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Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus Trichoderma reesei 4670

Zhang, Panpan, Deng, Yanlian, Lin, Xiaojing, Chen, Bin, Li, Jing, Liu, Hongju, Chen, Senhua, Liu, Lan
Journal of natural products 2019 v.82 no.4 pp. 947-957
Trichoderma reesei, X-ray diffraction, anti-inflammatory activity, fungi, inhibitory concentration 50, lipopolysaccharides, moieties, nitric oxide, nuclear magnetic resonance spectroscopy, spectral analysis, structure-activity relationships
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.