A Novel Ergot Alkaloid as a 5-HT<sub>1A</sub> Inhibitor Produced by <i>Dicyma </i>sp.

Vázquez, María J.; Roa, Ana; Reyes, Fernando; Vega, Alfonso; Rivera‐Sagredo, Alfonso; Thomas, David R.; Dı́ez, Elena; Hueso-Rodríguez, Juan A.

doi:10.1021/jm0341204

Cited by 18 publications

(12 citation statements)

References 20 publications

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“…In comparison, 1 H NMR analysis of a commercial sample of LSD tartrate showed the presence of a molar ratio of 1:1 for tartaric acid:LSD based on the integrals associated with the tartrate methine protons at 4.23 ppm (Supporting Information). The NMR data obtained for 1P‐LSD is consistent with its structure and closely related substances reported before . In the proton NMR spectrum, the chemical shifts linked to the propionyl group overlapped with the resonances associated with one of the methyl groups of the N , N ‐diethylamide group, H‐7α and H‐5β (Figure A), respectively.…”

Section: Resultsmentioning

confidence: 99%

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

Brandt

Kavanagh

Westphal³

et al. 2015

Drug Testing and Analysis

170

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1-Propionyl-d-lysergic acid diethylamide hemitartrate (1P-LSD) has become available as a ‘research chemical’ in form of blotters and powdered material. This non-controlled derivative of d-lysergic acid diethylamide (LSD) has previously not been described in the published literature despite being closely related to 1-acetyl-LSD (ALD-52), which was developed in the 1950s. This study describes the characterization of 1P-LSD in comparison with LSD using various chromatographic, mass spectrometric methods and nuclear magnetic resonance spectroscopy. An important feature common to LSD and other serotonergic hallucinogens is that they produce 5-HT2A-receptor activation and induce the head-twitch response (HTR) in rats and mice. In order to assess whether 1P-LSD displays LSD-like properties and activates the 5-HT2A receptor, male C57BL/6J mice were injected with vehicle (saline) or 1P-LSD (0.025–0.8 mg/kg, IP) and HTR assessed for 30 min using magnetometer coil recordings. It was found that 1P-LSD produced a dose-dependent increase in HTR counts, and that it had ~38% (ED50 = 349.6 nmol/kg) of the potency of LSD (ED50 = 132.8 nmol/kg). Furthermore, the HTR was abolished when 1P-LSD administration followed pre-treatment with the selective 5-HT2A receptor antagonist M100907 (0.1 mg/kg, SC), which confirms that the behavioral response is mediated by activation of the 5-HT2A receptor. These results indicate that 1P-LSD produces LSD-like effects in mice, consistent with its classification as a serotonergic hallucinogen. Nevertheless, the extent to which 1P-LSD might show psychoactive effects in humans similar to LSD remains to be investigated.

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Section: Resultsmentioning

confidence: 99%

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

Brandt

Kavanagh

Westphal³

et al. 2015

Drug Testing and Analysis

170

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show abstract

“…In that regard, a recent claim that EAS genes were horizontally transferred to Clavicipitaceae (Marcet-Houben and Gabaldón 2016) is dubious because it includes gene orthologs and paralogues in the phylogenetic analysis (a typical problem in HGT studies), and because the purported discontinuous distribution among fungal groups is overstated. Though best characterized in Clavicipitaceae and Trichocomaceae, an ergopeptine has been isolated from a Dicyma species (Xylariaceae) (Vazquez et al 2003), and ergot-alkaloid biosynthesis genes or close homologs have been identified in diverse fungi (Gerhards et al 2015) including a Malbranchea sp. (Myxotrichaceae) (Ding et al 2008).…”

Section: Ergot-alkaloid Diversification In the Clavicipitaceaementioning

confidence: 99%

Ergot Alkaloids of the Family Clavicipitaceae

2017

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Ergot alkaloids are highly diverse in structure, exhibit diverse effects on animals, and are produced by diverse fungi in the phylum Ascomycota, including pathogens and mutualistic symbionts of plants. These mycotoxins are best known from the fungal family Clavicipitaceae and are named for the ergot fungi that, through millennia, have contaminated grains and caused mass poisonings, with effects ranging from dry gangrene to convulsions and death. However, they are also useful sources of pharmaceuticals for a variety of medical purposes. More than a half-century of research has brought us extensive knowledge of ergot-alkaloid biosynthetic pathways from common early steps to several taxon-specific branches. Furthermore, a recent flurry of genome sequencing has revealed the genomic processes underlying ergot-alkaloid diversification. In this review, we discuss the evolution of ergot-alkaloid biosynthesis genes and gene clusters, including roles of gene recruitment, duplication and neofunctionalization, as well as gene loss, in diversifying structures of clavines, lysergic acid amides, and complex ergopeptines. Also reviewed are prospects for manipulating ergot-alkaloid profiles to enhance suitability of endophytes for forage grasses.

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“…Recentemente, esse fungo foi relatado no Japão, colonizando basidiomata de Aphyllophorales (Watanabe et al, 2003). O gênero Dicyma tem despertado interesse, também, no isolamento de novos compostos terapêuticos para uso humano (Vázquez et al,2003). Portanto, a conservação desse fungo é imprescindível para o desenvolvimento de processos e obtenção de produtos de interesse econômico.…”

Section: Dicyma Pulvinata Isolates Colonizing Microcyclus Ulei Stromaunclassified

Isolados de Dicyma pulvinata em estromas de Microcyclus ulei em seringueira

Mello

Santos

Silva

2006

Pesq. agropec. bras.

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Resumo -Dicyma pulvinata é um eficiente agente de biocontrole de Microcyclus ulei, causador do mal-dasfolhas da seringueira. O objetivo deste trabalho foi obter isolados com grande potencial antagônico. Em levantamentos realizados em 14 municípios produtores de borracha, localizados nos Estados do Acre, Amazonas, Bahia, Mato Grosso, Pará e Rondônia, obtiveram-se 52 isolados de D. pulvinata. O fungo antagônico, isolado diretamente em meio de cultura de batata-dextrose-ágar (BDA), foi identificado com base na morfologia dos conídios e conidióforos e preservado pelos métodos da liofilização, congelamento à temperatura de -80 o C e criopreservação em nitrogênio líquido, a fim de manter as características morfológicas e patogênicas dos isolados. O efeito antagônico foi testado por meio de inoculações de D. pulvinata em lesões de Fusicladium macrosporum induzidas em plantas de seringueira previamente infectadas. Todos os isolados foram incorporados à coleção de fungos da Embrapa Recursos Genéticos e Biotecnologia.Termos para indexação: Hevea, controle biológico, fungo antagonista. Dicyma pulvinata isolates colonizing Microcyclus ulei stromata in rubberAbstract -Dicyma pulvinata is an efficient biocontrol agent of Microcyclus ulei, causal agent of South American leaf blight. The objective of this work was to obtain strongly antagonistic isolates. A survey was carried out in rubber plantations located in 14 municipalities in the Sates of Acre, Amazonas, Bahia, Mato Grosso, Pará and Roraima, Brazil, obtaining 52 isolates of D. pulvinata. The antagonistic fungus was isolated on potato-dextroseagar (PDA) plates and identified based on morphological characteristics of conidiophores and conidia, and colony appearance. The antagonic effect was tested by inoculating D. pulvinata on Fusicladium macrosporum lesions induced on rubber plants, previously. In order to maintain the morphological and pathogenic traits, fungus isolates were preserved by lyophilization, deep freeze (-80 o C) and cryogeny. All isolates were introduced into Embrapa Recursos Genéticos e Biotecnologia fungus collection.

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A Novel Ergot Alkaloid as a 5-HT_1A Inhibitor Produced by Dicyma sp.

Cited by 18 publications

References 20 publications

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

Ergot Alkaloids of the Family Clavicipitaceae

Isolados de Dicyma pulvinata em estromas de Microcyclus ulei em seringueira

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A Novel Ergot Alkaloid as a 5-HT1A Inhibitor Produced by Dicyma sp.

Cited by 18 publications

References 20 publications

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD)

Ergot Alkaloids of the Family Clavicipitaceae

Isolados de Dicyma pulvinata em estromas de Microcyclus ulei em seringueira

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Product

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A Novel Ergot Alkaloid as a 5-HT_1A Inhibitor Produced by Dicyma sp.