Detection and identification of loline and its analogues in horse urine.

Takeda, Akira; Suzuki, Etsuko; Kamei, Katsutoshi; Nakata, Hisao

doi:10.1248/cpb.39.964

Cited by 12 publications

(9 citation statements)

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“…Several groups have published characteristic EI-MS data for the lolines (Akramov and Yunusov, 1966;Dannhardt and Steindl, 1985;Petroski et al, 1989;Robbins et al, 1972;Takeda et al, 1991). Takeda et al (1991) characterized the fragmentation of 2 (m/z 154).…”

Section: Methods For Isolation and Analysis Of Lolinesmentioning

confidence: 99%

“…In addition to 7, several other N-acylnorlolines (8-11) have been identified in Adenocarpus decorticans (Fabaceae) (Aasen and Culvenor, 1969;Powell and Petroski, 1992;Veen et al, 1992). Another acylnorloline, N-senecionoylloline (12) has been reported from horse urine and may be a metabolite of ingested lolines (Takeda et al, 1991). Lolidine (13), also reported from darnel, has one of the more unusual proposed structures: a loline alkaloid linked to another saturated pyrrolizidine that, instead of an ether bridge, has a chlorine atom at C-7 and is hydroxylated at C-2 (Batirov et al, 1977b).…”

Section: History Of Lolinesmentioning

confidence: 99%

“…In these studies, ergot alkaloids were several orders of magnitude more potent than the lolines. The identification of loline alkaloids in horse and bovine urine indicates that they are absorbed from feed; however, levels in blood plasma have been too low to detect, indicating that lolines are rapidly cleared (Takeda et al, 1991;TePaske et al, 1993b). Interestingly, a 10-1000 pM concentration of 3 exhibited a mitogenic effect on quiescent vascular smooth muscle cells, and also inhibited growing cells at 100-1000 pM (Strickland et al, 1996).…”

Section: Biological Activities Of Lolinesmentioning

confidence: 99%

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Loline alkaloids: Currencies of mutualism

et al. 2007

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Section: Methods For Isolation and Analysis Of Lolinesmentioning

confidence: 99%

Section: History Of Lolinesmentioning

confidence: 99%

Section: Biological Activities Of Lolinesmentioning

confidence: 99%

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Loline alkaloids: Currencies of mutualism

et al. 2007

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“…Crude loline salts were analyzed via gas chromatography (GC) and mass spectrometry (GC-MS), revealing a mixture of N-formylloline (m/z 183.3), loline (m/z 154) and trace amounts of N-acetylloline m/z 197.3). Loline species were then separated by thin layer chromatography and further characterized with GC-MS to compare peaks to reference data (Takeda et al, 1991;Justus et al, 1997).…”

Section: Alkaloid Extractionmentioning

confidence: 99%

Loline alkaloid production by fungal endophytes of Fescue species select for particular epiphytic bacterial microflora

Roberts

Lindow

2013

The ISME Journal

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The leaves of fescue grasses are protected from herbivores by the production of loline alkaloids by the mutualist fungal endophytes Neotyphodium sp. or Epichloë sp. Most bacteria that reside on the leaf surface of such grasses can consume these defensive chemicals. Loline-consuming bacteria are rare on the leaves of other plant species. Several bacterial species including Burkholderia ambifaria recovered from tall fescue could use N-formyl loline as a sole carbon and nitrogen source in culture and achieved population sizes that were about eightfold higher when inoculated onto plants harboring loline-producing fungal endophytes than on plants lacking such endophytes or which were colonized by fungal variants incapable of loline production. In contrast, mutants of B. ambifaria and other bacterial species incapable of loline catabolism achieved similarly low population sizes on tall fescue colonized by loline-producing Neotyphodium sp. and on plants lacking this endophytic fungus. Lolines that are released onto the surface of plants benefiting from a fungal mutualism thus appear to be a major resource that can be exploited by epiphytic bacteria, thereby driving the establishment of a characteristic bacterial community on such plants.

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“…Loline alkaloids are typically analyzed using capillary gas chromatography (GC) with a flame ionization detector 16−19 or gas chromatography−mass spectrometry (GC-MS) with electron ionization. 13,15,17,20 They have also been analyzed to some extent by NMR. 13,21 The high-performance liquid chromatographic (HPLC) analysis of loline alkaloids is very uncommon.…”

Section: ■ Introductionmentioning

confidence: 99%

Identification and Quantification of Loline-Type Alkaloids in Endophyte-Infected Grasses by LC-MS/MS

Adhikari

Boelt

Fomsgaard

2016

J. Agric. Food Chem.

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Lolines, fungal metabolites of the grass-endophyte association, were identified and quantified using newly developed LC-MS/MS methods in endophyte-infected grasses belonging to the Lolium and Festuca genera after extraction with three different solvents using two extraction methods. The shaking extraction method with isopropanol/water was superior to the other methods due to its high sensitivity, high accuracy (recovery within or close to the range of 80-120%), and high precision (coefficient of variation of <10%). Seven loline alkaloids were identified and quantified using our newly established LC-MS/MS methods, and N-formylloline was the most abundant (5 mg/g dry matter), followed by N-acetylloline. These LC-MS/MS methods used the shortest sample handling time and the fewest sample preparation steps and proved to be good alternatives to existing GC and GC-MS analytical methods without compromising analytical efficiency. In conclusion, we developed for the first time a highly sensitive quantitative LC-MS/MS analytical method for the accurate and reproducible quantification and a LightSight-assisted LC-QTRAP/MS qualitative method for the tentative identification of loline-type alkaloids in endophyte-infected grasses.

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Detection and identification of loline and its analogues in horse urine.

Cited by 12 publications

References 0 publications

Loline alkaloids: Currencies of mutualism

Loline alkaloids: Currencies of mutualism

Loline alkaloid production by fungal endophytes of Fescue species select for particular epiphytic bacterial microflora

Identification and Quantification of Loline-Type Alkaloids in Endophyte-Infected Grasses by LC-MS/MS

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