Cyclodepsipeptides, antibiotic

Bevan K, Davies JS, Hassall CH, Morton RB, Phillips DAS (1971) Amino-Acids and Peptides. Part X. Characterisation of the Monamycins, Members of a New Family of Cyclodepsipeptide Antibiotics. J Chem Soc (C) 514... 

H Tomoda, XH Huang, J Cao, H Nishida, R Nagoa, S Okuda, H Tanaka, S Omura. Inhibition of acyl-CoA cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiot 45 1626-1632, 1992. 

Destruxins and bassianolide have no importance in practical plant protection because their recovery is cumbersome, they are highly toxic to warm-blooded animals and, moreover, they are not contact poisons. Their activity as a stomach poison is greatly limited by their antifeedant effect. They are primarily products of theoretical interest, and it is to be hoped that study of them will clarify relationships concerning the mechanism of the insecticidal and antifeedant effects, and will help elucidate the biological effect of cyclodepsipeptide antibiotics of similar structure. 

Cyclodepsipeptide antibiotic. Isol. from Streptomyces sp. Used in complexation of K and its transport through a mitochondrial membrane. Cryst. (diisobutyl ether). Mp... 

The monamycins are a group of 15 antibiotic cyclodepsipeptides from Strepto-myces jamaicensis. After much structural elucidation work on the hydrolysis and degradation products (1050, 1051), the structures of the six chlorine-containing monamycins Gi (1015), G2 (1016), G3 (1017), H, (1018), H2 (1019), and I (1020) were determined (1052). 

T Sasaki, M Takagi, T Yaguchi, S Miyadoh, T Okada, M Koyama. A new anthelmintic cyclodepsipeptide PF1022. J Antibiot 45 692-697, 1992. 

Tyr substructures are, moreover, found within several peptidic antibiotics, for example the edeines 57 from Bacillus brevis, or within cyclodepsipeptides that have been isolated from marine sponges, for example jaspamides A-C 59 [106] or geo-diamolides H-I 58 [107] (Scheme 1.5.9). The chondramides 60 are closely related antibiotics that have been obtained from the myxobacterium Chondromyces croca-tus. Within the edeine biosynthesis D-/ -Tyr 9 seems to be a real precursor [89]. The biosynthesis of the jaspamides, the geodiamolides, or the chondramides has not yet been investigated. 

The antibiotic serratamolide (VI/119, Scheme VI/23), a naturally occurring cyclodepsipeptide, was isolated from a Serratia marcescens culture [90], Its synthesis is an application of the principal method described above. The hydro-genolysis of the diketopiperazine VI/117 gives the 0,0 -diacetyl derivative VI/118, which was converted into the antibiotic itself by mild hydrolysis [91]. 

Deffieux G, Merlet D, Baute R, Bourgeois G, Baute M-A, Neveu A. New insecticidal cyclodepsipeptides from the fungus Isariafelina. II. Structure elucidation of isariins B, C and D. J Antibiot 34 1266-1270, 1981. 

Tsuno, A., Kamijo, M., Taketomo, N., Sato, Y, and Ajisaka, K. (1997) Roseocardin, a novel cardiotonic cyclodepsipeptide from Trichothecium roseum.J. Antibiot., 50,1007-1013. 

Numerous a,P-dehydroamino acids have in recent years been identified as constituents of fungal metabolites. Their characterization and typical structural features are summarized in Table 1. In most of these metabolites, almost all of which are cyclic compounds (cyclopeptides or cyclodepsipeptides) and which frequently possess antibiotic properties, D-amino acids also occur. 

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