Special Issue "Secondary Metabolites and Metabolism"

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A special issue of Metabolites (ISSN 2218-1989).

Deadline for manuscript submissions: closed (30 November 2011)

Special Issue Editor

Guest Editor
Assoc. Prof. Dr. Silas G. Villas-Boas

Centre for Microbial Innovation, School of Biological Sciences, The University of Auckland, 3A Symonds Street, Auckland 1142, New Zealand
Website | E-Mail
Fax: +64 9 373 7416
Interests: microbial metabolomics; central carbon metabolism; microbial physiology; secondary metabolites; metabolic pathway analysis; mass spectrometry; gas chromatography; metabolic flux analysis; sample preparation for metabolome analysis; metabolic engineering

Special Issue Information

Dear Colleagues,

Secondary metabolites play fundamental role in chemical ecology, and humanity have long learned to exploit their properties to fight diseases, produce dyes for painting and food colouring as well as essential ingredients for cosmetics, fragrances and food flavouring.  Despite the enormous economic importance of secondary metabolites to our society, there are still numerous secondary metabolites yet to be discovered and chemically characterised. In addition, our current knowledge on secondary metabolism and its regulation is still very limited. Therefore, this special issue of Metabolites will be dedicated for publishing current advances on the discovery and characterisation of novel secondary metabolites, elucidation of metabolic pathways for biosynthesis of secondary metabolites any other aspect of the secondary metabolism in different organisms.

Dr. Silas G. Villas-Boas
Guest Editor

Keywords

  • secondary metabolites
  • bioactive compounds
  • natural products
  • isoprenoids
  • alkaloids
  • flavonoids
  • poliketides
  • phenylpropanoids
  • metabolism

Published Papers (8 papers)

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Research

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Open AccessArticle Atlantinone A, a Meroterpenoid Produced by Penicillium ribeum and Several Cheese Associated Penicillium Species
Metabolites 2012, 2(1), 214-220; doi:10.3390/metabo2010214
Received: 7 November 2011 / Revised: 30 December 2011 / Accepted: 10 February 2012 / Published: 23 February 2012
Cited by 4 | PDF Full-text (415 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Atlantinone A has been isolated from the psychrotolerant fungus Penicillium ribeum. The exact structure of the compound was confirmed by mass spectrometric and 1- and 2D NMR experiments. Atlantinone A was originally only produced upon chemical epigenetic manipulation of P. hirayamae,
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Atlantinone A has been isolated from the psychrotolerant fungus Penicillium ribeum. The exact structure of the compound was confirmed by mass spectrometric and 1- and 2D NMR experiments. Atlantinone A was originally only produced upon chemical epigenetic manipulation of P. hirayamae, however in this study the compound was found to be produced at standard growth conditions by the following species; P. solitum, P. discolor, P. commune, P. caseifulvum, P. palitans, P. novae-zeelandiae and P. monticola. A biosynthetic pathway to atlantinone A starting from andrastin A is proposed. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
Open AccessArticle Intracellular Metabolite Pool Changes in Response to Nutrient Depletion Induced Metabolic Switching in Streptomyces coelicolor
Metabolites 2012, 2(1), 178-194; doi:10.3390/metabo2010178
Received: 15 December 2011 / Revised: 18 January 2012 / Accepted: 10 February 2012 / Published: 17 February 2012
Cited by 7 | PDF Full-text (1274 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A metabolite profiling study of the antibiotic producing bacterium Streptomyces coelicolor A3(2) has been performed. The aim of this study was to monitor intracellular metabolite pool changes occurring as strains of S. coelicolor react to nutrient depletion with metabolic re-modeling, so-called metabolic switching,
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A metabolite profiling study of the antibiotic producing bacterium Streptomyces coelicolor A3(2) has been performed. The aim of this study was to monitor intracellular metabolite pool changes occurring as strains of S. coelicolor react to nutrient depletion with metabolic re-modeling, so-called metabolic switching, and transition from growth to secondary metabolite production phase. Two different culture media were applied, providing depletion of the key nutrients phosphate and L-glutamate, respectively, as the triggers for metabolic switching. Targeted GC-MS and LC-MS methods were employed to quantify important primary metabolite groups like amino acids, organic acids, sugar phosphates and other phosphorylated metabolites, and nucleotides in time-course samples withdrawn from fully-controlled batch fermentations. A general decline, starting already in the early growth phase, was observed for nucleotide pools and phosphorylated metabolite pools for both the phosphate and glutamate limited cultures. The change in amino acid and organic acid pools were more scattered, especially in the phosphate limited situation while a general decrease in amino acid and non-amino organic acid pools was observed in the L-glutamate limited situation. A phoP deletion mutant showed basically the same metabolite pool changes as the wild-type strain M145 when cultivated on phosphate limited medium. This implies that the inactivation of the phoP gene has only little effect on the detected metabolite levels in the cell. The energy charge was found to be relatively constant during growth, transition and secondary metabolite production phase. The results of this study and the employed targeted metabolite profiling methodology are directly relevant for the evaluation of precursor metabolite and energy supply for both natural and heterologous production of secondary metabolites in S. coelicolor. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
Open AccessArticle Investigation of Phenolic Acids in Suspension Cultures of Vitis vinifera Stimulated with Indanoyl-Isoleucine, N-Linolenoyl-L-Glutamine, Malonyl Coenzyme A and Insect Saliva
Metabolites 2012, 2(1), 165-177; doi:10.3390/metabo2010165
Received: 19 December 2011 / Revised: 25 January 2012 / Accepted: 8 February 2012 / Published: 15 February 2012
Cited by 1 | PDF Full-text (494 KB) | HTML Full-text | XML Full-text
Abstract
Vitis vinifera c.v. Muscat de Frontignan (grape) contains various high valuable bioactive phenolic compounds with pharmaceutical properties and industrial interest which are not fully exploited. The focus of this investigation consists in testing the effects of various biological elicitors on a non-morphogenic callus
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Vitis vinifera c.v. Muscat de Frontignan (grape) contains various high valuable bioactive phenolic compounds with pharmaceutical properties and industrial interest which are not fully exploited. The focus of this investigation consists in testing the effects of various biological elicitors on a non-morphogenic callus suspension culture of V. vinifera. The investigated elicitors: Indanoyl-isoleucine (IN), N-linolenoyl-L-glutamine (LG), insect saliva (IS) and malonyl coenzyme A (MCoA) were aimed at mimicking the influence of environmental pathogens on plants in their natural habitats and at provoking exogenous induction of the phenylpropanoid pathway. The elicitors’ indanoyl-isoleucine (IN), N-linolenoyl-L-glutamine (LG) and insect saliva (IS), as well as malonyl coenzyme A (MCoA), were independently inoculated to stimulate the synthesis of phenylpropanoids. All of the enhancers positively increased the concentration of phenolic compounds in grape cells. The highest concentration of phenolic acids was detected after 2 h for MCoA, after 48 h for IN and after 24 h for LG and IS respectively. At the maximum production time, treated grape cells had a 3.5-fold (MCoA), 1.6-fold (IN) and 1.5-fold (IS) higher phenolic acid content compared to the corresponding control samples. The HPLC results of grape cells showed two major resveratrol derivatives: 3-O-Glucosyl-resveratrol and 4-(3,5-dihydroxyphenyl)-phenol. Their influences of the different elicitors, time of harvest and biomass concentration (p < 0.0001) were statistically significant on the synthesis of phenolic compounds. The induction with MCoA was found to demonstrate the highest statistical effect corresponding to the strongest stress response within the phenylpropanoid pathway in grape cells. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
Open AccessArticle Comparative Chemistry of Aspergillus oryzae (RIB40) and A. flavus (NRRL 3357)
Metabolites 2012, 2(1), 39-56; doi:10.3390/metabo2010039
Received: 18 November 2011 / Revised: 14 December 2011 / Accepted: 22 December 2011 / Published: 5 January 2012
Cited by 19 | PDF Full-text (412 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Aspergillus oryzae and A. flavus are important species in industrial biotechnology and food safety and have been some of the first aspergilli to be fully genome sequenced. Bioinformatic analysis has revealed 99.5% gene homology between the two species pointing towards a large coherence
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Aspergillus oryzae and A. flavus are important species in industrial biotechnology and food safety and have been some of the first aspergilli to be fully genome sequenced. Bioinformatic analysis has revealed 99.5% gene homology between the two species pointing towards a large coherence in the secondary metabolite production. In this study we report on the first comparison of secondary metabolite production between the full genome sequenced strains of A. oryzae (RIB40) and A. flavus (NRRL 3357). Surprisingly, the overall chemical profiles of the two strains were mostly very different across 15 growth conditions. Contrary to previous studies we found the aflatrem precursor 13-desoxypaxilline to be a major metabolite from A. oryzae under certain growth conditions. For the first time, we additionally report A. oryzae to produce parasiticolide A and two new analogues hereof, along with four new alkaloids related to the A. flavus metabolites ditryptophenalines and miyakamides. Generally the secondary metabolite capability of A. oryzae presents several novel end products likely to result from the domestication process from A. flavus. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)

Review

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Open AccessReview A Historical Overview of Natural Products in Drug Discovery
Metabolites 2012, 2(2), 303-336; doi:10.3390/metabo2020303
Received: 1 March 2012 / Revised: 31 March 2012 / Accepted: 31 March 2012 / Published: 16 April 2012
Cited by 110 | PDF Full-text (542 KB) | HTML Full-text | XML Full-text
Abstract
Historically, natural products have been used since ancient times and in folklore for the treatment of many diseases and illnesses. Classical natural product chemistry methodologies enabled a vast array of bioactive secondary metabolites from terrestrial and marine sources to be discovered. Many of
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Historically, natural products have been used since ancient times and in folklore for the treatment of many diseases and illnesses. Classical natural product chemistry methodologies enabled a vast array of bioactive secondary metabolites from terrestrial and marine sources to be discovered. Many of these natural products have gone on to become current drug candidates. This brief review aims to highlight historically significant bioactive marine and terrestrial natural products, their use in folklore and dereplication techniques to rapidly facilitate their discovery. Furthermore a discussion of how natural product chemistry has resulted in the identification of many drug candidates; the application of advanced hyphenated spectroscopic techniques to aid in their discovery, the future of natural product chemistry and finally adopting metabolomic profiling and dereplication approaches for the comprehensive study of natural product extracts will be discussed. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
Open AccessReview Genetics of Polyketide Metabolism in Aspergillus nidulans
Metabolites 2012, 2(1), 100-133; doi:10.3390/metabo2010100
Received: 1 November 2011 / Revised: 23 December 2011 / Accepted: 17 January 2012 / Published: 30 January 2012
Cited by 6 | PDF Full-text (1121 KB) | HTML Full-text | XML Full-text
Abstract
Secondary metabolites are small molecules that show large structural diversity and a broad range of bioactivities. Some metabolites are attractive as drugs or pigments while others act as harmful mycotoxins. Filamentous fungi have the capacity to produce a wide array of secondary metabolites
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Secondary metabolites are small molecules that show large structural diversity and a broad range of bioactivities. Some metabolites are attractive as drugs or pigments while others act as harmful mycotoxins. Filamentous fungi have the capacity to produce a wide array of secondary metabolites including polyketides. The majority of genes required for production of these metabolites are mostly organized in gene clusters, which often are silent or barely expressed under laboratory conditions, making discovery and analysis difficult. Fortunately, the genome sequences of several filamentous fungi are publicly available, greatly facilitating the establishment of links between genes and metabolites. This review covers the attempts being made to trigger the activation of polyketide metabolism in the fungal model organism Aspergillus nidulans. Moreover, it will provide an overview of the pathways where ten polyketide synthase genes have been coupled to polyketide products. Therefore, the proposed biosynthesis of the following metabolites will be presented; naphthopyrone, sterigmatocystin, aspyridones, emericellamides, asperthecin, asperfuranone, monodictyphenone/emodin, orsellinic acid, and the austinols. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
Open AccessReview Role of Cereal Secondary Metabolites Involved in Mediating the Outcome of Plant-Pathogen Interactions
Metabolites 2011, 1(1), 64-78; doi:10.3390/metabo1010064
Received: 4 November 2011 / Revised: 21 November 2011 / Accepted: 29 November 2011 / Published: 15 December 2011
Cited by 11 | PDF Full-text (602 KB) | HTML Full-text | XML Full-text
Abstract
Cereal crops such as wheat, rice and barley underpin the staple diet for human consumption globally. A multitude of threats to stable and secure yields of these crops exist including from losses caused by pathogens, particularly fungal. Plants have evolved complex mechanisms to
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Cereal crops such as wheat, rice and barley underpin the staple diet for human consumption globally. A multitude of threats to stable and secure yields of these crops exist including from losses caused by pathogens, particularly fungal. Plants have evolved complex mechanisms to resist pathogens including programmed cell death responses, the release of pathogenicity-related proteins and oxidative bursts. Another such mechanism is the synthesis and release of secondary metabolites toxic to potential pathogens. Several classes of these compounds have been identified and their anti-fungal properties demonstrated. However the lack of suitable analytical techniques has hampered the progress of identifying and exploiting more of these novel metabolites. In this review, we summarise the role of the secondary metabolites in cereal crop diseases and briefly touch on the analytical techniques that hold the key to unlocking their potential in reducing yield losses. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
Open AccessReview Volatile Metabolites
Metabolites 2011, 1(1), 41-63; doi:10.3390/metabo1010041
Received: 21 October 2011 / Revised: 16 November 2011 / Accepted: 17 November 2011 / Published: 25 November 2011
Cited by 12 | PDF Full-text (247 KB) | HTML Full-text | XML Full-text
Abstract
Volatile organic compounds (volatiles) comprise a chemically diverse class of low molecular weight organic compounds having an appreciable vapor pressure under ambient conditions. Volatiles produced by plants attract pollinators and seed dispersers, and provide defense against pests and pathogens. For insects, volatiles may
[...] Read more.
Volatile organic compounds (volatiles) comprise a chemically diverse class of low molecular weight organic compounds having an appreciable vapor pressure under ambient conditions. Volatiles produced by plants attract pollinators and seed dispersers, and provide defense against pests and pathogens. For insects, volatiles may act as pheromones directing social behavior or as cues for finding hosts or prey. For humans, volatiles are important as flavorants and as possible disease biomarkers. The marine environment is also a major source of halogenated and sulfur-containing volatiles which participate in the global cycling of these elements. While volatile analysis commonly measures a rather restricted set of analytes, the diverse and extreme physical properties of volatiles provide unique analytical challenges. Volatiles constitute only a small proportion of the total number of metabolites produced by living organisms, however, because of their roles as signaling molecules (semiochemicals) both within and between organisms, accurately measuring and determining the roles of these compounds is crucial to an integrated understanding of living systems. This review summarizes recent developments in volatile research from a metabolomics perspective with a focus on the role of recent technical innovation in developing new areas of volatile research and expanding the range of ecological interactions which may be mediated by volatile organic metabolites. Full article
(This article belongs to the Special Issue Secondary Metabolites and Metabolism)
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