New opine type amino acids from a poisonous mushroom, Clitocybe acromelalga

Fushiya, Shinji; Matsuda, Masazumi; Yamada, S.; Nozoe, Shigeo

doi:10.1016/0040-4020(95)00929-9

Cited by 12 publications

(4 citation statements)

References 17 publications

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“…Heliopine, rideopine and lysopine have all been detected from crown gall tumours produced by rhizosphere bacteria Agrobacterium tumefaciens [34,43]. Valinopine has been detected from a poisonous mushroom Clitocybe acromelalga and is suggested being a fungal toxin [92]. In addition, we were able to observe a compound tentatively identified as saccharopine, which is a precursor of lysine in the fungal α-aminoadipate pathway [109].…”

Section: Resultsmentioning

confidence: 99%

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

et al. 2019

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Endophytes are microorganisms living inside plant hosts and are known to be beneficial for the host plant vitality. In this study, we isolated three endophytic fungus species from the roots of Scots pine seedlings growing on Finnish drained peatland setting. The isolated fungi belonged to dark septate endophytes (DSE). The metabolic profiles of the hot water extracts of the fungi were investigated using Ultrahigh Performance Liquid Chromatography with Diode Array Detection and Electron Spray Ionization source Mass Spectrometry with Orbitrap analyzer (UPLC–DAD–ESI–MS–Orbitrap). Out of 318 metabolites, we were able to identify 220, of which a majority was amino acids and peptides. Additionally, opine amino acids, amino acid quinones, Amadori compounds, cholines, nucleobases, nucleosides, nucleotides, siderophores, sugars, sugar alcohols and disaccharides were found, as well as other previously reported metabolites from plants or endophytes. Some differences of the metabolic profiles, regarding the amount and identity of the found metabolites, were observed even though the fungi were isolated from the same host. Many of the discovered metabolites have been described possessing biological activities and properties, which may make a favorable contribution to the host plant nutrient availability or abiotic and biotic stress tolerance.

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Section: Resultsmentioning

confidence: 99%

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

et al. 2019

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“…During the constituent analysis of dried fruiting bodies of I. hispidus in 2007, Politi et al identified a known compound, phenylalaninopine ( 53 ), by spectral and mass spectrometric characterization collected by LC-DAD-MS and comparing with the literature, while attempting to develop a phytochemical extraction method for mushrooms using hot water as a solvent [ 25 ] ( Figure 5 ). The compound was isolated initially from Clitocybe acromelalga, a poisonous mushroom [ 26 ]. Yang et al obtained two monosaccharides, D-arabitol ( 54 ) and D-glucose ( 55 ), along with the isolation of four triterpenoids [ 23 ].…”

Section: Compounds With Diverse Structuresmentioning

confidence: 99%

Diverse Metabolites and Pharmacological Effects from the Basidiomycetes Inonotus hispidus

et al. 2022

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Inonotus hispidus mushroom is a popular edible and medicinal mushroom with a long history of use. It is well known as a medicinal fungus with various health benefits for its significant anticancer and immunomodulatory activities. Over the last 60 years, secondary metabolites derived from I. hispidus and their biological activities have been discovered and investigated. Structurally, these compounds are mainly polyphenols and triterpenoids, which have anticancer, anti-inflammatory, antioxidant, antimicrobial, and enzyme inhibitor activities. Here, the secondary metabolites derived from I. hispidus and their activities were systematically and comprehensively classified and summarized, and the biosynthetic pathway of stylylpyrones was deduced and analyzed further. This review contributes to our understanding of I. hispidus and will help with research into natural product chemistry, pharmacology, and the biosynthesis of I. hispidus metabolites. According to this review, I. hispidus could be a promising source of bioactive compounds for health promotion and the development of functional foods.

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“…Opines have been structurally classified into several groups, among which two groups have a common secondary amine dicarboxylic acid structure. One group has been categorized as the N 2 -(l-D-carboxyethyl) derivatives of L-arginine (octopine), L-ornithine (octopinic acid), L-lysine (lysopine), L-histidine (histopine), L-methionine (methiopine), and L-phenylalanine (phenylalaninopine) [ 2 , 3 , 4 ]. The second group has been categorized as the N 2 -(1,3-D-dicarboxypropyl) derivatives of L-arginine (nopaline), L-ornithine (nopalinic acid (ornaline)), L-leucine (leucinopine), and L-asparagine (succinamopine) [ 5 , 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…[ 18 , 19 ] reported that Arthrobacter sp. strain 1C, isolated from soil, grew on N 2 -[l-D-(carboxyl)ethyl-L-phenylalanine] as the sole carbon source, and possessed NAD + -dependent dehydrogenase that catalyzed a reversible oxidization-reduction reaction of several octopine-type opines including N 2 -[l-D-(carboxyl)ethyl-L-methionine] and N 2 -[l-D-(carboxyl)ethyl-L-phenylalanine], which were later discovered in crown gall tumor tissues as methiopine [ 3 ] and phenylalaninopine [ 4 ]. The enzyme is sequentially homologous to OCS and NOS, while the corresponding gene is encoded on the chromosome (but not the plasmid).…”

Section: Introductionmentioning

confidence: 99%

Characterization of Flavin-Containing Opine Dehydrogenase from Bacteria

et al. 2015

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Opines, in particular nopaline and octopine, are specific compounds found in crown gall tumor tissues induced by infections with Agrobacterium species, and are synthesized by well-studied NAD(P)H-dependent dehydrogenases (synthases), which catalyze the reductive condensation of α-ketoglutarate or pyruvate with L-arginine. The corresponding genes are transferred into plant cells via a tumor-inducing (Ti) plasmid. In addition to the reverse oxidative reaction(s), the genes noxB-noxA and ooxB-ooxA are considered to be involved in opine catabolism as (membrane-associated) oxidases; however, their properties have not yet been elucidated in detail due to the difficulties associated with purification (and preservation). We herein successfully expressed Nox/Oox-like genes from Pseudomonas putida in P. putida cells. The purified protein consisted of different α-, β-, and γ-subunits encoded by the OdhA, OdhB, and OdhC genes, which were arranged in tandem on the chromosome (OdhB-C-A), and exhibited dehydrogenase (but not oxidase) activity toward nopaline in the presence of artificial electron acceptors such as 2,6-dichloroindophenol. The enzyme contained FAD, FMN, and [2Fe-2S]-iron sulfur as prosthetic groups. On the other hand, the gene cluster from Bradyrhizobium japonicum consisted of OdhB 1 -C-A-B 2, from which two proteins, OdhAB1C and OdhAB2C, appeared through the assembly of each β-subunit together with common α- and γ-subunits. A poor phylogenetic relationship was detected between OdhB1 and OdhB2 in spite of them both functioning as octopine dehydrogenases, which provided clear evidence for the acquisition of novel functions by “subunit-exchange”. To the best of our knowledge, this is the first study to have examined flavin-containing opine dehydrogenase.

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New opine type amino acids from a poisonous mushroom, Clitocybe acromelalga

Cited by 12 publications

References 17 publications

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

Diverse Metabolites and Pharmacological Effects from the Basidiomycetes Inonotus hispidus

Characterization of Flavin-Containing Opine Dehydrogenase from Bacteria

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