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  1. Article ; Online: Employing Two-stage Derivatisation and GC-MS to Assay for Cathine and Related Stimulant Alkaloids across the Celastraceae.

    Tembrock, Luke R / Broeckling, Corey D / Heuberger, Adam L / Simmons, Mark P / Stermitz, Frank R / Uvarov, Jessica M

    Phytochemical analysis : PCA

    2017  Volume 28, Issue 4, Page(s) 257–266

    Abstract: Introduction: Catha edulis (qat, khat, mirra) is a woody plant species that is grown and consumed in East Africa and Yemen for its stimulant alkaloids cathinone, cathine and norephedrine. Two Celastraceae species, in addition to qat, have been noted for ...

    Abstract Introduction: Catha edulis (qat, khat, mirra) is a woody plant species that is grown and consumed in East Africa and Yemen for its stimulant alkaloids cathinone, cathine and norephedrine. Two Celastraceae species, in addition to qat, have been noted for their stimulant properties in ethnobotanical literature. Recent phylogenetic reconstructions place four genera in a clade sister to Catha edulis, and these genera are primary candidates to search for cathine and related alkaloids.
    Objective: Determine if cathine or related alkaloids are present in species of Celastraceae other than Catha edulis.
    Methods: Leaf samples from 43 Celastraceae species were extracted in water followed by basification of the aqueous extract and partitioning with methyl-t-butyl ether to provide an alkaloid-enriched fraction. The extract was derivatised in a two-stage process and analysed using GC-MS for the presence of cathine. Related alkaloids and other metabolites in this alkaloid-enriched fraction were tentatively identified.
    Results: Cathinone, cathine and norephedrine were not detected in any of the 43 Celastraceae species assayed other than Catha edulis. However, the phenylalanine- or tyrosine-derived alkaloid phenylethylamine was identified in five species. Nine species were found to be enriched for numerous sterol- and terpene-like compounds.
    Conclusion: These results indicate that cathine is unique to Catha edulis, and not the compound responsible for the stimulant properties reported in related Celastraceae species. Copyright © 2017 John Wiley & Sons, Ltd.
    Language English
    Publishing date 2017-07
    Publishing country England
    Document type Journal Article
    ZDB-ID 1073576-8
    ISSN 1099-1565 ; 0958-0344
    ISSN (online) 1099-1565
    ISSN 0958-0344
    DOI 10.1002/pca.2671
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    Zs.A 4608: Show issues Location:
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  2. Article ; Online: Modulation of the antifungal activity of new medicinal plant extracts active on Candida glabrata by the major transporters and regulators of the pleiotropic drug-resistance network in Saccharomyces cerevisiae.

    Kolaczkowski, Marcin / Kolaczkowska, Anna / Stermitz, Frank R

    Microbial drug resistance (Larchmont, N.Y.)

    2009  Volume 15, Issue 1, Page(s) 11–17

    Abstract: The increased incidence of drug-resistant fungal infections, a process in which active efflux plays an important role, calls for the development of new treatments. Candida albicans and Candida glabrata are the most frequent human fungal pathogens. The ... ...

    Abstract The increased incidence of drug-resistant fungal infections, a process in which active efflux plays an important role, calls for the development of new treatments. Candida albicans and Candida glabrata are the most frequent human fungal pathogens. The latter, in spite of its increased azole tolerance, is rarely used in medicinal plant screening. Several extracts inhibiting the growth of this pathogenic yeast are identified here. The ethyl acetate extract of the herb Dalea formosa of the American Southwest, not previously known to possess antifungal activity, proved most active against azole-sensitive and azole-resistant isolates. The model yeast Saccharomyces cerevisiae, related to C. glabrata, was used to evaluate the influence of multidrug efflux on the antifungal activity of identified extracts and selected fractions from further purification steps, together with their ability to modulate ketoconazole resistance. The differential involvement of the major pleiotropic drug transporters of the ATP-binding cassette superfamily Pdr5p, Snq2p, and Yor1p as well as their transcriptional activators Pdr1p and Pdr3p in the detoxification of the antifungal constituents of several important medicinal plants is demonstrated. These include Artemisia annua and its widely used antimalarial component artemisinin. This approach revealed the concomitant presence of multidrug efflux pump substrates and modulators in the extract of A. annua and also allowed the identification of an extract not affected by the major pleiotropic drug-resistance genes.
    MeSH term(s) ATP Binding Cassette Transporter, Subfamily B/pharmacology ; ATP-Binding Cassette Transporters/genetics ; ATP-Binding Cassette Transporters/metabolism ; Antifungal Agents/pharmacology ; Artemisinins/pharmacology ; Azoles/pharmacology ; Candida glabrata/drug effects ; Carrier Proteins/genetics ; Carrier Proteins/physiology ; Drug Resistance, Fungal/genetics ; Genotype ; Indicators and Reagents ; Ketoconazole/pharmacology ; Microbial Sensitivity Tests ; Plant Extracts/pharmacology ; Plants, Medicinal/chemistry ; Saccharomyces cerevisiae/drug effects ; Saccharomyces cerevisiae/genetics
    Chemical Substances ATP Binding Cassette Transporter, Subfamily B ; ATP-Binding Cassette Transporters ; Antifungal Agents ; Artemisinins ; Azoles ; Carrier Proteins ; Indicators and Reagents ; Plant Extracts ; artemisinin (9RMU91N5K2) ; Ketoconazole (R9400W927I)
    Language English
    Publishing date 2009-02-07
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1290490-9
    ISSN 1931-8448 ; 1076-6294
    ISSN (online) 1931-8448
    ISSN 1076-6294
    DOI 10.1089/mdr.2009.0854
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    Zs.A 4435: Show issues Location:
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  3. Article: Retraction notice to 7,8-benzoflavone: a phytotoxin from root exudates of invasive Russian knapweed [Phytochemistry 64 (2003) 493-497].

    Stermitz, Frank R / Bais, Harsh P / Foderaro, Tommaso A / Vivanco, Jorge M

    Phytochemistry

    2009  Volume 70, Issue 1, Page(s) 156

    Language English
    Publishing date 2009-03-24
    Publishing country England
    Document type Retraction of Publication
    ZDB-ID 208884-8
    ISSN 1873-3700 ; 0031-9422
    ISSN (online) 1873-3700
    ISSN 0031-9422
    DOI 10.1016/j.phytochem.2008.11.009
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  4. Article ; Online: Phytotoxic compounds from roots of Centaurea diffusa Lam.

    Quintana, Naira / El Kassis, Elie G / Stermitz, Frank R / Vivanco, Jorge M

    Plant signaling & behavior

    2009  Volume 4, Issue 1, Page(s) 9–14

    Abstract: An extract of roots of Centaurea diffusa (diffuse knapweed) yielded caryophyllene oxide and linoleic acid which were shown to be phytotoxic. Also isolated were germacrene B, a previously-known phytotoxin as well as the inactive polyene aplotaxene. A ... ...

    Abstract An extract of roots of Centaurea diffusa (diffuse knapweed) yielded caryophyllene oxide and linoleic acid which were shown to be phytotoxic. Also isolated were germacrene B, a previously-known phytotoxin as well as the inactive polyene aplotaxene. A combination of these compounds, if transferred to the soil, could be one factor in the invasive behavior of this weed. Contrary to a literature report, 8-hydroxyquinoline was not detected in root exudates of in vitro grown C. diffusa nor could it be identified in the root extract. However, a recent report from a different group maintains that 8-hydroxyquinoline can be released from roots of C. diffusa following a diurnal rhythm.
    MeSH term(s) Arabidopsis/drug effects ; Centaurea/metabolism ; Chromatography, High Pressure Liquid ; Linoleic Acid/metabolism ; Linoleic Acid/toxicity ; Oxyquinoline/metabolism ; Oxyquinoline/toxicity ; Plant Roots/metabolism ; Polycyclic Sesquiterpenes ; Seedlings/drug effects ; Sesquiterpenes/metabolism ; Sesquiterpenes/toxicity ; Sesquiterpenes, Germacrane/metabolism ; Sesquiterpenes, Germacrane/toxicity
    Chemical Substances Polycyclic Sesquiterpenes ; Sesquiterpenes ; Sesquiterpenes, Germacrane ; Oxyquinoline (5UTX5635HP) ; Linoleic Acid (9KJL21T0QJ) ; caryophyllene oxide (S2XU9K448U)
    Language English
    Publishing date 2009-06-30
    Publishing country United States
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ISSN 1559-2324
    ISSN (online) 1559-2324
    DOI 10.4161/psb.4.1.7487
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Retraction. Metabolic profiling of root exudates of Arabidopsis thaliana.

    Walker, Travis S / Bais, Harsh Pal / Halligan, Kathleen M / Stermitz, Frank R / Vivanco, Jorge M

    Journal of agricultural and food chemistry

    2009  Volume 57, Issue 19, Page(s) 9346

    Language English
    Publishing date 2009-09-09
    Publishing country United States
    Document type Retraction of Publication
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/jf902670b
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    Zs.A 1172: Show issues Location:
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  6. Article ; Online: Inhibitors of bacterial multidrug efflux pumps potentiate antimicrobial photoinactivation.

    Tegos, George P / Masago, Kayo / Aziz, Fatima / Higginbotham, Andrew / Stermitz, Frank R / Hamblin, Michael R

    Antimicrobial agents and chemotherapy

    2008  Volume 52, Issue 9, Page(s) 3202–3209

    Abstract: Antimicrobial photodynamic inactivation (APDI) combines a nontoxic photoactivatable dye or photosensitizer (PS) with harmless visible light to generate singlet oxygen and reactive oxygen species that kill microbial cells. Cationic phenothiazinium dyes, ... ...

    Abstract Antimicrobial photodynamic inactivation (APDI) combines a nontoxic photoactivatable dye or photosensitizer (PS) with harmless visible light to generate singlet oxygen and reactive oxygen species that kill microbial cells. Cationic phenothiazinium dyes, such as toluidine blue O (TBO), are the only PS used clinically for APDI, and we recently reported that this class of PS are substrates of multidrug efflux pumps in both gram-positive and gram-negative bacteria. We now report that APDI can be significantly potentiated by combining the PS with an efflux pump inhibitor (EPI). Killing of Staphylococcus aureus mediated by TBO and red light is greatly increased by coincubation with known inhibitors of the major facilitator pump (NorA): the diphenyl urea INF271, reserpine, 5'-methoxyhydnocarpin, and the polyacylated neohesperidoside, ADH7. The potentiation effect is greatest in the case of S. aureus mutants that overexpress NorA and least in NorA null cells. Addition of the EPI before TBO has a bigger effect than addition of the EPI after TBO. Cellular uptake of TBO is increased by EPI. EPI increased photodynamic inactivation killing mediated by other phenothiazinium dyes, such as methylene blue and dimethylmethylene blue, but not that mediated by nonphenothiazinium PS, such as Rose Bengal and benzoporphyrin derivative. Killing of Pseudomonas aeruginosa mediated by TBO and light was also potentiated by the resistance nodulation division pump (MexAB-OprM) inhibitor phenylalanine-arginine beta-naphthylamide but to a lesser extent than for S. aureus. These data suggest that EPI could be used in combination with phenothiazinium salts and light to enhance their antimicrobial effect against localized infections.
    MeSH term(s) Bacterial Proteins/antagonists & inhibitors ; Carbanilides/chemistry ; Carbanilides/pharmacology ; Drug Resistance, Multiple, Bacterial/drug effects ; Drug Synergism ; Flavonoids/chemistry ; Flavonoids/pharmacology ; Light ; Methylene Blue/analogs & derivatives ; Methylene Blue/pharmacology ; Multidrug Resistance-Associated Proteins/antagonists & inhibitors ; Phenothiazines/chemistry ; Phenothiazines/pharmacology ; Photochemotherapy ; Photosensitizing Agents/chemistry ; Photosensitizing Agents/pharmacology ; Pseudomonas aeruginosa/drug effects ; Pseudomonas aeruginosa/growth & development ; Pseudomonas aeruginosa/radiation effects ; Staphylococcus aureus/drug effects ; Staphylococcus aureus/growth & development ; Staphylococcus aureus/radiation effects ; Tolonium Chloride/pharmacology
    Chemical Substances 5'-methoxyhydnocarpin ; Bacterial Proteins ; Carbanilides ; Flavonoids ; Multidrug Resistance-Associated Proteins ; Phenothiazines ; Photosensitizing Agents ; dimethylmethylene blue ; NorA protein, Staphylococcus (133135-40-7) ; Tolonium Chloride (15XUH0X66N) ; Methylene Blue (T42P99266K)
    Language English
    Publishing date 2008-05-12
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 217602-6
    ISSN 1098-6596 ; 0066-4804
    ISSN (online) 1098-6596
    ISSN 0066-4804
    DOI 10.1128/AAC.00006-08
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.A 809: Show issues Location:
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    Einzelsignatur: Show issues

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  7. Article: 7,8-Benzoflavone: a phytotoxin from root exudates of invasive Russian knapweed.

    Stermitz, Frank R / Bais, Harsh Pal / Foderaro, Tommaso A / Vivanco, Jorge M

    publication RETRACTED

    Phytochemistry

    2003  Volume 64, Issue 2, Page(s) 493–497

    Abstract: Root exudates from Acroptilon repens (Russian knapweed) were found to be phytotoxic and the phytotoxin in the exudate was identified as 7,8-benzoflavone (alpha-naphthoflavone), (1), not previously known as a natural product. In tests on growing seedlings ...

    Abstract Root exudates from Acroptilon repens (Russian knapweed) were found to be phytotoxic and the phytotoxin in the exudate was identified as 7,8-benzoflavone (alpha-naphthoflavone), (1), not previously known as a natural product. In tests on growing seedlings both 1 and its isomer 5,6-benzoflavone (2) were phytotoxic. Flavone, a structural analog of 1 and a known granular leaf and stem exudate of other plant species, was also phytotoxic and more potent than 1 or 2.
    MeSH term(s) Arabidopsis/drug effects ; Arabidopsis/growth & development ; Arabidopsis/ultrastructure ; Benzoflavones/chemistry ; Benzoflavones/isolation & purification ; Benzoflavones/toxicity ; Cell Death/drug effects ; Centaurea/chemistry ; Centaurea/drug effects ; Centaurea/growth & development ; Centaurea/ultrastructure ; Flavonoids/isolation & purification ; Flavonoids/toxicity ; Isomerism ; Photoperiod ; Plant Extracts/chemistry ; Plant Extracts/isolation & purification ; Plant Extracts/toxicity ; Plant Leaves/chemistry ; Plant Roots/chemistry ; Plant Roots/drug effects ; Plant Roots/growth & development ; Plant Stems/chemistry ; Seedlings/drug effects ; Seedlings/growth & development ; Time Factors ; beta-Naphthoflavone/isolation & purification ; beta-Naphthoflavone/toxicity
    Chemical Substances Benzoflavones ; Flavonoids ; Plant Extracts ; alpha-naphthoflavone (604-59-1) ; beta-Naphthoflavone (6051-87-2)
    Language English
    Publishing date 2003-05-01
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S. ; Retracted Publication
    ZDB-ID 208884-8
    ISSN 1873-3700 ; 0031-9422
    ISSN (online) 1873-3700
    ISSN 0031-9422
    DOI 10.1016/s0031-9422(03)00276-0
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    Z 1586: Show issues
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  8. Article: Isoflavones as potentiators of antibacterial activity.

    Morel, Cécile / Stermitz, Frank R / Tegos, George / Lewis, Kim

    Journal of agricultural and food chemistry

    2003  Volume 51, Issue 19, Page(s) 5677–5679

    Abstract: Isoflavones isolated from Lupinus argenteus were found to potentiate the antibacterial activity of alpha-linolenic acid, also found in the same plant. The isoflavones also potentiated the activity of the natural plant antibiotic berberine and the ... ...

    Abstract Isoflavones isolated from Lupinus argenteus were found to potentiate the antibacterial activity of alpha-linolenic acid, also found in the same plant. The isoflavones also potentiated the activity of the natural plant antibiotic berberine and the synthetic fluoroquinoline antibiotic norfloxacin. The isoflavones increased the uptake of berberine into Staphylococcus aureus cells, indicating that they may be inhibiting a multidrug resistance pump (MDR). Thus, L. argenteus contains a weak antibacterial and also MDR pump inhibitors, which increase its potency.
    MeSH term(s) ATP Binding Cassette Transporter, Sub-Family B/antagonists & inhibitors ; Anti-Bacterial Agents/pharmacology ; Berberine/metabolism ; Berberine/pharmacology ; Drug Synergism ; Isoflavones/pharmacology ; Lupinus/chemistry ; Norfloxacin/pharmacology ; Plant Leaves/chemistry ; Plant Stems/chemistry ; Staphylococcus aureus/drug effects ; Staphylococcus aureus/metabolism ; alpha-Linolenic Acid/pharmacology
    Chemical Substances ATP Binding Cassette Transporter, Sub-Family B ; Anti-Bacterial Agents ; Isoflavones ; Berberine (0I8Y3P32UF) ; alpha-Linolenic Acid (0RBV727H71) ; Norfloxacin (N0F8P22L1P)
    Language English
    Publishing date 2003-09-10
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, P.H.S.
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/jf0302714
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    Zs.A 1172: Show issues Location:
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  9. Article: Two flavonols from Artemisa annua which potentiate the activity of berberine and norfloxacin against a resistant strain of Staphylococcus aureus.

    Stermitz, Frank R / Scriven, Lacey N / Tegos, George / Lewis, Kim

    Planta medica

    2002  Volume 68, Issue 12, Page(s) 1140–1141

    Abstract: Bioassay-guided fractionation of an extract of Artemisia annua L. (Asteraceae) was conducted in order to assess the possible presence in the plant material of inhibitors of bacterial multidrug resistance pumps. Fractions were tested for Staphylococcus ... ...

    Abstract Bioassay-guided fractionation of an extract of Artemisia annua L. (Asteraceae) was conducted in order to assess the possible presence in the plant material of inhibitors of bacterial multidrug resistance pumps. Fractions were tested for Staphylococcus aureus growth inhibition in the presence of a subinhibitory dose of the weak antibacterial alkaloid berberine. Active fractions yielded the flavones chrysosplenol-D and chrysoplenetin, which themselves had very weak growth inhibitory action, but which made a potent combination with berberine. In comparison with work on other flavonols, it is likely that potentiation is due to the inhibition of an S. aureus multidrug resistance (MDR) pump. These same two flavonols were earlier reported to potentiate the activity of artemisinin against Plasmodium falciparum.
    MeSH term(s) Anti-Infective Agents/pharmacology ; Artemisia annua ; Berberine/pharmacology ; Drug Resistance, Bacterial ; Drug Synergism ; Flavonoids/chemistry ; Flavonoids/isolation & purification ; Flavonoids/pharmacology ; Molecular Structure ; Norfloxacin/pharmacology ; Plant Extracts/pharmacology ; Staphylococcus aureus/drug effects
    Chemical Substances Anti-Infective Agents ; Flavonoids ; Plant Extracts ; chrysoplenetin ; chrysoplenol D ; Berberine (0I8Y3P32UF) ; Norfloxacin (N0F8P22L1P)
    Language English
    Publishing date 2002-12
    Publishing country Germany
    Document type Letter ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, P.H.S.
    ZDB-ID 123545-x
    ISSN 1439-0221 ; 0032-0943
    ISSN (online) 1439-0221
    ISSN 0032-0943
    DOI 10.1055/s-2002-36347
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  10. Article: Phytotoxic Allelochemicals From Roots and Root Exudates of Leafy Spurge (Euphorbia esula L.).

    Qin, Bo / Perry, Laura G / Broeckling, Corey D / Du, Jiang / Stermitz, Frank R / Paschke, Mark W / Vivanco, Jorge M

    Plant signaling & behavior

    2009  Volume 1, Issue 6, Page(s) 323–327

    Abstract: Invasive plants are a widespread problem but the mechanisms used by these plants to become invasive are often unknown. The production of phytotoxic natural products by invasive weeds is one mechanism by which these species may become successful ... ...

    Abstract Invasive plants are a widespread problem but the mechanisms used by these plants to become invasive are often unknown. The production of phytotoxic natural products by invasive weeds is one mechanism by which these species may become successful competitors. Here we conducted a bioactivity-driven fractionation of root extracts and exudates from the invasive plant leafy spurge (Euphorbia esula L.), and structurally characterized jatrophane diterpenes and ellagic acid derivatives. Ellagic acid derivatives and one of the jatrophane diterpenes, esulone A, have been previously reported from leafy spurge, but another of the jatrophane diterpenes, kasuinine B, has not. We show that these compounds are phytotoxic but affect plants in different ways, either inducing overall plant necrosis or reducing root branching and elongation.
    Language English
    Publishing date 2009-05-31
    Publishing country United States
    Document type Journal Article
    ISSN 1559-2316
    ISSN 1559-2316
    DOI 10.4161/psb.1.6.3563
    Database MEDical Literature Analysis and Retrieval System OnLINE

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