Secondary metabolites with nematicidal and antimicrobial activity from nematophagous fungi and Ascomycetes

1995 ◽  
Vol 73 (S1) ◽  
pp. 932-939 ◽  
Author(s):  
H. Anke ◽  
M. Stadler ◽  
A. Mayer ◽  
O. Sterner
Keyword(s):  
Linoleic Acid ◽  
Secondary Metabolites ◽  
Biosynthetic Pathway ◽  
Nematophagous Fungi ◽  
Submerged Cultures ◽  
Daldinia Concentrica ◽  
Antimicrobial Metabolites ◽  
Natural Nematicides ◽  
Arthrobotrys Conoides ◽  
New Metabolites

Screening of nematode-trapping fungi for antimicrobial and nematicidal activities gave three new antimicrobial metabolites from cultures of five Arthrobotrys strains. The compounds exhibited no nematicidal activities towards Caenorhabditis elegans and Meloidogyne incognita. From trap-forming submerged cultures of Arthrobotrys conoides, linoleic acid was isolated as a nematicidal principle. Its production increased with the number of traps formed in both Arthrobotrys oligospora and Arthrobotrys conoides. Nematoctonus robustus and Nematoctonus concurrens produced pleurotin, dihydropleurotinic acid, and leucopleurotin, metabolites previously isolated from cultures of Hohenbuehelia species, suggesting that the same biosynthetic pathways function in both the teleomorph and anamorph. Several strains of Ascomycetes had nematicidal activities; linoleic acid was responsible for the activity in cultures of a Chlorosplenium species, 14-epicochlioquinone B in cultures of Neobulgaria pura, and two naphthalenes derived from the melanin biosynthetic pathway in Daldinia concentrica. 5-Pentyl-2-furaldehyde, previously known as a metabolite from a Basidiomycete, was produced by an unidentified Australian Ascomycete. More than 30 mostly new metabolites have been isolated from cultures of Lachnum papyraceum, many being chlorinated. Under different conditions the fungus incorporated bromine instead of chlorine. Key words: nematophagous fungi, natural nematicides, linoleic acid, chlorinated secondary metabolites.

Lactarane Type Sesquiterpenoids as Inhibitors of Leukotriene Biosynthesis and Other, New Metabolites from Submerged Cultures of Lentinellus cochleatus (Pers. ex Fr.) Karst

1996 ◽  
Vol 51 (7-8) ◽  
pp. 493-499 ◽  
Author(s):  
Annette Wunder ◽  
Timm Anke ◽  
Dörte Klostermeyer ◽  
Wolfgang Steglich
Keyword(s):  
Peripheral Blood ◽  
Human Peripheral Blood ◽  
Peripheral Blood Leukocytes ◽  
Submerged Cultures ◽  
Blood Leukocytes ◽  
Spectroscopic Investigations ◽  
Basophilic Leukemia ◽  
New Metabolites

Abstract Three known sesquiterpenoids of the lactarane and secolactarane type, deoxylactarorufin A (1), blennin A (2) and blennin C (3), have been obtained from cultures of Lentinellus cochleatus (Basidiomycetes) together with the new metabolites (Z)-2-chloro-3-(4-me-thoxyphenyl)-2-propen-l-ol (4) and lentinellone (5), a protoilludane derivative. The structures were determined by spectroscopic investigations. 1, 2 and 3 are potent inhibitors of leukotriene biosynthesis in rat basophilic leukemia (RBL-1) cells and human peripheral blood leukocytes (PBL).

Flavipucine and Brunnescin, Two Antibiotics from Cultures of the Mycophilic Fungus Cladobotryum rubrobrunnescens

1995 ◽  
Vol 50 (5-6) ◽  
pp. 358-364 ◽  
Author(s):  
Christian Wagner ◽  
Heidrun Anke ◽  
Helmut Besla ◽  
Olov Sterner
Keyword(s):  
The Other ◽  
Furan Derivative ◽  
Submerged Cultures ◽  
Cytotoxic Effects ◽  
Aspergillus Flavipes ◽  
Antimicrobial Metabolites ◽  
Agric Biol

Abstract Two antimicrobial metabolites were isolated from submerged cultures of Cladobotryum rubrobrunnescens, a mycophilic fungus growing on a Inocybe species. One of the compounds proved to be identical to flavipucine (2), an antibiotic previously isolated from Aspergillus flavipes (Casinovi et al., 1968) and from a Macrophoma species (Sassa T. and Onuma Y. (1983), Agric. Biol. Chem. 47, 1155-1157). The other metabolite, brunnescin (1), is a new tetrasubstituted furan derivative which exhibits antibacterial, antifungal and cytotoxic effects.

scholarly journals The fungal gene cluster for biosynthesis of the antibacterial agent viriditoxin

2019 ◽  
Author(s):  
Andrew S. Urquhart ◽  
Jinyu Hu ◽  
Yit-Heng Chooi ◽  
Alexander Idnurm
Keyword(s):  
Secondary Metabolites ◽  
Gene Cluster ◽  
Gene Disruption ◽  
Biosynthetic Pathway ◽  
Fluorescent Protein ◽  
Model Species ◽  
Paecilomyces Variotii ◽  
Bioinformatic Approaches ◽  
Green Fluorescent ◽  
Fungal Gene

AbstractBackgroundViriditoxin is one of the ‘classical’ secondary metabolites produced by fungi and that has antibacterial and other activities; however, the mechanism of its biosynthesis has remained unknown.ResultsHere, a gene cluster responsible for its synthesis was identified, using bioinformatic approaches from two species that produce viriditoxin and then through gene disruption and metabolite profiling. All eight genes in the cluster inPaecilomyces variotiiwere mutated, revealing their roles in the synthesis of this molecule and establishing its biosynthetic pathway which includes an interesting Baeyer-Villiger monooxygenase catalyzed reaction. Additionally, a candidate catalytically-inactive hydrolase was identified as being required for the stereoselective biosynthesis of (M)-viriditoxin. The localization of two proteins were assessed by fusing these proteins to green fluorescent protein, revealing that at least two intracellular structures are involved in the compartmentalization of the synthesis steps of this metabolite.ConclusionsThe full pathway for synthesis of viriditoxin was established by a combination of genomics, bioinformatics, gene disruption and chemical analysis processes. Hence, this work reveals the basis for the synthesis of an understudied class of fungal secondary metabolites and provides a new model species for understanding the synthesis of biaryl compounds with a chiral axis.

Secondary Metabolites of the Phytopathogen Peronophythora litchii

2010 ◽  
Vol 5 (2) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Haihui Xie ◽  
Yaoguang Liang ◽  
Jinghua Xue ◽  
Qiaolin Xu ◽  
Yueming Jiang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Spectrometric Data ◽  
Brine Shrimps ◽  
Hydroxybenzyl Alcohol ◽  
New Metabolites

Two new metabolites, 4R*-hydroxy-3,5R*-dimethoxycyclohex-2-enone (1) and 2-hydroxy-N-(2-hydroxyphenyl)propionamide (2), were isolated from solid cultures of the phytopathogen Peronophythora litchii, along with 4-hydroxybenzyl alcohol (3) and methyl D-indole-3-lactate (4). Their structures were elucidated on the basis of spectroscopic and spectrometric data. These metabolites were not toxic to brine shrimps (LC50 > 500 μg/mL).

New Metabolites of Streptomyces globisporus and Streptomyces griseus

1993 ◽  
Vol 58 (6) ◽  
pp. 1452-1456 ◽  
Author(s):  
Josef Jizba ◽  
Petr Sedmera ◽  
Marian Beran
Keyword(s):  
Streptomyces Griseus ◽  
Submerged Cultures ◽  
Spectroscopic Measurements ◽  
New Metabolites

5,6,7,7a-Tetrahydro-3H-pyrrolizin-7a-ol-3-one (VI) and N-[2-(1-hydroxy-4-methylpentyl)]acetamide (VII) were isolated from submerged cultures of the macrotetrolide-producing strains Streptomyces globisporus and S. griseus. Proposed structures are based on spectroscopic measurements.

scholarly journals Biosynthesis of Fusarubins Accounts for Pigmentation of Fusarium fujikuroi Perithecia

2012 ◽  
Vol 78 (12) ◽  
pp. 4468-4480 ◽  
Author(s):  
Lena Studt ◽  
Philipp Wiemann ◽  
Karin Kleigrewe ◽  
Hans-Ulrich Humpf ◽  
Bettina Tudzynski
Keyword(s):  
Secondary Metabolites ◽  
Gene Cluster ◽  
Biosynthetic Pathway ◽  
Polyketide Synthase ◽  
Biological Function ◽  
Fusarium Fujikuroi ◽  
Diverse Group ◽  
Fruiting Bodies ◽  
Content Type ◽  
Encoding Gene

ABSTRACTFusarium fujikuroiproduces a variety of secondary metabolites, of which polyketides form the most diverse group. Among these are the highly pigmented naphthoquinones, which have been shown to possess different functional properties for the fungus. A group of naphthoquinones, polyketides related to fusarubin, were identified inFusariumspp. more than 60 years ago, but neither the genes responsible for their formation nor their biological function has been discovered to date. In addition, although it is known that the sexual fruiting bodies in which the progeny of the fungus develops are darkly colored by a polyketide synthase (PKS)-derived pigment, the structure of this pigment has never been elucidated. Here we present data that link the fusarubin-type polyketides to a defined gene cluster, which we designatefsr, and demonstrate that the fusarubins are the pigments responsible for the coloration of the perithecia. We studied their regulation and the function of the single genes within the cluster by a combination of gene replacements and overexpression of the PKS-encoding gene, and we present a model for the biosynthetic pathway of the fusarubins based on these data.

scholarly journals Secondary metabolites of Phlebopus species from Northern Thailand

2020 ◽  
Vol 19 (12) ◽  
pp. 1525-1536
Author(s):  
Boontiya Chuankid ◽  
Hedda Schrey ◽  
Benjarong Thongbai ◽  
Olivier Raspé ◽  
Norbert Arnold ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Tumor Cell Lines ◽  
Submerged Cultures ◽  
Esi Ms ◽  
Spectroscopic Analyses ◽  
New Compounds ◽  
Comprehensive Characterization

AbstractSubmerged cultures of the edible mushrooms Phlebopus portentosus and Phlebopus spongiosus were screened for their secondary metabolites by HPLC-UV/Vis and HR-LC-ESI-MS. Two new compounds, 9′-hydroxyphenyl pulvinone (1), containing an unusual pulvinone structure, and phlebopyron (2), together with the seven known pigments, atromentic acid (3), xerocomic acid (4), variegatic acid (5), methyl atromentate (6), methyl isoxerocomate (7), methyl variegatate (8), and variegatorubin (9) were isolated from the cultures. Their structures were assigned on the basis of extensive 1D/2D NMR spectroscopic analyses, as well as HR-ESI-MS, and HR-ESI-MS/MS measurements. Furthermore, the isolated compounds were evaluated for their antimicrobial and cytotoxic properties. 9′-hydroxyphenyl pulvinone (1), xerocomic acid (4), and methyl variegatate (8) exhibited weak to moderate cytotoxic activities against several tumor cell lines. The present paper provides a comprehensive characterization of pigments from the class of pulvinic acids that are present in the basidiomes of many edible bolete species.

scholarly journals Secondary metabolites from marine microorganisms

2002 ◽  
Vol 74 (1) ◽  
pp. 151-170 ◽  
Author(s):  
ALPHONSE KELECOM
Keyword(s):  
Secondary Metabolites ◽  
Cyclic Peptides ◽  
Marine Invertebrates ◽  
Indole Alkaloids ◽  
Marine Sponges ◽  
Annual Reports ◽  
Marine Microorganisms ◽  
Mature Field ◽  
Bacteria And Fungi ◽  
New Metabolites

After 40 years of intensive research, chemistry of marine natural products has become a mature field. Since 1995, there are signals of decreased interest in the search of new metabolites from traditional sources such as macroalgae and octocorals, and the number of annual reports on marine sponges stabilized. On the contrary, metabolites from microorganisms is a rapidly growing field, due, at least in part, to the suspicion that a number of metabolites obtained from algae and invertebrates may be produced by associated microorganisms. Studies are concerned with bacteria and fungi, isolated from seawater, sediments, algae, fish and mainly from marine invertebrates such as sponges, mollusks, tunicates, coelenterates and crustaceans. Although it is still to early to define tendencies, it may be stated that the metabolites from microorganisms are in most cases quite different from those produced by the invertebrate hosts. Nitrogenated metabolites predominate over acetate derivatives, and terpenes are uncommon. Among the latter, sesquiterpenes, diterpenes and carotenes have been isolated; among nitrogenated metabolites, amides, cyclic peptides and indole alkaloids predominate.

INVESTIGATIONS INTO THE PRODUCTION OF LIPIDS BY SUBMERGED CULTURES OF THE MUSHROOM TRICHOLOMA NUDUM: I. FATTY ACID COMPOSITION OF NEUTRAL LIPIDS AND PHOSPHOLIPIDS AS A FUNCTION OF TIME

1962 ◽  
Vol 40 (7) ◽  
pp. 847-855 ◽  
Author(s):  
D. C. Leegwater ◽  
C. G. Youngs ◽  
J. F. T. Spencer ◽  
B. M. Craig
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Acid Composition ◽  
Neutral Lipids ◽  
Minor Component ◽  
Major Fatty Acid ◽  
Submerged Cultures

The production of neutral lipids and phospholipids by submerged cultures of the mushroom Tricholoma nudum, as well as the fatty acid composition of these two fractions, was studied as a function of time. The bulk of the neutral lipids was produced after 2 days when the organism appeared to be in a non-proliferative phase. The major fatty acids of the neutral lipids were palmitic, oleic, and linoleic acid (23–35% each); stearic acid was a minor component (8–13%); myristic, palmitoleic, and linolenic acid were present in small amounts (0.5–4.8%). The major fatty acid of the phospholipids was linoleic acid (55–70%); palmitic (15–19%), stearic (1.8–4.6%), and oleic (7–19%) acid were minor components; myristic, palmitoleic, and linolenic (0–2.3%) were present in small amounts. Linolenic acid was a major fatty acid (26–30%) only in the early stages of growth.A preliminary investigation was carried out with a 4-day-old culture to establish the identity of the various components of the neutral lipids and phospholipids. The neutral lipids were mainly triglycerides (92%). Small amounts of ergosterol esters (1%), free fatty acids (< 1%), ergosterol (1.7%), and unidentified non-saponifiable compounds were also present. The phospholipids contained phosphatidyl choline (59%) as the major component; phosphatidyl ethanolamine (26%), phosphatidyl serine and phosphatidic acid (7.8%), and an inositol containing phospholipid were minor components.Some of the techniques applied were specially developed for the present type of studies and are described in detail.

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