Callyspongia fibrosa

Alkylpyridines supposedly lie also along another biosynthetic route, affording pofymeric pyridinium compounds in marine haliclonid sponges the Indo-Pacific Callyspongia fibrosa (Davies-Coleman 1993), the Caribbean Amphimedon compressa (Albrizio 1995), and the Mediterranean Reniera sarai (Sep5i6 1997). 

The next group of 3-AP polymers comprises the EGF-active factors (76), Fig. (21) from the sponge Callyspongia fibrosa [33]. They are... 

Fig. (31). Di-, tri-, tetra- and oligomeric alkylpyridinium compounds related to natural EGF-active factors from Callyspongia fibrosa...

It is interesting to note that a large oligomeric or polymeric 1,3-dialkylsubstituted pyridinium compound, which is an inhibitor of epidermal growth factor, has been isolated from the Micronesian sponge Callyspongia fibrosa [132]. 

Another quaternary alkyl piridinium salt (36) was isolated from an extract of the Micronesian sponge Callyspongia fibrosa [37]. A cyclic structure for this compound was first proposed on the basis of ion-spray mass spectrometry. However, a theoretically identical sample (36a) produced by an efficient synthetic route (see Scheme 7) revealed that the EGF active constituent must be a large oligomer or polymer of (36). 

Mantella Alkaloid 161, A-20082 Mantella Alkaloid 189, see T-20042 Mantella Alkaloid 191, A-20083 Mantella Alkaloid 317, A-20084 Aglaia odorata Alkaloid, A-20077 Callyspongia fibrosa Alkaloid, A-20078 Crotalaria retusa Alkaloid, A-10043 Dictyodendrilla Alkaloid, A-20081 Fromia monilis Alkaloid, A-30051 Pseudoceratina crassa Alkaloid, see B-30080 Zizyphus mucronata Alkaloid, A-20085 Alkaloid A, in B-I002I Mantella Alkaloid 384A, A-20086 Securidaca longipedunculata Alkaloid A, A-20087... 

The oligomeric pyridinium salts such as niphatoxins A-C and polymers such as halitoxin and amphitoxin have been isolated from aqueous or methanolic extracts of haplosderid sponges (Talpir et al, 1992). One derivative isolated from Callyspongia fibrosa is an inhibitor of the epidermal growth factor (EGF) receptor, with a molecular weight greater than 5000 Da, and may be a polymer of a... 

Davies-Coleman, M.T., Faulkner, D.J., Dubowchik, G.M., Roth, G.P., Poison, C., and Fairchild, C. (1993) A new EGF-active polymeric pyridinium alkaloid from the sponge Callyspongia fibrosa. J. Org. Chem., 58, 5925-5930. 

---