Absolute stereostructures of chaetomugilins G and H produced by a marine-fish-derived Chaetomium species

Abstract

Chaetomugilins G and H were isolated from a strain of Chaetomium globosum that was originally isolated from the marine fish, Mugil cephalus, and their absolute stereostructures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, and chemical transformation. In addition, the absolute configuration of chaetoviridin C was established by derivatization from chaetomugilin A. These compounds exhibited a growth inhibitory activity against cultured P388, HL-60, L1210 and KB cells.

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

“…Chaetomugilins G (91) and H (92) were obtained from the same strain C. globosum OUPS-T106B-6 [91]. In addition, the absolute configuration of chaetoviridin C (79) was established by derivatization from chaetomugilin A (85 against cultured P388, HL-60, L1210 and KB cells.…”

New Azaphilones and Chlorinated Phenolic Glycosides from Chaetomium elatum with Caspase-3 Inhibitory Activity

“…Therefore, 5 was determined as the acetylated derivation of 4, 5chloro-2-hydroxy-4-methoxy-6-propyl-phenol-(6-O-acetyl)-β-D-glucopyranoside, which was named globosumoside B. On the basis of the Osmanovaʼs review and recently published work [11][12][13][14][15][16], more than 30 azaphilones have been isolated from Chaetomium spp., possessing a five-membered lactone ring fused to chlorinated isochromen at C-7/C-8 with a 7S absolute configuration and a C 6 side chain [(E)-3-methyl-1-pentenyl or (E)-4-hydroxy-3-methyl-1-pentenyl] at C-3. Compounds 1-3 are the first examples of 7R-configurated azaphilones with a chlorinated isochromen from Chaetomium spp.…”

“…13 C NMR (100 MHz) and 1 H NMR (400 MHz) data of compound 1 and key signals of HMBC, 1 H-1 H COSY, and ROESY.…”

Three new azaphilones produced by a marine fish-derived chaetomium globosum

“…[1][2][3][4][5][6][7] The EtOAc extract of the culture filtrate was purified, employing Sephadex LH-20, silica gel column chromatography and the reverse phased HPLC, to afford chaetomugilins S (1), dechlorochaetomugilin A (2) and dechloro-chaetomugilin D (3) (Figure 1). …”

“…We already reported their absolute stereostructures and cytotoxic activities. [1][2][3][4][5][6][7] Our continuing search for cytotoxic metabolites from this fungal strain led to the isolation of three new azaphilones designated as chaetomugilins S-U (1-3). Azaphilones have various bioactivities such as antimicrobial activity, nitric oxide inhibition (cohaerins), 8 gp120-CD4-binding inhibition (isochromophiliones, ochrephilone, screotiorin and rubrorotiorin), 9 monoamine oxidase inhibition (luteusins, TL-1, TL-2 and chaetoviridins), 10,11 plateletderived growth factor-binding inhibition (RP-1551s) 12 and antimalarial activity (cochliodones).…”