Marine Vanadium-Dependent Haloperoxidases, Their Isolation, Characterization, and Application

Wever, Ron; Krenn, Bea E.; Renirie, Rokus

doi:10.1016/bs.mie.2018.02.026

Cited by 53 publications

(57 citation statements)

References 149 publications

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“…This result was explained because of the production of a diffusible hypobromous acid, which would depart the active site of the enzyme and then would brominate the substrate in a nonspecific manner. Indeed, the involvement of a hypohalous acid (HOX species) in this mechanism is widely accepted for vanadium-dependent haloperoxidases (VHPOs) from algae and fungi, which do not exhibit specificity [32], while for VCPOs from Streptomycetes it has been postulated that an enzyme-bound chlorine species would make possible the stereoselective halogenation [33,34].…”

Section: Discussionmentioning

confidence: 99%

New Napyradiomycin Analogues from Streptomyces sp. Strain CA-271078

et al. 2019

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As part of our continuing efforts to discover new bioactive compounds from microbial sources, a reinvestigation of extracts of scaled-up cultures of the marine-derived Streptomyces sp. strain CA-271078 resulted in the isolation and structural elucidation of four new napyradiomycins (1–3, 5). The known napyradiomycin SC (4), whose structural details had not been previously described in detail, and another ten related known compounds (6–15). The structures of the new napyradiomycins were characterized by HRMS and 1D- and 2D-NMR spectroscopies and their relative configurations were established through a combination of molecular modelling with nOe and coupling constants NMR analysis. The absolute configuration of each compound is also proposed based on biosynthetic arguments and the comparison of specific rotation data with those of related compounds. Among the new compounds, 1 was determined to be the first non-halogenated member of napyradiomycin A series containing a functionalized prenyl side chain, while 2–4 harbor in their structures the characteristic chloro-cyclohexane ring of the napyradiomycin B series. Remarkably, compound 5 displays an unprecedented 14-membered cyclic ether ring between the prenyl side chain and the chromophore, thus representing the first member of a new class of napyradiomycins that we have designated as napyradiomycin D1. Anti-infective and cytotoxic properties for all isolated compounds were evaluated against a set of pathogenic microorganisms and the HepG2 cell line, respectively. Among the new compounds, napyradiomycin D1 exhibited significant growth-inhibitory activity against methicillin-resistant Staphylococcus aureus, Mycobacterium tuberculosis, and HepG2.

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Section: Discussionmentioning

confidence: 99%

New Napyradiomycin Analogues from Streptomyces sp. Strain CA-271078

et al. 2019

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“…In this section, the following aspects would be addressed: the role of vanadium (a) in enzymes (haloperoxidases, nitrogenases), (b) the role of vanadium in ascidians and fan worms, (c) microbial use of vanadium and its transformation, (d) its physiological aspects (the phosphate/vanadate antagonism), including potential medicinal applications. Several reviews concerning these aspects have been published previously [5][6][7].…”

Section: Biological Aspectsmentioning

confidence: 99%

“…Vanadate-dependent haloperoxidase (VHPO) enzymes have been isolated from marine algae (in particular, Ascophyllum nodosum; Figure 1, right) and from hyphomycetes fungi such as the mold Curvularia inaequalis; these enzymes may also be present in certain cyanobacteria [7]. Haloperoxidases catalyze the two-electron oxidation of halides (iodide and bromide in particular, although chloride and pseudohalides such as thiocyanate may also serve as substrates for this reaction) to hypohalous acids or hypohalites, in the presence of a peroxide (hydrogen peroxide), as depicted in Figure 1 and eq.…”

Section: Vanadium-dependent Enzymesmentioning

confidence: 99%

Vanadium: Biological, Environmental, and Engineering Aspects

Rehder¹

2019

acr

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Vanadium is an element that is widely distributed in Earth's crust as well as in seawater and groundwater reservoirs. Therefore, it exerts a great influence on the issues related to life and environment. Vanadium is utilized by several marine organisms. For example, there are vanadate-dependent haloperoxidases in algae and several bacteria, e.g., Azotobacter, use it for nitrogen fixation and bacterial reduction involves the conversion of vanadate to oxidovanadium (IV). The similarity between vanadate and phosphate imparts a physiological functional role to vanadate (V), and consequently, several aspects of medicinal potential to vanadate and vanadium coordination compounds, such as their use in the treatment of diabetes, cancer, and cardiovascular problems, which may be explained in conjunction with vanadate/phosphate antagonism. Similar considerations apply to the efficacy of vanadium compounds in the treatment of HIV and [tropical] diseases caused by bacteria and protozoa. In addition to this biological efficacy, vanadium plays an increasingly recognized role in industrial processes, such as steel production, oxidation catalysis, and vanadium-based energy storage (batteries) and solar cells.

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“…Several species of macro-algae in the marine environment ( Figure 2) are able to catalyze the oxidation of the halide Xˉ (Xˉ = Iˉ, Brˉ, Clˉ) to hypohalous acid [14][15][16][17], as exemplified for the bromide oxidation in eqn. (1).…”

Section: Vanadium In Marine Algaementioning

confidence: 99%

“…The several steps of this sequence are shown in Figure 4. [16]). The intermittently formed active hydroperoxido complex transfers a hydroxide to the halide X -.…”

Section: Vanadium In Marine Algaementioning

confidence: 99%