Diagnostically analyzing 1H NMR spectra of sub-types in chaetoglobosins for dereplication

1H-NMR spectra provide abundant diagnostic information including chemical shift values, splitting patterns, coupling constants, and integrals. Thus some key functional groups, and even planar structures could be elucidated on the basis of carefully analyzing the corresponding 1H NMR spectrum. In this paper, the different sub-types of chaetoglobosins are classified according to the structural features, of which the 1H NMR spectra are systematically summed up. Thus diagnostically analyzing the 1H-NMR spectra could identify possible sub-types of chaetoglobosins, which could be used for dereplication. According to the analysis of this report, it implies that different new sub-types or new sub-type combinations in the key skeleton of chaetoglobosins might exist in nature. More importantly, dereplication based on 1H NMR spectral analysis will not only provide a useful approach to determine the chaetoglobosins structures quickly, but also could set a good example for structural dereplication of other NPs.

[1]  Ernö Pretsch,et al.  Structure Determination of Organic Compounds: Tables of Spectral Data , 2020 .

[2]  W. Kang,et al.  Chaetomadrasins A and B, Two New Cytotoxic Cytochalasans from Desert Soil-Derived Fungus Chaetomium madrasense 375 , 2019, Molecules.

[3]  Xuewei Wang,et al.  Overexpression of the Global Regulator LaeA in Chaetomium globosum Leads to the Biosynthesis of Chaetoglobosin Z. , 2016, Journal of natural products.

[4]  Yonghui Zhang,et al.  Nine new cytochalasan alkaloids from Chaetomium globosum TW1-1 (Ascomycota, Sordariales) , 2016, Scientific Reports.

[5]  W. Gerwick,et al.  Biosynthesis-assisted structural elucidation of the bartolosides, chlorinated aromatic glycolipids from cyanobacteria. , 2015, Angewandte Chemie.

[6]  Yonghui Zhang,et al.  Armochaetoglobins K–R, Anti‐HIV Pyrrole‐Based Cytochalasans from Chaetomium globosum TW1‐1 , 2015 .

[7]  Taichi Inui,et al.  Essential Parameters for Structural Analysis and Dereplication by 1H NMR Spectroscopy , 2014, Journal of natural products.

[8]  Guo-dong Chen,et al.  Chaetoglobosin Y, a new cytochalasan from Chaetomium globosum. , 2014, Fitoterapia.

[9]  He Li,et al.  Chaetoglobosin Vb from endophytic Chaetomium globosum: absolute configuration of chaetoglobosins. , 2012, Chirality.

[10]  David J Newman,et al.  Natural products as sources of new drugs over the 30 years from 1981 to 2010. , 2012, Journal of natural products.

[11]  A. Zhang,et al.  Chemical and bioactive diversities of the genus Chaetomium secondary metabolites. , 2012, Mini reviews in medicinal chemistry.

[12]  K. Soytong,et al.  Cytotoxic 10-(indol-3-yl)-[13]cytochalasans from the fungus Chaetomium elatum ChE01 , 2010, Archives of pharmacal research.

[13]  C. Hertweck,et al.  The chemistry and biology of cytochalasans. , 2010, Natural product reports.

[14]  H. Ge,et al.  Cytotoxic chaetoglobosins from the endophyte Chaetomium globosum. , 2010, Planta medica.

[15]  P. Proksch,et al.  Cytoglobosins A-G, cytochalasans from a marine-derived endophytic fungus, Chaetomium globosum QEN-14. , 2010, Journal of natural products.

[16]  C. Hertweck,et al.  Molecular basis of cytochalasan biosynthesis in fungi: gene cluster analysis and evidence for the involvement of a PKS-NRPS hybrid synthase by RNA silencing. , 2007, Journal of the American Chemical Society.

[17]  D. Newman,et al.  Natural products as sources of new drugs over the last 25 years. , 2007, Journal of natural products.

[18]  H. Ge,et al.  Chaetoglobosin U, a cytochalasan alkaloid from endophytic Chaetomium globosum IFB-E019 , 2006 .

[19]  A. Cole,et al.  Chaetoglobosins Q, R, and T, three further new metabolites from Chaetomium globosum. , 2004, Journal of natural products.

[20]  A. Numata,et al.  Cytotoxic cytochalasans from a Penicillium species separated from a marine alga , 2001 .

[21]  K. Katayama,et al.  Chaetoglobosin O and Other Phytotoxic Metabolites from Cylindrocladium floridanum, a Causal Fungus of Alfalfa Black Rot Disease. , 1996, Bioscience, biotechnology, and biochemistry.

[22]  H. Oikawa,et al.  20-Ketoreductase Activity of Chaetoglobosin A and Prochaetoglobosins in a Cell-free System of Chaetomium subaffine and the Isolation of New Chaetoglobosins , 1993 .

[23]  H. Oikawa,et al.  Useful approach to find the plausible biosynthetic precursors of secondary metabolites using P-450 inhibitors: postulated intermediates of chaetoglobosin A , 1992 .

[24]  J. Luche,et al.  Nucleophilic properties of butyllithium versus free carboxylic acids , 1991 .

[25]  S. Natori,et al.  Chaetoglobosins, Cytotoxic 10-(Indo-3-yl)-[13] cytochalasans from Chaetomium spp. II. Structures of Chaetoglobosins A, B, and D , 1982 .

[26]  S. Natori,et al.  Chaetoglobosins G and J, cytotoxic indol-3-yl[13]-cytochalasans from Chaetomium globosum , 1977 .