Stachartins A – E, Phenylspirodrimanes from the Tin Mine Tailings‐Associated Fungus Stachybotrys chartarum

Abstract

Eight phenylspirodrimane-type analogues, including five new compounds, named stachartins A -E (1, 3, 6 -8), were isolated from cultures of the tin mine tailings-associated fungus Stachybotrys chartarum. Their structures were elucidated by spectroscopic methods including extensive 2D-NMR techniques.

Antiviral and anti-inflammatory meroterpenoids: stachybonoids A–F from the crinoid-derived fungus Stachybotrys chartarum 952

“…8). Thus, compound 7 was identied and named as stachybonoid F. The known compounds were identied as stachybotrylactone (8) 13 and stachartin B (9) 13,14 on the basis of NMR data and mass spectrometric analysis and a comparison of their spectroscopic data with published values. The absolute conguration of compound 8 was further established by a singlecrystal X-ray diffraction experiment using Cu Ka radiation (ESI †).…”

“…H (400 MHz) and13 C (100 MHz) NMR data of compounds 5-7 (in pyridine-d 5 , J in Hz) , m; 1.63, dd (3.5, 11.9) 31 7,. CH 2 1.98, t (14.0); 1.75, m 26.6, CH 2 1.73, m; 1.99, m 26.6, CH 2 2 5.45, m 68.9, CH 2.33, td (12.8, 3.5); 1.14, dt (12.8, 6.1) 25.2, CH 2 2.38, m; 1.…”

Stachybotrysins A–G, Phenylspirodrimane Derivatives from the Fungus Stachybotrys chartarum

“…Stachybotrys is a genus of filamentous fungi comprising approximately 100 species and is widely distributed, generally found in soil and various decaying plant substrates . These fungi are known for the production of a variety of secondary metabolites including trichothecene mycotoxins, , diterpenes, isochroman, cochlioquinones, and the prenylated phenol derivatives ranging from chartarutines, S. microspora triprenyl phenols, stachybotrins, kampanols, stachyflins, and bisabosquals to phenylspirodrimanes. , These metabolites exhibit a wide range of bioactivities including the inhibition of pancreatic cholesterol esterase, anticomplement and antiviral activity, , enhancers of fibrinolytic plasminogen, and inhibitors of TNF-α liberation and cytotoxicity . In the course of our search for new phenylspirodrimane derivatives with structural novelty and pharmacological potency, a 70 L fermentation of S. chartarum CGMCC 3.5365 from China General Microbiological Culture Collection Center (CGMCC) was performed.…”

“…In the course of our search for new phenylspirodrimane derivatives with structural novelty and pharmacological potency, a 70 L fermentation of S. chartarum CGMCC 3.5365 from China General Microbiological Culture Collection Center (CGMCC) was performed. The HPLC-UV-guided fractionation and purification of the EtOAc extract led to the isolation of seven new phenylspirodrimane derivatives, stachybotrysins A–G ( 2 – 8 ), along with five known compounds, F1839-I ( 1 ), stachybotrysin ( 9 ), , Mer-NF5003E ( 10 ), stachybotrylactone acetate ( 11 ), and stachybotryslactone B ( 12 ). , The structures of these compounds were determined by spectroscopic data analysis and comparison with reported data. Herein, we report the detailed isolation, structure elucidation, and biological activities of these compounds.…”

“…13,14 These metabolites exhibit a wide range of bioactivities including the inhibition of pancreatic cholesterol esterase, 15 anticomplement 16 and antiviral activity, 13,14 enhancers of fibrinolytic plasminogen, 8 and inhibitors of TNF-α liberation and cytotoxicity. 17 In the course of our search for new phenylspirodrimane derivatives with structural novelty and pharmacological potency, a 70 L fermentation of S. chartarum CGMCC 3.5365 from China General Microbiological Culture Collection Center (CGMCC) was performed. The HPLC-UV-guided fractionation and purification of the EtOAc extract led to the isolation of seven new phenylspirodrimane derivatives, stachybotrysins A−G (2− 8), along with five known compounds, F1839-I (1), 15 stachybotrysin (9), 17,18 Mer-NF5003E (10), 19 stachybotrylactone acetate (11), 2 and stachybotryslactone B (12).…”