
Ralph L ReedOregon State University | OSU · College of Pharmacy
Ralph L Reed
Ph.D.
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61
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August 1978 - present
Publications
Publications (61)
Powdery mildew, caused by Podosphaera macularis, is one of the most important diseases of hop in the Pacific Northwest of the United States. Resistant cultivars exist; however, recently, the pathogen has overcome two sources of resistance in popular cultivars. Breeding for new, emerging races of the pathogen is thus a continuing priority. We used R...
Phytochemicals from the genus, Fagonia, have been attracting increasing attention due to their potential beneficial effects on human health. Fagonia species contain various types of phytochemicals such as flavonoids, alkaloids, saponins, terpenoids, coumarins and tannins. In this study, we investigated the phytochemical composition of unhydrolyzed...
Introduction
The phytochemical composition of plant material governs the bioactivity and potential health benefits as well as the outcomes and reproducibility of laboratory studies and clinical trials.
Objective
The objective of this work was to develop an efficient method for the in‐depth characterisation of plant extracts and quantification of m...
Vitamin C (L-ascorbic acid, AA) is an essential cellular antioxidant and cofactor for several α-ketoglutarate-dependent dioxygenases. As an antioxidant, AA interacts with vitamin E to control oxidative stress. While several reports suggest an interaction of AA with folate (vitamin B9) in animals and humans, little is known about the nature of the i...
Exposure to ultraviolet B (UVB) irradiation of the skin leads to numerous dermatological concerns including skin cancer and accelerated aging. Natural product glucosinolate derivatives, like sulforaphane, have been shown to exhibit chemopreventive and photoprotective properties. In this study, we examined meadowfoam (Limnanthes alba) glucosinolate...
Xanthohumol (XN), a prenylated flavonoid from hops, improves dysfunctional glucose and lipid metabolism in animal models of metabolic syndrome (MetS). However, its metabolic transformation into the estrogenic metabolite, 8-prenylnaringenin (8-PN), poses a potential health concern for its use in humans. To address this concern, we evaluated two hydr...
Scope:
Xanthohumol (XN), a prenylated flavonoid found in hops, exhibits anti-inflammatory and antioxidant properties. However, poor bioavailability may limit therapeutic applications. As food components are known to modulate polyphenol absorption, the objective was to determine whether a protein matrix could enhance the bioavailability of XN post...
Buprenorphine is a partial μ-opioid agonist used for analgesia. Due to the small size of laboratory rodents, buprenorphine HCl is typically diluted 10- or 20-fold with a sterile diluent, such as saline, for accurate dosing. Protocols for preparing and storing diluted buprenorphine vary by institution, and little published information is available r...
Buprenorphine is a partial μ-opioid agonist used for analgesia. Due to the small size of laboratory rodents, buprenorphineHCl is typically diluted 10- or 20-fold with a sterile diluent, such as saline, for accurate dosing. Protocols for preparing andstoring diluted buprenorphine vary by institution, and little published information is available reg...
Buprenorphine is a partial μ-opioid agonist used for analgesia. Due to the small size of laboratory rodents, buprenorphineHCl is typically diluted 10- or 20-fold with a sterile diluent, such as saline, for accurate dosing. Protocols for preparing andstoring diluted buprenorphine vary by institution, and little published information is available reg...
Xanthohumol (XN) is a prenylated flavonoid found in hops (Humulus lupulus) and beer. The dose-dependent effects of XN on glucose and lipid metabolism in a preclinical model of metabolic syndrome were the focus of our study. Forty-eight male C57BL/6J mice, 9 weeks of age, were randomly divided into three XN dose groups of 16 animals. The mice were f...
Meadowfoam (Limnanthes alba) is a commercial oilseed annual crop grown in Oregon. After extracting oil from seed, the remaining seed meal is rich in the secondary plant metabolite glucolimnanthin, which can be converted into pesticidal compounds such as 3-methoxybenzyl isothiocyanate (ITC) and 3-methoxyphenylacetonitrile (nitrite) in the presence o...
Particular aspects provide methods for converting glucosinolate in a glucosinolate-containing plant material to glucosinolate breakdown products (GBPs), comprising: providing an amount of processed glucosinolate-containing plant material, the processed material being depleted of oil and glucosinolate converting enzyme activity by virtue of said pro...
Meadowfoam (Limnanthes alba Hartw. ex Benth.) is an oilseed crop in the Willamette Valley of Oregon. Meadowfoam seed meal (MSM), a by-product after oil extraction, contains 2 to 4% glucosinolate (glucolimnanthin). Activated MSM, produced by adding freshly ground myrosinase-active meadowfoam seeds to MSM, facilitates myrosinase-mediated formation of...
Xanthohumol (XN) is a bioactive prenylflavonoid from hops. A single-dose pharmacokinetic (PK) study was conducted in men (n = 24) and women (n = 24) to determine dose-concentration relationships.
Subjects received a single oral dose of 20, 60, or 180 mg XN. Blood was collected at 0, 0.25, 0.5, 1, 2, 4, 8, 12, 24, 48, 72, 96, and 120 h. Plasma level...
Recent advances in sampling techniques in the pharmaceutical industry sparked significant interest in applying improvements to extraction methods for greater analyte detection and quantitation. In particular, the dried blood spot (DBS) sampling technique has numerous advantages compared to traditional methods such as liquid-liquid extraction, inclu...
Current findings suggest flavonoids might aid in prevention and/or mitigation of cardiovascular disease and type II diabetes. Specifically, xanthohumol (XN), a prenylflavonoid from hops, has recently been shown to improve glucose and lipid homeostasis in obese rodents. However, there is limited data on XN metabolism in humans. A study was conducted...
Obesity contributes to increased risk for several chronic diseases including cardiovascular disease and type 2 diabetes. Xanthohumol, a prenylated flavonoid from hops (Humulus lupulus), was tested for efficacy on biomarkers of metabolic syndrome in 4week old Zucker fa/fa rats, a rodent model of obesity. Rats received daily oral doses of xanthohumol...
Metabolic syndrome is a leading public health concern with over 50 million Americans being affected and at increased risk for other chronic diseases including cardiovascular disease, obesity and type II diabetes. Xanthohumol, a prenylated flavonoid from hops (Humulus lupulus), was tested for efficacy on biomarkers of metabolic syndrome in 4 week ol...
Xanthohumol (XN), a dietary flavonoid found in hops, may have health-protective actions against cardiovascular disease and type 2 diabetes. Yet, there are limited data on the pharmacokinetics (PK) of XN. This study provides PK parameters for XN and its major metabolites in rats.
A PK study was conducted in male jugular vein-cannulated Sprague-Dawle...
Meadowfoam (Limnanthes alba L.) is a herbaceous winter-spring annual grown as a commercial oilseed crop. The meal remaining after oil extraction from the seed contains up to 4% of the glucosinolate glucolimnanthin. Degradation of glucolimnanthin yields toxic breakdown products, and therefore the meal may have potential in the management of soilborn...
With 5 figures and 4 tables
Meadowfoam, an oilseed crop grown in the Willamette Valley of Oregon, was developed from Limnanthes alba (Benth.), an herbaceous winter annual native to the west coast of North America. Meadowfoam oil is valued for unique properties attributed to the predominance of very long-chain fatty acids and desaturation at the Δ5...
4-Hydroxy-2(E)-nonenal (HNE), a reactive aldehyde derived from oxidized lipids, has been implicated in the pathogenesis of cardiovascular and neurological diseases, in part by its ability to induce oxidative stress and by protein carbonylation in target cells. The effects of intracellular ascorbic acid (vitamin C) on HNE-induced cytotoxicity and pr...
Meadowfoam ( Limnanthes alba ) is an oilseed crop grown in western Oregon. After extraction of the oil from the seeds, the remaining seed meal contains 2-4% of the glucosinolate glucolimnanthin. This study investigated the effect of fermentation of seed meal on its chemical composition and the effect of the altered composition on downy brome ( Brom...
Meadowfoam ( Limnanthes alba) is an oilseed crop grown in western Oregon. The seed meal has potential value as a biopesticide due to glucosinolate degradation products and phytoecdysteroids, a group of polyhydroxylated triterpenoids with potent activities as arthropod molting hormones. Liquid chromatography in combination with tandem mass spectrome...
At many trichloroethene (TCE)-contaminated field sites, microbial transformation of TCE results in the accumulation of vinyl chloride (VC), a known carcinogen and neurotoxin. Quantitative tools are needed to determine the in situ rates of VC transformation to ethene in contaminated groundwater. For this study, E-/Z-chlorofluoroethene (E-/Z-CFE) was...
Trichlorofluoroethene (TCFE) was used as a reactive tracer to determine the in situ rate of reductive dechlorination in treatment zones impacted by three large-diameter permeable columns (LDPCs) that were installed at a trichloroethene (TCE)–contaminated site. The LDPCs were part of a pilot study to evaluate the effectiveness of hydrogen, lactate,...
Little is known about the occurrence and distribution of the herbicide diuron [3-(3,4-dichlorophenyl)-1,1-dimethyl urea] in soil, ground water, and surface water in areas affected by grass-seed production. A field study was designed to investigate the occurrence and distribution of diuron and its transformation products at a poorly drained field si...
Subcritical (hot) water with ethanol as modifier was used to extract nonylphenol polyethoxy carboxylates (NPECs) with 1−4 ethoxy groups from sludge samples. Quantitative recovery of native NPECs from sludge was accomplished by extracting 0.25 g samples for 20 min with 30% (v/v) ethanol in water at 75 °C and 150 bar. NPECs in the water/ethanol extra...
Dacthal and its mono- and diacid metabolites were sequentially extracted from soils by first performing a supercritical carbon dioxide extraction to recover Dacthal, followed by a subcritical (hot) water extraction step to recover metabolites. Dacthal was recovered from soil in 15 min by supercritical carbon dioxide at 150 °C and 400 bar. The mono-...
A simple and rapid method was developed to determine concentrations of diuron [N'-(3,4-dichlorophenyl)-N,N-dimethylurea] and three of its major metabolites, N'-(3,4-dichlorophenyl)-N-methylurea (DCPMU), 3,4-dichlorophenylurea (DCPU), and 3,4-dichloroaniline (DCA), in ground water and surface water. The analytical method utilizes a 25 mm C-18 Empore...
Because of their weakly estrogenic properties, interest in nonylphenol polyethoxylates and their carboxylated metabolites is resurging. To assess their occurrence in surface waters impacted by municipal and industrial effluents, an analytical method was developed for the quantitative determination of nonylphenol polyethoxy carboxylate (NPEC) metabo...
Profound sex-related differences in P450 levels and P450 activities in rainbow trout trunk kidney occur during the time of spawning. Since spawning in salmonids can be induced by certain analogues of luteinizing hormone-releasing hormone (LHRH), the role of the analogue, [D-Ala6, Pro9-NHEt]-LHRH (LHRH-A) in the expression of selected P450 enzymes i...
Monocrotaline (MCT) is a pyrrolizidine alkaloid which has been shown to induce immunotoxicity in mice. We hypothesized that metabolic activation of MCT by mixed-function oxygenases (MFO) to dehydromonocrotaline (MCTP) is a prerequisite for its immunotoxicity, as has been shown for other toxic effects of MCT. To test this hypothesis, we compared the...
Immunoblots (Western blot) of mullet liver microsomes revealed the presence of multiple forms of P-450 that appear to be structurally related to rainbow trout CYP1A1 and CYP2K1 and to P-450 LMC1 and LMC4, but not to LMC5. 3-Methylcholanthrene but not beta-naphthoflavone induced a major 58 kDa liver protein and a minor 56 kDa protein in mullet that...
1. Pyrrolizidine alkaloids (PAs) are metabolized primarily to putative dehydroalkaloid (PA pyrrole) metabolites and to PA N-oxide by rat liver microsomal monooxygenases. 2. The dehydroalkaloids are highly reactive and either bind covalentely to tissue nucleophiles or are hydrolysed to the more stable pyrrole, (R,S)-6,7-dihydro-7-hydroxy-1-hydroxyme...
Evidence based on optimal pH, thermal stability, and enzyme inhibition data suggests that the NADPH-dependent microsomal N-oxidation of the pyrrolizidine alkaloid senecionine is carried out largely by flavin-containing monooxygenase in guinea pig liver, lung, and kidney. In contrast, the hepatic microsomal conversion of senecionine to the pyrrole m...
Studies were carried out to investigate the metabolism of senecionine by human liver microsomes and the role of human cytochrome
P450IIIA4 in this process. Human liver microsomes metabolized senecionine to two major products, (±)-6,7-dihydro-7-hydroxy-l-hydroxymethyl-5H-pyrrolizine (DHP) and senecionine N-oxide. The rates of product formation (DHP...
The pyrrolizidine alkaloids (PAs) constitute a large group of hepatotoxic and carcinogenic plant constituents of wide geographic and botanical distribution. These alkaloids are responsible for the death of livestock throughout the world and for occasional human poisonings following the consumption of contaminated foods or the injudicious use of her...
A series of Senecio alkaloid and alkaloid N-oxide standards has been analyzed using positive and negative ion thermospray liquid chromatography/mass spectrometry (LC/MS) with an ammonium acetate-containing mobile phase. On-line separations of pyrrolizidine alkaloids from extracts of Senecio jacobaea (tansy ragwort) and Senecio vulgaris (common grou...
The pyrrolizidine alkaloid, senecionine, is N-oxidized by purified pig liver flavin-containing monooxygenase but not by purified rabbit lung flavin-containing monooxygenase. The activity of the pig liver enzyme toward senecionine was linear with time and amount of enzyme. The oxygenation was not due to some indirect mechanism, such as O2- release f...
Rats display a marked sex difference in the oxidation of the pyrrolizidine alkaloid senecionine, especially with respect to N-oxidation. This sex difference was largely eliminated following treatment with dexamethasone. These observations suggested the potential involvement of the male-specific cytochrome P-450 UT-A and the P-450 PCN-E in the metab...
Dehydroretronecine (DHR), a major metabolite of the pyr-rolizidine alkaloids, has been shown to bind and crosslink pBR322
plasmid DNA and M13 viral DNA, as monitored by electron microscopy and agarose gel electrophoresis. The crosslinking was alkali-stable
and varied with time, temperature, pH and reactant ratios. Although the binding of DHR to sin...
A new method was developed for the preparation of tritiated putrescine dihydrochloride ([2,3-3H]-1,4-diaminobutane dihydrochloride) from succinonitrile (1,4-butanedinitrile) and 3H2O, with a radiochemical yield of 16%. Tritiated jacobine and other pyrrolizidine alkaloids were then biosynthesized in Seneciojacobaea using 3H-putrescine·2HC as the pre...
AbstractA new method was developed for the preparation of tritiated putrescine dihydrochloride ([2,3‐3H]‐1,4‐diaminobutane dihydrochloride) from succinonitrile (1,4‐butanedinitrile) and 3H2O, with a radiochemical yield of 16%. Tritiated jacobine and other pyrrolizidine alkaloids were then biosynthesized in Senecio jacobaea using 3H‐putrescine·2HC a...
The influence of Zn on the acute hepatotoxicity of pyrrolizidine alkaloids (PAs) was determined in male rats. Zinc, 72 mumol/kg as ZnCl2, was administered ip for 3 consecutive days, followed 16 h after the last dose by a single ip injection of purified mixed PAs (80, 120, or 160 mg/kg) obtained from tansy ragwort (Senecio jacobaea). Hepatotoxicity...
Dietary butylated hydroxyanisole (BHA) at levels of 0.25 and 0.75% was found to protect young female mice against the acute toxicity of monocrotaline. The protective effect was associated with reduced levels of pyrrole metabolites in liver, decreased activity of hepatic aminopyrine demethylase, and a reduced rate of in vitro microsomal conversion o...
Meadowfoam (Limnanthes alba Hartw. ex Benth., Limnanthaceae) is an oilseed crop grown in western Oregon. The seed meal contains the glucosinolate, glucolimnanthin
(2–4%). The herbicidal potency of the seed meal depends on the enzyme-mediated conversion of the relatively inactive glucolimnanthin
into the more potent herbicidal compounds, 3-methoxybe...
Our hypotheses are that 1) xanthohumol (XN) and/or its metabolites can inhibit ABC-mediated efflux of dietary cholesterol by binding to the efflux transporters, ABCA1 and ABCG5/G8 as well as 2) XN and/or its metabolites can up-regulate ABCG5/G8 in Caco-2 cells. The combined effects of XN binding to ABC-transporters and XN-induced upregulation of AB...
About Meadowfoam Limnanthes alba Benth. and related species are native plants adapted to vernal pools of the Pacific Northwest. Meadowfoam seed oil contains novel long-chain fatty acids (C 20 -C 22) with an unusual Δ5 desaturation. The oil is light-colored, odor free, and has exceptional oxidative stability. Current market for oil is in personal ca...