Transvalencin Z was isolated from a culture broth of Nocardia transvalensis IFM 10065, a clinical isolate from a Japanese patient with actinomycotic mycetoma. The transvalencin Z structure was determined using NMR and mass spectrometric analyses. The structure is similar to a partial structure of siderophores such as mycobactins and nocobactins, but the compound has no cytotoxic activity. Transvalencin Z shows a strong antimicrobial activity against Gram-positive bacteria, but shows no activity against Gram-negative bacteria, fungi and tumor cells.
Keywords transvalencin Z, siderophores, Nocardia transvalensis, nocobactin
IntroductionMost Nocardia species can cause human infections called nocardiosis. The infections that are caused by Nocardia are considered rare, but infectious cases have been increasingly reported, especially with the increase of immunocompromised patients [1,2]. During our screening program of bioactive compounds from pathogenic actinomycetes, we found that most of the culture broth of Nocardia clinical isolates produce anti-tumor compounds that are extractable using hydrophobic solvents such as ethyl ether or n-hexane [3,4]. Our studies suggest that most of the active compounds from these pathogenic bacteria belong to siderophore-class antibiotics such as brasilibactin A [4], madurastatin [5] and asterobactin [6]. These siderophores are characterized as having salicylic acid moieties in their structures. We previously reported that N. transvalensis IFM 10065 produces a novel zinc-containing antibiotic, transvalencin A [6,7]. Our continuous screening of new bioactive metabolites from that bacterium has led to isolation of a novel antimicrobial compound with a salicylic acid moiety in its structure, designated as transvalencin Z (Fig. 1, 1). In this paper, we describe its production, isolation, physicochemical properties, structural characterization and biological activity.