UAH

Bernhard Vogler

vogler b

Associate Professor, Chemistry

Office: MSB 321
Phone: 256.824.6267
Fax: 256.824.6349
Email: bvogler@chemistry.uah.edu

Résumé

Research Interests

Drug Discovery and Structure Elucidation

My expertise lies in structure elucidation of Natural Products by NMR. Special emphasis goes to the efficient implementation of On-line techniques like HPLC-NMR and HPLC-MS for screening purposes. This structural information is linked whenever possible to biological activity. Several biochemical screens are set up for this purpose. Compounds studied for this purpose stem mostly from plant sources.

  • REU-program

Publications

Fakhouri, Walid; Walker, Frank; Vogler, Bernhard; Armbruster, Wolfgang; Buchenauer, Heinrich: Isolation and identification of N-mercapto-4-formylcarbostyril, an antibiotic produced by Pseudomonas fluorescens.Phytochemistry (2001), 58(8), 1297-1303 [abstract]

Papajewski, S.; Vogler, B.; Conrad, J.; Klaiber, I.; Roos, G.; Walter, C. U.; Sussmuth, R.; Kraus, W. Papajewski, S.; Vogler, B.; Conrad, J.; Klaiber, I.; Roos, G.; Walter, C. U.; Sussmuth, R.; Kraus, W. Planta Med. (2001), 67(8), 732-736 [abstract]

Kato, M.; Kosugi, H.; Ichiyanagi, T.; Hagiwara, H.; Kodaira, A.; Kusakari, T.; Suzuki, T.; Ando, M.; Lee, J.; Drechsel, P.; Vogler, B. New entry to the synthesis of clerodane diterpenes. The first enantioselective syntheses of 7-oxo-kolavenic acid and methyl solidagonate. Tetrahedron (2001), 57(39), 8243-8256. [abstract]

Vardamides, J. C.; Dongo, E.; Nkengfack, A. E.; Fomum, Z. T.; Ngando, T. M.; Vogler, B.; Kraus, W. Diterpenoid and limonoids from the stem of Pterorhachis zenkeri. Fitoterapia (2001), 72(4), 386-393. [abstract]

Conrad, Jurgen; Vogler, Bernhard; Klaiber, Iris; Reeb, Sabine; Guse, Jan-Hinrich; Roos, Gudrun; Kraus, Wolfgang. Vanillic acid 4-O-beta-D-(6'-O-galloyl) glucopyranoside and other constituents from the bark of Terminalia macroptera Guill. et Perr. Nat. Prod. Lett. (2001), 15(1), 35-42. [abstract]

Spring, O.; Zipper, R.; Reeb, S.; Vogler, B.; Da Costa, F. B. Sesquiterpene lactones and a myoinositol from glandular trichomes of Viguiera quinqueremis (Heliantheae; Asteraceae). Phytochemistry (2001), 57(2), 267-272. [abstract]

Setzer, William N.; Holland, Michael T.; Bozeman, Carey A.; Rozmus, Glenn F.; Setzer, Mary C.; Moriarity, Debra M.; Reeb, Sabine; Vogler, Bernhard; Bates, Robert B.; Haber, William A. Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis. Planta Med. (2001), 67(1), 65-69. [abstract]

Conrad, Juergen; Vogler, Bernhard; Reeb, Sabine; Klaiber, Iris; Papajewski, Stefan; Roos, Gudrun; Vasquez, Erlinda; Setzer, Mary C.; Kraus, Wolfgang. Isoterchebulin and 4,6-O-isoterchebuloyl-D-glucose, novel hydrolyzable tannins from Terminalia macroptera. J. Nat. Prod. (2001), 64(3), 294-299. [abstract]

Vogler, B.; Spring, O. Application of LC-NMR measurements in phytochemical studies. Recent Res. Dev. Phytochem. (2000), 4 207-222. [abstract]

Todorova, Milka N.; Vogler, Bernhard; Tsankova, Elena T. Acrifolide, a novel sesquiterpene lactone from Achillea crithmifolia. Nat. Prod. Lett. (2000), 14(6), 463-468.

Todorova, Milka; Vogler, Bernhard; Tsankova, Elena. Terpenoids from Achillea setacea. Z. Naturforsch., C: J. Biosci. (2000), 55(9/10), 840-842.

Setzer, W. N.; Setzer, M. C.; Schmidt, J. M.; Moriarity, D. M.; Vogler, B.; Reeb, S.; Holmes, A. M.; Haber, W. A.: Cytotoxic components from the bark of Stauranthus perforatus from Monteverde, Costa Rica . Planta Med. (2000), 66(5), 493-494.

Spring, O.; Zipper, R..; Klaiber, I.; Reeb, S.; Vogler, B.: Sesquiterpene lactones in Viguiera eriophora and Viguiera puruana (Heliantheae; Asteraceae). Phytochemistry (2000), 55(3), 255-261.

Jaki B; Orjala J; Heilmann J; Linden A; Vogler B; Sticher O. Novel extracellular diterpenoids with biological activity from the cyanobacterium Nostoc commune. J.Nat. Prod. (2000 Mar), 63(3), 339-43.

Kostova, I.; Iossifova, T.; Rostan, J.; Vogler, B.; Kraus, W.; Navas, H.: Chemical and biological studies on Croton panamensis latex (Dragon's Blood). Pharm. Pharmacol. Lett. (1999), 9(1), 34-36.

Moser, D.; Klaiber, I.; Vogler, B.; Kraus, W.: Molluscicidal and antibacterial compounds from Petunia hybrida. Pestic. Sci. (1999), 55(3), 336-339.

Renukappa, T.; Roos, G.; Klaiber, I.; Vogler, B.; Kraus, W.: Application of high-performance liquid chromatography coupled to nuclear magnetic resonance spectrometry, mass spectrometry and bioassay for the determination of active saponins from Bacopa monniera Wettst.. J.of Chromatography. A (1999 Jun 25), 847(1-2), 109-16.

Spring, O.; Zipper, R.; Vogler, B.; Lopes, J. L. C.; Vichnewski, W.; Dias, D. A.; Cunha, W. R.: Sesquiterpene lactones in Blainvillea rhomboidea. . Phytochemistry (1999), 52(1), 79-85.

Conrad, J.; Vogler, B.; Klaiber, I.; Roos, G.; Walter, C. U.; Kraus, W.: Two Triterpene esters from Terminalia macroptera bark. Phytochemistry (1998), 48(4), 647-650.

Iossifova, T.; Vogler, B.; Kostova, I.: Secoiridoid glucosides from Fraxinus ornus bark.

Iossifova, T.; Vogler, B.; Klaiber, I.; Kostova, I.; Kraus, W.: Caffeic acid esters of phenylethanoid glycosides from Fraxinus ornus bark. Phytochemistry 1999, 50(2), 297-301

Keige, A.; Vogler, B.; Klaiber, I.; Kraus, W.: Novel Coumarins and Sesquiterpene Lactones from Vernonia brachycalyx. Pharm. Pharmacol. Lett. (1998), 8(1), 43-45.

Moser, D.; Klaiber, I.; Vogler, B.; Kraus, W.: Molluscicidal and Bactericidal Compounds from Petunia hybrida Vilm. (Solanaceae).

Papajewski, S.; Guse, J.-H.; Klaiber, I.; Roos, G.; Suessmuth, R.; Vogler, B.; Walter, C. U.; Kraus, W.: Bioassay guided isolation of a new C18-polyacetylene, (+)-9(Z),17-octadecadiene-12,14-diyne-1,11,16-triol, from Cussonia barterii.Planta Med. (1998), 64(5), 479-481.

Roos, G.; Prawat, H.; Walter, C. U.; Klaiber, I.; Vogler, B.; Guse, J.-H.; Kraus, W.: New sesquiterpene lactones with antibacterial activity from Vernonia fastigiata. Planta Med. (1998), 64(7), 673-674.

Schulze, B.; Vogler, B.; Renz, P.: Biosynthesis of vitamin B12 in anaerobic bacteria: Experiments with Eubacterium limosum of the transformation of 5-hydroxy-6-mehtyl-benimidazole, its nucleoside, its cobamides, and of 5-hydroxybenzimidazolylcobamide into vitamin B12. Eur J. of Biochem, (1998 Jun 15), 254(3), 620-5.

Steffensky, M.; Li, S.-M.;Vogler, B.; Heide, L.: Novobiocin biosynthesis in Streptomyces spheroides: identification of a dimethylallyl diphosphate: 4-hydroxyphenylpyruvate dimethylallyl transferase. FEMS Microbiol. Lett. (1998), 161(1), 69-74.

Vogler, B.; Klaiber, I.; Roos, G.; Walter, C. U.; Hiller, W.; Sandor, P.; Kraus, W.: Combination of LC-MS and LC-NMR as a Tool for Structure Determination of Natural Products. . J. Nat. Prod. (1998), 61(2), 175-178.

Bugge, J.; Klaiber, I.; Vogler, B.; Kraus, W.: Molluscicidal Pterocarpanes from Erythrina burana and a new Indole Alkaloid from Erythrina brucei. Pharm. Pharmacol. Lett. (1997), 7(4), 155-156.

Einholz, W.; Schaefer, R.; Keller, W.; Vogler, B.: Twelve-vertex heteroborane clusters by copyrolysis of tetrachlorodiborane(4) and element halides. Z. Naturforsch., B: Chem. Sci. (1997), 52(2), 221-226.

Kato, M.; Kosugi, H.; Kodaira, A.; Hagiwara, H.; Vogler, B.: Stereocontrolled synthesis of the key intermediate for the enantioselective synthesis of clerodane natural products. Tetrahedron Lett. (1997), 38(39), 6845-6848.

Kraus, W.; Maile, R.; Vogler, B.; Wundrak, B.: 1-Tigloyl-3-acetylazadirachtol, a new Limonoid from the Marrango Tree, Azadirachta excelsa Jack (Meliaceae). J. Indian Chem. Soc. (1997), 74(11-12), 870-873.

Moser, D.; Klaiber, I.; Vogler, B.; Kraus, W.: Molluscicidal and Bactericidal Compounds from Petunia hybrida Vilm.. Pharm. Pharmacol. Lett. (1997), 7(4), 148-151.

Spring, O.; Heil, N.; Vogler, B.: Sesquiterpene Lactones and Flavanones in Scalesia species (Heliantheae: Asteraceae). Phytochemistry (1997), 46(8), 1369-1373.

Braun, N. A.; Klein, I.; Spitzner, D.;Vogler B.; Borrmann, H.; Simon, A.: Diastereoselective Synthesis of Tricyclo[3.2.1.0]octanes; Chiral Building Blocks for Terpenes. Liebigs Ann. (1995), (12), 2165-9.

Braun, N. A.; Klein, I.; Spitzner, D.;Vogler B.; Braun, S.; Borrmann, H.; Simon, A.: Cascade Reactions with Chiral Michael Acceptors; Synthesis of Enantiomerically Pure Tricyclo[3.2.1.0]- and Bicyclo[3.2.1]octanes. Tetrahedron Lett. (1995), 36(21), 3675-8.

Endres B; Wurfel A; Vogler B; Renz P. 7-Azabenzimidazolylcobamide and 5,6-dimethyl-7-azabenzimidazolylcobamide, new vitamin B12-analogs synthesized from 4(5)-aminoimidazole by Eubacterium limosum. Biol. Chem.Hoppe-Seyler (1995 Oct), 376(10), 595-601.

Spring, O.; Buschmann, H.; Vogler, B.; Schilling, E. E.; Spraul, M.; Hoffmann, M.: Sesquiterpene lactone chemistry of Zaluzania grayana from online LC-NMR measurements. Phytochemistry (1995), 39(3), 609-12.

Sutthivaiyakit, S.; Pakakatsama, P.; Kraus, W.; Vogler, B.: Constituents of Diospyros rhodocalyx. Planta Med. (1995), 61(3), 295.

Guimares, D. H.; Weber, A.; Klaiber, I.; Vogler, B.; Renz, P.: Guanylcobamide and hypoxanthylcobamide. Corrinoids formed by Desulfovibrio vulgaris. Arch. Microbiol. (1994), 162(4), 272-6.

Kraus, W.; Köll-Weber, M. Maile, R.; Wunder, T.; Vogler, B.: Biologically Active constituents of tropical and subtropical plants. Pure Appl. Chem. (1994), 66(10/11), 2347-52.

Schulze, B.; Ruoff, D.; Vogler, B.; Renz, P.: Mode of Transformation of [1-15N]5-hydroxybenzimidazole and [1-15N]5-hydroxy-6-methyl-benzimidazole into the 5,6-dimethylbenzimidazolmoiety of Vitamin B12. Biol. Chem. Hoppe-Seyler (1994), 375(11), 785-8.

Wieser M; Eberspacher J; Vogler B; Lingens F . Metabolism of 4-chlorophenol by Azotobacter sp. GP1: structure of the meta cleavage product of 4-chlorocatechol. FEMS Microbio. Letters (1994 Feb 1), 116(1), 73-8.

Fetzner, S.; Vogler, B.; Lingens, F.: Transformation of 2-chloroquinoline to 2-chloro-cis-7,8-dihydro-7,8-dihydroxyquinoline by quinoline-grown resting cells of Pseudomonas putida 86. FEMS Microbio Letters (1993 Sep 1), 112(2), 151-7.

Kraus, W.; Bokel, M.; Schwinger, M.; Vogler, B.; Soellner, R.; Wendisch, D.; Steffens, R.; Wachendorff, U. The chemistry of azadirachtin and other insecticidal constituents of Meliaceae. Proc. Phytochem. Soc. Eur. (1993), 34(PHYTOCHEMISTRY AND AGRICULTURE), 18-39.

Kato, Michiharu; Watanabe, Masataka; Tooyama, Youichi; Vogler, Bernhard; Yoshikoshi, Akira. Efficient and convenient syntheses of (R)-(-)-cryptone and (S)-(-)-4-isopropenyl-2-cyclohexen-1-one. Synthesis (1992), (11), 1055-7.

Lingens, B.; Schild, T. A.; Vogler, B.; Renz, P.: Biosynthesis of vitamin B12. Transformation of riboflavin deuterium-labeled in the 1'R position or 1'S position into 5,6-dimethylbenzimidazole. Eur. J. Biochem. (1992), 207(3), 981-5.

Munder, M.; Vogt, J. R. A.; Vogler, B.; Renz, P.: Biosynthesis of Vitamin B12 in anaerobic bacteria. Eur. J. Biochem. (1992), 204(2), 679-83.

Kato, M.; Vogler, B.; Yoshikoshi, A.: Acid-catalyzed double-bond isomerization of 8a-substituted 5,5-dimethyl-3,5,6,7,8,8a-hexahydronaphthalen-2(1H)-ones. . J. Chem. Res., Synop. (1991), (5), 114-15.

Kato, M.; Watanabe, M.; Awen, B. Z.; Vogler, B.: Regio- and diastereoselective alkylation of (1R,5S)-4-ethyl-6,6-dimethyl-3-(phenylsulfonyl)bicyclo[3.1.1]hept-3-en-2-one. Tetrahedron Lett. (1991), 32(50), 7439-42.

Kato, M.; Watanabe, M.; Vogler, B.; Awen, B. Z.; Masuda, Y.; Tooyama, Y.; Yoshikoshi, A.: The use of 4,4-disubstituted nopinones for natural-product synthesis. Synthesis of elemanoid sesquiterpenes. J. Org. Chem. (1991), 56(25), 7071-6.

Kato, Michiharu; Watanabe, Masataka; Vogler, Berhard; Tooyama, Youichi; Yoshikoshi, Akira. Efficient preparation of (R)-(-)-cryptone from (+)-nopinone and its transformation into noroxopenlanfuran. J. Chem. Soc., Chem. Commun. (1990), (23), 1706-7

Kato, M.; Vogler, B.; Tooyama, Y.; Yoshikoshi, A.: A key intermediate for the chiral synthesis of elemanoids. Synthesis of (+)-.beta.-elemenone. Chem. Lett. (1990), (1), 151-4.

Kato, M.; Vogler, B.; Kamat, V. P.; Tooyama, Y.; Yoshikoshi, A.: Cyclobutane ring cleavage of nopinone derivatives and application to natural product synthesis. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (1989), 31st 88-95.

Vogler, B.; Bayer, R.; Meller, M.; Kraus, W.; Schell, F. M.: Photo-aza-Claisen rearrangements of cyclic enaminones. J. Org. Chem. (1989), 54(17), 4165-8.

Kraus, W.; Bokel, M.; Bruhn, A.; Cramer, R.; Klaiber, I.; Klenk, A.; Nagl, G.; Poehnl, H.; Sadlo, H.; Vogler, B.: Structure determination by NMR of azadirachtin and related compounds from Azadirachta indica A. Juss (Meliaceae). Tetrahedron (1987), 43(12), 2817-30.

Kraus, W.; Klenk, A.; Bokel, M.; Vogler, B.: Tetranortriterpenoid lactams with insect antifeeding activity from Azadirachta indica A. Juss (Meliaceae). Liebigs Ann. Chem. (1987), (4), 337-40.

Short Lectures and Posters at Meetings

2001: Vogler, Tania; Vogler, Bernhard; Kostova, Ivanka. . Acid methanolysis of macrocyclic secoiridoid glucosides. Abstracts of Papers, 222nd ACS National Meeting, Chicago, IL, United States, August 26-30, 2001 .

2001: Kostova, Ivanka; Vogler, Tania; Vogler, Bernhard. Phenolic compounds from Bulgarian Fraxinus species. Abstracts of Papers, 222nd ACS National Meeting, Chicago, IL, United States, August 26-30, 2001.

1999:Pérez-Bermúdez, P.; Vogler, B.; Seitz, H.U.; Gavidia, I.: Micropropagation of Isoplexis Spp and Terpenoid Analysis of Clonally Propagated Plants.

1999:Vasquez, E.A.; Vogler, B.; Reeb, S.; Zebitz, C.; Kraus, W.: Biological Activities of Sesquiterpene Lactones Dihydromikanolide and Dihydrocandenolide from Mikania cordata (BURM.) B.L. Robinson (Compositae).

1999:Vogler, B.; Roos, G.; Klaiber, I.; Waiblinger, J.; Guse, J.-H.; Walter, C.-U.; Kraus, W.: LC-Coupled NMR and MS - Investigations on Thamnosma africana ENGL. (Rutaceae).

1999:Vogler, B.; Stöhr, J.R.; Klaiber, I.; Bauer R.: Online Structure Elucidation of Amides and Polyoxigenated Cylcohexane Derivatives by LC-NMR and LC-MS form Crude Extracts of Piper Species.

1998:Bauer, R.; Klaiber, I.; Vogler, B.; Zschocke, S.: LC-Coupeled spectroscopic studies of Angelica dahurica and Ligusticum chianxiong with emphasis on LC-NMR.

1998:Conrad J.; Vogler, B.; Klaiber, I.; Roos, G.; Walter, C.U.; Kraus, W.: Bioassay Guided Isolation of Triterpene Glucopyranosyl Esters from Terminalia macroptera Bark.

1998:Hiller, W.; Vogler, B.: Tube-less NMR: From Research LC-NMR to Automated High-Throughput NMR.

1998:Iossifova, T.; Klaiber, I.; Vogler, B.; Evstatieva, L.; Kostova, I.; Kraus, W.: LC-Coupled spectroscopic investigation of Fraxinus pallisiae bark.

1998:Iossifova, T.; Vogler, B.; Klaiber, I.; Kostova, I.; Kraus, W.: Caffeic acid esters of phenylethanoid glycosides from Fraxinus ornus bark.

1998:Papajewski, S.; Vogler, B.; Klaiber, I.; Walter, C.U.; Roos, G.; Süßmuth, R.; Kraus, W.: Biosassay guided isolation of a novel type of quinic acis esters fro Cussonia bateri (Araliaceae).

1998:Roos, G.; Guse, J.-H.; Klaiber, I.; Vogler, B.; Walter C. U.; Kraus, W.: Phytochemical Analysis of Thamnosma africana Engl. (Rutaceae) roots.

1998:Roos, G.; Waiblinger, J.; Klaiber, I.; Vogler, B.; Kraus, W.: Phytochemical Analysis of Emilia marlothina (Asteraceae).

1998:Conrad, J.; Vogler, B.; Klaiber, I.; Reeb, S.; Roos, G.; Kraus, W.: Hydrolyzable Tannins and a New Phenolic Gycoside Gallate from Terminalia macroptera Bark.

1998:Rostan, J.; Vogler, B.; Klaiber, I.; Kostova, I.; Navas, H.; Nicholson, G.; Walk, T.; Kraus, W.: First report on cyclic peptides in Croton species.

1998:Thejavathi, Renukappa., Roos G.; Klaiber, I.; Vogler B.; Kraus, W.: Bioassay-guided Isolation of Active Principles from Bacopa monniera Wettst..

1998:Vasquez, E.A.; Gutke, H.-J.; Roos, G.; Vogler, B.; Rejesus, B.M.; Kraus, W.: Chemical and Biological Studies on the Essential Oil of Coleus amboinicus Lour..

1998:Moser, D.; Klaiber, I.; Vogler,B.; Kraus, W.: Molluscicidal Sucrose Esters form Petunia hybrida Vilm..

1997:Conrad, J.; Vogler, B.; Klaiber, I.; Walter, C. U.; Roos, G.; Guse, J.-H.; Kraus, W.: Bioassay guided isolation of triterpenes from Terminalia macroptera.

1998:Vogler, B.; Conrad, J.; Hiller, W.; Klaiber, I.; Roos, G.; Sandor, P.: Can HPLC-NMR serve as a Tool for Natural Products Isolation.

1997:Roos, G.; Klaiber, I.; Vogler, B.; Walter, C. U.; Kraus, W.: Bactericidal Sesquiterpene Lactones from Vernonia fastigiata (Asteraceae).

1997:Roos, G.; Klaiber, I.; Vogler, B.; Walter, C.U.; Kraus, W.: Bioassay directed determination of natural products with anthelmintic activity.

1997:Roos, G.; Klaiber, I;. Vogler, B.; Walter, C. U.; Kraus, W.: Phytochemical Analysis of Thamnosma africana roots.

1997:Rostan, J.; Iossifova, T.; Klaiber, I.; Kostova, I.; Kraus, W.; Navas, B.; Vogler, B.: Chemical and biological studies on Croton panamensis latex (Dragon's Blood).

1997:Keige, A.; Vogler, B.; Klaiber, I.; Kraus, W.: Novel Coumarins and Sesquiterpene Lactones from Vernonia brachycalyx.

1996:Bugge, J.; Keige, A.; Klaiber, I.; Vogler, B.; Kraus, W.: Pflanzeninhaltsstoffe mit antibakterieller und antimykotischer Wirkung.

1996:Jandl, A.; Roos, G.; Walter, C. U.; Guse, J.-H.; Klaiber, I.; Vogler, B.; Kraus, W.: Pflanzeninhaltsstoffe mit nematizider Wirkung.

1996:Klaiber, I.; Walter, C. U.; Prawat, H.; Guse, J.-H.; Vogler, B.; Kraus, W.: HPLC-MS as a tool for natural products isolation.

1996:Prawat, H.; Klaiber, I.; Roos, G.; Vogler, B.; Walter, C. U.; Kraus, W.: Biologically active constituents of Vernonia fastigiata.

1996:Roos, G.; Walter, C. U.; Prawat, H.; Guse, J.-H.; Klaiber, I.; Vogler, B.; Kraus, W.: Bioassay directed isolation of sesquiterpene lactones from african asteraceae.

1996:Spring, O.; Vogler, B.; Klaiber, I.: Neue Analysetechniken zur Nutzung phytochemischer Merkmale in der Taxonomie von Asteraceen .

1996:Walter, C. U. ; Roos, G.; Prawat, H.; Guse, J.-H.; Klaiber, I.; Vogler, B.; Kraus, W.: Screening of biologically active compounds from Vernonia fastigiata.