Eight new dimeric sorbicillinoids
(1–3, 5–9) and 12 new monomeric
sorbicillinoids (10–20, 25), along with five known analogues (4 and 21–24), were isolated from the marine-derived fungus Trichoderma reesei 4670. Their structures were elucidated
on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS,
and ECD) and X-ray crystallography. Compound 1, containing
a pyrrolidin-2-one moiety, is reported for the first time in the sorbicillinoid
family. Compounds 8 and 9 are the first
examples of bisorbicillinoids possessing a benzofuro[2,3-h]chromene scaffold from a natural source. Compounds 3–11, 13–16, 18, 21, 22, 24, and 25 exhibited potent anti-inflammatory activity by inhibiting
the production of NO in RAW264.7 cells activated by lipopolysaccharide
with IC50 values in the range from 0.94 to 38 μM.
Structure–activity relationships of the sorbicillinoids were
discussed.
Two new spiromeroterpenoids, namely fusariumin A (1) and B (2), along with four known terpenoids, asperterpenoid A (3), agathic acid (4), guignardone N (5), and trametenolic acid (6), were obtained from the endophytic fungus Fusarium sp. YD-2, derived from the twigs of Santalum album. Their structures were elucidated by a combination of spectroscopic analyses. The absolute configuration of 1 was determined by single-crystal X-ray diffraction using Cu Ka radiation, and that of 2 was elucidated on the basis of experimental and calculated electronic circular dichroism spectra. Compound 2 exhibited moderate anti-inflammatory activity in vitro by inhibiting nitric oxide (NO) production in lipopolysaccharide activated RAW264.7 cells with an IC 50 value of 50 mM, and compound 3 showed strong anti-inflammatory activity with an IC 50 value of 1.6 mM. In the antibacterial assay, compound 1 displayed significant activities against Staphylococcus aureus and Pseudomonas aeruginosa with an MIC value of 6.3 mg mL À1 , and compound 3 showed moderate activities against Salmonella enteritidis and Micrococcus luteus with MIC values of 6.3 and 25.2 mg mL À1 , respectively.
Ascidian-derived microorganisms are a significant source of pharmacologically active metabolites with interesting structural properties. When discovering bioactive molecules from ascidian-derived fungi, two new phenols, roussoelins A (1) and B (2), and ten known polyketides (3–12) were isolated from the ascidian-derived fungus Roussoella siamensis SYSU-MS4723. The planar structure of compounds 1 and 2 was established by analysis of HR-ESIMS and NMR data. The conformational analysis of the new compounds was assigned according to coupling constants and selective gradient NOESY experiments, and absolute configurations were completed by the modified Mosher’s method. Among the isolated compounds, 1, 2, and 9 showed moderate antioxidant capacity.
Graphical abstract
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