Mycale

Two other pyrrolopyrimidine nucleoside antibiotics, mycalisines A and B (56,57), have been isolated from the sponge Mycale sp. (173). These bioactive marine metaboHtes inhibit cell division of starfish eggs. 

Northcote, P. T., Blunt, J. W., andMunro, M. H. G. (1991). Pateamine A potent cytotoxin from the New Zealand marine sponge, Mycale sp. Tetrahedron Lett. 32, 6411—6414. 

Rzasa, R. M., Shea, H. A., and Romo, D. (1998). Total synthesis of the novel, immunosuppressive agent (-)-Pateamine A from Mycale sp. Employing a b-lactam-based macrocyclization. J. Am. Chem. Soc. 120, 591—592. 

The toxic effect of various species of rove beetles pertaining to the genus Paederus on the skin and eyes of mammals, including man, are due to the presence in their hemolymph of three vesicant amides pederin (104), pederone (105) and pseudopederin (106) (Fig. 18) [94,95], pederin being the major and most active of the three compounds. Their structure determination [96, 97] revealed rather unique substances until similar natural products with comparable biological activities were isolated from sponges of the genera Mycale [98,99], Stylinos [100] and Theonella [101-104]. 

Azumamide E is a cyclotetrapeptide natural product isolated from marine sponge Mycale izuensis. Like most cyclopeptide HDAC inhibitors, these compounds contain D-a-amino acids (D-Phe, D-Tyr, D-Ala, D-Val) which relieve ring strain (Fig. 7). However, they are unique from other natural cyclopeptide HDAC inhibitors with a retroenantio arrangement. 

Nakao Y, Yoshida S, Matsunaga S, Shindoh N, Terada Y, Nagai K, Yamashita JK, Ganesan A, van Soest RWM, Fusetani N. (2006) Azumamides A-E Histone deacetylase inhibitory cyclic tetrapeptides from the marine spong Mycale izuensis. Angew Chem Int Ed 45 7553-7557. 

Nakao, Y, Yoshida, S., Matsunaga, S., Shindoh, N., Terada, Y, Nagai, K et al. (2006) Azumamides A-E histone deacetylase inhibitory cydic tetrapeptides from the marine sponge. Mycale izuensis Angewandte Chemie (International Edition in En ish), 45, 7553-7557. 

Polyket mixed biogenesis macrolides (pateamine A from Mycale sp., Poecil., Porif from NZ Northcote 1991) macrocyclic ethers y-pyrones (Phaceiocarpus sp., Gigartinales, Rhodoph. from SE Australia and Tasmania Murray 1995). 

Pateamine (606), a potent cytotoxin containing a dilactone functionality, was isolated from a New Zealand species of Mycale and identified by analysis of spectral data [480]. Total synthesis of pateamine A (606) involved a (3-lactam based macrocyclisation [481,482], while another total synthesis of pateamine employed a concise and convergent route [483]. 

Mycale sp. from Japan contained thiomycalolides A (619) and B (620) as minor metabolites. They are highly cytotoxic glutathione adducts of the known metabolites mycalolides A and B [494]. 

Hiburipyranone (82), a brominated isocoumarine from the sponge Mycale adhaerens collected off Hiburi Island, Japan, is cytotoxic against P-388 cells with an IC50 value of 0.19 pg/ml [72]. 

Mycalamides A (286) (233) and B (287) 234) were isolated from a New Zealand sponge of the genus Mycale and exhibit significant in vivo antiviral and antitumor activity. From an Okinawan sponge Theonella sp.) onna-mide A (288) with a structure closely related to mycalamides was isolated,... 

Peloruside A 14 (Scheme 6.1 Part 2) was isolated from a New Zealand Mycale hentschei marine sponge and initially showed activity against P388 murine leukaemia cells at 10 ng/mL.98 Peloruside s cytotoxicity profile and structural similarity to bryostatin led to the examination of protein kinase C (PKC) as a possible mode of action.242 This was determined to be incorrect and it was soon established that the remarkable activity of peloruside was through the stabilisation of microtubules at a site distinct from the taxoid site.243... 

Peloruside A (31), which is a 16-membered, highly oxidized macrolide from the sponge Mycale hentscheli, induces tubulin polymerization (2). 13-Deoxytedanolide (32) isolated from Japanese sponges of the genus Mycale shows promising antitumor activity. It inhibits protein synthesis by binding to a 70 S large subunit of eukaryotic ribosome (17). 

Pateamine (39) is a macrolide isolated from a marine sponge Mycale sp. Its potent cytotoxicity is attribnted to inhibition of transcriptional initiation (19). 

---