Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus Trichoderma reesei 4670.
Pan-Pan ZhangYanlian DengXiaojing LinBin ChenJing LiHongju LiuSen-Hua ChenLan LiuPublished in: Journal of natural products (2019)
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.
Keyphrases
- anti inflammatory
- high resolution
- molecular docking
- induced apoptosis
- cell cycle arrest
- signaling pathway
- magnetic resonance
- inflammatory response
- toll like receptor
- endoplasmic reticulum stress
- lps induced
- mass spectrometry
- immune response
- structure activity relationship
- cell proliferation
- molecular dynamics simulations
- electron microscopy