Stachybotrylactam

Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347.[Pubmed:24694571]

Mar Drugs. 2014 Apr 1;12(4):1924-38.

A novel spirocyclic drimane coupled by two drimane fragment building blocks 2 and a new drimane 1 were identified in mycelia and culture broth of Stachybotrys sp. MF347. Their structures were established by spectroscopic means. This is the first example of spirocyclic drimane coupled by a spirodihydrobenzofuranlactam unit and a spirodihydroisobenzofuran unit; and the connecting position being N-C instead of an N and N connecting unit. Strain MF347 produced also the known spirocyclic drimanes stachybocin A (12) and stachybocin B (11) featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue; the known spirocyclic drimanes chartarlactam O (5); chartarlactam K (6); F1839A (7); Stachybotrylactam (8); stachybotramide (9); and 2alpha-acetoxyStachybotrylactam acetate (10); as well as ilicicolin B (13), a known sesquiterpene. The relative configuration of two known spirobenzofuranlactams (3 and 4) was determined. All compounds were subjected to biological activity tests. The spirocyclic drimane 2, 11, and 12, as well as the sesquiterpene 13, exhibited antibacterial activity against the clinically relevant methicillin-resistant Staphylococcus aureus (MRSA).

Evaluation of settled floor dust for the presence of microbial metabolites and volatile anthropogenic chemicals in indoor environments by LC-MS/MS and GC-MS methods.[Pubmed:21872054]

Talanta. 2011 Sep 30;85(4):2027-38.

This study reports on detection of a large number of biological and anthropogenic pollutants using LC-MS/MS and GC-MS technologies in settled floor dust (SFD). The latter technique was applied to obtain a general picture on the presence of microbial as well as non-microbial volatile organic compounds, whereas the targeted LC-MS/MS analysis focused on identification of species specific secondary metabolites. In the absence of moisture monitoring data the relevance of finding of Stachybotrylactam and other metabolites of tertiary colonizers are confined only to accidental direct exposure to SFD. To the best of our knowledge 30 of the 71 identified volatile organic compounds (VOCs) are newly reported in SFD matrix. Coordinated application of "AMDIS and Spectconnect" was found beneficial for the evaluation and identification of prime volatile pollutants in complex environmental samples. Principal component analysis (PCA) of peak areas of 18 microbial volatile organic compounds (MVOCs) resulted in identification of nonanal as potential MVOC marker. Two more volatiles toluene and 1-tetradecanol though had discriminative influence, are not regarded as MVOC markers, considering their probable alternate origin from paints and cosmetics, respectively.

Total synthesis and structure revision of stachybotrys spirolactams.[Pubmed:12968895]

J Org Chem. 2003 Sep 19;68(19):7422-7.

The spirolactam structure 1 reported in 1996 by Roggo et al. has been enantioselectively synthesized in 20 steps from (+)-Wieland-Miescher ketone. Spectra of this synthetic lactam differed from those of the natural spirolactam from the Roggo group, leading to the hypothesis that the natural lactam may be the regioisomer 27, a structure previously ascribed by Jarvis et al. to the natural product Stachybotrylactam. This hypothesis was confirmed by the first total synthesis of (-)-Stachybotrylactam (27). Double reductive amination of two molecules of aldehyde 29 with one molecule of l-lysine led by analogous chemistry to the first synthesis of the pseudosymmetric "dimer" 30, whose spectra corresponded to those of the natural "dimer" originally assigned structure 5 by the Roggo group.