Chaetoglobosins

Sekita S, Yoshihira K, Natori S, Kuwano H, Structures of chaetoglobosin A and... 

Sekita S, Yoshihira K, Natori S, Kuwano H, Structures of chaetoglobosins C, D, E, and F, cytotoxic indol-3-yl-[13]cytochalasans from Chaetomium globosum, Tetrahedron Lett 1351—1354, 1976. 

Jiao W, Feng Y, Blunt JW, Cole ALJ, Munro MHG, Chaetoglobosins Q, R, andT, three further new metabolites from Chaetomium globosum, J Nat Prod 67 1722— 1725, 2004. 

Zhang L et al. Isolation and determination of the anti-cancer substance chaetoglobosin A from endophytic fungus oiMaytenus hookerii, Zhongguo Yaoxue... 

For the purpose of this review, it has been necessary to circumscribe the type of tetramic acid metabolites to be considered. Thus, the large group of cytochalasins, chaetoglobosins and penchalasins, e.g. 3, will not be included here as they have been covered in detail elsewhere [5-7]. For these metabolites, a tetramic acid species has been postulated as the putative precursor 4 that undergoes a Diels-Alder reaction [8-10],... 

A new toxic cytochalasin, chaetoglobosin K, isolated from Diplodia macro-spora, has the structure (24), according to the X-ray crystal-structure determination.24 Compared with chaetoglobosin A, metabolite K has additional methyl groups at positions 10 and 11 this raises the interesting possibility (among others) that propionic acid may be implicated in its biosynthesis. 

There are, perhaps, several reasons as to why far more detailed research has been conducted with both the cytochalasins and chaetoglobosins in zoological models than plant (agricultural) systems. First, cellular activity against animal systems implies that a potential pharmaceutical market may exist, especially if the... 

Matesic, D. F., Blomme, I., Sunman, J. A., Cutler, S. J., and Cutler, H. G. 2001. Prevention of organochlorine-induced inhibition of gap junctional communication by chaetoglobosin K in astricytes. Cell Biol. Toxicol. 17, 395-408... 

Other effects of cytochalasins on plant growth have been reported 11481. Chaetoglobosin K was Isolated from Dlolodla macrosDora and shown to be structurally related to the cytochalasins 11461. Phytotoxicity tests Indicated Inhibition to wheat coleoptlles at 10 N and may be the most active cytochalasin tested. 

Chatoglobosin A (58) and the related compounds are mycotoxins produced by various iungi such as Chaetomium sp. These mycotoxins are acutely toxic to mammals [46]. Chaetoglobosin O was isolated from Cylindrocladium Jloridanum causal fungus of black rot disease to alfalfa [47]. Biosynthetic studies using the cheatoglobosin-produc-ed strain Chaetomium subqffine revealed that the incorporation of the precursor [1- C, 02]-, H3]-acetate, labeled methionin and... 

Kig. 15.1, ess oxidized products using P450 inhibitor in the biosynthesis of chaetoglobosin A (58)... 

Andersen, B., Smedsgaard, J., and Frisvad, J.C. 2004. Penicillium expansum Consistent production of patulin, chaetoglobosins, and other secondary metabolites in culture and their natural occurrence in fruit products. J. Agric. Food. Chem. 52, 2421-2428. 

Penicillium expansum consistent production of patulin, chaetoglobosins and other secondary metabolites and their natural occurrence in fruit products,... 

---