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

J Nat Prod. 2019 Apr 26;82(4):947-957. doi: 10.1021/acs.jnatprod.8b01029.

Panpan Zhang ¹, Yanlian Deng ², Xiaojing Lin ³, Bin Chen ¹, Jing Li ¹, Hongju Liu ², Senhua Chen ¹ ⁴, Lan Liu ¹ ⁵ ⁴

Affiliations

1 School of Marine Sciences , Sun Yat-Sen University , Guangzhou 510006 , People's Republic of China.
2 School of Pharmacy , Guangdong Medical University , Dongguan 523808 , People's Republic of China.
3 Research Center of Chinese Herbal Resource Science and Engineering , Guangzhou University of Chinese Medicine , Guangzhou 510006 , People's Republic of China.
4 Southern Laboratory of Ocean Science and Engineering , Zhuhai 519080 , People's Republic of China.
5 Key Laboratory of Functional Molecules from Oceanic Microorganisms, Department of Education of Guangdong Province , Sun Yat-Sen University , Guangzhou 510006 , People's Republic of China.

PMID: 30920218 DOI: 10.1021/acs.jnatprod.8b01029

Abstract

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.

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