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Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens

Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two new benzyl derivatives, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol (1) and (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol (2) along with seven kno...

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मुख्य लेखकों:	Gao, Jiangtao, León, Francisco, Radwan, Mohamed M., Dale, Olivia R., Husni, Afeef S., Manley, Susan P., Lupien, Shari, Wang, Xiaoning, Hill, Robert A., Dugan, Frank M., Cutler, Horace G., Cutler, Stephen J.
स्वरूप:	Artigo
भाषा:	Inglês
प्रकाशित:	2011
विषय:	Article
ऑनलाइन पहुंच:	https://ncbi.nlm.nih.gov/pmc/articles/PMC3142309/ https://ncbi.nlm.nih.gov/pubmed/21667972 https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/np200147c
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id	pubmed-3142309
record_format	dspace
spelling	pubmed-31423092012-07-22 Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens Gao, Jiangtao León, Francisco Radwan, Mohamed M. Dale, Olivia R. Husni, Afeef S. Manley, Susan P. Lupien, Shari Wang, Xiaoning Hill, Robert A. Dugan, Frank M. Cutler, Horace G. Cutler, Stephen J. J Nat Prod Article Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two new benzyl derivatives, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol (1) and (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol (2) along with seven known compounds (3–9) including five benzaldehyde compounds, flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglaucin (5), auroglaucin (6) and 2-(2′,3-epoxy-1′,3′-heptadienyl)- 6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (7), one diketopiperazine alkaloid echinulin (8), and 5,7-dihydroxy-4-methylphthalide (9). The chemical structures of these compounds were established on the basis of extensive 1D, 2D NMR and HRMS data. Compounds 1–4 and 6 showed good binding affinity for human opioid or cannabinoid receptors. These findings have important implications for psychoactive studies with this class of compounds. 2011-06-13 2011-07-22 /pmc/articles/PMC3142309/ /pubmed/21667972 http://dx.doi.org/10.1021/np200147c Text en
institution	US NLM
collection	PubMed Central
language	Inglês
format	Artigo
topic	Article
spellingShingle	Article Gao, Jiangtao León, Francisco Radwan, Mohamed M. Dale, Olivia R. Husni, Afeef S. Manley, Susan P. Lupien, Shari Wang, Xiaoning Hill, Robert A. Dugan, Frank M. Cutler, Horace G. Cutler, Stephen J. Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens
description	Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two new benzyl derivatives, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol (1) and (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol (2) along with seven known compounds (3–9) including five benzaldehyde compounds, flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglaucin (5), auroglaucin (6) and 2-(2′,3-epoxy-1′,3′-heptadienyl)- 6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (7), one diketopiperazine alkaloid echinulin (8), and 5,7-dihydroxy-4-methylphthalide (9). The chemical structures of these compounds were established on the basis of extensive 1D, 2D NMR and HRMS data. Compounds 1–4 and 6 showed good binding affinity for human opioid or cannabinoid receptors. These findings have important implications for psychoactive studies with this class of compounds.
author	Gao, Jiangtao León, Francisco Radwan, Mohamed M. Dale, Olivia R. Husni, Afeef S. Manley, Susan P. Lupien, Shari Wang, Xiaoning Hill, Robert A. Dugan, Frank M. Cutler, Horace G. Cutler, Stephen J.
author_facet	Gao, Jiangtao León, Francisco Radwan, Mohamed M. Dale, Olivia R. Husni, Afeef S. Manley, Susan P. Lupien, Shari Wang, Xiaoning Hill, Robert A. Dugan, Frank M. Cutler, Horace G. Cutler, Stephen J.
author_sort	Gao, Jiangtao
title	Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens
title_short	Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens
title_full	Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens
title_fullStr	Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens
title_full_unstemmed	Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens
title_sort	benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus eurotium repens
publishDate	2011
url	https://ncbi.nlm.nih.gov/pmc/articles/PMC3142309/ https://ncbi.nlm.nih.gov/pubmed/21667972 https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/np200147c
_version_	1755557698572648448

Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens

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