37 results on '"Wolfgang Schühly"'
Search Results
2. Preparation of new 1,3-dibenzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities
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Nadine Kretschmer, Marcel Kaiser, Muaaz Alajlani, Robert Weis, Robert Saf, Adelheid Brantner, Werner Seebacher, Rudolf Bauer, Noor-ul-Amin Mohsin, Wolfgang Schühly, Ferdinand Belaj, Johanna Dolensky, Markus Petritsch, Pascal Mäser, and Patrick Hochegger
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Staphylococcus aureus ,Antifungal Agents ,Cell Survival ,Plasmodium falciparum ,Antineoplastic Agents ,Microbial Sensitivity Tests ,01 natural sciences ,Cell Line ,Antimalarials ,Mice ,Structure-Activity Relationship ,03 medical and health sciences ,chemistry.chemical_compound ,Parasitic Sensitivity Tests ,Candida albicans ,Drug Discovery ,Escherichia coli ,Animals ,Humans ,Cytotoxic T cell ,Ammonium ,Cell Proliferation ,030304 developmental biology ,Pharmacology ,0303 health sciences ,Dose-Response Relationship, Drug ,Molecular Structure ,Strain (chemistry) ,biology ,010405 organic chemistry ,Organic Chemistry ,General Medicine ,Antimicrobial ,biology.organism_classification ,Yeast ,Anti-Bacterial Agents ,Rats ,0104 chemical sciences ,Quaternary Ammonium Compounds ,chemistry ,Biochemistry ,Cell culture ,Pseudomonas aeruginosa ,Female ,Salts ,Drug Screening Assays, Antitumor ,Epidermis ,Bacteria - Abstract
New 1,3 dibenzyl -tetrahydropyridinylidene ammonium salts have been prepared from unsubstituted or N-benzylated tetrahydropyridinylidene ammonium salts. The antiplasmodial and antitrypanosomal activities as well as their cytotoxic effects were determined using microplate assays. In addition, their activities against two gram positive and two gram negative bacteria strains and a yeast strain were examined. Furthermore, anticancer effects against two cell lines were investigated. Physicochemical parameters were calculated and structure-activity-relationships discussed. One compound showed antiplasmodial activity against a multiresistant strain of Plasmodium falciparum in subnanomolar concentration. Antitrypanosomal activities were detected in low nanomolar concentrations. A single compound was active against grampositive and gramnegative bacteria, as well as yeast. One compound inhibited the growth of a HCT cell line in low concentration.
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- 2021
3. Lignans and sesquiterpene lactones from Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae)
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Helle Wangensteen, Ulrich Girreser, Christoph van Thriel, Karin Jöhrer, Malte Mäder, Alfonso Mangoni, Richard Greil, Serhat Sezai Çiçek, Oleksandr Shulha, Wolfgang Schühly, Janina Kroes, Laura Grauso, Christian Zidorn, Jandirk Sendker, Shulha, O., Cicek, S. S., Wangensteen, H., Kroes, J., Mader, M., Girreser, U., Sendker, J., Johrer, K., Greil, R., Schuhly, W., Mangoni, A., Grauso, L., van Thriel, C., and Zidorn, C.
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Sesquiterpene ,0106 biological sciences ,Circular dichroism ,Cytotoxicity ,Lignan ,Hypochaeris radicata subsp. neapolitana, Asteraceae ,Plant Science ,Asteraceae ,Sesquiterpene lactone ,01 natural sciences ,Biochemistry ,Lactones ,chemistry.chemical_compound ,Phenylpropanoid ,Hydroxymethyl ,chemistry.chemical_classification ,Molecular Structure ,biology ,Sesquiterpenoid ,Stringhalt ,General Medicine ,Lactone ,Multiple Myeloma ,Sesquiterpenes ,Human ,Stereochemistry ,Horticulture ,Lignans ,Botanical systematic ,Structure-Activity Relationship ,Hypochaeris ,food ,Cell Line, Tumor ,Neurotoxicity ,Humans ,Molecular Biology ,Cell Proliferation ,Dose-Response Relationship, Drug ,010405 organic chemistry ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,food.food ,0104 chemical sciences ,chemistry ,Cichorieae ,Drug Screening Assays, Antitumor ,010606 plant biology & botany - Abstract
Four undescribed lignans and two undescribed sesquiterpenic acids, together with three known compounds (hypochoeroside C, hypochoeroside D, and 5- O -caffeoylshikimic acid) were isolated from the roots of Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae). The lignans were identified as 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy- O -β-D-glucopyranoside, 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy- O -β-D-glucopyranosyl-2′- O -methacrylate, (7 S ,8 R ,8′ R )-7-(3,4-dihydroxyphenyl)-3′,4′-dihydroxy-7,8,7′,8′-tetrahydronaphtho [8,8′-c]furan-1(3H)-one, and (7 S ,8 R ,8′ R )-7-(3,4-dihydroxyphenyl)-3′,4′-dihydroxy-8'-(hydroxymethyl)-7,8,7′,8′-tetrahydronaphthalen-8-carboxylic acid. The two sesquiterpenic acids were identified as the ring open precursors of hypochoerosides C and D. Structures were elucidated using NMR and HRMS. Absolute configurations of (7 S ,8 R ,8′ R )-7-(3,4-dihydroxyphenyl)-3′,4′-dihydroxy-7,8,7′,8′-tetrahydronaphtho [8,8′-c]furan-1(3H)-one and (7 S ,8 R ,8′ R )-7-(3,4-dihydroxyphenyl)-3′,4′-dihydroxy-8'-(hydroxymethyl)-7,8,7′,8′-tetrahydronaphthalen-8-carboxylic acid were determined using electronic circular dichroism (ECD) spectroscopy. 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy- O -β-D-glucopyranoside was evaluated for its anti-proliferative activity against myeloma cell lines MM1S, U266, and NCI-H929 and showed cytotoxicity at 100 mM against MM1S strain. No neurotoxicity was observed for major compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy- O -β-D-glucopyranoside, hypochoeroside C, and hypochoeroside D in a fluorescence assay measuring neurite outgrowth in dorsal root ganglion (DRG) neurons. Additionally, compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy- O -β-D-glucopyranoside, hypochoeroside C, hypochoeroside D, and hypochoerosidic acid D were quantified in unstressed and drought-stressed plants using HPLC-DAD. Drought-stressed plants were found to contain lower concentrations of the lignan 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy- O -β-D-glucopyranoside and sesquiterpene lactone hypochoeroside C.
- Published
- 2019
4. Activities of Psilostachyin A and Cynaropicrin against Trypanosoma cruzi In Vitro and In Vivo
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Marcos Meuser Batista, Wolfgang Schühly, Denise da Gama Jaen Batista, Elen Mello de Souza, Maria De Mieri, Michael Adams, Cristiane França da Silva, Julianna Siciliano de Araújo, Matthias Hamburger, Erica Ripoll Hammer, Stefanie Zimmermann, Reto Brun, Maria de Nazaré Correia Soeiro, Jessica Lionel, and Patrícia Bernardino da Silva
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Male ,Chagas disease ,Trypanosoma cruzi ,Parasitemia ,Pharmacology ,Lactones ,Mice ,03 medical and health sciences ,chemistry.chemical_compound ,Microscopy, Electron, Transmission ,Parasitic Sensitivity Tests ,In vivo ,parasitic diseases ,Autophagy ,medicine ,Animal mortality ,Animals ,Experimental Therapeutics ,Chagas Disease ,Pharmacology (medical) ,Treatment Failure ,030304 developmental biology ,0303 health sciences ,biology ,030306 microbiology ,Cell Membrane ,medicine.disease ,biology.organism_classification ,Survival Analysis ,Trypanocidal Agents ,Cynaropicrin ,3. Good health ,Infectious Diseases ,Liver ,chemistry ,Nitroimidazoles ,Benznidazole ,Vacuoles ,Immunology ,Toxicity ,Sesquiterpenes ,medicine.drug - Abstract
In vitro and in vivo activities against Trypanosoma cruzi were evaluated for two sesquiterpene lactones: psilostachyin A and cynaropicrin. Cynaropicrin had previously been shown to potently inhibit African trypanosomes in vivo , and psilostachyin A had been reported to show in vivo effects against T. cruzi , albeit in another test design. In vitro data showed that cynaropicrin was more effective than psilostachyin A. Ultrastructural alterations induced by cynaropicrin included shedding events, detachment of large portions of the plasma membrane, and vesicular bodies and large vacuoles containing membranous structures, suggestive of parasite autophagy. Acute toxicity studies showed that one of two mice died at a cynaropicrin dose of 400 mg/kg of body weight given intraperitoneally (i.p.). Although no major plasma biochemical alterations could be detected, histopathology demonstrated that the liver was the most affected organ in cynaropicrin-treated animals. Although cynaropicrin was as effective as benznidazole against trypomastigotes in vitro , the treatment (once or twice a day) of T. cruzi -infected mice (up to 50 mg/kg/day cynaropicrin) did not suppress parasitemia or protect against mortality induced by the Y and Colombiana strains. Psilostachyin A (0.5 to 50 mg/kg/day given once a day) was not effective in the acute model of T. cruzi infection (Y strain), reaching 100% animal mortality. Our data demonstrate that although it is very promising against African trypanosomes, cynaropicrin does not show efficacy compared to benznidazole in acute mouse models of T. cruzi infection.
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- 2013
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5. In vitro metabolism and disposition of honokiol in rat and human livers
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Gottfried Reznicek, Wolfgang Schühly, Alexandra Maier-Salamon, Michaela Böhmdorfer, Walter Jäger, Theresia Thalhammer, Steffen Hering, Barbara Taferner, and Antje Hüfner
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Male ,Honokiol ,Insecta ,Metabolite ,Glucuronidation ,Pharmaceutical Science ,In Vitro Techniques ,Pharmacology ,Lignans ,chemistry.chemical_compound ,Cytosol ,Sulfation ,Glucuronic Acid ,Species Specificity ,In vivo ,Animals ,Bile ,Humans ,Tissue Distribution ,Rats, Wistar ,Biotransformation ,Chromatography, High Pressure Liquid ,biology ,Biphenyl Compounds ,Sulfuric Acids ,biology.organism_classification ,Rats ,Perfusion ,Magnolia officinalis ,Liver ,chemistry ,Magnolia ,Microsomes, Liver ,Microsome ,Metabolic Detoxication, Phase I ,Drug metabolism - Abstract
The biotransformation of honokiol, a major constituent of the bark of Magnolia officinalis , was investigated in rat and human livers. When isolated, rat livers were perfused with 10 µM honokiol and two metabolites, namely hydroxylated honokiol conjugated with glucuronic and sulfuric acid (M1) and honokiol monoglucuronide (M2), were quantified in bile and perfusate by high‐performance liquid chromatography. The hepatic extraction ratio and clearance of honokiol was very high in rat liver ( E : 0.99 ± 0.01 and 35.8 ± 0.04 mL/min, respectively) leading to very low bioavailability ( F = 0.007 ± 0.001). M2 formation was also highly efficient in human liver microsomes [ V max / K m = 78.1 ± 6.73 µL/(min mg)], which appeared to be catalyzed mainly by UDP‐glucuronosyltransferases 1A1, A3, 1A8, and 1A10, indicating hepatic and extrahepatic glucuronidation. Monosulfation of honokiol to the minor metabolite honokiol monosulfate [ V max / K m = 27.9 ± 4.33 µL/(min mg)] by human liver cytosol was less pronounced and is mediated by sulfotransferases 1A1* 1, 1A1* 2, 1A2, 1A3, 1B1, and 1E1. P450‐mediated oxidation of honokiol by liver microsomes, however, was below detection limit. In summary, this study established that glucuronidation and sulfation are the main metabolic pathways for honokiol in rat and human liver, suggesting their major contribution to clearance in vivo . © 2011 Wiley‐Liss, Inc. and the American Pharmacists Association J Pharm Sci 100:3506–3516, 2011
- Published
- 2011
6. Erratum to: Hypericum species in the Páramos of Central and South America: a special focus upon H. irazuense Kuntze ex N. Robson
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Sara Crockett, Marianne Eberhardt, Olaf Kunert, and Wolfgang Schühly
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Plant Science ,Biotechnology - Published
- 2017
7. Antiplasmodial and leishmanicidal activity of biflavonoids from Indian Selaginella bryopteris
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Marcel Kaiser, Rumalla Chidananda Swamy, Achanta Venkata Narasimha Appa Rao, Wolfgang Schühly, Armin Presser, Silke Buzzi, and Olaf Kunert
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Biflavonoids ,Traditional medicine ,biology ,medicine.drug_class ,Stereochemistry ,Selaginella bryopteris ,Trypanosoma brucei rhodesiense ,Plasmodium falciparum ,Plant Science ,Amentoflavone ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,chemistry ,parasitic diseases ,Antiprotozoal ,medicine ,Plasmodium berghei ,Trypanosoma cruzi ,Agronomy and Crop Science ,Biotechnology - Abstract
A series of eleven biflavonoids containing amentoflavone and hinokiflavone derivatives from the Indian medicinal herb Selaginella bryopteris has been investigated for their antiprotozoal activity using in vitro assays against the K1 strain of Plasmodium falciparum, Leishmania donovani, Trypanosoma brucei rhodesiense and Trypanosoma cruzi. The highest antiprotozoal activity was displayed by 7,4′,7″-tri-O-methylamentoflavone which exhibited an IC50 of 0.26 μM. This compound showed no significant cytotoxicity (IC50 > 150 μM) evaluated using L-6 cells. The strongest activity against Leishmania was detected for 2,3-dihydrohinokiflavone (IC50 = 1.6 μM), whereas for Trypanosoma no significant activity was observed (IC50 > 12.5 μg/mL for the extract). To evaluate the in vivo activity against Plasmodium of the most active compound, trimethylated amentoflavones were obtained by partial synthesis starting from amentoflavone. The synthesized mixture of trimethylated amentoflavones did not show activity in the Plasmodium berghei mouse model against female NMRI mice at 50 mg/kg.
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- 2008
8. Secondary metabolites from the aerial parts of Verbascum dudleyanum and their biological activities
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Zeliha S. Akdemir, Erdal Bedir, I. Irem Tatli, Olaf Kunert, and Wolfgang Schühly
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chemistry.chemical_classification ,Iridoid Glycosides ,biology ,Scrophulariaceae ,Picein ,Flavonoid ,Plant Science ,General Chemistry ,biology.organism_classification ,General Biochemistry, Genetics and Molecular Biology ,Catalpol ,chemistry.chemical_compound ,chemistry ,Glucoside ,Verbascum ,Organic chemistry ,Aucubin - Abstract
From the overground parts of Verbascum dudleyanum, six iridoid glycosides, aucubin, ajugol, catalpol, 6-O-α-L-rhamnopyranosylcatalpol, saccatoside, and 6-O-(3″-O-trans-p-coumaroyl)-α-L-rhamnopyranosylcatalpol, and two saponins, ilwensisaponin A and C, as well as a flavonoid, luteolin-7-O-β-glucopyranoside, together with an acetophenone glucoside, picein, were isolated. The structures of isolated compounds were elucidated by spectroscopic methods. These compounds showed biological acitivites.
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- 2008
9. Pflanzliche Antiemetika. Inhaltsstoffe, Molekulare Wirkmechanismen und Klinische Evidenz
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Wolfgang Schühly, Rudolf Bauer, and Sara L. Crockett
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Pharmacology ,Gynecology ,medicine.medical_specialty ,business.industry ,Pharmaceutical Science ,Medicine ,Pharmacology (medical) ,business - Abstract
In Mitteleuropa werden viele Medizinalpflanzen gegen Ubelkeit und Erbrechen verwendet. Pflanzenextrakte mit reinen oder aromatischen Bitterstoffen, atherischem Ol oder anderen speziellen Wirkstoffen konnen Verdauungsstorungen verringern, Magen- und Darmkrampfe lindern und/oder gegen spezifische Gehirn- oder Magenrezeptoren wirken, die Erbrechen auslosen. Die Wirkungen von Cannabis sativa und Zingiber officinale, die in der traditionellen Medizin Anwendung bei Erbrechen finden, sind durch klinische Studien abgesichert. Jedoch sind uber die Wirkung und den Wirkungsmechanismus von Pflanzenextrakten und deren Inhaltsstoffen gegenuber Rezeptoren, die im Geschehen von Ubelkeit und Erbrechen eine Rolle spielen, wie z.B. die 5-HT3-, 5-HT4, M3- oder H3-Rezeptoren, noch wenig gesicherte Erkenntnisse vorhanden. Diese Tatsache weist auf die Bedeutung weiterfuhrender Forschung auf diesem Gebiet hin.
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- 2007
10. Structurally Unique Biflavonoids fromSelaginella chrysocaulos andSelaginella bryopteris
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Achanta Venkata Narasimha Appa Rao, Daneel Ferreira, Vanapatla Swarupa Rani, Wolfgang Schühly, Ramalla Chidananda Swamy, Bobbala Ravi Kumar, Olaf Kunert, and Franz Bucar
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Flavonoids ,Selaginellaceae ,Biflavonoids ,Molecular Structure ,biology ,Plant Extracts ,Stereochemistry ,Selaginella bryopteris ,Bioengineering ,General Chemistry ,General Medicine ,Plant Components, Aerial ,Amentoflavone ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Selaginella chrysocaulos ,chemistry ,Molecular Medicine ,Bryopteris ,Molecular Biology ,Flavanone - Abstract
Chemical investigation of Selaginella chrysocaulos from Northeast India yielded three new (i.e., 1-3) and two known biflavonoids. From Selaginella bryopteris, collected in the southern part of India, one new (11) and eleven known biflavonoids of the amentoflavone- and hinokiflavone-type were isolated and identified. The structures of the compounds were elucidated by 1D- and 2D-NMR spectroscopy, and by mass spectrometry. The absolute configurations of chiral biflavonoids with flavanone subunits (from S. bryopteris) were determined with the aid of circular-dichroism (CD) spectroscopy. Several very rare or even unprecedented substructures in biflavonoids were found.
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- 2006
11. Novel Steroidal Glycosides from two IndianCaralluma species,C. stalagmifera andC. indica
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Olaf Kunert, Nebojsa Simic, Gummadi Sridhar Babu, Bobbala Ravi Kumar, Doris Kühnelt, Achanta Venkata Narasimha Appa Rao, Medaboyina Padmavathi, Robert Michael Alex, Wolfgang Schühly, and Belvotagi Venkatrao Adavi Rao
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chemistry.chemical_classification ,Steroidal glycosides ,Caralluma ,biology ,Stereochemistry ,Organic Chemistry ,Glycoside ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,Biochemistry ,Catalysis ,Inorganic Chemistry ,chemistry ,Drug Discovery ,Caralluma stalagmifera ,Physical and Theoretical Chemistry ,Caralluma indica - Abstract
New steroidal glycosides, stalagmosides I–V (1–5) and indicosides I and II (7 and 8), together with the known compounds carumbelloside III, lasianthoside A, and lasianthoside B, were isolated from whole plants of Caralluma stalagmifera and Caralluma indica, respectively. Their structures were elucidated by extensive NMR spectroscopic studies.
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- 2006
12. Hyperolactone C: Determination of its absolute configuration by comparison of experimental and calculated CD spectra
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Sara L. Crockett, Wolfgang Schühly, and Walter M. F. Fabian
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Pharmacology ,Circular dichroism ,Chemistry ,Organic Chemistry ,Solvation ,Absolute configuration ,Analytical chemistry ,Time-dependent density functional theory ,Polarizable continuum model ,Catalysis ,Molecular electronic transition ,Spectral line ,Analytical Chemistry ,Drug Discovery ,Density functional theory ,Spectroscopy - Abstract
A detailed conformational analysis of hyperolactone C diastereomers and enantiomers ((5R,9R),(5S,9S) and (5S,9R),(5R,9S)) was done with molecular mechanics and density functional theory methods. Time-dependent density functional theory (B3PW91/TZVP) was used to calculate electronic transition energies (UV/vis spectra) and rotational strengths of the respective conformations. The effect of solvation (acetonitrile solution) on excitation energies and electronic circular dichroism was approximated by the polarizable continuum model. By comparison of the simulated CD spectrum with that measured for hyperolactone C isolated from Hypericum lloydii, its absolute configuration can be assigned as (5S,9S).
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- 2005
13. Iridoid and Phenylethanoid Glycosides fromPhlomis longifoliavar.longifolia
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Ihsan Calis, Wolfgang Schühly, Nedjalka Handjieva, Otto Sticher, Tayfun Ersöz, and Simeon Popov
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Spectrometry, Mass, Electrospray Ionization ,Spectrophotometry, Infrared ,Turkey ,Iridoid ,Stereochemistry ,medicine.drug_class ,Iridoid Glucosides ,chemistry.chemical_compound ,Verbascoside ,Glucosides ,Chlorogenic acid ,Spectroscopy, Fourier Transform Infrared ,Caffeic acid ,medicine ,Iridoids ,Nuclear Magnetic Resonance, Biomolecular ,Pyrans ,chemistry.chemical_classification ,Lamiaceae ,Plants, Medicinal ,Molecular Structure ,Glycoside ,Phenylethanoid ,chemistry ,Molecular Medicine ,Spectrophotometry, Ultraviolet ,Phlomis longifolia ,Chromatography, Liquid - Abstract
From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6). leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, ID- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail.
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- 2001
14. Novel Triterpene Saponins from Zizyphus joazeiro
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Otto Sticher, Wolfgang Schühly, Jörg Heilmann, and Ihsan Calis
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chemistry.chemical_classification ,Stem bark ,Chemistry ,Stereochemistry ,Chemical structure ,Plant composition ,Organic Chemistry ,Saponin ,Biochemistry ,Jujubogenin ,Catalysis ,Inorganic Chemistry ,chemistry.chemical_compound ,Triterpene ,Drug Discovery ,Triol ,Physical and Theoretical Chemistry - Abstract
Two dammarane-type saponins with a novel aglycon derived from the parent 16,22-epoxy-24-methylidenedammarane and lotoside A, a new lotogenin deriv., were isolated from the MeOH ext. of the stem bark of the Brazilian medicinal plant Zizyphus joazeiro, in addn. to the known saponin 3beta -{[O-[O-[alpha -L-arabinofuranosyl-(1 -> 2)]-O-[beta -D-glucopyranosyl-(1 -> 3)]]-alpha -L-arabinopyranosyl]oxy}jujubogenin. The structures of the new compds. were detd. as 16,22-epoxy-3beta -[(beta -D-glucopyranosyl)oxy]-24-methylidenedammarane-15alpha ,16alpha ,20beta -triol, 16,22-epoxy-3beta -{{O-[O-[beta -D-glucopyranosyl-(1 -> 2)]-O-[beta -D-apiofuranosyl-(1 -> 3)]]-beta -D-glucopyranosyl-(1 -> 2)-alpha -L-arabinopyranosyl}oxy}-24-methylidenedammarane-15alpha ,16alpha ,20beta -triol, and 3beta -{[O-[O-[beta -D-glucopyranosyl-(1 -> 2)]-O-[beta -D-apiofuranosyl-(1 -> 3)]]-beta -D-glucopyranosyl-(1 -> 2)-alpha -L-arabinopyranosyl]oxy}lotogenin by means of 1D- and 2D-NMR spectroscopy, as well as FAB mass spectrometry. For the novel aglycon, we propose the name joazeirogenin and, for the new saponins, joazeiroside A and B. Joazeirogenin was found to be 16,22-epoxy-24-methylidenedammarane-3beta ,15alpha ,16alpha ,20beta -tetrol.
- Published
- 2000
15. Multiple screening of medicinal plants from Oaxaca, Mexico: ethnobotany and bioassays as a basis for phytochemical investigation
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Otto Sticher, Michael Heinrich, Joachim Schmitt, P. M. Bork, C. Volken, Birgit U. Jaki, Michaela Kuhnt, Takeshi Kato, Dieter Herrmann, Barbara Frei, and Wolfgang Schühly
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Pharmacology ,Traditional medicine ,biology ,In vitro toxicology ,Pharmaceutical Science ,Brine shrimp ,Fungus ,biology.organism_classification ,Antimicrobial ,Complementary and alternative medicine ,Phytochemical ,Ethnobotany ,Drug Discovery ,Molecular Medicine ,Bioassay ,Medicinal plants - Abstract
Summary Based on ethnobotanical data collected among Zapotec Indians in Mexico, nine species traditionally applied to treat skin diseases and two species used to treat gastrointestinal disorders were subjected to several bioassays as further selection criteria for phytochemical investigation. Ten were active against at least one of the pathogenic and/or non-pathogenic bacteria and one against a non-pathogenic fungus in bioautographic TLC and agar diffusion tests. Cytotoxic/antitumor potential was found for one plant species with cell lines (KB, Caco-2) and for six with the brine shrimp assay. In the NF-κB- and the HET-CAM-test used to test for anti-inflammatory potential, two respectively one plant extract showed noteworthy activity. Furthermore, a potentially immunomodulating activity was investigated by evaluating the influence of extracts in various in vitro assays using murine and human lymphoid cells. In addition to the reported biological activities of the eleven plant species, comparisons of the ethnobotanical data and strategies for the selection for further phytochemical investigations are discussed.
- Published
- 1998
16. Hyperolactone C
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Sara L. Crockett, Wolfgang Schühly, Ferdinand Belaj, and Ikhlas A. Khan
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General Materials Science ,General Chemistry ,Condensed Matter Physics - Published
- 2004
17. Hypericum species in the Páramos of Central and South America: a special focus upon H. irazuense Kuntze ex N. Robson
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Sara L. Crockett, Marianne Eberhardt, Olaf Kunert, and Wolfgang Schühly
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Hypericum species ,biology ,Ecology ,Clusiaceae ,Plant Science ,Vegetation ,biology.organism_classification ,Article ,Habitat ,Botany ,Flowering plant ,Medicinal plants ,Hypericum ,Endemism ,Biotechnology - Abstract
Knowledge about members of the flowering plant family Clusiaceae occurring in the tropical mountain regions of the world is limited, in part due to endemism and restricted distributions. High altitude vegetation habitats (Paramos) in Central and South America are home to numerous native Hypericum species. Information related to the phytochemistry of paramo Hypericum, as well as ecological factors with the potential to influence chemical defenses in these plants, is briefly reviewed. Results of the phytochemical analysis of Hypericum irazuense, a species collected in the paramo of the Cordillera de Talamanca in Costa Rica, are presented. Lastly, guidelines for the viable and sustainable collections of plant material, to facilitate future investigations of these interesting plants, are given.
- Published
- 2010
18. Chemical differentiation of Berberis croatica and B. vulgaris using HPLC fingerprinting
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Marijana Zovko Končić, Dario Kremer, Wolfgang Schühly, Adelheid Brantner, Ksenija Karlović, and Zdenka Kalođera
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Berberis vulgaris ,chemotaxonomy ,Berberis croatica ,HPLC fingerprinting ,HPLC ,BIOMEDICINA I ZDRAVSTVO. Farmacija. Farmacija ,BIOMEDICINE AND HEALTHCARE. Pharmacy. Pharmacy - Abstract
In Croatia, two indigenous species of the genus Berberis L. occur: common barberry (B. vulgaris L.) and Croatian barberry (B. croatica Horvat), endemic to the Balkano-Illyric region. As a contribution to the chemotaxonomy of the two species, differences of their RP-HPLC chromatograms were investigated. A HPLC method combined with Unweighted Pair Group Method with Arithmetic means (UPGMA) was developed for species differentiation and compared to several previously described procedures for the differentiation of other species. The results indicate that common and Croatian barberry are closely related species, but can be differentiated according to their HPLC fingerprints under appropriate chromatographic conditions and selection of clustering variables. Generally, the amount of berberine was higher in samples obtained from B. vulgaris than from B. croatica.
- Published
- 2010
19. Radical Scavenger Activity of Phenylethanoid Glycosides in FMLP Stimulated Human Polymorphonuclear Leukocytes: Structure-Activity Relationships
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Hasan Kırmızıbekmez, Otto Sticher, Sebnem Harput, Ihsan Calis, Wolfgang Schühly, and Jörg Heilmann
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Antioxidant ,Neutrophils ,Stereochemistry ,medicine.medical_treatment ,Pharmaceutical Science ,Analytical Chemistry ,Structure-Activity Relationship ,chemistry.chemical_compound ,Drug Discovery ,medicine ,Humans ,Moiety ,Glycosides ,Pharmacology ,chemistry.chemical_classification ,Reactive oxygen species ,Organic Chemistry ,Glycoside ,Biological activity ,Free Radical Scavengers ,Phenylethanoid ,Syringic acid ,N-Formylmethionine Leucyl-Phenylalanine ,Complementary and alternative medicine ,chemistry ,Lipophilicity ,Molecular Medicine - Abstract
Radical scavenger activities of 21 phenylethanoid glycosides, including 15 ester derivatives of caffeic, ferulic, vanillic and syringic acid as well as 6 deacyl derivatives were determined by quantifying their effects on the production of reactive oxygen species (ROS) in a luminol-enhanced chemiluminescence assay with formyl-methionyl-leucyl-phenylalanine (FMLP) stimulated human polymorphonuclear neutrophils (PMNs). All phenylethanoids acylated with phenolic acids showed strong antioxidant activity whereas the deacyl derivatives were more than 30-fold less active. Therefore, the antioxidant activity is mainly related to the number of aromatic methoxy and hydroxy groups and the structure of the acyl moiety (C6-C1 or C6-C3). In contrast, modification of the sugar chain or replacement of hydroxy groups by methoxy groups in the acyl or the phenylethanoid moiety is of minor importance. The position of the acyl moiety is without significance. Free caffeic, ferulic, vanillic and syringic acid are less active compared to the phenylethanoid derivatives. This points to the importance of dissociation and lipophilicity of these acids in a cellular test system.
- Published
- 2000
20. Assessment of anti-protozoal activity of plants traditionally used in Ecuador in the treatment of leishmaniasis
- Author
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Wolfgang Schühly, Javier Salazar Lecaro, Rudolf Bauer, Hugo Navarrete, María Salomé Gachet, Marcel Kaiser, Ricardo Muñoz, and Reto Brun
- Subjects
Veterinary medicine ,Plasmodium falciparum ,Leishmania donovani ,Antiprotozoal Agents ,Cell Line ,Scoparia dulcis ,parasitic diseases ,Drug Discovery ,Brugmansia ,Medicine ,Animals ,Trypanosoma cruzi ,Leishmaniasis ,Pharmacology ,Plants, Medicinal ,biology ,Traditional medicine ,business.industry ,Trypanosoma brucei rhodesiense ,biology.organism_classification ,medicine.disease ,Elephantopus mollis ,Rats ,Minquartia ,Ecuador ,business - Abstract
Aim of the Study For the assessment of the in vitro anti-protozoal potential of plants traditionally used in Ecuador in the treatment of leishmaniasis, a combined approach based on interviews with healers as well as a literature search was carried out. Materials and Methods From three regions of Ecuador, 256 local healers called “Agents of Traditional Medicine” (ATMs) were interviewed about their knowledge of the use of plants to treat and heal the illness recognized by the ATMs as leishmaniasis. From literature sources, 14 plants were identified as being used in the treatment of leishmaniasis. Subsequently, plant material was collected from a representative selection of 39 species. A total of 140 extracts were screened in vitro against Leishmania donovani , Plasmodium falciparum , Trypanosoma brucei rhodesiense and Trypanosoma cruzi . Additionally, these extracts were evaluated for their anti-microbial activities using five gram-positive and -negative bacteria as well as Candida albicans . Results and Conclusions The survey resulted in 431 use-records for 145 plant-taxa used for the treatment of leishmaniasis. The 10 most frequently reported taxa accounted for 37.7% of all records. In the case of leishmaniasis, activity was observed for Elephantopus mollis , Minquartia guianensis , Bocconia integrifolia , Gouania lupuloides , Scoparia dulcis , an as-yet-unidentified species of Piper and Brugmansia . For the leaves of M. guianensis and the twigs and bark of G. lupuloides a good selectivity index (SI) was found. IC 50 values and the SI of active plant extracts are presented.
- Published
- 2009
21. Derivatives of schisandrin with increased inhibitory potential on prostaglandin E(2) and leukotriene B(4) formation in vitro
- Author
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Robert Saf, Walter M. F. Fabian, Martina Blunder, Rudolf Bauer, Antje Hüfner, Eva M. Pferschy-Wenzig, Olaf Kunert, and Wolfgang Schühly
- Subjects
Circular dichroism ,Spectrometry, Mass, Electrospray Ionization ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Schisandra chinensis ,Clinical Biochemistry ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Schisandrin ,Biochemistry ,Leukotriene B4 ,Dinoprostone ,Lignans ,chemistry.chemical_compound ,Cyclooctanes ,Structure-Activity Relationship ,Drug Discovery ,Cyclooxygenase Inhibitors ,Polycyclic Compounds ,Lipoxygenase Inhibitors ,Molecular Biology ,Schisandra ,Lignan ,Arachidonate 5-Lipoxygenase ,biology ,Cyclooxygenase 2 Inhibitors ,Circular Dichroism ,Organic Chemistry ,Chemical modification ,biology.organism_classification ,chemistry ,Axial chirality ,Cyclooxygenase 1 ,Molecular Medicine ,Cycloheptene ,Indicators and Reagents ,Cyclooctadiene - Abstract
Four derivatives of schisandrin, a major dibenzo[a,c]cyclooctadiene lignan of Schisandra chinensis (Turcz.) Baillon were synthesized and structurally characterized by means of NMR and mass spectroscopy. Furthermore, axial chirality of the biphenyl system was determined by comparison of calculated with measured circular dichroism (CD) spectra. Three of the obtained derivatives showed a ring contraction during chemical modification. While the original lignans were inactive on the performed bioassays, the compounds which showed the cycloheptadiene skeleton revealed remarkable activities. For the inhibition of LTB(4) production the IC(50) values of aR-6,7-dihydro-6-(1'-hydroxyethyl)-3,9-dimethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,10,11-tetraol (6) and aR-6-(1'-iodoethyl)-1,2,3,9,10,11-hexamethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene (8) were 4.2+/-0.3microM and 4.5+/-0.2microM, respectively. aR-6,7-Dihydro-6-(1'-hydroxyethyl)-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,3,9,10,11-hexaol (5) revealed dual inhibition on COX-2 (IC(50) 32.1+/-2.5microM) and on LTB(4) production (37.3+/-5.5% inhibition at 50microM).
- Published
- 2009
22. Absolute configuration of eremophilane sesquiterpenes from Petasites hybridus: comparison of experimental and calculated circular dichroism spectra
- Author
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Olaf Kunert, Wolfgang Schühly, Walter M. F. Fabian, Ferdinand Belaj, Rudolf Bauer, Sajid Jahangir, and Antje Bodensieck
- Subjects
Circular dichroism ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Protein Conformation ,Molecular Conformation ,Catalysis ,Molecular electronic transition ,Analytical Chemistry ,Substrate Specificity ,Structure-Activity Relationship ,Eremophila Plant ,Drug Discovery ,Spectroscopy ,Pharmacology ,biology ,Molecular Structure ,Chemistry ,Circular Dichroism ,Organic Chemistry ,Absolute configuration ,Stereoisomerism ,Time-dependent density functional theory ,Petasites ,biology.organism_classification ,Crystallography ,Models, Chemical ,Proton NMR ,Petasites hybridus ,Density functional theory ,Chirality (chemistry) ,Sesquiterpenes - Abstract
In-depth conformational analyses of 10 known eremophilane (= (1S,4aR,7R,8aR)-decahydro-1,8a-dimethyl-7-(1-methylethyl)napththalene) sesquiterpenes, 1–10, from Petasites hybridus were performed with molecular mechanics as well as density functional theory methods. Electronic transition energies and rotational strengths of these eight eremophilane lactones and two petasins were calculated by time-dependent density functional theory (B3PW91/TZVP). The absolute configurations of the constituents could be assigned by comparison of their simulated and experimental circular dichroism (CD) spectra in methanol as (4S,5R,8S,10R) (1, 2), (2R,4S,5R,8S,10R) (3, 4, 5), (2R,4S,5R,8R,9R,10R) (6), (2R,4S,5R,8R,10R) (7, 8), and (3R,4R,5R) (9, 10). Single-crystal X-ray diffraction data of 8β-hydroxyeremophilanolide ((8S)-8-hydroxyeremophil-7(11)-en-12,8-olide) (1) served as starting point for the theoretical conformational calculations of the 8β-epimers of the eremophilane lactones. Experimental CD spectra as well as 1H NMR spectra of compound 1 in methanol were considerably dependent on sample concentration. Chirality, 2010. © 2009 Wiley-Liss, Inc.
- Published
- 2009
23. Evaluation of the Anti-inflammatory Potential of Chinese Botanicals
- Author
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Michael Adams, Wolfgang Schühly, Rudolf Bauer, S Gusenleitner, and M Fischer
- Subjects
Pharmacology ,Complementary and alternative medicine ,Traditional medicine ,medicine.drug_class ,business.industry ,Organic Chemistry ,Drug Discovery ,medicine ,Pharmaceutical Science ,Molecular Medicine ,business ,Anti-inflammatory ,Analytical Chemistry - Published
- 2009
24. Design and synthesis of ten biphenyl-neolignan derivatives and their in vitro inhibitory potency against cyclooxygenase-1/2 activity and 5-lipoxygenase-mediated LTB4-formation
- Author
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Olaf Kunert, Wolfgang Schühly, Asije Oluwemimo, Ernst Haslinger, Eva M. Pferschy-Wenzig, Antje Bodensieck, Antje Hüfner, Rudolf Bauer, Elke Prettner, and Michael Adams
- Subjects
Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Biochemistry ,Chemical synthesis ,Leukotriene B4 ,Lignans ,Lipoxygenase ,Structure-Activity Relationship ,Drug Discovery ,Leukocytes ,Structure–activity relationship ,Humans ,Cyclooxygenase Inhibitors ,Molecular Biology ,chemistry.chemical_classification ,Arachidonate 5-Lipoxygenase ,biology ,Chemistry ,Organic Chemistry ,Biphenyl Compounds ,In vitro ,Biphenyl compound ,Enzyme ,Cyclooxygenase 2 ,Magnolia ,Prostaglandin-Endoperoxide Synthases ,Arachidonate 5-lipoxygenase ,biology.protein ,Cyclooxygenase 1 ,Molecular Medicine ,Cyclooxygenase - Abstract
A set of ten derivatives of methylhonokiol, an anti-inflammatory active biphenyl-type neolignan from Magnolia grandiflora, has been evaluated for their in vitro cyclooxygenase-1/2 (COX-1/2) inhibitory activity using assays with purified prostaglandin H synthase (PGHS)-1 and PGHS-2 enzymes as well as for their 5-lipoxygenase (5-LOX) mediated LTB(4) formation inhibitory activity using an assay with activated human polymorphonuclear leukocytes. The derivatization reactions included methylation, acetylation, hydrogenation, epoxydation and isomerization. Five of the derivatives are new to science. The most active compound against COX-1 and COX-2 was methylhonokiol with IC(50) values of 0.1 microM, whereas the most active compound against LTB(4) formation was (E)-3'-propenyl-5-(2-propenyl)-biphenyl-2,4'-diol with an IC(50) value of 1.0 microM. Structure-activity relationship studies showed that the polarity of the derivatives plays a crucial role in their activity towards COX-1/2 enzyme and 5-LOX mediated LTB(4) formation.
- Published
- 2008
25. Jacaranda--an ethnopharmacological and phytochemical review
- Author
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Wolfgang Schühly and María Salomé Gachet
- Subjects
Pharmacology ,Traditional medicine ,biology ,Plant Extracts ,Antiprotozoal Agents ,Bignoniaceae ,Tribe (biology) ,biology.organism_classification ,Tecomeae ,Antineoplastic Agents, Phytogenic ,Jacaranda ,Phytochemical ,Genus ,Ethnobotany ,Drug Discovery ,Botany ,Animals ,Humans ,Medicine, Traditional ,Medicinal plants - Abstract
The genus Jacaranda, an important representative of the tribe Tecomeae in the family Bignoniaceae, is interesting from both biological and chemical perspectives. In this review, a contemporary summary of biological and pharmacological research on Jacaranda species will be presented and critically evaluated. Significant findings in the treatment of protozoa-caused diseases as well as of skin illnesses have been presented in ethnobotanical reports and recent studies were performed on crude extracts for certain Jacaranda species. Jacaranone, the most important constituent isolated is known to possess anti-cancer activity. Recently, high cutaneous toxicity together with moderate activity against leishmaniasis was described. Very few additional data are available on the biological activities and cytotoxicity of pure compounds from Jacaranda. Thirteen of the forty-nine distinguished species of Jacaranda have been reported in scientific literature as ethnobotanically used or phytochemically investigated. However, information about a chemical profile is available only for six species. The following article gives a critical assessment of the literature to date and aims to show that the pharmaceutical potential of this genus has been underestimated and deserves closer attention.
- Published
- 2008
26. Chromatographic fingerprinting of Berberis croatica vs. B. vulgaris (Common and Croatian barberry) using HPLC
- Author
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Adelheid Brantner, Z. Kaloðera, Dario Kremer, Ksenija Karlović, Marijana Zovko, and Wolfgang Schühly
- Subjects
Pharmacology ,Croatian ,Chromatography ,biology ,Traditional medicine ,Berberis croatica ,Organic Chemistry ,UPGMA ,Pharmaceutical Science ,biology.organism_classification ,High-performance liquid chromatography ,language.human_language ,Analytical Chemistry ,chemistry.chemical_compound ,Berberine ,Complementary and alternative medicine ,chemistry ,Chemotaxonomy ,Genus ,Drug Discovery ,language ,Berberis ,Molecular Medicine ,fingerprinting ,Berberis vulgaris ,HPLC - Abstract
In Croatia, two indigenous species of the Berberis L. genus, common barberry (B. vulgaris L.) and Croatian barberry (B. croatica Horvat), occur. While common barberry is a well known species growing in many parts of Europe, Croatian barberry is endemic to the illyric-balcanic region (Croatia, Bosnia and Herzegovina, Montenegro, and Macedonia) [1]. As a contribution to chemotaxonomy, differences of RP-HPLC chromatograms of B. croatica and B. vulgaris were investigated. Herbal samples were collected at six different locations (three locations per species) in Croatia. Methanolic extracts of roots, twigs, leaves and fruit were analysed with regard to their berberine content and chromatographic fingerprints. The HPLC conditions were: isocratic (TEA-adjusted 0.02 mol L-1 H3PO4 (pH 4.82)– acetonitrile (75:25)) and gradient elution (H2O/HCOOH, 9:1 followed by acetonitrile/HCOOH). Signals were detected at 205.4, 254.2 and 330.2 nm. Cluster analysis (UPGMA) was employed for evaluation of fingerprints. The average quantity of berberine in extracts of B. vulgaris was higher than in extracts of B. croatica. In extracts of roots it ranged from 7.85 to 12.19% and from 2.44 to 7.29%, for B. vulgaris and B. croatica, respectively. The quantity of berberine in extracts of twigs varied from 0.82 to 1.53% and from 0.48 to 0.63%, for B. vulgaris and B. croatica, respectively. Even though differences in the individual chromatograms of two species could be noted and UPGMA tended to group samples of the same species together, cluster analyses of fingerprints did not reveal important differences between the two species. This finding indicates that common and Croatian barberry are probably very closely related.
- Published
- 2008
27. Structure and Absolute Configuration of Loliolide Isomers Determined by Comparison of Calculated and Experimental CD Spectra
- Author
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Wolfgang Schühly, Walter M. F. Fabian, Sajid Jahangirb, and Christine Fabiana
- Subjects
Physics ,Wavelength ,Basis (linear algebra) ,Absolute configuration ,Structure (category theory) ,Time-dependent density functional theory ,Circular dichroism spectra ,Molecular physics ,Spectral line ,Excitation - Abstract
The circular dichroism spectra of the four possible configurations [(R,R), (R,S), (S,R), (S,S)] of loliolides are simulated on the basis of electronic excitation energies (wavelength) and rotational strengths R (nm) calculated by time dependent density functional theory using three density functionals (B3PW91 , PBE0 , B3LYP) and three basis sets [TZVP, SVP, 6-31G (d)]. All three basis sets give almost similar l and R with B3PW91 and B3LYP methods but with the PBE0 method, lower values of l and R were observed.
- Published
- 2007
28. [Contents, molecular action mechanism and clinical evidence. Plant derived antiemetics]
- Author
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Sara L, Crockett, Wolfgang, Schühly, and Rudolf, Bauer
- Subjects
Alkaloids ,Plants, Medicinal ,Vomiting ,Animals ,Antiemetics ,Humans ,Nausea - Published
- 2007
29. Processing of a sesquiterpene lactone by Papilio glaucus caterpillars
- Author
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Wolfgang Schühly, Cheryl Frankfater, Frank R. Fronczek, and Marc Slattery
- Subjects
Magnolia virginiana ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Glaucus ,Sesquiterpene ,Sesquiterpene lactone ,Biochemistry ,chemistry.chemical_compound ,Lactones ,Botany ,Animals ,Parthenolide ,Ecology, Evolution, Behavior and Systematics ,chemistry.chemical_classification ,biology ,fungi ,General Medicine ,biology.organism_classification ,Adaptation, Physiological ,Magnoliaceae ,Lepidoptera ,Plant Leaves ,Plants, Toxic ,chemistry ,Papilio glaucus ,Larva ,Sesquiterpenes ,Lactone - Abstract
Papilio glaucus caterpillars encounter a diverse array of sesquiterpene lactones, including parthenolide, in the leaves of host plants Liriodendron tulipifera and Magnolia virginiana. These compounds are toxic to unadapted herbivores, and the development of P. glaucus caterpillars likely depends on their ability to excrete or detoxify them efficiently. A new metabolite of parthenolide, 2-alpha-hydroxydihydroparthenolide, identified by crystal structure determination and nuclear magnetic resonance, was present in the waste of the caterpillars. The parent compound was modified by the reduction of an alpha-methylene group, rendering the compound less reactive, and the addition of a hydroxyl group, which increases the polarity and prepares it for the conjugation reactions of phase II metabolism. Unmetabolized parthenolide was also present in large amounts in waste. P. glaucus larvae are apparently capable of excreting intact sesquiterpene lactones and sesquiterpene lactone metabolites during consumption of foliage rich in these compounds.
- Published
- 2005
30. Hyperolactone C: determination of its absolute configuration by comparison of experimental and calculated CD spectra
- Author
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Wolfgang, Schühly, Sara L, Crockett, and Walter M F, Fabian
- Subjects
Models, Molecular ,Acetonitriles ,Models, Chemical ,Protein Conformation ,Ultraviolet Rays ,Circular Dichroism ,Molecular Conformation ,Solvents ,Electrons ,Models, Theoretical ,Furans - Abstract
A detailed conformational analysis of hyperolactone C diastereomers and enantiomers ((5R,9R),(5S,9S) and (5S,9R),(5R,9S)) was done with molecular mechanics and density functional theory methods. Time-dependent density functional theory (B3PW91/TZVP) was used to calculate electronic transition energies (UV/vis spectra) and rotational strengths of the respective conformations. The effect of solvation (acetonitrile solution) on excitation energies and electronic circular dichroism was approximated by the polarizable continuum model. By comparison of the simulated CD spectrum with that measured for hyperolactone C isolated from Hypericum lloydii, its absolute configuration can be assigned as (5S,9S).
- Published
- 2005
31. Absolute Configuration of Hyperolactone C Determined by Comparison of Calculated and Experimental CD Spectra
- Author
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Wolfgang Schühly, Sara L. Crockett, and Walter M. F. Fabian
- Subjects
Materials science ,Absolute configuration ,Analytical chemistry ,Hyperolactone C ,Spectral line - Published
- 2004
32. New triterpenoids with antibacterial activity from Zizyphus joazeiro
- Author
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Jörg Heilmann, Wolfgang Schühly, Ihsan Calis, and Otto Sticher
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,Pharmaceutical Science ,Microbial Sensitivity Tests ,Pharmacognosy ,Gram-Positive Bacteria ,Analytical Chemistry ,chemistry.chemical_compound ,Triterpene ,Betulinic acid ,Drug Discovery ,Antibacterial agent ,Pharmacology ,chemistry.chemical_classification ,Plants, Medicinal ,Traditional medicine ,biology ,Molecular Structure ,Organic Chemistry ,biology.organism_classification ,Terpenoid ,Triterpenes ,Anti-Bacterial Agents ,Complementary and alternative medicine ,chemistry ,visual_art ,Rhamnaceae ,visual_art.visual_art_medium ,Molecular Medicine ,Bark ,Antibacterial activity - Abstract
The stem bark of the Brazilian medicinal plant Zizyphus joazeiro C. Mart. was phytochemically investigated. Three known compounds (betulinic, ursolic and alphitolic acid) and three new derivatives of betulinic acid, 7 beta-(4-hydroxybenzoyloxy)-betulinic acid, 7 beta-(4-hydroxy-3'-methoxybenzoyloxy)-betulinic acid and 27-(4-hydroxy-3'-methoxybenzoyloxy)-betulinic acid which showed a considerable activity against Gram-positive bacteria were isolated from the dichloromethane extract. The structures were established on the basis of NMR spectroscopy and mass spectrometry.
- Published
- 2000
33. Major herbs of ayurveda
- Author
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Wolfgang Schühly
- Subjects
Pharmacology ,Complementary and alternative medicine ,Drug Discovery ,Pharmaceutical Science ,Molecular Medicine ,Biology - Published
- 2004
34. Cycloartane Triterpenes from Dikamali, the Gum Resin ofGardenia gummiferaandGardenia lucida
- Author
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Achanta Venkata Narasimha Appa Rao, Marupaka Radhakishan, Bobbala Ravi Kumar, Gandhe Sreekanth, Wolfgang Schühly, Gummadi Sreedhar Babu, Olaf Kunert, Belvotagi Venkatrao Adavi Rao, and Robert Saf
- Subjects
Methicillin-Resistant Staphylococcus aureus ,Gardenia gummifera ,Spectrometry, Mass, Electrospray Ionization ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Flavonoid ,Bioengineering ,Biochemistry ,Terpene ,Triterpenoid ,Candida albicans ,Plant Gums ,Medicinal plants ,Molecular Biology ,chemistry.chemical_classification ,Rubiaceae ,biology ,Traditional medicine ,Chemistry ,General Chemistry ,General Medicine ,biology.organism_classification ,Gardenia ,Triterpenes ,Anti-Bacterial Agents ,Molecular Medicine ,Resins, Plant - Abstract
We report on the chemical investigation of dikamali gum, which is the resin of Gardenia gummifera and G. lucida (Rubiaceae). Six new cycloartane triterpenes, dikamaliartanes A-F (1-6, resp.), together with a known flavonoid (7), were isolated and identified by NMR spectroscopy. All six cycloartanes are characterized by an open A-ring with a free COOH group at C(3). In four of them, the C-atoms C(23)-C(27) form a 4-methylfuran-2-yl moiety. Bacterial assays using Staphylococcus aureus, Candida albicans, and Mycobacteria have been carried out but did not reveal significant activity.
- Published
- 2009
35. [Untitled]
- Author
-
Wolfgang Schühly
- Subjects
Pharmacology ,Complementary and alternative medicine ,Drug Discovery ,Pharmaceutical Science ,Molecular Medicine - Published
- 2005
36. Processing of a Sesquiterpene Lactone by Papilio glaucus Caterpillars.
- Author
-
Cheryl Frankfater, Wolfgang Schühly, Frank Fronczek, and Marc Slattery
- Abstract
Papilio glaucus caterpillars encounter a diverse array of sesquiterpene lactones, including parthenolide, in the leaves of host plants Liriodendron tulipifera and Magnolia virginiana. These compounds are toxic to unadapted herbivores, and the development of P. glaucus caterpillars likely depends on their ability to excrete or detoxify them efficiently. A new metabolite of parthenolide, 2-α-hydroxydihydroparthenolide, identified by crystal structure determination and nuclear magnetic resonance, was present in the waste of the caterpillars. The parent compound was modified by the reduction of an α-methylene group, rendering the compound less reactive, and the addition of a hydroxyl group, which increases the polarity and prepares it for the conjugation reactions of phase II metabolism. Unmetabolized parthenolide was also present in large amounts in waste. P. glaucus larvae are apparently capable of excreting intact sesquiterpene lactones and sesquiterpene lactone metabolites during consumption of foliage rich in these compounds. [ABSTRACT FROM AUTHOR]
- Published
- 2005
- Full Text
- View/download PDF
37. Chemical characterization of Magnolia biondii (Flos Magnoliae, Xin Yi)
- Author
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Jeannette Skarbina, Olaf Kunert, Rudolf Bauer, Owi I. Nandi, and Wolfgang Schühly
- Subjects
Pharmacology ,chemistry.chemical_classification ,Molecular Structure ,biology ,Plant composition ,Magnolia biondii ,Flos ,Flowers ,Naphthols ,Plant Science ,General Medicine ,biology.organism_classification ,Sesquiterpene ,Sesquiterpene lactone ,Lignans ,chemistry.chemical_compound ,Complementary and alternative medicine ,chemistry ,Phytochemical ,Magnolia ,Drug Discovery ,Botany ,Parthenolide ,Medicinal plants - Abstract
Samples of Magnolia biondii buds (Xin Yi, Flos Magnoliae) from different sources were subjected to phytochemical analysis and compared to samples of M. denudata and M. liliiflora. Among the compounds found in the flower buds of M. biondii were eight tetrahydrofurofuran lignans as well as the sesquiterpene lactone parthenolide and the sesquiterpene alcohol oplodiol. A rapid TLC-method for the identification of plant material from M. biondii and its distinction from M. liliiflora was developed. Structure elucidation was carried out by means of NMR (1- and 2-D) and LC-MS.
Catalog
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