancer promoter that was fonnd to be cansed by potent inhibition of protein phosphatases 1 and 2A (1). More than 15 calycnlin derivatives were isolated from several marine sponges, which indicates the involvement of symbiotic microorganisms in the prodnction of calycnhns (6). 

Nakao Y, Takada K, Matsunaga S, Fusetani N. Calyceramides A-C neuraminidase inhibitory sulfated ceramides from the marine sponge Discodermia calyx. Tetrahedron 2001 57 3013-3017. 

Calyculins A-H are bioactive metabolites isolated from the sponge Discodermia calyx Calyculins are potent serine-threonine protein phosphatase (PPl and PP2A) inhibitors and endowed with remarkable cell membrane permeability. The absolute stereochemistry of calyculins and its C33—C37 portion has been investigated. The relative configuration of the stereocenters was determined by X-ray analysis. ... 

Senecio vernalis (senecivernine), 244 Sesbania drummodii seeds (sesbanimide A and sesbanimide B), 182 Sesbania punicea (sesbanimide A and sesbanimide B), 182 sponge Discodermia calyx (calyculin),... 

Matsunaga, S. et al., Calycnlins E, E, G and H, additional inhibitors of protein phosphatases 1 and 2A from the marine sponge Discodermia Calyx, Tetrahedron 47, 2999, 1991. 

The calyculins make up a family of potent, selective serine-threonine phosphatase inhibitors, which have been isolated from the Japanese sponge Discodermia calyx.There are at least 13 different members of this family, and the most abundant are calyculin A 1189a and calyculin C 1189c." As nanomolar inhibitors of protein phosphatases 1 and 2A (PPl and PP2A), 1189a and analogs have... 

Calyctiins, Strongly antitumor active metabolites from the Japanese marine sponge Discodermia calyx. Phosphatases 1 and 2A have been identified as the molecular sites of action. IC50O.5-2 nM(PPl) 0.1 -1 nM (PP2A). With regard to PPl C. A is about 30-200 times more effective than okadaic acid. Acidic, alkaline, and protein-tyrosine phosphatases are not affected. C. is cell permeable and can be used to study... 

Calyculin A Discodermia calyx (Sponge) — Inhibitor of protein phosphatases 250/10 pg... 

Specific Clycolipids of Theonella swinhoei, Discodermia calyx and D. dissoluta... 

Calyceramides A-C, isolated from Discodermia calyx harvested in Japan, are inhibitors of neuraminidase, an enzyme on the surface of the influenza virus, which acts during the process of the spread of viral infection by degrading glycoconjuguates of sialic acid (N-acetylneura-minic acid). Neuraminidase inhibitors are rare, and sul-fated ceramides could be good models for study (Nakao et al., 2001). 

Kato, Y, Fusetani, N., Matsunaga, S., Hashimoto, K., Fujita, S., and Furuya, T. (1986a) Calyculin A, a novel antitumor metabolite from the marine sponge Discodermia calyx. J. Am. Chem. Soc., 108, 2780-2781. 

Matsunaga, S., Wakimoto, T, Fusetani, N and Suganuma, M. (1997a) Isolation of four new calyculins from the marine sponge Discodermia calyx. /. Org. Chem., 62, 2640-2642. Addition/correction J. Org. Chem., 62, 9388. 

The lithistid sponge Discodermia calyx led to the isolation of icadamide C, a polyketide closely related to theopederin K, isolated from Theonella sp. Icadamide C and theopederin K are strongly cytotoxic against A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15 cancer cell lines with ICso values of 19, 25, 10, 17, and 14ngml and 0.3, 0.5, 0.1, 0.1, and O.lngml", respectively, for icadamide C and theopederin K (Shinde et al, 2007). 

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