Abstract
A novel chaetoglobosin named penochalasin I (1) with a unprecedented six-cyclic 6/5/6/5/6/13 fused ring system, and another new chaetoglobosin named penochalasin J (2), along with chaetoglobosins G, F, C, A, E, armochaetoglobosin I, and cytoglobosin C (3–9) were isolated from the culture of Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound 1 was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2′ of the chaetoglobosin class. Compounds 5–8 remarkably inhibited the plant pathogenic fungus R. solani (minimum inhibitory concentrations (MICs) = 11.79–23.66 μM), and compounds 2, 6, and 7 greatly inhibited C. gloeosporioides (MICs = 23.58–47.35 μM), showing an antifungal activity higher than that of carbendazim. Compound 1 exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC50 < 10 μM), and compounds 6 and 9 showed potent cytotoxicity against SGC-7901 and A549 cells (IC50 < 10 μM).
Highlights
Chaetoglobosins are one class belonging to the cytochalasan alkaloids, containing a 10-(indol-3-yl) group and a tricyclic core in which a macrocyclic ring is commonly fused to a perhydroisoindolone moiety [1,2,3,4]
About 80 chaetoglobosins have been found from some fungi belonging to the genera Chaetomium [5,6,7], Discosia [8], Cylindrocladium [9], Penicillium [10,11], Calonectria [12], Diplodia [13], and Phomopsis [14], most belonging to the genus Chaetomium
There were no previous reports on the cytotoxicity of these chaetoglobosins to MDA-MB-435, A549 and SGC-7901 cell lines, except compounds 8 and 9, which were tested on the A549 cell line [28,29] with IC50 values almost identical to our current results
Summary
Chaetoglobosins are one class belonging to the cytochalasan alkaloids, containing a 10-(indol-3-yl) group and a tricyclic core in which a macrocyclic ring is commonly fused to a perhydroisoindolone moiety [1,2,3,4]. Marine mangrove endophytic fungi have attracted significant attention for their notable ability to produce metabolites with novel structures and biological activities [21,22]. As part of our ongoing search for biologically active and/or structurally novel metabolites of the endophytic fungi from. Myoporum bontioides [24,25], the fungus Penicillium chrysogenum (collection No V11) harbored inside. I (1) bearing an unprecedented carried and in resulted a novel chaetoglobosin termed Penochalasin. 6/5/6/5/6/13 six polycyclicsix system, and asystem, new chaetoglobosin named Penochalasin (2), along withJ unprecedented. 6/5/6/5/6/13 polycyclic and a new chaetoglobosin namedJ Penochalasin seven known chaetoglobosins, chaetoglobosin. Structure characterization, and bioactivity evaluationand are (8) [28], and cytoglobosin C (9) [29] (Figure 1).
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