The IR spectrum exhibited absorptions at 3649 (hydroxy group) and 1735 cm в€’1 (carbonyl group). Subsequent fractionation by silica gel column chromatography (CC), octadecylsilyl (ODS) CC, Sephadex LH-20 and semi-preparative reversed-phase HPLC yielded 1 (4.3 mg).ДЄspergiloid I ( 1) was isolated as a colorless lamellar crystal, with the molecular formula C 18H 26O 4 (6 double-bond equivalents) as derived from the ESI high-resolution mass spectrometry ( + at m/ z 329.1729, calculated 329.1723) and NMR data ( TableВ 1). The obtained fermented broth (~45 L) was extracted four times with EtOAc (v/v, 1:1) to afford a brown crude extract (9.1 g). A preliminary survey of the fractionation by 1H NMR and LCвЂ“MS revealed the presence of the molecule we eventually named aspergiloid I ( 1), which had a low-resolution mass ( + at m/ z 329) spectrum that did not match any previously isolated compounds, prompted us to purify it further.

YXf3 was extracted with EtOAc and separated by a combination of column chromatographic methods. Herein, we report the production, isolation, structure characterization, and biological activity of 1, a rare spirolactone metabolite with a novel carbon skeleton.ДЄ large-scale culture broth of Aspergillus sp. YXf3 and isolated a novel norditerpenoid, namely, aspergiloid I ( 1) ( FigureВ 1). We further focused on the fractionation containing the minor terpenoid constituents with characteristic signals for terminal vinyl group detected by 1H NMR from the liquid fermentation broth of Aspergillus sp. Interestingly, sphaeropsidins A and B were also discovered from both Aspergillus chevalieri and phytopathogenic fungus Sphaeropsis sapinea, displaying anti-gram-positive bacterial, antiviral, antiprotozoal and phytotoxic activity. YXf3 associated with Ginkgo biloba led to the isolation of new p-terphenyls and novel types of diterpenoids including pimarane-type diterpenoids (sphaeropsidins A and B, aspergiloids D and E), a cleistanthane-type diterpenoid (aspergiloid C), and norcleistanthane-type diterpenoids (asergiloids A, B, and FвЂ“H), many of which were reported from this microorganism for the first time. Our previous chemical investigation of the bioactive secondary metabolites produced by the endophytic Aspergillus sp. Recently, a wide variety of biologically active and structurally unique metabolites were isolated from these types of microorganisms, demonstrating their promise as a source of novel and/or bioactive natural products. Plant-derived fungi, which have drawn considerable attention from natural product chemists, have been proved to be a rich source of bioactive natural compounds.

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