Antibacterial metabolite

C-Methylation also features in the biosynthesis of usnic acid (Figure 3.41), an antibacterial metabolite found in many lichens, e.g. Usnea and Clado-nia species, which are symbiotic combinations of alga and fungus. However, the principal structural modification encountered involves phenolic oxidative coupling (see page 28). Two molecules of methylphloracetophenone are incorporated, and these are known to derive from a pre-aromatization methylation reaction and not by... 

The marine bacterium Chromobacterium sp. produces 2,3,4,5-tetrabromopyrrole (1) <74MB281>, and the marine acorn worm Polyphysia crassa has yielded the antibacterial metabolite 2,3,4-tribromopyrrole (2), an extremely labile compound <90JNP703>. The Red Sea sponge Acanthella carteri contains bromopyrrole amide (3) <97JNP180>, and the isomeric... 

In a screening of myxobacteria for antibacterial metabolites, the Sorangium cellulosum strain So ce678 was selected for its activity against Staphylococcus aureus [55]. The active compounds were produced as two rather lipophilic active compounds, i.e. tartrolons B (16) and C (17). Tartrolon B was identified as a boric acid ester of tartrolon A3, whereas tartrolon A1 and tartrolon A2 are stereoisomers of tartrolon A3. All components could be chemically converted into eaeh other. 

McConnell, O.J. and Fenical, W., 1977a. Polyhalogenated l-octene-3-ones, antibacterial metabolites from the red seaweed Bonnemaisonia asparagoides. Tetrahedron Lett., 1977 1851-1854. 

C14H10O5. Mr 258.23, mp. 350 °C, (decomp.). Phytotoxic, cytotoxic, and antibacterial metabolite of Alter-naria dauci, A. tenuis, and A. cucumerina. 

C12H20N2O2, Mr 224.30, pale yellow needles, mp. 97-99 C, [a]o+13.3° red complex with Fe, green Cu(ll) salts. Toxic, antibacterial metabolite from Af-pergillus flavus, A. sojae, and A. quercinus, LD50 (mouse p.o.) 4-5 mg/kg. A. is formed from leucine and isoleucine. Other amino acids can be built-in by specific feeding during the fermentation, e.g., neoaspergillic acid (2 mol. leucine). 

Stewart M, Capon R, White J, Lacey E, Tennant S, Gill J, Shaddock M (2004) Rugulotrosins A and B Two New Antibacterial Metabolites from an Australian Isolate of a Penicillium sp. J Nat Prod 67 728. 

Broadbent D, Mabelis RP, Spencer H (1975) 3,6,8-Trihydroxy-l-methylxanthone -an Antibacterial Metabolite from PeniciUbm patulum. Phytochemistry 14 2082... 

Ohzeki, T. and Mori, K. (2001) Synthetic microbial chemistry, part XXXV. Synthesis of corollosporine, an antibacterial metabolite of the marine fungus CoroUospora maritima. Biosci. Biotechnol. Biochem., 65, 172-175. 

Vanisree, M. and Subbaraju, G.V. (2002) Alcyonacean metabolites VIII-antibacterial metabolites from Lobophytum crassum of the Indian Ocean. Asian J. Chem., 14, 957—960. 

Ciminiello, P., Fattorusso, E., and Magno, S. (1988) BucdnulLii, an antibacterial metabolite from the Mediterranean whelk Buccinulum comeum. Gazz. Chim. Hal., 118, 105-107. 

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