Cytotoxic trichothecene-type sesquiterpenes from the sponge-derived fungusStachybotrys chartarumwith tyrosine kinase inhibition

Abstract

Bioassay-guided fractionation of a sponge associated fungus Stachybotrys chartarum resulted in the isolation of 15 trichothecene-based sesquiterpenes with inhibitory effects against tumor cell lines.

Reisolation and NMR characterization of the satratoxins G and H

“…A recent publication outlined the isolation and characterization of several new trichothecene metabolites—among them were satratoxins G and H . The authors reported their sample of satratoxin G to furnish crystals suitable for x‐ray crystallographic analysis, to which they were able to resolve the absolute configuration of the compound.…”

“…Initially identified by Eppley and Bailey, satratoxins G and H were characterized in full, but the contemporary spectral details are not readily available, even though numerical values have been updated . These compounds have been implicated as the causative agents in animal and human toxicosis, in particular neurotoxicity and inflammation as a result of inhalation leading to respiratory disorders .…”

“…The authors reported their sample of satratoxin G to furnish crystals suitable for x‐ray crystallographic analysis, to which they were able to resolve the absolute configuration of the compound. However, upon closer examination of the crystallographic data, we suggest the compound is in fact mycotoxin A (compound 5 in Li et al) of which in their work 199 mg was isolated (c.f. 2.4 mg for satratoxin G).…”

“…We used the x‐ray structure of mycotoxin A to interpret the nuclear Overhauser effect (NOE) data of satratoxin G and to guide the assignment of the relative configuration about the six‐membered ring defined by C‐3'–C‐12′. The reasoning was that, on occasion, satratoxins G and H are drawn as 12'S or not defined, while the original data and later reports suggest it is 12'R, (isosatratoxin G being tentatively assigned as the C‐12′ epimer. ) The configurational structure shown in Figure a demonstrates a series of self‐consistent through‐space interactions (recorded in CDCl 3 for satratoxin G) that arranges the H‐2′, H‐12′, H‐7′, and H‐8′ protons in close proximity, consistent with molecular modeling distance calculations (see Table S4).…”

Recent Advances on Macrocyclic Trichothecenes, Their Bioactivities and Biosynthetic Pathway

“…[ 7 , 10 , 28 ]. Macrocyclic trichothecenes are produced by the genera Myrothecium [ 29 , 30 , 31 ], Podostroma [ 32 ], Stachybotrys [ 33 ], Calcarisporium [ 34 ], Cercophora [ 35 ], Cylindrocarpon [ 36 ], Dendrodochium [ 37 ], Phomopsis [ 38 ], and Verticinimonosporium [ 39 ]. It is worth noting that Baccharis , belonging to the Asteraceae family, is the only plant genus that can produce trichothecenes [ 40 ].…”