Novel Metabolites from the Endophytic Fungus Chaetomium subaffine L01

Abstract

One natural p-terphenyl glycoside, gliocladinin C, and two furano-polyene derivatives, chaetominins A and B, were isolated from potato endophytic fungus Chaetomium subaffine. The absolute configurations of these compounds were elucidated by HR-ESI-MS, NMR, the DP4 + probabilities and electronic circular dichroism (ECD) spectra. Furthermore, gliocladinin C and chaetominin A showed cytotoxic activity against two selected human tumor cell lines (Hep-2 and HepG-2).

One New Terphenyl Glycoside From a Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)

“…Infrared (IR) spectrum was recorded on a Nicolet-Nexus-470 FT-IR spectrometer with potassium bromide (KBr) pellets. 1 H, 13 C NMR spectra were recorded on a JEOLJNM-ECP NMR spectrometer (500/125 MHz for 1 H and 13 C), using tetramethylsilane as an internal standard. High-performance liquid chromatography (HPLC) separation was attained by utilizing a Hitachi LA-2000 preparative-HPLC system, along with a Hitachi L-2455 photodiode array detector.…”

“…11,12 Moreover, the terphenyl family exhibited extensive activities, including antitumor, antibacterial, antiaging, anticoagulant, neuroprotective, immunosuppressive, and α-glucosidase inhibitory effects. 9 A literature survey revealed that p -terphenyl glycosides exhibited cytotoxic 13,14 and antibacterial activities. 14 For example, gliocladinin C, a p -terphenyl glycoside isolated from a potato-derived fungus Chaetomium subaffine L01 showed strong cytotoxic activity against human tumor cell lines Hep-2 and HepG-2.…”

“…14 For example, gliocladinin C, a p -terphenyl glycoside isolated from a potato-derived fungus Chaetomium subaffine L01 showed strong cytotoxic activity against human tumor cell lines Hep-2 and HepG-2. 13…”

“…These NMR spectral features of 1 were in close resemblance to that of the reported gliocladinin C from the fungus Chaetomium subaffine L01 isolated from a potato tissue. 13 The obvious difference is the addition of a methoxy signal, which was connected to C-6′ based on the heteronuclear multiple bond correlation (HMBC) (Figure 1) from the proton signal ( δ H 3.23) to C-6′. In addition, the methoxy group ( δ C 60.4, δ H 3.40) and aromatic quaternary carbon (C-3′, δ C 141.4; C-5′, δ C 143.7) in 1 replaced the methoxy group ( δ C 54.9, δ H 3.70) and aromatic quaternary carbon (C-3′, δ C 148.0; C-5′, 154.6) in gliocladinin C. The HMBC (Figure 1) from the proton signal ( δ H 3.40) to C-3′ indicated that the methoxy group was attached to C-3′ rather than C-5′.…”

“…14 For example, gliocladinin C, a pterphenyl glycoside isolated from a potato-derived fungus Chaetomium subaffine L01 showed strong cytotoxic activity against human tumor cell lines Hep-2 and HepG-2. 13 Large number of terphenyl derivatives have been reported from marine sources. For example, 2 new terphenyl derivatives, terphyl acid, and terphyl diacid, along with 6 known terphenyls, possessing cytotoxic activity were reported from the marine-derived Aspergillus sp.…”