Expanding the chemical diversity of an endophytic fungus Bulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach
An endophytic fungus Bulgaria inquinans (isolate MSp3-1), isolated from mistletoe (Viscum album), was subjected to fermentation on solid Czapek medium. Chromatographic workup of the crude EtOAc extract yielded five new natural products (1–5). Subsequent application of the “One Strain, MAny Compounds” (OSMAC) strategy on this strain by the addition of a mixture of salts (MgSO4, NaNO3 and NaCl) to solid Czapek medium induced the accumulation of nine additional new secondary metabolites (6–13, 16), with most of them (8, 10–12) not detectable in cultures lacking the salt mixture. The structures of the new compounds were established on the basis of the 1D/2D NMR and HRESIMS data. The TDDFT-ECD m…
Indole Diterpenoids from an Endophytic Penicillium sp.
A chemical investigation of the endophyte Penicillium sp. (strain ZO-R1-1), isolated from roots of the medicinal plant Zingiber officinale, yielded nine new indole diterpenoids (1-9), together with 13 known congeners (10-22). The structures of the new compounds were elucidated by 1D and 2D NMR analysis in combination with HRESIMS data. The absolute configuration of the new natural products 1, 3, and 7 was determined using the TDDFT-ECD approach and confirmed for 1 by single-crystal X-ray determination through anomalous dispersion. The isolated compounds were tested for cytotoxicity against L5178Y, A2780, J82, and HEK-293 cell lines. Compound 1 was the most active metabolite toward L5178Y ce…
Fusaristatins D–F and (7S,8R)-(−)-chlamydospordiol from Fusarium sp. BZCB-CA, an endophyte of Bothriospermum chinense
Abstract Three new lipodepsipeptides, fusaristatins D–F (1–3) and a new α-pyrone derivative, (7S,8R)-(−)-chlamydospordiol (5), together with eight known compounds (4, 6–12) were obtained from solid rice cultures of Fusarium sp. BZCB-CA, an endophyte of the Chinese medicinal plant, Bothriospermum chinense. The planar structures of the new metabolites (1–3, 5) were established by spectroscopic techniques (1D/2D NMR and HRESIMS). Marfey’s method was applied to determine the absolute configuration of 1, while the absolute configuration of 5 was determined by single-crystal X-ray crystallography analysis in addition to Mosher’s method. Crystallographic data of inflatin C (7) are also supplied he…
Didymellanosine, a new decahydrofluorene analogue, and ascolactone C from Didymella sp. IEA-3B.1, an endophyte of Terminalia catappa
Didymellanosine (1), the first analogue of the decahydrofluorene-class of natural products bearing a 13-membered macrocyclic alkaloid conjugated with adenosine, and a new benzolactone derivative, ascolactone C (4) along with eight known compounds (2, 3, 5–10), were isolated from a solid rice fermentation of the endophytic fungus Didymella sp. IEA-3B.1 derived from the host plant Terminalia catappa. In addition, ascochitamine (11) was obtained when (NH4)2SO4 was added to rice medium and is reported here for the first time as a natural product. Didymellanosine (1) displayed strong activity against the murine lymphoma cell line L5178Y, Burkitt's lymphoma B cells (Ramos) and adult lymphoblastic…
CCDC 1968535: Experimental Crystal Structure Determination
Related Article: Ni Putu Ariantari, Marian Frank, Ying Gao, Fabian Stuhldreier, Anna-Lene Kiffe-Delf, Rudolf Hartmann, Simon-Patrick Höfert, Christoph Janiak, Sebastian Wesselborg, Werner E.G. Müller, Rainer Kalscheuer, Zhen Liu, Peter Proksch|2021|Tetrahedron|85|132065|doi:10.1016/j.tet.2021.132065
CCDC 1968536: Experimental Crystal Structure Determination
Related Article: Ni Putu Ariantari, Marian Frank, Ying Gao, Fabian Stuhldreier, Anna-Lene Kiffe-Delf, Rudolf Hartmann, Simon-Patrick Höfert, Christoph Janiak, Sebastian Wesselborg, Werner E.G. Müller, Rainer Kalscheuer, Zhen Liu, Peter Proksch|2021|Tetrahedron|85|132065|doi:10.1016/j.tet.2021.132065