Abstract
A new prenylated indole diketopiperazine alkaloid, cristatumin F (1), and four known metabolites, echinulin (2), dehydroechinulin (3), neoechinulin A (4) and variecolorin O (5), were isolated from the crude extract of the fungus Eurotium cristatum. The structure of 1 was elucidated primarily by NMR and MS methods. The absolute configuration of 1 was assigned using Marfey’s method applied to its acid hydrolyzate. Cristatumin F (1) showed modest radical scavenging activity against DPPH radicals, and exhibited marginal attenuation of 3T3L1 pre-adipocytes.
Highlights
Prenylated indole diketopiperazines are an important class of compounds with diverse chemical structures and biological activities [1]
The linkage of the prenylated indole core with the diketopiperazine part through the methylene bridge was revealed by the HMBC correlations from H2-8 to C-3 and C-9
The culture of E. cristatum was isolated from a sample of fuzhuan brick tea collected from Yiyang city, Hunan Province, People’s Republic of China, in May 2012
Summary
Prenylated indole diketopiperazines are an important class of compounds with diverse chemical structures and biological activities [1]. Prenylated indole alkaloids, generally characterized by a reverse isoprenic chain in the C-2 position of the indole nucleus, are often found in fungal sources. This group of alkaloids are an important class of molecules possessing a variety of biological activities, including antibacterial [2,3], immunosuppressive [4,5], brine shrimp inhibition [3], radical scavenging [6,7], UV-A protecting [7,8], and cytotoxicity properties [9]. During our ongoing search for new bioactive natural products from unique fungal species, a subculture of an isolate of E. cristatum, a fungus isolated from a sample of fuzhuan brick tea, was grown in solid-substrate fermentation culture. Structure elucidation, and biological activities of these compounds are reported
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