Cephalosporium caerulens

Because of the unique expression of FASN in tumors, much emphasis has been put toward the development of pharmacological agents that inhibit FASN activity and, therefore, inhibit tumor growth and progression. Historically, a Cephalosporium caerulens mycotoxin metabolite known as cerulenin [(2S, 3R)-... 

The utility of this methodology is illustrated by the stereoselective synthesis of ( + )-cer-ulenin (759), an antifungal antibiotic first isolated from the culture filtrate of Cephalosporium caerulens. Its ability to inhibit lipid biosynthesis in Escherichia coli by irreversibly binding P-keto-acyl-carrier protein synthetase, the enzyme responsible for the chain lengthening reaction in fatty acid synthesis, has attracted interest in its mechanism of action. D-Tartaric acid... 

Protostane and their 29-nor-derivatives denoted as fusidanes are fimgal metabolites. Cephalosporium caerulens, for instance, produces (-l-)-protosta-17(20)-( -24-diene-3p-ol. Fusidanes sueh as helvolic acid from the Helvola mutant of the mold Aspergillus fumigatus and related structures are widely used as antibacterials. Fusi-dic acid isolated from the fermentation broth of Fusidium coccineum and related tribes is an example. Its sodium salt has immunosuppressive and antibacterial properties, and is applied in ointments against multiresistant staphylococci during the therapy of wound infections... 

C12H17NO3 M 223.271 Isol. from Cephalosporium caerulens. Antifungal antibiotic. Inhibitor of the biosynth. of fatty acids and steroids. Needles (CCI4 or C6H6). Mp 93 . Bp 000001 120 . [a] 6 +63 (c, 2 in MeOH). 

Cerulenin was discovered by Hata et al. in 1960 from Cephalosporium caerulens strains [136]. Some years later, the antibiotic was isolated and the incorrect structure 122 was proposed [137]. The initial assignment was subsequently revised to the isomer 121 on the basis of high-resolution NMR measurements [138], and the correct absolute configuration of (-l-)-cerulenin was independently established by two groups [139, 140]. Cerulenin is also produced by Helicoceras oryzae, Sartorya sp., and Acrocylindrium sp. Strains (Figure 3.40) [141]. 

Isol. from Cephalosporium caerulens, also obt. by mild hydrol. of Helvolic acid. Needles. Mp 202.5-203°. -88.9° (c, 1 in CHCI3). 

Cerulenin is produced by the fungus Cephalosporium caerulens. Cerulenin... 

The two ketoacyl-synthetases present in the fatty-acid synthetase complexes of higher plants exhibit differential sensitivities against cerulenin. In plants the B-ketoacyl-synthetase I (de novo fatty acid synthesis) is affected by cerulenin, whereas the B-ketoacylsynthetase II, which catalyzes the elongation from 16 0 to 18 0 is relatively insensitive (Jaworski et al. 1974). The B-ketoacylsynthetase of Cephalosporium caerulens, which produces cerulenin, is much less sensitive than the yeast enzyme (Kawaguchi et al. 1979) and in Escherichia coli two sensitive and one insensitive synthetase were described (Jackowski and Rock 1987). 

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