TY  - JOUR
A1  - Abdissa, Negera
A1  - Heydenreich, Matthias
A1  - Midiwo, Jacob O.
A1  - Ndakala, Albert
A1  - Majer, Zsuzsanna
A1  - Neumann, Beate
A1  - Stammler, Hans-Georg
A1  - Sewald, Norbert
A1  - Yenesew, Abiy
T1  - A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones
JF  - Phytochemistry letters
N2  - Phytochemical investigation of the dichloromethane/methanol (1:1) extract of the roots of Bulbine frutescens led to the isolation of a new xanthone, 8-hydroxy-6-methylxanthone-1-carboxylic acid (1) and a new phenylanthraquinone, 6',8-O-dimethylknipholone (2) along with six known compounds. The structures were elucidated on the basis of NMR and MS spectral data analyses. The structure of compound 1 was confirmed through X-ray crystallography which was then used as a reference to propose the revision of the structures of six seco-anthraquinones into xanthones. The isolated compounds were evaluated for cytotoxicity against human cervix carcinoma KB-3-1 cells with the phenylanthraquinone knipholone being the most active (IC50 = 0.43 mu M). Two semi-synthetic knipholone derivatives, knipholone Mannich base and knipholone-1,3-oxazine, were prepared and tested for cytotoxic activity; both showed moderate activities (IC50 value of 1.89 and 2.50 mu M, respectively). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
KW  - Bulbine frutescens
KW  - Xanthone
KW  - seco-Anthraquinone
KW  - Phenylanthraquinone
KW  - Cytotoxicity
KW  - Structure revision
Y1  - 2014
U6  - https://doi.org/10.1016/j.phytol.2014.04.004
SN  - 1874-3900
SN  - 1876-7486
VL  - 9
SP  - 67
EP  - 73
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Abdissa, Negera
A1  - Induli, Martha
A1  - Akala, Hoseah M.
A1  - Heydenreich, Matthias
A1  - Midiwo, Jacob O.
A1  - Ndakala, Albert
A1  - Yenesew, Abiy
T1  - Knipholone cyclooxanthrone and an anthraquinone dimer with antiplasmodial activities from the roots of Kniphofia foliosa
JF  - Phytochemistry letters
N2  - A new phenylanthrone, named knipholone cyclooxanthrone and a dimeric anthraquinone, 10-methoxy-10,7'-(chrysophanol anthrone)-chrysophanol were isolated from the roots of Kniphofia foliosa together with the rare naphthalene glycoside, dianellin. The structures were determined by NMR and mass spectroscopic techniques. The compounds showed antiplasmodial activities against the chloroquine-resistant (W2) and chloroquine-sensitive (D6) strains of Plasmodium falciparum with 10-methoxy-10,7'-(chrysophanol anthrone)-chrysophanol being the most active with IC50 values of 1.17 +/- 0.12 and 4.07 +/- 1.54 mu g/ml, respectively.
KW  - Kniphofia foliosa
KW  - Asphodelaceae
KW  - Roots
KW  - Anthraquinone
KW  - Knipholone cyclooxanthrone
KW  - 10-Methoxy-10,7 '-(chrysophanol anthrone)-chrysophanol
KW  - Dianellin
KW  - Malaria
Y1  - 2013
U6  - https://doi.org/10.1016/j.phytol.2013.02.005
SN  - 1874-3900
VL  - 6
IS  - 2
SP  - 241
EP  - 245
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Adem, Fozia A.
A1  - Mbaveng, Armelle T.
A1  - Kuete, Victor
A1  - Heydenreich, Matthias
A1  - Ndakala, Albert
A1  - Irungu, Beatrice
A1  - Yenesew, Abiy
A1  - Efferth, Thomas
T1  - Cytotoxicity of isoflavones and biflavonoids from Ormocarpum kirkii towards multi-factorial drug resistant cancer
JF  - Phytomedicine : international journal of phytotherapy and phytopharmacology
N2  - Background: While incidences of cancer are continuously increasing, drug resistance of malignant cells is observed towards almost all pharmaceuticals. Several isoflavonoids and flavonoids are known for their cytotoxicity towards various cancer cells. Methods: The cytotoxicity of compounds was determined based on the resazurin reduction assay. Caspases activation was evaluated using the caspase-Glo assay. Flow cytometry was used to analyze the cell cycle (propodium iodide (PI) staining), apoptosis (annexin V/PI staining), mitochondrial membrane potential (MMP) (JC-1) and reactive oxygen species (ROS) (H2DCFH-DA). CCRF-CEM leukemia cells were used as model cells for mechanistic studies. Results: Compounds 1, 2 and 4 displayed IC50 values below 20 mu M towards CCRF-CEM and CEM/ADR5000 leukemia cells, and were further tested towards a panel of 7 carcinoma cells. The IC50 values of the compounds against carcinoma cells varied from 16.90 mu M (in resistant U87MG.Delta EGFR glioblastoma cells) to 48.67 mu M (against HepG2 hepatocarcinoma cells) for 1, from 7.85 mu M (in U87MG.Delta EGFR cells) to 14.44 mu M (in resistant MDA-MB231/BCRP breast adenocarcinoma cells) for 2, from 4.96 mu M (towards U87MG.Delta EGFRcells) to 7.76 mu M (against MDA-MB231/BCRP cells) for 4, and from 0.07 mu M (against MDA-MB231 cells) to 2.15 mu M (against HepG2 cells) for doxorubicin. Compounds 2 and 4 induced apoptosis in CCRF-CEM cells mediated by MMP alteration and increased ROS production. Conclusion: The present report indicates that isoflavones and biflavonoids from Ormocarpum kirkii are cytotoxic compounds with the potential of being exploited in cancer chemotherapy. Compounds 2 and 4 deserve further studies to develop new anticancer drugs to fight sensitive and resistant cancer cell lines.
KW  - Apoptosis
KW  - Cancer
KW  - Ormocarpum kirkii
KW  - Isoflavone
KW  - Biflavonoid
KW  - Multi-drug resistance
Y1  - 2019
U6  - https://doi.org/10.1016/j.phymed.2019.152853
SN  - 0944-7113
SN  - 1618-095X
VL  - 58
PB  - Elsevier
CY  - München
ER  - 
TY  - JOUR
A1  - Akampurira, Denis
A1  - Akala, Hoseah M.
A1  - Derese, Solomon
A1  - Heydenreich, Matthias
A1  - Yenesew, Abiy
T1  - A new C-C linked benzophenathridine-2-quinoline dimer, and the antiplasmodial activity of alkaloids from Zanthoxylum holstzianum
JF  - Natural product research
N2  - The CH2Cl2/MeOH (1:1) extract of Zanthoxylum holstzianum stem bark showed good antiplasmodial activity (IC50 2.5 +/- 0.3 and 2.6 +/- 0.3 mu g/mL against the W2 and D6 strains of Plasmodium falciparum, respectively). From the extract five benzophenanthridine alkaloids [8-acetonyldihydrochelerythrine (1), nitidine (2), dihydrochelerythine (3), norchelerythrine (5), arnottianamide (8)]; a 2-quinolone alkaloid [N-methylflindersine (4)]; a lignan [4,4 '-dihydroxy-3,3 '-dimethoxylignan-9,9 '-diyl diacetate (7)] and a dimer of a benzophenanthridine and 2-quinoline [holstzianoquinoline (6)] were isolated. The CH2Cl2/MeOH (1:1) extract of the root bark afforded 1, 3-6, 8, chelerythridimerine (9) and 9-demethyloxychelerythrine (10). Holstzianoquinoline (6) is new, and is the second dimer linked by a C-C bond of a benzophenanthridine and a 2-quinoline reported thus far. The compounds were identified based on spectroscopic evidence. Amongst five compounds (1-5) tested against two strains of P. falciparum, nitidine (IC50 0.11 +/- 0.01 mu g/mL against W2 and D6 strains) and norchelerythrine (IC50 value of 0.15 +/- 0.01 mu g/mL against D6 strain) were the most active.
KW  - Antiplasmodial
KW  - benzophenanthridine alkaloid
KW  - holstzianoquinoline;
KW  - rutaceae
KW  - Zanthoxylum holstzianum
Y1  - 2022
U6  - https://doi.org/10.1080/14786419.2022.2034810
SN  - 1478-6419
SN  - 1478-6427
VL  - 37
IS  - 13
SP  - 2161
EP  - 2171
PB  - Taylor & Francis
CY  - London [u.a.]
ER  - 
TY  - JOUR
A1  - Andayi, Andrew W.
A1  - Yenesew, Abiy
A1  - Derese, Solomon
A1  - Midiwo, Jacob O.
A1  - Gitu, Peter M.
A1  - Jondiko, Ogoche J. I.
A1  - Akala, Hoseah M.
A1  - Liyala, Pamela
A1  - Wangui, Julia
A1  - Waters, Norman C.
A1  - Heydenreich, Matthias
A1  - Peter, Martin G.
T1  - Antiplasmodial flavonoids from Erythrina sacleuxii
N2  - The acetone extracts of the root bark and stem bark of Erythrina sacleuxii showed antiplasmodial activities against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Chromatographic separation of the acetone extract of the root bark afforded a new isoflavone, 7-hydroxy-4 -methoxy-3'- prenylisoflavone (trivial name 5-deoxy-3' - prenylbiochanin A) along with known isoflavonoids as the antiplasmodial principles. Flavonoids and isoflavonoids isolated from the stem bark of E. sucleuxii were also tested and showed antiplasmodial activities. The structures were determined on the basis of spectroscopic evidence
Y1  - 2006
UR  - http://www.thieme-connect.com/ejournals/toc/plantamedica
U6  - https://doi.org/10.1055/s-2005-873200
SN  - 0032-0943
ER  - 
TY  - JOUR
A1  - Arias, Hugo R.
A1  - Feuerbach, Dominik
A1  - Schmidt, Bernd
A1  - Heydenreich, Matthias
A1  - Paz, Cristian
A1  - Ortells, Marcelo O.
T1  - Drimane Sesquiterpenoids Noncompetitively Inhibit Human alpha 4 beta 2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human alpha 3 beta 4 and alpha 7 Subtypes
JF  - Journal of natural products
N2  - The drimane sesquiterpenoids drimenin, cinnamolide, dendocarbin A, and polygodial were purified from the Canelo tree (Drimys winteri) and chemically characterized by spectroscopic methods. The pharmacological activity of these natural compounds were determined on hα4β2, hα3β4, and hα7 nicotinic acetylcholine receptors (AChRs) by Ca2+ influx measurements. The results established that drimane sesquiterpenoids inhibit AChRs with the following selectivity: hα4β2 > hα3β4 > hα7. In the case of hα4β2 AChRs, the following potency rank order was determined (IC50’s in μM): drimenin (0.97 ± 0.35) > cinnamolide (1.57 ± 0.36) > polygodial (62.5 ± 19.9) ≫ dendocarbin A (no activity). To determine putative structural features underlying the differences in inhibitory potency at hα4β2 AChRs, additional structure–activity relationship and molecular docking experiments were performed. The Ca2+ influx and structural results supported a noncompetitive mechanism of inhibition, where drimenin interacted with luminal and nonluminal (TMD-β2 intrasubunit) sites. The structure–activity relationship results, i.e., the lower the ligand polarity, the higher the inhibitory potency, supported the nonluminal interaction. Ligand binding to both sites might inhibit the hα4β2 AChR by a cooperative mechanism, as shown experimentally (nH > 1). Drimenin could be used as a molecular scaffold for the development of more potent inhibitors with higher selectivity for the hα4β2 AChR.
Y1  - 2018
U6  - https://doi.org/10.1021/acs.jnatprod.7b00893
SN  - 0163-3864
SN  - 1520-6025
VL  - 81
IS  - 4
SP  - 811
EP  - 817
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Atilaw, Yoseph
A1  - Duffy, Sandra
A1  - Heydenreich, Matthias
A1  - Muiva-Mutisya, Lois
A1  - Avery, Vicky M.
A1  - Erdelyi, Mate
A1  - Yenesew, Abiy
T1  - Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata
JF  - Molecules
N2  - In our search for new antiplasmodial agents, the CH2Cl2/CH3OH (1:1) extract of the roots of Tephrosia aequilata was investigated, and observed to cause 100% mortality of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at a 10 mg/mL concentration. From this extract three new chalconoids, E-2,6-dimethoxy-3,4-(2,2-dimethyl)pyranoretrochalcone (1, aequichalcone A), Z-2,6-dimethoxy-3,4-(2,2-dimethyl)pyranoretrochalcone (2, aequichalcone B), 4-ethoxy-3-hydroxypraecansone B (3, aequichalcone C) and a new pterocarpene, 3,4:8,9-dimethylenedioxy-6a,11a-pterocarpene (4), along with seven known compounds were isolated. The purified compounds were characterized by NMR spectroscopic and mass spectrometric analyses. Compound 1 slowly converts into 2 in solution, and thus the latter may have been enriched, or formed, during the extraction and separation process. The isomeric compounds 1 and 2 were both observed in the crude extract. Some of the isolated constituents showed good to moderate antiplasmodial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum.
KW  - Tephrosia aequilata
KW  - chalcone
KW  - retrochalcone
KW  - aequichalcone A
KW  - aequichalcone B
KW  - aequichalcone C
KW  - pterocarpene
KW  - antiplasmodial
Y1  - 2017
U6  - https://doi.org/10.3390/molecules22020318
SN  - 1420-3049
VL  - 22
IS  - 2
PB  - MDPI
CY  - Basel
ER  - 
TY  - JOUR
A1  - Atilaw, Yoseph
A1  - Heydenreich, Matthias
A1  - Ndakala, Albert
A1  - Akala, Hoseah M.
A1  - Kamau, Edwin
A1  - Yenesew, Abiy
T1  - 3-Oxo-14 alpha, 15 alpha-epoxyschizozygine: A new schizozygane indoline alkaloid from Schizozygia coffaeoides
JF  - Phytochemistry letters
N2  - The stem bark extract of Schizozygia coffaeoides (Apocynaceae) showed moderate antiplasmodial activity (IC50 = 8-12 mu g/mL) against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Chromatographic separation of the extract led to the isolation of a new schizozygane indoline alkaloid, named 3-oxo-14 alpha, 15 alpha-epoxyschizozygine. In addition, two dimeric anthraquinones, cassiamin A and cassiamin B, were identified for the first time in the family Apocynaceae. The structures of the isolated compounds were deduced on the basis of spectroscopic evidence. The schizozygane indole alkaloids showed good to moderate antiplasmodial activities (IC50 = 13-52 mu m). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
KW  - Schizozygia coffaeoides
KW  - Schizozygane indoline alkaloid
KW  - 3-Oxo-14 alpha, 15 alpha-epoxyschizozygine
KW  - Dimeric anthraquinone
KW  - Cassiamin A
KW  - Cassiamin B
Y1  - 2014
U6  - https://doi.org/10.1016/j.phytol.2014.07.003
SN  - 1874-3900
SN  - 1876-7486
VL  - 10
SP  - 28
EP  - 31
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Baraza, Lilechi D.
A1  - Neser, Wekesa
A1  - Jackson, Korir Cheruiyot
A1  - Fredrick, Juma B.
A1  - Dennis, Ochieno
A1  - Wairimu, Kamau R.
A1  - Keya, Aggrey Osogo
A1  - Heydenreich, Matthias
T1  - Antimicrobial Coumarins from the Oyster Culinary-Medicinal Mushroom, Pleurotus ostreatus (Agaricomycetes), from Kenya
JF  - International journal of medicinal mushrooms
N2  - Pleurotus ostreatus has been widely used as food because of its nutritional and medicinal properties. These have been attributed to the presence of macronutrients, minerals, vitamins, and amino acids, among other secondary metabolites. There are, however, few reports on the antimicrobial activities of different classes of purified compounds from P. ostreatus. This led to the current study, the objective of which was to chemically characterize the antibiotic activities of P. ()streams against selected human pathogenic bacteria and endophytic fungi. Chemical structures were determined using spectroscopic methods and by comparison with values of related structures reported in the literature. Pure compounds from P. ostreatus were tested in vitro against pathogenic bacteria (Staphylococcus aureus and Escherichia coli) and endophytic fungi (Pencillium digitatum and Fusarium prolferatum). A new compound, (E)-5,7-dimethoxy-6-(3-methylbuta-1,3-dienyl)-2H-chromen-2-one (5-methoxy-(E)-suberodiene) (compound 2), along with ergosterol (compound I.) and 5,7-dimethoxy-6-(3-methylbut-2-enyl)-2H-chromen-2-one (toddaculin; compound 3), were isolated from the fruiting bodies of P. ostreatus. The growth of S. aureus,E proliferatum, and P. digitatum colonies was inhibited in media containing compound 2, with minimum inhibitory concentrations closely comparable to those of conventional antibiotics.
KW  - Escherichia coli
KW  - Fusarium proliferatum
KW  - medicinal mushrooms
KW  - Penicillium digitatum
KW  - Pleurotus ostreatus
KW  - Staphylococcus aureus
Y1  - 2016
U6  - https://doi.org/10.1615/IntJMedMushrooms.v18.i10.60
SN  - 1521-9437
SN  - 1940-4344
VL  - 18
SP  - 905
EP  - 913
PB  - Begell House
CY  - Danbury
ER  - 
TY  - JOUR
A1  - Barta, Petra
A1  - Szatmari, Istvan
A1  - Fueloep, Ferenc
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kleinpeter, Erich
T1  - Synthesis and stereochemistry of new naphth[1,3]oxazino[3,2-a] benzazepine and naphth[1,3]oxazino[3,2-e]thienopyridine derivatives
JF  - Tetrahedron
N2  - Through the reactions of 1- or 2-naphthol and 4,5-dihydro-3H-benz[c]azepine or 6,7-dihydrothieno[3,2-c]pyridine, new aminonaphthol derivatives were prepared. The syntheses were extended by using N-containing naphthol analogues such as 5-hydroxyisoquinoline and 6-hydroxyquinoline. The ring closures of the novel bifunctional compounds were also achieved, resulting in new naphth[2,1-e][1,3]oxazines, naphth[1,2-e][1,3]oxazines, isoquinolino[5,6-e][1,3]oxazines and quinolino[5,6-e][1,3]oxazines. H-1 NMR spectra of the target heterocycles 16, 20 and 21 were sufficiently resolved to indentify the present stereochemistry; therefore, beside computed structures, spatial experimental (dipolar coupling-NOE) and computed (ring current effect of the naphthyl moiety-TSNMRS) NMR studies were employed. The studied heterocycles exist exclusively as S(14b),R(N), R(14b),S(N), and S(16b)S(N) isomers, respectively. The flexible moieties of the studied compounds prefer. (C) 2016 Elsevier Ltd. All rights reserved.
KW  - Modified Mannich reaction
KW  - Thienopyridine
KW  - Benzazepine
KW  - NMR spectroscopy
KW  - Stereochemistry
KW  - Theoretical calculations
Y1  - 2016
U6  - https://doi.org/10.1016/j.tet.2016.03.058
SN  - 0040-4020
VL  - 72
SP  - 2402
EP  - 2410
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Belasri, Khadija
A1  - Topal, Leila
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kleinpeter, Erich
A1  - Fulop, Ferenc
A1  - Szatmari, Istvan
T1  - Synthesis and conformational analysis of naphthoxazine-fused phenanthrene derivatives
JF  - Molecules
N2  - The synthesis of new phenanthr[9,10-e][1,3]oxazines was achieved by the direct coupling of 9-phenanthrol with cyclic imines in the modified aza-Friedel-Crafts reaction followed by the ring closure of the resulting bifunctional aminophenanthrols with formaldehyde. Aminophenanthrol-type Mannich bases were synthesised and transformed to phenanthr[9,10-e][1,3]oxazines via [4 + 2] cycloaddition. Detailed NMR structural analyses of the new polyheterocycles as well as conformational studies including Density Functional Theory (DFT) modelling were performed. The relative stability of ortho-quinone methides (o-QMs) was calculated, the geometries obtained were compared with the experimentally determined NMR structures, and thereby, the regioselectivity of the reactions has been assigned.
KW  - modified Mannich reaction
KW  - cyclic imines
KW  - [4+2] cycloaddition
KW  - NMR
KW  - spectroscopy
KW  - conformational analysis
KW  - DFT calculations
Y1  - 2020
U6  - https://doi.org/10.3390/molecules25112524
SN  - 1420-3049
VL  - 25
IS  - 11
PB  - MDPI
CY  - Basel
ER  - 
TY  - JOUR
A1  - Benassi, Rois
A1  - Bregulla, Antje
A1  - Friedrich, Alwin
A1  - Henning, Dietrich
A1  - Heydenreich, Matthias
A1  - Mickler, Wulfhard
A1  - Kleinpeter, Erich
A1  - Kempter, Gerhard
A1  - Schilde, Uwe
A1  - Taddei, F.
T1  - NMR spectroscopic and theoretical structural study of 5-exo-methylene-substituted hydantoins
Y1  - 1998
ER  - 
TY  - JOUR
A1  - Benassi, Rois
A1  - Bregulla, Antje
A1  - Henning, Dietrich
A1  - Heydenreich, Matthias
A1  - Kempter, Gerhard
A1  - Kleinpeter, Erich
A1  - Taddei, F.
T1  - NMR-spectroscopic and theoretical structural analysis of 5-benzyl subtituted hydantoins in solutions
Y1  - 1999
ER  - 
TY  - JOUR
A1  - Bringmann, Gerhard
A1  - Mutanyatta-Comar, Joan
A1  - Maksimenka, Katja
A1  - Wanjohi, John M.
A1  - Heydenreich, Matthias
A1  - Brun, Reto
A1  - Müller, Werner E. G.
A1  - Peter, Martin G.
A1  - Midiwo, Jacob O.
A1  - Yenesew, Abiy
T1  - Joziknipholones A and B : the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens
N2  - From the roots of the African plant Bulbine frutescens (Asphodelaceae), two unprecedented novel dimeric phenylanthraquinones, named joziknipholones A and B, possessing axial and centrochirality, were isolated, together with six known compounds. Structural elucidation of the new metabolites was achieved by spectroscopic and chiroptical methods, by reductive cleavage of the central bond between the monomeric phenylanthraquinone and -anthrone portions with sodium dithionite, and by quantum chemical CD calculations. Based on the recently revised absolute axial configuration of the parent phenylanthraquinones, knipholone and knipholone anthrone, the new dimers were attributed to possess the P- configuration (i.e., with the acetyl portions below the anthraquinone plane) at both axes in the case of joziknipholone A, whereas in joziknipholone B, the knipholone part was found to be M-configured. Joziknipholones A and B are active against the chloroquine resistant strain K1 of the malaria pathogen, Plasmodium falciparum, and show moderate activity against murine leukemic lymphoma L5178y cells.
Y1  - 2008
UR  - http://www3.interscience.wiley.com/journal/26293/home?CRETRY=1&SRETRY=0
SN  - 0947-6539
ER  - 
TY  - JOUR
A1  - Buyinza, Daniel
A1  - Derese, Solomon
A1  - Ndakala, Albert
A1  - Heydenreich, Matthias
A1  - Yenesew, Abiy
A1  - Koch, Andreas
A1  - Oriko, Richard
T1  - A coumestan and a coumaronochromone from Millettia lasiantha
JF  - Biochemical systematics and ecology
N2  - The manuscript describes the phytochemical investigation of the roots, leaves and stem bark of Millettia lasiantha resulting in the isolation of twelve compounds including two new isomeric isoflavones lascoumestan and las-coumaronochromone. The structures of the new compounds were determined using different spectroscopic techniques.
KW  - Millettia lasiantha
KW  - Leguminosae
KW  - Coumestan
KW  - Coumaronochromone
Y1  - 2021
U6  - https://doi.org/10.1016/j.bse.2021.104277
SN  - 0305-1978
SN  - 1873-2925
VL  - 97
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Böhmer, Volker
A1  - Dörrenbächer, Ralph
A1  - Frings, Michael
A1  - Heydenreich, Matthias
A1  - DePaoli, Diana
A1  - Vogt, Walter
A1  - Ferguson, George
A1  - Thondorf, Iris
T1  - Annelated calixarenes composed of Calix[4]arenes with hydroxy groups in the endo and exo position
Y1  - 1996
ER  - 
TY  - JOUR
A1  - Chepkirui, Carolyne
A1  - Ochieng, Purity J.
A1  - Sarkar, Biswajyoti
A1  - Hussain, Aabid
A1  - Pal, Chiranjib
A1  - Yang, Li Jun
A1  - Coghi, Paolo
A1  - Akala, Hoseah M.
A1  - Derese, Solomon
A1  - Ndakala, Albert
A1  - Heydenreich, Matthias
A1  - Wong, Vincent K. W.
A1  - Erdelyi, Mate
A1  - Yenesew, Abiy
T1  - Antiplasmodial and antileishmanial flavonoids from Mundulea sericea
JF  - Fitoterapia
N2  - Five known compounds (1-5) were isolated from the extract of Mundulea sericea leaves. Similar investigation of the roots of this plant afforded an additional three known compounds (6-8). The structures were elucidated using NMR spectroscopic and mass spectrometric analyses. The absolute configuration of 1 was established using ECD spectroscopy. In an antiplasmodial activity assay, compound 1 showed good activity with an IC50 of 2.0 mu M against chloroquine-resistant W2, and 6.6 mu M against the chloroquine-sensitive 3D7 strains of Plasmodium falciparum. Some of the compounds were also tested for antileishmanial activity. Dehydrolupinifolinol (2) and sericetin (5) were active against drug-sensitive Leishmania donovani (MHOM/IN/83/AG83) with IC50 values of 9.0 and 5.0 mu M, respectively. In a cytotoxicity assay, lupinifolin (3) showed significant activity on BEAS-2B (IC50 4.9 mu M) and HePG2 (IC50 10.8 mu M) human cell lines. All the other compounds showed low cytotoxicity (IC50 > 30 mu M) against human lung adenocarcinoma cells (A549), human liver cancer cells (HepG2), lung/bronchus cells (epithelial virus transformed) (BEAS-2B) and immortal human hepatocytes (LO2)
KW  - Mundulea sericea
KW  - leguminosae
KW  - flavanonol
KW  - flavonol
KW  - antiplasmodial
KW  - antileishmanial
KW  - cytotoxicity
Y1  - 2020
U6  - https://doi.org/10.1016/j.fitote.2020.104796
SN  - 0367-326X
SN  - 1873-6971
VL  - 149
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Csuetoertoeki, Renata
A1  - Szatmari, Istvan
A1  - Koch, Andreas
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
A1  - Fueloep, Ferenc
T1  - Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives
JF  - Tetrahedron
N2  - A new highly functionalized aminonaphthol derivative, 1-(amino(2-aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde. benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.
KW  - Naphthoxazinoquinazolines
KW  - NMR
KW  - Conformational analysis
KW  - DFT calculations
KW  - Hammett-Brown plots
Y1  - 2011
U6  - https://doi.org/10.1016/j.tet.2011.08.074
SN  - 0040-4020
VL  - 67
IS  - 44
SP  - 8564
EP  - 8571
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Csütörtöki, Renata
A1  - Szatmari, Istvan
A1  - Koch, Andreas
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
A1  - Fulop, Ferenc
T1  - Syntheses and conformational analyses of new naphth[1,2-e][1,3]oxazino[3,2-c] quinazolin-13-ones
JF  - Tetrahedron
N2  - The syntheses of naphth[1,2-e][1,3]oxazino[3,2-c]quinazolin-13-one derivatives (3a-f) were achieved by the solvent-free heating of benzyloxycarbonyl-protected intermediates (2a-f) with MeONa. For intermediates 2a-f, prepared by the reactions of substituted aminonaphthols with benzyl N-(2-formylphenyl)carbamate, not only the expected trans ring form B and chain form A(1), but also the rearranged chain form A(2) as a new tautomer were detected in DMSO at room temperature. The quantity of A(2) in the tautomeric mixture was changed with time.
 Conformational analyses of the target heterocycles 3a-f by NMR spectroscopy and accompanying theoretical calculations at the DFT level of theory revealed that the oxazine ring preferred a twisted chair conformation and the quinazolone ring was planar. Besides the conformations, both the configurations at C-7a and C-15 and the preferred rotamers of the 1-naphthyl substituent at C-15 were assigned, which allowed evaluation of the aryl substituent-dependent steric hindrance in this part of the molecules. Configurational assignments were corroborated by quantifying the ring current effect of 15-aryl in terms of spatial NICS.
KW  - Naphthoxazinoquinazolinones
KW  - Aminonaphthols
KW  - NMR spectroscopy
KW  - Conformational analysis
KW  - Theoretical calculations
KW  - Ring current effect
Y1  - 2012
U6  - https://doi.org/10.1016/j.tet.2012.04.026
SN  - 0040-4020
VL  - 68
IS  - 24
SP  - 4600
EP  - 4608
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Csütörtöki, Renáta
A1  - Szatmári, István
A1  - Koch, Andreas
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
A1  - Fulop, Ferenc
T1  - Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives
Y1  - 2011
SN  - 0040-4020
ER  - 
TY  - JOUR
A1  - Derese, Solomon
A1  - Barasa, Leonard
A1  - Akala, Hoseah M.
A1  - Yusuf, Amir O.
A1  - Kamau, Edwin
A1  - Heydenreich, Matthias
A1  - Yenesew, Abiy
T1  - 4 '-Prenyloxyderrone from the stem bark of Millettia oblata ssp  teitensis and the antiplasmodial activities of isoflavones from some Millettia species
JF  - Phytochemistry letters
N2  - The CH2Cl2/MeOH (1: 1) extract of the stem bark of Millettia oblata ssp. teitensis showed antiplasmodial activity (IC50 = 10-12 mu g/mL) against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Chromatographic separation of the extract led to the isolation of a new isoflavone, 4'-prenyloxyderrone (1), together with known isoflavones (8-O-methylretusin, durmillone, maximaisoflavone B, maximaisoflavone H and maximaisoflavone J), a rotenoid (tephrosin) and a triterpene (lupeol). Similar investigation of Millettia leucantha resulted in the identification of the isoflavones afrormosin and wistin, and the flavone chrysin. The identification of these compounds was based on their spectroscopic data. Five of the isoflavones isolated from these plants as well as 11 previously reported compounds from Millettia dura were tested and showed good to moderate antiplasmodial activities (IC50 = 13-53 mu M), with the new compound, 4'-prenyloxyderrone, being the most active (IC50 = 13-15 mu M).
KW  - Millettia oblata ssp teitensis
KW  - Millettia leucantha
KW  - Millettia dura;
Y1  - 2014
U6  - https://doi.org/10.1016/j.phytol.2014.02.001
SN  - 1874-3900
SN  - 1876-7486
VL  - 8
SP  - 69
EP  - 72
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Deyou, Tsegaye
A1  - Marco, Makungu
A1  - Heydenreich, Matthias
A1  - Pan, Fangfang
A1  - Gruhonjic, Amra
A1  - Fitzpatrick, Paul A.
A1  - Koch, Andreas
A1  - Derese, Solomon
A1  - Pelletier, Jerry
A1  - Rissanen, Kari
A1  - Yenesew, Abiy
A1  - Erdelyi, Mate
T1  - Isoflavones and Rotenoids from the Leaves of Millettia oblata ssp teitensis
JF  - Journal of natural products
N2  - A new isoflavone, 8-prenylmilldrone (1), and four new rotenoids, oblarotenoids A-D (2-5), along with nine known compounds (6-14), were isolated from the CH2Cl2/CH3OH (1:1) extract of the leaves of Millettia oblata ssp. teitensis by chromatographic separation. The purified compounds were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of the rotenoids were established on the basis of chiroptical data and in some cases by single-crystal X-ray crystallography. Maximaisoflavone J (11) and oblarotenoid C (4) showed weak activity against the human breast cancer cell line MDA-MB-231 with IC50 values of 33.3 and 93.8 mu M, respectively.
Y1  - 2017
U6  - https://doi.org/10.1021/acs.jnatprod.7b00255
SN  - 0163-3864
SN  - 1520-6025
VL  - 80
SP  - 2060
EP  - 2066
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Fotie, J.
A1  - Nkengfack, A. E.
A1  - Peter, Martin G.
A1  - Heydenreich, Matthias
A1  - Fomum, Z. T.
T1  - Chemical constituents of the ethyl acetate extracts of the stem bark and fruits of Dichrostachys cinerea and the roots of Parkia bicolor
N2  - The antibacterial activities of ethyl acetate, methanol and aqueous extracts of the stem bark of Dichrostachys cinerea and the roots of Parkia bicolor have been evaluated. Ethyl acetate extracts have been investigated, studies that led to a series of known compounds, amongst which many are reported here for the very first time from both the species
Y1  - 2004
SN  - 1011-3924
ER  - 
TY  - JOUR
A1  - Gonzalez-Chavarria, Ivan
A1  - Duprat, Felix
A1  - Roa, Francisco J.
A1  - Jara, Nery
A1  - Toledo, Jorge R.
A1  - Miranda, Felipe
A1  - Becerra, Jose
A1  - Inostroza, Alejandro
A1  - Kelling, Alexandra
A1  - Schilde, Uwe
A1  - Heydenreich, Matthias
A1  - Paz, Cristian
T1  - Maytenus disticha extract and an isolated β-Dihydroagarofuran induce mitochondrial depolarization and apoptosis in human cancer cells by increasing mitochondrial reactive oxygen species
JF  - Biomolecules
N2  - Maytenus disticha (Hook F.), belonging to the Celastraceae family, is an evergreen shrub, native of the central southern mountains of Chile. Previous studies demonstrated that the total extract of M. disticha (MD) has an acetylcholinesterase inhibitory activity along with growth regulatory and insecticidal activities. beta-Dihydroagarofurans sesquiterpenes are the most active components in the plant. However, its activity in cancer has not been analyzed yet. Here, we demonstrate that MD has a cytotoxic activity on breast (MCF-7), lung (PC9), and prostate (C4-2B) human cancer cells with an IC50 (mu g/mL) of 40, 4.7, and 5 mu g/mL, respectively, an increasing Bax/Bcl2 ratio, and inducing a mitochondrial membrane depolarization. The beta-dihydroagarofuran-type sesquiterpene (MD-6), dihydromyricetin (MD-9), and dihydromyricetin-3-O-beta-glucoside (MD-10) were isolated as the major compounds from MD extracts. From these compounds, only MD-6 showed cytotoxic activity on MCF-7, PC9, and C4-2B with an IC50 of 31.02, 17.58, and 42.19 mu M, respectively. Furthermore, the MD-6 increases cell ROS generation, and MD and MD-6 induce a mitochondrial superoxide generation and apoptosis on MCF-7, PC9, and C4-2B, which suggests that the cytotoxic effect of MD is mediated in part by the beta-dihydroagarofuran-type that induces apoptosis by a mitochondrial dysfunction.
KW  - Maytenus disticha
KW  - beta-dihydroagarofuran-type sesquiterpene
KW  - dihydromyricetin
KW  - dihydromyricetin-3-O-beta-glucoside
KW  - cytotoxic
KW  - activity
KW  - Mitochondrial ROS
Y1  - 2020
U6  - https://doi.org/10.3390/biom10030377
SN  - 2218-273X
VL  - 10
IS  - 3
PB  - MDPI
CY  - Basel
ER  - 
TY  - JOUR
A1  - Gress, Anja
A1  - Heilig, Anne
A1  - Smarsly, Bernd M.
A1  - Heydenreich, Matthias
A1  - Schlaad, Helmut
T1  - Hydrogen-bonded polymer nanotubes in water
N2  - Intermolecular hydrogen bonding, not hydrophobic interaction, is the driving force for the spontaneous self- assembly of glycosylated polyoxazoline chains into nanotubes in dilute aqueous solution. The structural information is encoded in the relatively simple molecular structure of chains consisting of a tertiary polyamide backbone (hydrogen- accepting) and glucose side chains (hydrogen-donating). The formation of the nanotubes should occur through bending and closing of a 2D hydrogen-bonded layer of interdigitated polymer chains.
Y1  - 2009
UR  - http://pubs.acs.org/loi/mamobx
U6  - https://doi.org/10.1021/Ma900227t
SN  - 0024-9297
ER  - 
TY  - JOUR
A1  - Gumula, Ivan
A1  - Heydenreich, Matthias
A1  - Derese, Solomon
A1  - Ndiege, Isaiah O.
A1  - Yenesew, Abiy
T1  - Four isoflavanones from the stem bark of Platycelphium voense
JF  - Phytochemistry letters
N2  - From the stem bark of Platycelphium voense (Leguminosae) four new isoflavanones were isolated and characterized as (S)-5,7-dihydroxy-2 ',4 '-dimethoxy-3 '-(3 ''-methylbut-2 ''-enyl)-isoflavanone (trivial name platyisoflavanone A), (+)-5,7,2 '-trihydroxy-4 '-methoxy-3 '-(3 ''-methylbut-2 ''-enyl)-isoflavanone (platyisoflavanone B), 5,7-dihydroxy-4 '-methoxy-2 ''-(2 '''-hydroxyisopropyl)-dihydrofurano-[4 '',5 '':3 ',2 ']-isoflavanone (platyisoflavanone C) and 5,7,2 ',3 ''-tetrahydroxy-2 '',2 ''-dimethyldihydropyrano-[5 '',6 '':3 ',4 ']-isoflavanone (platyisoflavanone D). In addition, the known isoflavanones, sophoraisoflavanone A and glyasperin F; the isoflavone, formononetin; two flavones, kumatakenin and isokaempferide; as well as two triterpenes, betulin and beta-amyrin were identified. The structures were elucidated on the basis of spectroscopic evidence. Platyisoflavanone A showed antibacterial activity against Mycobacterium tuberculosis in the microplate alamar blue assay (MABA) with MIC = 23.7 mu M, but also showed cytotoxicity (IC50 = 21.1 mu M) in the vero cell test.
KW  - Platycelphium voense
KW  - Stem bark
KW  - Leguminosae
KW  - Isoflavanones
KW  - Platyisoflavanone
KW  - Mycobacterium tuberculosis
Y1  - 2012
U6  - https://doi.org/10.1016/j.phytol.2011.11.012
SN  - 1874-3900
VL  - 5
IS  - 1
SP  - 150
EP  - 154
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Haebel, Sophie
A1  - Hejazi, Mahdi
A1  - Frohberg, Claus
A1  - Heydenreich, Matthias
A1  - Ritte, Gerhard
T1  - Mass spectrometric quantification of the relative amounts of C6 and C3 position phosphorylated glucosyl residues in starch
N2  - The quantification of phosphate bound to the C6 and C3 positions of glucose residues in starch has received increasing interest since the importance of starch phosphorylation for plant metabolism was discovered. The method described here is based on the observation that the isobaric compounds glucose-6-phosphate (Glc6P) and glucose-3- phosphate (Glc3P) exhibit significantly different fragmentation patterns in negative ion electrospray tandem mass spectrometry (MS/MS). A simple experiment involving collision-induced dissociation (CID) MS2 spectra of the sample and the two reference substances Glc3P and Glc6P permitted the quantification of the relative amounts of the two compounds in monosaccharide mixtures generated by acid hydrolysis of starch. The method was tested on well-characterized potato tuber starch. The results are consistent with those obtained by NMR analysis. In contrast to NMR, however, the presented method is fast and can be performed on less than 1 mg of starch. Starch samples of other origins exhibiting a variety of phosphorylation degrees were analyzed to assess the sensitivity and robustness of the method.
Y1  - 2008
UR  - http://www.sciencedirect.com/science/journal/00032697
SN  - 0003-2697
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kleinpeter, Erich
A1  - Zimmermann, Thomas
T1  - Dynamic NMR study of the flexibility of 2-amino-3-aroyl-4,6-diaryl-pyrylium salts
Y1  - 1997
UR  - http://www.springerlink.com/content/110258
U6  - https://doi.org/10.1007/s002160050205
SN  - 0937-0633
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Klod, Sabrina
A1  - Szatmari, Istvan
A1  - Fulop, Ferenc
A1  - Kleinpeter, Erich
T1  - Synthesis and conformational analysis of naphth[1', 2':5,6][1,3]oxazino[3,2-c][1,3]benzoxazine and naphth[1', 2':5,6][1,3]oxazino[3,4-c][1,3]benzoxazine derivatives
JF  - Tetrahedron
N2  - A new functional group, the hydroxy group, was inserted into a Betti base by reaction with salicylaldehyde, and the naphthoxazine derivatives thus obtained were converted by ring-closure reactions with formaldehyde, acetaldehyde, propionaldehyde or phosgene to the corresponding naphth[1',2':5,6][1,3]oxazino[3,2-c][1,3]benzoxazine derivatives. Further, the conformational analysis of these polycyclic compounds by NMR spectroscopy and an accompanying molecular modelling are reported; especially, both quantitative anisotropic ring current effects of the aromatic moieties in these compounds and steric substituent effects were employed to determine the stereochemistry of the naphthoxazinobenzoxazine derivatives.
Y1  - 2006
UR  - http://www.sciencedirect.com/science/journal/00404020
U6  - https://doi.org/10.1016/j.tet.2006.09.037
SN  - 0040-4020
VL  - 62
IS  - 48
SP  - 11081
EP  - 11089
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kovacs, J.
A1  - Toth, G.
A1  - Kleinpeter, Erich
T1  - Electronic influences on (3)J(C,H) coupling constants via -S-, -S(O)- and -SO2--: their determination, calculation and comparison of detection methods
N2  - (3)J(C,H) coupling constants via a sulfur atom in two series of compounds, both including a sulfide, a sulfoxide and a sulfone, were detected experimentally and calculated by quantum mechanical methods. In the first series (1-3) the coupling between a hydrogen, bonded to an Sp(3) carbon, and an Sp(2) carbon is treated; the second series (4- 6) deals with the coupling between a hydrogen, bonded to an Sp3 carbon, and an Sp3 carbon. Different pulse sequences (broadband HMBC, SelJres, 1D HSQMBC, J-HMBC-2, selective J-resolved long-range experiment and IMPEACH-MBC) proved to be useful in determining the long-range (3)J(C,H) coupling constants. However, the dynamic behaviour of two of the compounds (4 and 6) led to weighted averages of the two coupling constants expected (concerning equatorial and axial positions of the corresponding hydrogens). DFT calculations proved to be useful to calculate not only the (3)J(C,H) coupling constants but also the different contributions of FC, PSO, DSO and SD terms; the calculation of the Fermi contact term (FC) was found to be sufficient for the correct estimation of (3)J(C,H) coupling constants. Copyright (C) 2004 John Wiley Sons, Ltd
Y1  - 2004
SN  - 0749-1581
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Ristau, Thomas
A1  - Knoll, Susanne
A1  - Heinicke, Jochen
A1  - Sieler, Joachim
A1  - Niemitz, Matthias
A1  - Mühlstädt, Manfred
A1  - Kleinpeter, Erich
T1  - Conformational analysis of sulfur-containing heterocycles ; part I: synthesis and structural determination of diastereomerically pure 4,6-bis(phenoxymethyl)-1,2,5-trithiepanes
Y1  - 1998
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Sarodnick, Gerhard
A1  - Kleinpeter, Erich
T1  - Quinoxalines XIV : Synthesis, H-1, C-13, N-15 NMR spectroscopic, and quantum chemical study of 1H-pyrazolo[3,4- b]quinoxalines (flavazoles)
N2  - The synthesis of a series of 1H-pyrazolo[3,4-b]quinoxalines (flavazoles) by acylation, alkylation, halogenation, and aminomethylation of the parent compound is reported and their structure is investigated by H-1, C-13 and N-15 NMR spectroscopy. The restricted rotation about the partial C, N double bond of the N-acyl derivatives 7-10 is studied by dynamic NMR spectroscopy and the barriers to rotation are determined. In order to assign unequivocally the 15 N chemical shifts of N-4 and N-9, in case of 3-substituted flavazoles, exemplary the H-1, C-13, and N-15 NMR chemical shifts of 34, 35, and 39 are also theoretically calculated by quantum chemical methods [ab initio at different levels of theory (HF/6-3G* and B3LYP/6-31G*)]. (C) 2005 Elsevier Ltd. All rights reserved
Y1  - 2005
SN  - 0040-4020
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Szatmári, István
A1  - Fulop, Ferenc
A1  - Kleinpeter, Erich
T1  - Synthesis and conformational analysis of naphth[1,2-e][1,3]oxazino[4,3-a][1,3]isoquinoline and naphth[2,1- e][1,3]oxazino[4,3-a]isoquinoline derivatives
N2  - Through the cyclization of 1-(;-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinoline and 1-(;- hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinoline with formaldehyde, phosgene, p-nitrobenzaldehyde or p-chlorophenyl isothiocyanate, 8-substituted 10,11-dihydro-8H,15bH-naphth[1,2-e][1,3]oxazino[4,3-a]isoquinolines (3 and 4) and 10,11- dihydro-8H,15bH-naphth[2,1-e][1,3]oxazino[4,3-a]isoquinolines (15 and 16) were prepared. Conformational analysis of both the piperidine and the 1,3-oxazine moieties of these heterocycles by NMR spectroscopy and an accompanying theoretical study revealed that these two conformationally flexible six-membered ring moieties prefer twisted chair conformers.
Y1  - 2008
UR  - http://www.sciencedirect.com/science/article/pii/S0040402008009150
U6  - https://doi.org/10.1016/j.tet.2008.05.025
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Poleschner, Helmut
A1  - Schilde, Uwe
T1  - Fluoroselenenylation of Acetylenes with Xenon Difluoride-Diorganyl Diselenides : synthesis and structure elucidation of functionalized Vicinal (E)-Fluoro(organylseleno)olefins
Y1  - 1996
ER  - 
TY  - JOUR
A1  - Heydenreich, Matthias
A1  - Wolf, G.
A1  - Woller, Jochen
A1  - Kleinpeter, Erich
T1  - Restricted rotation of the amino group and ring inversion in highly substituted anilines. A dynamic NMR and computational study
N2  - The reaction of cyclic ylidene malononitriles with acetylene (di)carboxylic acid esters led to the production of nine bicyclic systems incorporating highly substituted (5/6) anilines. The free energy of activation (DeltaG(#)) for the restricted rotation about the aniline-NH2 bond was experimentally measured in each case and a correlation was evident between the increase in steric strain in the ground state, the electron withdrawing capabilities of the ring substituents, and a reduction in the rotational barrier. For four of the compounds, the slow ring interconversion (chairreversible arrowchair) for the annelated saturated seven-membered ring that formed part of the bicyclic system was also evident. In these four compounds, both dynamic processes were also studied theoretically using ab initio methods whilst the ring interconversion was additionally studied using molecular dynamic simulations. The interconversion between the two stable chair forms was deemed to occur via a conformation series consisting of chairreversible arrowboatreversible arrowtwist-boatreversible arrowboatreversible arrowchair. (C) 2004 Elsevier Ltd. All rights reserved
Y1  - 2004
SN  - 0040-4020
ER  - 
TY  - JOUR
A1  - Holdt, Hans-Jürgen
A1  - Müller, Holger
A1  - Potter, Matthias
A1  - Kelling, Alexandra
A1  - Schilde, Uwe
A1  - Starke, Ines
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
T1  - The first sandwich complex with an octa(thioether) coordination sphere : Bis(maleonitrile-tetrathia-12-crown- 4)silver(I)
N2  - The new tetrathiacrown ethers maleonitrile-tetrathia-12-crown-4 (mn12S(4)) and maleonitrile-tetrathia-13-crown- 4 (mn13S(4)) have been prepared and characterised by X-ray crystallographic analysis. These crown ethers form 2:1, 3:2 and 1: 1 complexes with AgY (Y = BF4, PF6). The crystal structures of [Ag(mn12S(4))(2)]BF4 (3a), [Ag(mn13S(4))(2)]BF4 (4a) and [Ag-2(mn13S(4))(3)](PF6)(2) (6b) have been determined. Compound 3a contains the centrosymmetric sandwich complex cation [Ag(mn12S(4))(2)](+) where each mn12S(4) ligand is coordinated to the Ag centre in an endo manner through all four S atoms. The 2:1 complex [Ag(mn12S(4))(2)](+) is the first sandwich complex with a tetrathiacrown ether and the first complex with an octa(thioether) coordination sphere. The crystal structure of compound 4a also reveals a 2:1 complex. This complex, [Ag(mnl3S(4))(2)](+), exhibits a half-sandwich structure. One mn13S(4) ligand coordinates to Ag+ by all four S donor atoms and the other 13S(4) crown by only one S atom. Compound 6b contains a dinuclear Ag complex. The Ag complexes 3a,b-8a,b were also studied by electrospray ionisation mass spectrometry. Collision-induced dissociation (CID) was used to compare the relative stability of 2:1 complexes [AgL2]+ and 1:1 complexes [AgL](+) (L = mn12S(4), mn13S(4)). The C-13 NMR chemical shifts of 2:1 and 1:1 Ag complexes and their corresponding free ligands were also estimated and compared. The free energy of the barrier of ring inversion (Delta G(double dagger)) for [Ag(mn12S(4))(2)](+) was determined to be 64 kJmol(-1).
Y1  - 2006
UR  - http://www3.interscience.wiley.com/cgi-bin/jhome/27721/
U6  - https://doi.org/10.1002/ejic.200501109
SN  - 1434-1948
ER  - 
TY  - JOUR
A1  - Irungu, Beatrice N.
A1  - Adipo, Nicholas
A1  - Orwa, Jennifer A.
A1  - Kimani, Francis
A1  - Heydenreich, Matthias
A1  - Midiwo, Jacob O.
A1  - Bjoremark, Per Martin
A1  - Hakansson, Mikael
A1  - Yenesew, Abiy
A1  - Erdelyi, Mate
T1  - Antiplasmodial and cytotoxic activities of the constituents of Turraea robusta and Turraea nilotica
JF  - Journal of ethnopharmacology : an interdisciplinary journal devoted to bioscientific research on indigenous drugs
N2  - Ethnopharmacological relevance: Turraea robusta and Turraea nilotica are African medicinal plants used for the treatment of a wide variety of diseases, including malaria. The genus Turraea is rich in limonoids and other triterpenoids known to possess various biological activities.
 Materials and methods: From the stem bark of T. robusta six compounds, and from various parts of T nilotica eleven compounds were isolated by the use of a combination of chromatographic techniques. The structures of the isolated compounds were elucidated using NMR and MS, whilst the relative configuration of one of the isolated compounds, toonapubesin F, was established by X-ray crystallography. The antiplasmodial activities of the crude extracts and the isolated constituents against the D6 and W2 strains of Plasmodium falciparum were determined using the semiautomated micro dilution technique that measures the ability of the extracts to inhibit the incorporation of (G-H-3, where G is guanine) hypoxanthine into the malaria parasite. The cytotoxicity of the crude extracts and their isolated constituents was evaluated against the mammalian cell lines African monkey kidney (vero), mouse breast cancer (4T1) and human larynx carcinoma (HEp2).
 Results: The extracts showed good to moderate antiplasmodial activities, where the extract of the stem bark of T. robusta was also cytotoxic against the 4T1 and the HEp2 cells (IC50 < 10 mu g/ml). The compounds isolated from these extracts were characterized as limonoids, protolimonoids and phytosterol glucosides. These compounds showed good to moderate activities with the most active one being azadironolide, IC50 2.4 +/- 0.03 mu M and 1.1 +/- 0.01 mu M against the D6 and W2 strains of Plasmodium falciparum, respectively; all other compounds possessed IC50 14.4-40.5 mu M. None of the compounds showed significant cytotoxicity against vero cells, yet four of them were toxic against the 4T1 and HEp2 cancer cell lines with piscidinol A having IC50 8.0 +/- 0.03 and 8.4 +/- 0.01 mu M against the 4T1 and HEp2 cells, respectively. Diacetylation of piscidinol A resulted in reduced cytotoxicity.
 Conclusion: From the medicinal plants T. robusta and T. nilotica, twelve compounds were isolated and characterized; two of the isolated compounds, namely 11-epi-toonacilin and azadironolide showed good antiplasmodial activity with the highest selectivity indices. (C) 2015 The Authors. Published by Elsevier Ireland Ltd.
KW  - Turraea robusta
KW  - Turraea nilotica
KW  - Antiplasmodial activity
KW  - Cytotoxicity
KW  - Limonoid
KW  - Toonapubesins F
KW  - Toonacilin
KW  - Azadironolide
Y1  - 2015
U6  - https://doi.org/10.1016/j.jep.2015.08.039
SN  - 0378-8741
VL  - 174
SP  - 419
EP  - 425
PB  - Elsevier
CY  - Clare
ER  - 
TY  - JOUR
A1  - Juma, Wanyama P.
A1  - Akala, Hoseah M.
A1  - Eyase, Fredrick L.
A1  - Muiva, Lois M.
A1  - Heydenreich, Matthias
A1  - Okalebo, Faith A.
A1  - Gitu, Peter M.
A1  - Peter, Martin G.
A1  - Walsh, Douglas S.
A1  - Imbuga, Mabel
A1  - Yenesew, Abiy
T1  - Terpurinflavone an antiplasmodial flavone from the stem of Tephrosia Purpurea
JF  - Phytochemistry letters
N2  - The stem extract of Tephrosia purpurea showed antiplasmodial activity against the D6 (chloroquine-sensitive) and W2 (chloroquine-resistant) strains of Plasmodium falciparum with IC(50) values of 10.47 +/- 2.22 mu g/ml and 12.06 +/- 2.54 mu g/ml, respectively. A new prenylated flavone, named terpurinflavone, along with the known compounds lanceolatin A, (-)-semiglabrin and lanceolatin B have been isolated from this extract. The new compound, terpurinflavone, showed the highest antiplasmodial activity with IC(50) values of 3.12 +/- 0.28 mu M (D6) and 6.26 +/- 2.66 mu M (W2). The structures were determined on the basis of spectroscopic evidence.
KW  - Tephrosia purpurea
KW  - Leguminosae
KW  - Stem
KW  - Flavone
KW  - Terpurinflavone
KW  - Antiplasmodial
Y1  - 2011
U6  - https://doi.org/10.1016/j.phytol.2011.02.010
SN  - 1874-3900
VL  - 4
IS  - 2
SP  - 176
EP  - 178
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Kerubo, Leonidah Omosa
A1  - Midiwo, Jacob Ogweno
A1  - Derese, Solomon
A1  - Langat, Moses K.
A1  - Akala, Hoseah M.
A1  - Waters, Norman C.
A1  - Peter, Martin
A1  - Heydenreich, Matthias
T1  - Antiplasmodial activity of compounds from the surface exudates of senecio roseiflorus
JF  - Natural product communications : an international journal for communications and reviews
N2  - From the surface exudates of Senecio roseiflorus fourteen known methylated flavonoids and one phenol were isolated and characterized. The structures of these compounds were determined on the basis of their spectroscopic analysis. The surface exudate and the flavonoids isolated showed moderate to good antiplasmodial activity with 5,4'-dihydroxy-7-dimethoxyflavanone having the highest activity against chloroquine-sensitive (D6) and resistant (W2) strains of Plasmodium falciparum, with IC50 values of 3.2 +/- 0.8 and 4.4 +/- 0.01 mu g/mL respectively.
KW  - Senecio roseiflorus
KW  - Asteraceae
KW  - Surface exudates
KW  - Antiplasmodial activity
Y1  - 2013
SN  - 1934-578X
VL  - 8
IS  - 2
SP  - 175
EP  - 176
PB  - NPC
CY  - Westerville
ER  - 
TY  - JOUR
A1  - Kihampa, Charles
A1  - Nkunya, Mayunga H. H.
A1  - Joseph, Cosam C.
A1  - Magesa, Stephen M.
A1  - Hassanali, Ahmed
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
T1  - Antimosquito and antimicrobial clerodanoids and a chlorobenzoid from Tessmannia species
N2  - The clerodane diterpenoids trans-kolavenolic acid, 18-oxocleroda-3,13(E)-dien-15-oic acid, ent-(18- hydroxycarbonyl)-cleroda- 3,13(E)-dien-15-oate, 2-oxo-ent-cleroda-3,13(Z)-dien-15-oic acid and trans-2-oxo-ent-cleroda- 13(Z)-en-15-oic acid, and the chlorobenzenoid O-(3-hydroxy-4-hydroxycarbonyl-5-pentylphenyl)-3-chloro-4-methoxy-6-pentyl- 2-oxybenzoic acid were isolated from Tessmannia martiniana var pauloi and T. martiniana var matiniana. Structures were established based on interpretation of spectroscopic data. Some of the compounds exhibited significant antimosquito, antifungal and antibacterial activities.
Y1  - 2010
UR  - http://www.naturalproduct.us/
SN  - 1934-578X
ER  - 
TY  - JOUR
A1  - Kihampa, Charles
A1  - Nkunya, Mayunga H. H.
A1  - Joseph, Cosam C.
A1  - Magesa, Stephen M.
A1  - Hassanali, Ahmed
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
T1  - Anti-mosquito and antimicrobial nor-halimanoids, isocoumarins and an anilinoid from Tessmannia densiflora
N2  - The nor-halimane diterpenoid tessmannic acid and its methyl, 2-methylisopropyl and 1-methylbutyl esters, the unusual isocoumarins 8-hydroxy-6-methoxy-3-pentylisocoumarin and 7-chloro-8-hydroxy-6-methoxy-3-pentylisocoumarin, and 5- pentyl-3-methoxy-N-butylaniline were isolated from the stem and root bark extracts of Tessmannia densiflora Harms (Caesalpiniaceae) that showed mosquito larvicidal activity. The structures were determined on interpretation of spectroscopic data. Tessmannic acid and its methyl ester exhibited antibacterial and antifungal activity. The compounds also caused high larvae and adult Anopheles gambiae mosquitoe mortality effects, and stronger mosquito repellency than that shown by the standard repellent DEET, hence indicating Tessmannia species to be potential sources of bioactive natural products.
Y1  - 2009
UR  - http://www.sciencedirect.com/science/journal/00319422
U6  - https://doi.org/10.1016/j.phytochem.2009.07.024
SN  - 0031-9422
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Csütörtöki, Renáta
A1  - Szatmári, István
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Starke, Ines
A1  - Fulop, Ferenc
T1  - Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines-synthesis and conformational study
N2  - The reactions of 1-(amino(2-hydroxyphenyl)methyl)-2-naphthol (3) and 1-(amino(2-aminophenyl)methyl)-2-naphthol (6) with glutardialdehyde resulted in the formation of piperidine-fused benzoxazinonaphthoxazine 4 and quinazolinonaphthoxazine 7, respectively, both in diastereopure form. The full conformational search protocols of 4 and 7 were successfully carried out by NMR spectroscopy and accompanying molecular modelling; the global minimum-energy conformers of all diastereomers were computed, and the assignments of the most stable stereoisomers, Gtct1 for 4 and Gtct1 for 7, were corroborated by spatial NOE information relating to the H7a-H10a-H15b and H,H coupling patterns of the protons in the flexible part of the piperidine moiety. Additionally, mass spectrometric fragmentation was investigated in collision-induced dissociation experiments. The elemental compositions of the ions were determined by accurate mass measurements.
Y1  - 2012
SN  - 0040-4020
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Chatterjee, S. K.
A1  - Rudorf, Wolf-Dieter
T1  - Study of the pi-electron distribution in push-pull alkenes by 1H and 13C NMR spectroscopy, III : the conformation of 3,4-Dihydro-4-oxo-2H-thiins
Y1  - 1994
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Chatterjee, S. K.
A1  - Rudorf, Wolf-Dieter
T1  - Study of the pi-electron distribution in push-pull alkenes by 1H and 13C NMR spectroscopy
Y1  - 1994
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Kalder, L.
A1  - Koch, Andreas
A1  - Henning, Dietrich
A1  - Kempter, Gerhard
T1  - NMR spectroscopic and theoretical structural analysis of 5,5-disubstituted hydantoins in solution
Y1  - 1997
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Kalder, L.
A1  - Koch, Andreas
A1  - Henning, Dietrich
A1  - Kempter, Gerhard
A1  - Benassi, Rois
A1  - Taddei, F.
T1  - NMR spectroscopic and theoretical structural analysis of 5,5-disubstituted hydantoins in solution
Y1  - 1997
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Krtitschka, Angela
A1  - Krüger, Tobias
A1  - Linker, Torsten
T1  - NMR spectroscopic conformational analysis of 4-methylene-cyclohexyl pivalateThe effect of sp(2) hybridization
JF  - Magnetic resonance in chemistry
N2  - The conformational equilibrium of the axial/equatorial conformers of 4-methylene-cyclohexyl pivalate is studied by dynamic NMR spectroscopy in a methylene chloride/freon mixture. At 153K, the ring interconversion gets slow on the nuclear magnetic resonance timescale, the conformational equilibrium (-G degrees) can be examined, and the barrier to ring interconversion (G(#)) can be determined. The structural influence of sp(2) hybridization on both G degrees and G(#) of the cyclohexyl moiety can be quantified.
KW  - 4-methylene-cyclohexyl pivalate
KW  - conformational analysis
KW  - dynamic NMR spectroscopy
KW  - exo-methylene conformational effect at cyclohexane
KW  - quantum chemical calculations
Y1  - 2017
U6  - https://doi.org/10.1002/mrc.4630
SN  - 0749-1581
SN  - 1097-458X
VL  - 55
SP  - 1073
EP  - 1078
PB  - Wiley
CY  - Hoboken
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Linker, Torsten
T1  - Synthesis and NMR spectroscopic conformational analysis of esters of 4-hydroxy-cyclohexanone-the more polar the molecule the more stable the axial conformer
N2  - The esters of 4-hydroxy-cyclohexanone and a series of carboxylic acids R-COOH with R of different electronic and steric influence (R=Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, sec-Bu, t-Bu, CF3, CH2Cl, CHCl2, CCl3, CH2Br, CHBr2, and CBr3) were synthesized and the conformational equilibria studied by 1H and 13C NMR spectroscopy at 103 K and at 295 K, respectively. The geometry of optimized structures of the axial/equatorial chair conformers was computed at the ab initio MO and DFT levels of theory. Only one preferred conformation was obtained for the axial and the equatorial conformer as well. When comparing the conformational equilibria of the cyclohexanone esters with those of the corresponding cyclohexyl esters a certain polarity contribution of the cyclohexanone framework was revealed, which is independent of the substituent effects and increases the stability of the axial conformers by a constant amount.
Y1  - 2012
SN  - 0040-4020
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Linker, Torsten
T1  - Synthesis and NMR spectroscopic conformational analysis of esters of 4-hydroxy-cyclohexanone-the more polar the molecule the more stable the axial conformer
JF  - Tetrahedron
N2  - The esters of 4-hydroxy-cyclohexanone and a series of carboxylic acids R-COOH with R of different electronic and steric influence (R=Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, sec-Bu, t-Bu, CF3, CH2Cl, CHCl2, CCl3, CH2Br, CHBr2, and CBr3) were synthesized and the conformational equilibria studied by H-1 and C-13 NMR spectroscopy at 103 K and at 295 K, respectively. The geometry of optimized structures of the axial 'equatorial chair conformers was computed at the ab initio MO and DFT levels of theory. Only one preferred conformation was obtained for the axial and the equatorial conformer as well. When comparing the conformational equilibria of the cyclohexanone esters with those of the corresponding cyclohexyl esters a certain polarity contribution of the cyclohexanone framework was revealed, which is independent of the substituent effects and increases the stability of the axial conformers by a constant amount.
KW  - 4-Substituted cyclohexanones
KW  - Conformational analysis
KW  - Dynamic NMR
KW  - Simulation of H-1 NMR spectra
KW  - Quantum chemical calculations
KW  - ALTONA equation
Y1  - 2012
U6  - https://doi.org/10.1016/j.tet.2012.01.022
SN  - 0040-4020
VL  - 68
IS  - 10
SP  - 2363
EP  - 2373
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Heydenreich, Matthias
A1  - Shainyan, Bagrat A.
T1  - At the experimental limit of the NMR conformational analysis
BT  - Si-29 and C-13 NMR study of the conformational equilibrium of 1-phenyl-1-tert-butylsilacyclohexane
JF  - Organic letters
N2  - The low temperature (95 K) NMR study of 1-Ph-1-t-Bu-silacyclohexane (1) showed the conformational equilibrium to be extremely one-sided toward thePh(ax),t-Bueq conformer. The barrier to interconversion has been measured (4.2-4.6 kcal/mol) and the conformational equilibrium [Delta nu = 1990.64 ppm (Si-29), 618.9 ppm (C-13), 1-Ph-ax:1-Pheq = (95.6-96.6%):(3.4-4.4%), K = 25 +/- 3, Delta G degrees = -RT ln K = 0.58-0.63 kcal/mol] analyzed. The assignment and quantification of the NMR signals is supported by MP2 and DFT calculations.
Y1  - 2021
U6  - https://doi.org/10.1021/acs.orglett.0c03878
SN  - 1523-7060
SN  - 1523-7052
VL  - 23
IS  - 2
SP  - 405
EP  - 409
PB  - American Chemical Society
CY  - Washington
ER  -