TMC-169, a New Antibiotic of the Aspochalasin Group Produced by Aspergillus flavipes.

Abstract

In the course of screening for new bioactive compounds,a newantibiotic has been isolated from a fungal strain Aspergillus flavipes TC 1446 and was designated TMC-169. Spectroscopic analyses revealed that TMC-169 was a new analog of the aspochalasin group, represented by aspochalasins A~GX~3) and phomacin C4). This paper briefly describes the taxonomy, isolation, physico-chemical properties, structure elucidation and biological activity of TMC-169. The producing strain TCI446, a soil isolate, was S. Suzuki, T. Uchida & S. Komatsubara: TMC-1 A, B, C and D, new antibiotics of the manumycin group produced by Streptomyces sp. Taxonomy, production, isolation, physico-chemical properties, structure elucidation and biological properties.

A Novel Aspochalasin with HIV-1 Integrase Inhibitory Activity from Aspergillus flavipes

“…The positive ESI mass spectrum of 1 revealed a sodiated ion at m/z 472. Accurate mass measurement of the ion confirmed a molecular formula of C 25 H 39 NO 6 Na indicative of seven double bond equivalences. Investigation of the NMR data (Table 1) COSY and gHMBC correlations to C-3.…”

“…AJ117509 [3,4]; aspochalasins G and F from Aspergillus sp. [5], TMC-169 from Aspergillus flavipes strain TC1446 [6] and aspochalasins IϳK from Aspergillus flavipes [7]. However, they have also been identified from a species of Phoma (phomacins AϳC) [8] and from an unidentified fungus (aspochalasins C and E) [9].…”

Methylthio-Aspochalasins from a Marine-Derived Fungus Aspergillus sp.

“…These compounds contained almost the same carbon skeleton and their structural diversity included a double bond shift (C5/C6 or C6/C7) in the isoindolone unit together with ketone, hydroxyl, methoxyl and double bond reduction in the macrocylic ring. Aspochalasins showed various bioactivities such as antibiotic [ 15 , 16 , 17 ], cytotoxicity [ 13 , 18 ], anti-HIV [ 19 ], TNF-alpha [ 20 ] and melanogenesis [ 21 ] inhibitors. Herein, we describe the isolation, structural elucidation, and cytotoxic activity of these two new aspochalasins.…”

Chemical investigations of secondary metabolites from selected fungi and from peanut seeds challenged by Aspergillus caelatus

“…Our initial interest in fungal endophytes related to those found in corn plants because of the prominence of corn in the economy of the Midwest, and 130 and J (29), 130 and TMC-169 (30). 131 The extract showed moderate antifungal activity against F. verticillioides but showed potent antiinsectan activity against the fall armyworm, killing 58% of the test insects while reducing the growth of the survivors by more than 75%. Compound 25 is known to display a wide variety of activities including antifungal, 132 and anti-tumor effects, 133 inhibition of plant pathogens, 127 and antibacterial activity against Pseudomonas syringae.…”

“…Compound 25 is known to display a wide variety of activities including antifungal, 132 and anti-tumor effects, 133 inhibition of plant pathogens, 127 and antibacterial activity against Pseudomonas syringae. 133 Members of the aspochalasin family are known to exhibit cytotoxicity against tumor cell lines 130,131 and antimicrobial activity against bacteria, fungi, and yeasts. [139][140][141] and it also possesses antifungal and antiinsectan activity.…”