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Drug metabolism and drug interactions | 1995

Cytochrome P450 Limonene Hydroxylases of Mentha Species

Shari L. Lupien; Frank Karp; Krishan Ponnamperuma; Mark R. Wildung; Rodney Croteau

The oxygenation pattern of the monoterpenoids of mint (Mentha) species is determined by regiospecific cytochrome P450-catalyzed hydroxylation of the common olefinic precursor (-)-limonene. In peppermint, C3-allylic hydroxylation leads to (-)-trans-isopiperitenol that ultimately is converted to (-)-menthol, whereas in spearmint, C6-allylic hydroxylation leads to (-)-trans-carveol that is oxidized to (-)-carvone. The limonene-6-hydroxylase and the cytochrome P450 reductase were purified from the oil glands of spearmint, and the system was reconstituted. Amino acid sequences from the purified hydroxylase were utilized to design primers with which a large, non-degenerate PCR product was prepared. This probe was employed to screen a spearmint oil gland cDNA library from which the corresponding full-length cDNA was isolated. This clone provides the tool for isolating the homologous cDNA species from peppermint and related Mentha species.


Journal of Natural Products | 2013

Neocosmospora sp.-derived resorcylic acid lactones with in vitro binding affinity for human opioid and cannabinoid receptors.

Jiangtao Gao; Mohamed M. Radwan; Francisco León; Olivia R. Dale; Afeef S. Husni; Yunshan Wu; Shari L. Lupien; Xiaoning Wang; Susan P. Manly; Robert A. Hill; Frank M. Dugan; Horace G. Cutler; Stephen J. Cutler

Bioassay-guided fractionation of a fungus Neocosmospora sp. (UM-031509) resulted in the isolation of three new resorcylic acid lactones, neocosmosin A (2), neocosmosin B (3), and neocosmosin C (4). Three known resorcylic acid lactones, monocillin IV (1), monocillin II (5), and radicicol (6), were also isolated and identified. The structures of these compounds were established on the basis of extensive 1D and 2D NMR spectroscopic analysis, mass spectrometric (ESIMS) data, and X-ray crystallography. Compounds 4-6 show good binding affinity for the human opioid receptors. These findings have important implications for evaluating the potential psychoactive effects with this class of compounds.


Biocontrol Science and Technology | 2009

Ascochyta blight of chickpea reduced 38% by application of Aureobasidium pullulans (anamorphic Dothioraceae, Dothideales) to post-harvest debris

Frank M. Dugan; Hajime Akamatsu; Shari L. Lupien; Weidong Chen; Martin L. Chilvers; Tobin L. Peever

Abstract In 2004–2005, application of non-amended suspensions of Aureobasidium pullulans conidia to post-harvest chickpea debris resulted in 37.9% fewer Ascochyta blight lesions on chickpea test plants relative to controls. Analogous tests in 2006–2007 resulted in 38.4% fewer lesions. Ascospores released from debris were predominantly Davidiella sp. (anamorph, Cladosporium sp.), followed by Didymella rabiei (anamorph, Ascochyta rabiei, agent of Ascochyta blight).


Archives of Biochemistry and Biophysics | 1999

Regiospecific Cytochrome P450 Limonene Hydroxylases from Mint (Mentha) Species: cDNA Isolation, Characterization, and Functional Expression of (−)-4S-Limonene-3-hydroxylase and (−)-4S-Limonene-6-hydroxylase☆

Shari L. Lupien; Frank Karp; Mark R. Wildung; Rodney Croteau


Plant Pathology | 2003

First report of Fusarium proliferatum causing rot of garlic bulbs in North America

Frank M. Dugan; Barbara C. Hellier; Shari L. Lupien


Journal of Phytopathology | 2002

Incidence, aggressiveness and in planta interactions of Botrytis cinerea and other filamentous fungi quiescent in grape berries and dormant buds in central Washington State

Frank M. Dugan; Shari L. Lupien; Gary G. Grove


Journal of Natural Products | 2011

Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.

Jiangtao Gao; Francisco León; Mohamed M. Radwan; Olivia R. Dale; Afeef S. Husni; Susan P. Manly; Shari L. Lupien; Xiaoning Wang; Robert A. Hill; Frank M. Dugan; Horace G. Cutler; Stephen J. Cutler


Journal of Phytopathology | 2005

Fungi Resident in Chickpea Debris and their Suppression of Growth and Reproduction of Didymella rabiei under Laboratory Conditions

Frank M. Dugan; Shari L. Lupien; M. Hernandez-Bello; T. L. Peever; Weidong Chen


Journal of Phytopathology | 2007

Pathogenic Fungi in Garlic Seed Cloves from the United States and China, and Efficacy of Fungicides Against Pathogens in Garlic Germplasm in Washington State

Frank M. Dugan; Barbara C. Hellier; Shari L. Lupien


Archive | 1998

Recombinant materials and methods for production of limonene hydroxylases

Rodney Croteau; Shari L. Lupien; Frank Karp

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Frank M. Dugan

Washington State University

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Barbara C. Hellier

Washington State University

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Jiangtao Gao

University of Mississippi

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Xiaoning Wang

University of Mississippi

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Francisco León

Spanish National Research Council

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Afeef S. Husni

University of Mississippi

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Frank Karp

Washington State University

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