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At least 19 recordsLinked to original sources
PubMed2026

Trichoderma specialized metabolites in biocontrol: gene-metabolite links, ecological functions, and translational bottlenecks.

Trichoderma spp. produce a diverse repertoire of metabolites with specific activities that contribute to biocontrol through direct antagonism, ecological signalling, and modulation of plant responses. However, current knowledge remains uneven: many metabolites are chemically described, whereas fewer are supported by robust gene-metabolite associations, experimentally validated ecological functions, and realistic translational evidence. Progress in this field will depend less on expanding compound catalogues than on integrating mechanistic, ecological, and translational evidence. This review examines the specialized metabolism of Trichoderma with emphasis on biosynthetic gene clusters, regulatory networks, ecological roles, and biosafety constraints relevant to biocontrol. Major metabolite classes, including polyketides, terpenoids, peptaibols, siderophores, diketopiperazines, and volatile organic compounds, are discussed together with representative case studies for which genetic and functional evidence is available. We further propose a translational framework to distinguish metabolites with mainly descriptive support from those approaching application readiness, based on four criteria: gene-level validation, demonstrated ecological role, manageable biosafety profile, and feasible delivery/stability. This perspective helps explain why metabolite inventories continue to expand faster than field translation. Recent advances in genomics, transcriptomics, metabolomics, genome editing, and formulation science are reshaping how Trichoderma metabolites are prioritized for future development.

Biosafety↗
PubMed2026

Genetic and metabolite diversity of Sundaland Heptapleurum (Araliaceae) insight into evolutionary and specialized metabolite.

BACKGROUND: The genus Heptapleurum Gaertn (previously treated as Schefflera J.R.Forst. & G.Forst.) within the Araliaceae family is recognized for its significant medicinal value and complex taxonomy. However, an integrated understanding of its evolutionary and metabolite diversity remains unexplored, especially in the Sundaland region (i.e., Java and Sumatra). Here, we integrate genomics and metabolomics to unravel the evolutionary relationships and metabolite diversity of 10 Heptapleurum species from Sundaland. RESULTS: We assembled 10 new complete plastid genomes (plastomes) and 45S nuclear ribosomal DNA (nrDNA) sequences, identifying significant variation and potential key molecular markers. Metabolomics identified 152 metabolites, mainly phenolics and terpenoids. Metabolite profiles of H. rhynchocarpum and H. capituliferum were more correlated with phylogeny than with geography; these two species were separate from the main Heptapleurum clade. Four species, H. farinosum, H. longifolium, H. rigidum, and H. fastigiatum, have almost identical plastomes and 45S nrDNA structures, suggesting they may represent closely related species with different phenotypes, as evidenced by distinctive metabolite compositions. CONCLUSIONS: Crucially, there is an incongruence between the genetic and chemical phylogenies, underscoring that while chemotaxonomy reflects functional diversity, genetic data remains the definitive standard for evolutionary inference, with the potential for reclassifying H. rhynchocarpum and H. capituliferum. This study provides a foundation for future taxonomic revisions, conservation, and drug discovery of Heptapleurum.

Phylogeny↗
PubMed1975

Isolation and mass spectral identification of blood metabolites of cyclophosphamide: evidence for phosphoramide mustard as the biologically active metabolite.

Thin-layer chromatography and mass spectrometry were used to isolate and identify cyclophosphamide metabolites present in blood of mice. Blood was removed 5, 15, 30 and 45 minutes after intraperitoneal administration and extracted with chloroform followed by methanol. Thin-layer chromatography of the two extracts and the residual solid with or without prior methylation, collection of resulting alkylating components, determination of radioactivity and mass spectral analysis, served to identify cyclophosphamide, 4-ketocyclophosphamide, alcophosphamide, N-dechloroethylcyclophosphamide, carboxyphosphamide, phosphoramide mustard and nor-HN2. The absence of detectable levels of 4-hydroxycyclophosphamide or aldophosphamide in the blood of cyclophosphamide-treated mice suggests that cyclophosphamide is converted rapidly in the liver to carboxyphosphamide, 4-ketocyclophosphamide, phosphoramide mustard and nor-HN2. Direct administration of synthetic 4-hydroxycyclophosphamide to mice and extraction of blood with chloroform demonstrated the recovery of this metabolite in vivo. Analysis of extracts of blood from mice treated with phosphoramide mustard indicated the presence of nor-HN2, 3-(2-chloroethyl)-1,3-oxazolidin-2-one and unchanged drug. Consideration of blood levels, cytotoxicity and alkylating activity of metabolites identified, in or inferred from, this study, implicates phosphoramide mustard as a leading condidate for the biologically active form of cyclophosphamide.

Animals↗
PubMed1979

Antiestrogens and antiestrogen metabolites: preparation of tritium-labeled (+/-)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxyl]-1,2-propanediol (U-23469) and characterization and synthesis of a biologically important metabolite.

The Upjohn antiestrogen (+/-)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol (2b, U 23469) has been prepared in tritium-labeled form by reduction of an unsaturated dihydronaphthalene precursor with carrier-free tritium gas over a palladium catalyst followed by alkylation with 3-iodo-1,2-propanediol. After extensive chromatographic purification, the final material was obtained with a specific activity of 13 Ci/mmol and a radiochemical purity of 94%. In vivo studies with immature rats show that [3H]2b is slowly converted to a more polar metabolite that is selectively accumulated in the nuclear fraction of the uterus where it is bound to the estrogen receptor. Chromatographic comparisons indicate that this metabolite is the demethylated analogue 2c, a compound that has an affinity for estrogen receptor more than 300 times greater than that of 2b. These studies suggest that the demethylated analogue 2c may be a biologically important metabolite of 2b that is involved in the action of this antiestrogen.

Animals↗
PubMed1992

[Synthesis of metabolites of mosapramine. II. Synthesis of phenolic metabolites of mosapramine and their pharmacological activities].

Four phenolic metabolites of (+-)-3-chloro-5-[3-(2-oxo-1,2,3,5,6,7,8,8a-octahydroimidazo[1,2- a]pyridine-3-spiro-4'-piperidino)propyl]-10,11-dihydro-5H-dibenz [b,f]azepine (mosapramine), a new antipsychotic drug, were synthesized in order to determine their chemical structures. Pharmacological activities of the three main metabolites were compared with those of mosapramine. The activities of the metabolites were far less potent than those of mosapramine.

Animals↗
PubMed1977

Marihuana metabolites in urine of man. VII. Excretion patterns of acidic metabolites detected by sequential thin layer chromatography.

The 11-oic acid metabolites of delta-9-tetrahydrocannabinol (THC), cannabinol (CBN), and cannabidiol (CBD) can be identified presumptively in human urine using standard thin layer chromatographic procedures. Other acidic metabolites are also excreted but these are not yet identified. These acidic metabolites appear in urine soon after exposure but persist for at least 48 to 72 hours. Such long persistence does not permit their detection to be used for forensic purposes. Using only simple chemical methods, we have been able to identify presumptively the 11-oic acids of THC, CBN and CBD in the urine of persons taking these materials. A sequential thin-layer chromatography system we have devised provided the basis for this first report of such isolation without the use of labeled drug or mass spectrometric methods.

Cannabidiol↗
PubMed1978

Determination of the metabolites of bezitramide in urine. II. The basic metabolite.

A high-performance liquid chromatographic method for the determination of low levels (less than 1 microgram/ml) of the basic metabolite of bezitramide, 1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one, in human urine is described. Special attention is given to the separation from the basic metabolite of droperidol, a drug frequently co-administered with bezitramide.

Analgesics↗
PubMed1992

[Synthesis of metabolites of mosapramine. I. Synthesis of alcoholic metabolites].

Four alcoholic metabolites of (+-)-3-chloro-5-[3-(2-oxo-1,2,3,5,6,7,8,8a-octahydroimidazo[1,2-a] pyridine-3-spiro-4'-peperidino)propyl]-10,11-dihydro-5'-dibenz[b,f ] azepine(mosapramine), a new antipsychotic drug, were synthesized in order to determine their chemical structures. A mixture of 10-ethoxy-3-chloro-10,11-dihydro-5H-dibenz[b,f]azepine and 11-ethoxy isomer was used as a starting material. Isomeric intermediates, i.e. 10-oxo-3-chloro-5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine and 11-oxo isomer, were separated by chromatography with silica gel. The metabolites were obtained by NaBH4 reduction of the corresponding 10-oxo or 11-oxo compounds followed by introduction of spiro-piperidine moieties into propyl side chain.

Antipsychotic Agents↗
PubMed1978

Determination of the metabolites of bezitramide in urine. I. Acidic metabolite.

Two methylation methods are compared in relation to the determination of low levels (less than microgram/ml) of the acidic metabolite of bezitramide in human urine. It was necessary to use alkali flame ionisation detector, which specifically detects nitrogen-containing compounds. Several difficulties associated with the use of this detector are described.

Analgesics↗
PubMed1977

Metabolites of gentamicin-producing Micromonospora species I. Isolation and identification of metabolites.

From the cultural broth of a Micromonospora species 25 aminocyclitol antibiotics were isolated by repeated ion-exchange chromatographic processes. The main components of the metabolites were identified as gentamicin C1, C2, and C1a. The other previously reported gentamicin type antibiotics and some other degradation products including gentamicin A, B, B1, X2, sisomicin, garamine, gentamines etc., were identified by chemical, PMR, and mass spectroscopic studies. Besides these, seven new gentamicin type antibiotics were isolated and characterized.

Bacteria↗
PubMed1975

[Quantitative determination of the main metabolites of acetylsalicylic acid. 1. A method for the quantitative determination of salicylic acid and its metabolites. Studies in healthy individuals].

For special purposes a combination of methods is described which allows to determine salicylic acid (including acetylsalicylic acid) and its main metabolites in blood plasma and urine separately and quantitatively. Salicylic acid (SA) and salicyluric acid (SU) are extracted from the acidified fluid with ether and afterwards reextracted in an aqueous phase. By fluorometry at different wavelengths, it is possible to differentiate between SA and SU. The conjugates of SA and SU are hydrolyzed with sulfuric acid and then extracted in the form of SA and SU. The four analyses (SA, SU and their conjugates) are of satisfying accuracy and sensitivity. To test the validity of the method in vivo, the concentrations of SA and its conjugates were determined in the plasma and urines of healthy volunteers. By a simplified, but nevertheless accurate, modification of the described method total salicylate in the urine can be determined.

Adult↗
PubMed1975

[Quantitative determination of the main metabolites of acetylsalicylic acid/2nd communication: the concentrations of salicylic acid and its metabolites in patients with renal insufficiency (author's transl)].

Quantitative Determination of the Main Metabolites of Acetylsalicylic Acid / 2nd Communication: The concentrations of salicylic acid and its metabolies in patients with renal insufficiency 9 patients suffering from renal insufficiencies of varing degrees and treated regularly by hemodialysis were given 1.5 g Colfarit (microcapsulated acetyl salicylic acid) as a single dose. The concentrations of salicylic acid (SA), salicyluric acid (SU), further salicylic acid conjugates (SAC) and salicyluric acid conjugates (SUC) were determined in the blood plasma. Likewise urea and creatinine were determined. SA concentration decreased continually and, at the end of the trial (72 h after application), had vanished almost completely from the plasma of most patients. SU increased at first and decreased afterwards. With the exception of the dailysis time SAC and SUC increased during the trial. After 3 days the SUC level was more than 50% of total salicylate (SSS) in most patients. SSS (the sum of SA + SU + SAC + SUC) did not change very much before dialysis, but showed a rather high decrease during the first hours of dialysis. tafter dialysis the SSS levels rose again, apparently as a consequence of a redistribution and of the synthesis of conjugates with decreased tissue affinity. It could be shown that SSS in the blood plasma does not parallel SSS in the whole body. The interindividual variation of SA metabolism as well as the variation of the biological blank values was rather high. The results are discussed with regard to salicylate pharmacokinetics in renal insufficiency and to normal salicylate metabolism.

Adult↗
PubMed1977

[Prevention and therapy of respiratory distress syndrome in premature infants by means of bromhexine metabolite VIII. Animal experimental studies on the therapeutic efficacy of bromhexine metabolite VIII in premature respiratory distress syndrome].

In preparing a clinical study 14C-labelled bromhexine metabolite VIII was applied intraamnially in animal experiments. The distribution was measured in different maternal and fetal organs by thinlayer chromatography and autoradiography. A complete placental passage was found in both directions. An organspecific accumulation in the fetal lungs could not be demonstrated.

Ambroxol↗