DOCSLIB.ORG

Occurrence and Properties of Thiosilvatins

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Occurrence and Properties of Thiosilvatins marine drugs Review Occurrence and Properties of Thiosilvatins Maria Michela Salvatore 1 , Rosario Nicoletti 2,3 , Marina DellaGreca 1 and Anna Andolfi 1,* 1 Department of Chemical Sciences, University of Naples ‘Federico II’, 80126 Naples, Italy; [email protected] (M.M.S.); [email protected] (M.D.) 2 Council for Agricultural Research and Economics, Research Centre for Olive, Citrus and Tree Fruit, 81100 Caserta, Italy; [email protected] 3 Department of Agriculture, University of Naples ‘Federico II’, 80055 Portici, Italy * Correspondence: andolfi@unina.it; Tel.: +39-081-2539179 Received: 27 September 2019; Accepted: 21 November 2019; Published: 26 November 2019 Abstract: The spread of studies on biodiversity in different environmental contexts is particularly fruitful for natural product discovery, with the finding of novel secondary metabolites and structural models, which are sometimes specific to certain organisms. Within the large class of the epipolythiodioxopiperazines, which are typical of fungi, thiosilvatins represent a homogeneous family that, so far, has been reported in low frequency in both marine and terrestrial contexts. However, recent observations indicate that these compounds have been possibly neglected in the metabolomic characterization of fungi, particularly from marine sources. Aspects concerning occurrence, bioactivities, structural, and biosynthetic properties of thiosilvatins are reviewed in this paper. Keywords: thiosilvatins; secondary metabolites; diketopiperazines; epipolythiodioxopiperazines; fungi; biological activities 1. Introduction A huge chapter on research on biodiversity is represented by studies concerning the biochemical properties of the manifold organisms which are part of natural ecosystems. Novel secondary metabolites are continuously discovered, disclosing a surprising chemodiversity in terms of both structural and biosynthetic aspects. Although most classes of compounds are spread throughout the several kingdoms of nature, a certain specificity results in some cases. An example in this respect is represented by the epipolythiodioxopiperazines (ETPs), so far only reported from fungi [1]. ETPs are a large and structurally diverse class of bioactive secondary metabolites originating from diketopiperazines and characterized by the presence of a disulfide bridge or a polysulfide dioxopiperazine six-membered ring. Due to their bioactivities, ETPs are receiving attention in recent years [2]. This review is focused on thiosilvatins, a specific family of ETPs resulting from the enzymatic assemblage of two amino acids (i.e., l-tyrosine/l-phenylalanine and glycine), generally integrated with two methylated sulfur atoms. Unlike a related family including hyalodendrin, gliovictin, and their analogues, in this homogeneous group of compounds, the pivotal nitrogen deriving from the aromatic amino acid is not engaged in structural modifications other than methylation (Figure1). Mar. Drugs 2019, 17, 664; doi:10.3390/md17120664 www.mdpi.com/journal/marinedrugs Mar.Mar. Drugs Drugs 20192019, 17, 17, x, FOR 664 2 of2 of13 14 Mar. Drugs 2019, 17, x FOR 2 of 13 Figure 1. Basic structure of thiosilvatins. Figure 1. Basic structure of thiosilvatins. The finding of natural products displaying this kind of molecular structure only started in the The finding of natural products displaying this kind of molecular structure only started in the 1980s [3],The and finding even of nowadays natural products reports aredisplaying quite infrequent. this kind Theof molecular present paper structure provides only starteda review in ofthe 1980s [3], and even nowadays reports are quite infrequent. The present paper provides a review of the the1980s current [3], andknowledge even nowadays concerning repo occurrence,rts are quite bioact infrequent.ivities, structural,The present and paper biosynthetic provides aspectsa review of of current knowledge concerning occurrence, bioactivities, structural, and biosynthetic aspects of these thesethe currentcompounds. knowledge To ensure concerning a comparative occurrence, examinat bioactionivities, of the severalstructural, structures and biosynthetic reviewed herewith, aspects of compounds. To ensure a comparative examination of the several structures reviewed herewith, the thethese name compounds. of some compounds To ensure wasa comparative adapted to examinat conformion to previouslyof the several characterized structures reviewed analogs. herewith, namethe name of some of some compounds compounds was was adapted adapted to conform to conform to previously to previously characterized characterized analogs. analogs. 2. Structures and Chemical Properties 2. Structures and Chemical Properties (3R,6R)-1,4-Dimethyl-3-(4-(3-methyl-2-butenyloxy)benzyl)-3,6-bis(methylthio)piperazine-2,5- (3R,6,6RR)-1,4-Dimethyl-3-(4-(3-methyl-2-butenyloxy)benzyl)-3,6-bis(methylthio)piperazine-2,5-dione)-1,4-Dimethyl-3-(4-(3-methyl-2-butenyloxy)benzyl)-3,6-bis(methylthio)piperazine-2,5- dione(1), the (1), founder the founder product product of this of compound this compound series, series was, isolated was isolated for the for first the time first in time 1981 in along 1981 withalong its withdione its (deprenyl1), the founder analogue product (16) [3] of. thisSubsequently, compound 1 series was named, was isolated cis-bis(methylthio)silvatin for the first time in when1981 along the deprenylwith its deprenyl analogue analogue (16)[3]. Subsequently, (16) [3]. Subsequently,1 was named 1 wascis -bis(methylthio)silvatinnamed cis-bis(methylthio)silvatin when the only when sulfur the onlybridged sulfur thiosilvatin, bridged thiosilvatin, dithiosilvatin dithiosilvatin (2), was characterized (2), was characterized and submitted and tosubmitted a reductive to a methylation reductive methylationonly sulfur giving bridged 1 and thiosilvatin, its epimer dithiosilvatin in C-6 (3) [4] ((Figure2), was 2).characterized and submitted to a reductive givingmethylation1 and giving its epimer 1 and in its C-6 epimer (3)[4] in (Figure C-6 (23).) [4] (Figure 2). 1 2 3 1 2 3 Figure 2. Structures of cis-bis(methylthio)silvatin (1, NM = 408 U), dithiosilvatin (2, NM = 378 U), Figuretrans-bis(methylthio)silvatin 2. Structures of cis-bis(methylthio)silvatin (3, NM = 408 U). (1, NM = 408 U), dithiosilvatin (2, NM = 378 U), transFigure-bis(methylthio)silvatin 2. Structures of cis-bis(methylthio)silvatin (3, NM = 408 U). (1, NM = 408 U), dithiosilvatin (2, NM = 378 U), trans-bis(methylthio)silvatin (3, NM = 408 U). The most relevant structural modifications observed in this class of compounds are in the numberThe most of sulfurs, relevant the structural degree ofmodifications methylation obse of heteroatoms,rved in this class and theof compounds presence of are a dimethyl in the The most relevant structural modifications observed in this class of compounds are in the numberallylic of chain sulfurs, (Table the3 ).degree A controversial of methylation issue of he concerningteroatoms, thiosilvatinsand the presence could of bea dimethyl represented allylic by number of sulfurs, the degree of methylation of heteroatoms, and the presence of a dimethyl allylic chainnomenclature. (Table 1). A controversial In fact, several issue compounds concerning werethiosilvatins inconsistently could be designatedrepresented with by nomenclature. trivial names, chain (Table 1). A controversial issue concerning thiosilvatins could be represented by nomenclature. Inabbreviations, fact, several compounds or according were to inconsistently the IUPAC standards, designated which with trivial generally names, are abbreviations, not linked to or the In fact, several compounds were inconsistently designated with trivial names, abbreviations, or accordingname of to the the founder IUPAC compound.standards, which For generally instance, are Sch not 54794 linked (4) to and the Sch name 54796 of the (5) founder have the according to the IUPAC standards, which generally are not linked to the name of the founder compound.same structures For instance, and stereostructures Sch 54794 ( of4) 1andand Sch3, but 54796 their (5 amino) have functions the same are structures not methylated; and compound. For instance, Sch 54794 (4) and Sch 54796 (5) have the same structures and stereostructuresconsequently, theyof 1 and could 3, but be their respectively amino functions named cis are- andnot metransthylated;-dinor-bis(methylthio)silvatin consequently, they could [5 ]. stereostructures of 1 and 3, but their amino functions are not methylated; consequently, they could beLikewise, respectivelycis-3-(4-hydroxybenzyl)-1,4-dimethyl-3,6-bis(methylthio)-2,5-piperazinedione named cis- and trans-dinor-bis(methylthio)silvatin [5]. Likewise, cis (16-3-(4-) and be respectively named cis- and trans-dinor-bis(methylthio)silvatin [5]. Likewise, cis-3-(4- hydroxybenzyl)-1,4-dimethyl-3,6-bis(methylthio)-2,5-piperazinedionetrans-6-(4-hydroxybenzyl)-1,4-dimethyl-3,6-bis(methylthio)piperazine-2,5-dione (16) (17and) were namedtrans-6-(4- in the hydroxybenzyl)-1,4-dimethyl-3,6-bis(methylthio)-2,5-piperazinedione (16) and trans-6-(4- hydroxybenzyl)-1,4-dimethyl-3,6-bis(original manuscripts according to IUPACmethylthio)piperazine-2,5-dione standards [3,6], but they could (17 be) easilywere namednamed respectively in the hydroxybenzyl)-1,4-dimethyl-3,6-bis(methylthio)piperazine-2,5-dione (17) were named in the originalcis- and manuscriptstrans-deprenyl-bis(methylthio)silvatin. according to IUPAC standards [3,6], but they could be easily named respectivelyoriginal manuscripts cis-
Load more

Recommended publications
  • Incorporating Fermentation Into Undergraduate Laboratory Courses
    Athens Journal of Sciences- Volume 2, Issue 4 – Pages 257-264 Incorporating Fermentation into Undergraduate Laboratory Courses By Claire Gober Madeleine Joullie† Laboratory courses in universities have a responsibility to introduce current research practices and trends in scientific research to adequately prepare students for work in the field. One such research practice gaining popularity in recent years is that of green chemistry. Since the 1960s, increasing concern over the release of toxic chemicals into the environment has led to a push for more environmentally responsible chemistry. A growing faction of chemists has begun to adopt methods to eliminate chemical waste and support green chemistry. Fermentation is an ideal technique to demonstrate environmentally sustainable chemistry in an undergraduate laboratory class. Fermentation of complex natural products, as opposed to traditional organic synthesis, is beneficial as it supports a number of principles of green chemistry; it is conducted at ambient temperature and pressure, uses inexpensive and innocuous materials, makes use of renewable resources, and does not require a fume hood. Skills implemented during fermentation can be easily taught to upper-level Chemistry and Biochemistry undergraduate students, who typically have limited exposure to complex natural products in their coursework. Such a course would be interdisciplinary in nature, incorporating fungal biology and metabolism as well as organic chemistry. Students would learn a variety of skills, including growth media selection and preparation, inoculation of fungal cultures, extraction of natural products, and purification and characterization of metabolites. Experiments of this nature would allow for discussions of several areas of research: green chemistry, natural products and their application to medicine, identification of functional groups in complex molecules by spectroscopy, and introduction to biochemistry and metabolism.
    [Show full text]
  • Penitrem a Peer-Reviewed Journal Articles
    ________________________________________________________________________ ________________________________________________________________________ Penitrem A Peer-Reviewed Journal Articles Literature Review by Lisa Petrison, Ph.D. Neurotoxic Effects: Berntsen H. F., Wigestrand M. B., Bogen I. L., Fonnum F., Walaas S. I., Moldes-Anaya A.. Mechanisms of penitrem-induced cerebellar granule neuron death in vitro: possible involvement of GABAA receptors and oxidative processes. Neurotoxicology. 2013;35:129–136. Moldes-Anaya Angel, Rundberget Thomas, Fæste Christiane K., Eriksen Gunnar S., Bernhoft Aksel. Neurotoxicity of Penicillium crustosum secondary metabolites: tremorgenic activity of orally administered penitrem A and thomitrem A and E in mice. Toxicon. 2012;60:1428–1435. Moldes-Anaya Angel S., Fonnum Frode, Eriksen Gunnar S., Rundberget Thomas, Walaas S. Ivar, Wigestrand Mattis B.. In vitro neuropharmacological evaluation of penitrem-induced tremorgenic syndromes: importance of the GABAergic system. Neurochemistry international. 2011;59:1074–1081. Lu Hai-Xia X., Levis Hannah, Liu Yong, Parker Terry. Organotypic slices culture model for cerebellar ataxia: potential use to study Purkinje cell induction from neural stem cells. Brain research bulletin. 2011;84:169–173. Namiranian Khodadad, Lloyd Eric E., Crossland Randy F., et al. Cerebrovascular responses in mice deficient in the potassium channel, TREK-1. American journal of physiology. Regulatory, integrative and comparative physiology. 2010;299. Ohno Akitoshi, Ohya Susumu, Yamamura Hisao,
    [Show full text]
  • Roquefortine C (SML0406)
    Roquefortine C from Penicillium roqueforti Catalog Number SML0406 Storage Temperature –20 °C CAS RN 58735-64-1 Precautions and Disclaimer Synonym: Roquefortine This product is for R&D use only, not for drug, household, or other uses. Please consult the Material Safety Data Sheet for information regarding hazards and safe handling practices. Preparation Instructions Roquefortine C is soluble in methanol (10 mg/mL), DMSO (10 mg/mL), ethyl acetate (1 mg/mL), and chloroform (1 mg/mL). Storage/Stability Store the product sealed at –20 °C. Under these conditions the product is stable for at least 4 years. A DMSO solution (10 mg/mL) is stable for 3 months at Product Description –20 °C. Molecular formula: C22H23N5O2 Molecular weight: 389.45 References 1. Kopp-Holtwiesche, B., and Rehm, H.J., Roquefortine C is a paralytic neurotoxin with a Antimicrobial action of roquefortine. J. Environ. dioxopiperazine structure produced by a diverse range Pathol. Toxicol. Oncol., 10, 41-44 (1990). 1 of fungi, most notably Penicillium species. It has been 2. Wagener, R.E. et al., Penitrem A and Roquefortine 2 found in blue cheese and in many other food products Production by Penicillium commune. App. Environ. 3 due to natural occurrence and contamination. Microbiol., 39, 882-887 (1980). 3. Shangguan, N. et al., The total synthesis of Roquefortine C was found to be active on a wide range roquefortine C and a rationale for the of organisms. It inhibits the growth of Gram-positive thermodynamic stability of isoroquefortine C over bacteria, and cockerels treated with roquefortine lost roquefortine C. J. Am.
    [Show full text]
  • By Penicillium Paneum Frisvad and Penicillium Roqueforti Thom Isolated from Baled Grass Silage in Ireland
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Online Research Database In Technology 9268 J. Agric. Food Chem. 2006, 54, 9268−9276 Mycotoxins and Other Secondary Metabolites Produced in Vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom Isolated from Baled Grass Silage in Ireland MARTIN O’BRIEN,*,†,# KRISTIAN F. NIELSEN,‡ PADRAIG O’KIELY,† PATRICK D. FORRISTAL,§ HUBERT T. FULLER,# AND JENS C. FRISVAD‡ Teagasc, Grange Beef Research Centre, Dunsany, Co. Meath, Ireland; Center for Microbial Biotechnology, BioCentrum-DTU, Technical University of Denmark, Building 221, DK-2800 Kgs. Lyngby, Denmark; Teagasc, Crops Research Centre, Oak Park, Co. Carlow, Ireland; and School of Biology and Environmental Science, College of Life Sciences, University College Dublin, Belfield, Dublin 4, Ireland Secondary metabolites produced by Penicillium paneum and Penicillium roqueforti from baled grass silage were analyzed. A total of 157 isolates were investigated, comprising 78 P. paneum and 79 P. roqueforti isolates randomly selected from more than 900 colonies cultured from bales. The findings mostly agreed with the literature, although some metabolites were not consistently produced by either fungus. Roquefortine C, marcfortine A, and andrastin A were consistently produced, whereas PR toxin and patulin were not. Five silage samples were screened for fungal metabolites, with two visually moldy samples containing up to 20 mg/kg of roquefortine C, mycophenolic acid, and andrastin A along with minor quantities (0.1-5 mg/kg) of roquefortines A, B, and D, festuclavine, marcfortine A, and agroclavine. Three visually nonmoldy samples contained low amounts of mycophenolic acid and andrastin A.
    [Show full text]
  • Putative Neuromycotoxicoses in an Adult Male Following Ingestion of Moldy Walnuts
    Short research communication Putative neuromycotoxicoses in an adult male following ingestion of moldy walnuts Authors: C. J. Botha1 C. M. Visagie2 M. Sulyok3 Affiliations: 1 Department of Paraclinical Sciences, Faculty of Veterinary Science, University of Pretoria, Private bag X04, Onderstepoort, 0110, South Africa 2 Biosystematics Division, Agricultural Research Council – Plant Health and Protection, Private Bag X134, Queenswood, Pretoria, 0121, South Africa 3 Centre for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Konrad Lorenzstr. 20, A-3430, Tulln, Austria CJ Botha [email protected] Tel.: +27 125298023; fax +27 125298304. ORCID CJ Botha 0000 0003 1535 9270 ORCID CM Visagie 0000-0003-2367-5353 ORCID M Sulyok 0000-0002-3302-0732 1 Abstract A tremorgenic syndrome occurs in dogs following ingestion of moldy walnuts and Penicillium crustosum has been implicated as the offending fungus. This is the first report of suspected moldy walnut toxicosis in man. An adult male ingested approximately 8 fungal-infected walnut kernels and after 12 hours experienced tremors, generalized pain, incoordination, confusion, anxiety and diaphoresis. Following symptomatic and supportive treatment at a local hospital the man made an uneventful recovery. A batch of walnuts (approximately 20) were submitted for mycological culturing and identification as well as for mycotoxin analysis. Penicillium crustosum Thom was the most abundant fungus present on walnut samples, often occurring as monocultures on isolation plates. Identifications were confirmed with DNA sequences. The kernels and shells of the moldy walnuts as well as P. crustosum isolates plated on Yeast Extract Sucrose (YES) and Czapek Yeast Autolysate (CYA) agars and incubated in the dark at 25 ºC for 7 days were screened for tremorgenic mycotoxins and known P.
    [Show full text]
  • Preservation Stress Resistance of Melanin Deficient Conidia From
    Seekles et al. Fungal Biol Biotechnol (2021) 8:4 https://doi.org/10.1186/s40694-021-00111-w Fungal Biology and Biotechnology RESEARCH Open Access Preservation stress resistance of melanin defcient conidia from Paecilomyces variotii and Penicillium roqueforti mutants generated via CRISPR/Cas9 genome editing Sjoerd J. Seekles1,2, Pepijn P. P. Teunisse1,2, Maarten Punt1,3, Tom van den Brule1,4, Jan Dijksterhuis1,4, Jos Houbraken1,4, Han A. B. Wösten1,3 and Arthur F. J. Ram1,2* Abstract Background: The flamentous fungi Paecilomyces variotii and Penicillium roqueforti are prevalent food spoilers and are of interest as potential future cell factories. A functional CRISPR/Cas9 genome editing system would be benefcial for biotechnological advances as well as future (genetic) research in P. variotii and P. roqueforti. Results: Here we describe the successful implementation of an efcient AMA1-based CRISPR/Cas9 genome edit- ing system developed for Aspergillus niger in P. variotii and P. roqueforti in order to create melanin defcient strains. Additionally, kusA− mutant strains with a disrupted non-homologous end-joining repair mechanism were created to further optimize and facilitate efcient genome editing in these species. The efect of melanin on the resistance of conidia against the food preservation stressors heat and UV-C radiation was assessed by comparing wild-type and melanin defcient mutant conidia. Conclusions: Our fndings show the successful use of CRISPR/Cas9 genome editing and its high efciency in P. vari- otii and P. roqueforti in both wild-type strains as well as kusA− mutant background strains. Additionally, we observed that melanin defcient conidia of three food spoiling fungi were not altered in their heat resistance.
    [Show full text]
  • The Brla Gene Deletion Reveals That Patulin Biosynthesis Is Not Related to Conidiation in Penicillium Expansum
    International Journal of Molecular Sciences Article The brlA Gene Deletion Reveals That Patulin Biosynthesis Is Not Related to Conidiation in Penicillium expansum Chrystian Zetina-Serrano, Ophélie Rocher, Claire Naylies, Yannick Lippi , Isabelle P. Oswald , Sophie Lorber and Olivier Puel * Toxalim (Research Centre in Food Toxicology), Université de Toulouse, INRAE, ENVT, INP-Purpan, UPS, 31027 Toulouse, France; [email protected] (C.Z.-S.); [email protected] (O.R.); [email protected] (C.N.); [email protected] (Y.L.); [email protected] (I.P.O.); [email protected] (S.L.) * Correspondence: [email protected]; Tel.: +33-582-066-336 Received: 7 August 2020; Accepted: 8 September 2020; Published: 11 September 2020 Abstract: Dissemination and survival of ascomycetes is through asexual spores. The brlA gene encodes a C2H2-type zinc-finger transcription factor, which is essential for asexual development. Penicillium expansum causes blue mold disease and is the main source of patulin, a mycotoxin that contaminates apple-based food. A P. expansum PeDbrlA deficient strain was generated by homologous recombination. In vivo, suppression of brlA completely blocked the development of conidiophores that takes place after the formation of coremia/synnemata, a required step for the perforation of the apple epicarp. Metabolome analysis displayed that patulin production was enhanced by brlA suppression, explaining a higher in vivo aggressiveness compared to the wild type (WT) strain. No patulin was detected in the synnemata, suggesting that patulin biosynthesis stopped when the fungus exited the apple. In vitro transcriptome analysis of PeDbrlA unveiled an up-regulated biosynthetic gene cluster (PEXP_073960-PEXP_074060) that shares high similarity with the chaetoglobosin gene cluster of Chaetomium globosum.
    [Show full text]
  • Synthetic Studies of Roquefortine C: Synthesis of Isoroquefortine
    Synthetic studies of roquefortine C: SPECIAL FEATURE Synthesis of isoroquefortine C and a heterocycle David J. Richard, Bruno Schiavi, and Madeleine M. Joullie´ * Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323 Edited by Kyriacos C. Nicolaou, The Scripps Research Institute, La Jolla, CA, and approved April 14, 2004 (received for review April 9, 2004) The syntheses of isoroquefortine C and a related heterocycle were achieved by implementation of both intra- and intermolecular vinyl amidation reactions. These accomplishments represent a signifi- cant advance in the use of these strategies in the generation of complex molecules. etabolites produced by fungi represent one of the largest Mclasses of natural products. Such compounds vary widely in their structural composition and have found application in pharmaceuticals such as antibiotics, immunosuppressants, anti- fungal agents, and growth promoters (1). Other congeners Fig. 1. The roquefortine class of natural products. within this class display biological properties harmful to humans and other animals. These natural products have been classified as mycotoxins and are produced as secondary metabolites by an containing hemins but no potency toward Gram-negative or- CHEMISTRY array of soilborne and airborne fungi (2). Mycotoxins have been ganisms (15). Additional studies led to the finding that roque- isolated as contaminants of a variety of grain products and have fortine C inhibited bacterial RNA synthesis but only modestly been a topic of great interest for scientists concerned with affected DNA and protein production (16). veterinary health and agricultural safety. The lack of consistent toxicological data, along with the In most cases, eradication of the fungal infection responsible ubiquitous nature of P.
    [Show full text]
  • Patulin Fact Sheet
    Patulin Fact Sheet Background Information: Patulin takes it’s name from the fungus from which it was first isolated, Penicillium patulum. It is most likely to occur in moldy fruits, such as apples, but may also be found in grains, especially wet grains, and silages. Patulin may be associated with problems in silages, however the data on that aspect has not been well established. Since Patulin is associated with storage molds, it should be considered when investigating silage problems, specifically regarding dairy catte. Can co-contaminate feedstuffs with other Penicillium toxins, such as, Ochratoxin A (OTA), Citrinin, Roquefortine C, Mycophenolic Acid (MPA), and Cyclopiazonic Acid. Major crops affected: Corn, Barley, Wheat, & Rye, their associated silages, and Fruits. Associated Mold: Penicillium sp., Aspergillus sp., and Byssochlamys sp. Conditions favoring production: Penicillium is a major silage mold and may be a greater silage problem because it can grow at lower pH than do other molds. Considered to be more prevalent from a storage mold situation, rather than field/growing condition mold situation. Symptoms: Patulin is an antibiotic against gram-positive bacteria. In ruminants, Patulin has been shown to reduce VFA production, fiber digestion, and bacterial yield. Also, nephrotoxic (kidney) and immunotoxic effects. Gastrointestinal symptoms like gastric ulcers, intestinal hemorrages, lesions in the duodenum, and alteration of intestinal barrier function. Detection Limit: 200 ppb Dairyland Labs Packages that include Patulin: • Mycotoxin Select Package • Mycotoxin Complete Package Sources Diaz, D.E., W.M. Hagler, and L.W. Whitlow. “Mycotoxins in Feeds.” Feedstuffs. 15 Sep. 2010. Gallo, A., G. Giubuerti, J.C. Frisvad, T. Bertuzzi, and K.F.
    [Show full text]
  • Targeted and Untargeted Analysis of Secondary Fungal Metabolites by Liquid Chromatography-Mass Spectrometry
    Targeted and untargeted analysis of secondary fungal metabolites by liquid chromatography-mass spectrometry Svetlana V. Malysheva Promoter: Prof. Dr. Sarah De Saeger Co-promoters: Prof. Dr. Irina Yu. Goryacheva Dr. José Diana Di Mavungu 2013 THESIS SUBMITTED IN FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR IN PHARMACEUTICAL SCIENCES PROEFSCHRIFT VOORGELEGD TOT HET BEKOMEN VAN DE GRAAD VAN DOCTOR IN DE FARMACEUTISCHE WETENSCHAPPEN Targeted and untargeted analysis of secondary fungal metabolites by liquid chromatography-mass spectrometry Svetlana V. Malysheva Promoter: Prof. Dr. Sarah De Saeger Co-promoters: Prof. Dr. Irina Yu. Goryacheva Dr. José Diana Di Mavungu 2013 THESIS SUBMITTED IN FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR IN PHARMACEUTICAL SCIENCES PROEFSCHRIFT VOORGELEGD TOT HET BEKOMEN VAN DE GRAAD VAN DOCTOR IN DE FARMACEUTISCHE WETENSCHAPPEN PhD thesis Title: Targeted and untargeted analysis of secondary fungal metabolites by liquid chromatography – mass spectrometry Author: Svetlana V. Malysheva Year: 2013 Pages: 338 ISBN: 978-94-6197-128-9 Printer: University Press, Zelzate, Belgium Refer to this thesis as follows: Malysheva SV (2013). Targeted and untargeted analysis of secondary fungal metabolites by liquid chromatography – mass spectrometry. Thesis submitted in fulfilment of the requirements of the degree of Doctor (Ph.D.) in Pharmaceutical Sciences. Faculty of Pharmaceutical Sciences, Ghent University Promoter: Prof. Sarah De Saeger (Faculty of Pharmaceutical Sciences, Ghent University, Ghent, Belgium) Co-promoters: Prof. Irina Yu. Goryacheva (Chemistry Institute, Saratov State University, Russia) Dr. José Diana Di Mavungu (Faculty of Pharmaceutical Sciences, Ghent University, Ghent, Belgium) Members of the reading committee: Prof. Ann Van Schepdael (Faculty of Pharmaceutical Sciences, KU Leuven, Belgium) Prof.
    [Show full text]
  • Modelling Fungal Growth, Mycotoxin Production and Release in Grana Cheese
    microorganisms Article Modelling Fungal Growth, Mycotoxin Production and Release in Grana Cheese Marco Camardo Leggieri 1 , Amedeo Pietri 2 and Paola Battilani 1,* 1 Department of Sustinable Crop Production, Università Cattolica del Sacro Cuore, Via E. Parmense, 84, 29122 Piacenza, Italy; [email protected] 2 Department of Animal Science, Food and Nutrition, Università Cattolica del Sacro Cuore, Via E. Parmense, 84, 29122 Piacenza, Italy; [email protected] * Correspondence: [email protected]; Tel.: +39-0523-599-254 Received: 29 November 2019; Accepted: 31 December 2019; Published: 2 January 2020 Abstract: No information is available in the literature about the influence of temperature (T) on Penicillium and Aspergillus spp. growth and mycotoxin production on cheese rinds. The aim of this work was to: (i) study fungal ecology on cheese in terms of T requirements, focusing on the partitioning of mycotoxins between the rind and mycelium; and (ii) validate predictive models previously developed by in vitro trials. Grana cheese rind blocks were inoculated with A. versicolor, P. crustosum, P. nordicum, P. roqueforti, and P. verrucosum, incubated at different T regimes (10–30 ◦C, step 5 ◦C) and after 14 days the production of mycotoxins (ochratoxin A (OTA); sterigmatocystin (STC); roquefortine C (ROQ-C), mycophenolic acid (MPA), Pr toxin (PR-Tox), citrinin (CIT), cyclopiazonic acid (CPA)) was quantified. All the fungi grew optimally around 15–25 ◦C and produced the expected mycotoxins (except MPA, Pr-Tox, and CIT). The majority of the mycotoxins produced remained in the mycelium (~90%) in three out of five fungal species (P. crustosum, P. nordicum, and P.
    [Show full text]
  • A Thesis in Plant Pathology
    The Pennsylvania State University The Graduate School College of Agricultural Sciences FUNGI AND MYCOTOXINS IN FRESH AND ENSILED MAIZE AND THE AFFECTS OF AGRONOMIC PRACTICES, WEATHER CONDITIONS AND SILAGE CHARACTERISTICS ON TOXIN CONTAMINATION A Thesis in Plant Pathology by Michele A. Mansfield © 2005 Michele A. Mansfield Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy December 2005 The thesis of Michele A. Mansfield was reviewed and approved* by the following: Gretchen A. Kuldau Assistant Professor of Plant Pathology Thesis Advisor Chair of Committee David M. Geiser Associate Professor of Plant Pathology Erick D. DeWolf Assistant Professor of Plant Pathology Seogchan Kang Associate Professor of Plant Pathology A. Daniel Jones Professor of Biochemistry and Molecular Biology and Professor of Chemistry at Michigan State University (current) Senior Scientist at The Pennsylvania State University (former) *Signatures are on file in the Graduate School ii DISSERTATION ABSTRACT Maize silage, which constitutes a significant portion of the cattle diet, can become contaminated by mycotoxins produced by Aspergillus, Alternaria, Fusarium and Penicillium and the presence of these toxins has been associated with serious herd health problems (226). The objectives of this work were to study the mycoflora and mycotoxins in maize silage and investigate how agronomic practices, weather conditions and the process of ensiling affect the frequency and concentrations of several classes of mycotoxins. Silage was collected in Pennsylvania from 30-40 dairies during harvest and six months after storage in 2001 and 2002. Fusarium and Penicillium were the most commonly occurring toxigenic fungi although Aspergillus fumigatus, two Alternaria species and a novel species, Penicillium farinosum, were also present.
    [Show full text]