@article{PazBecerraSilvaetal.2016, author = {Paz, Cristian and Becerra, Jose and Silva, Mario and Cabrera-Pardo, Jaime and Burgos, Viviana and Heydenreich, Matthias and Schmidt, Bernd}, title = {(-)-8-Oxohobartine a New Indole Alkaloid from Aristotelia chilensis (Mol.) Stuntz}, series = {Records of Natural Products}, volume = {10}, journal = {Records of Natural Products}, publisher = {ACG Publications}, address = {Gebze-Kocaeli}, issn = {1307-6167}, pages = {68 -- 73}, year = {2016}, abstract = {The fruit of Aristotelia chilensis is considered a "super fruit" due to its high concentration of polyphenols displaying exceptional antioxidant capacities ORAC. From maqui berries have been reported several anthocyanins and glycosylated flavonoids, those benefits increase the attention to restudy the plant. From the leaves of A. chilensis several indole alkaloids have been reported, we in addition to aristoteline, aristone, aristoquinoline and 3-fromylindole report the spectroscopic elucidation of 8-oxo-9-dehydromakomakine (1), hobartine (2) and a new alkaloid named 8-oxohobartine (3). Compound 1 to 3 did not show bactericidal activity against E. coli and S. aureus till 200 mu g.}, language = {en} } @article{PazBecerraSilvaetal.2015, author = {Paz, Cristian and Becerra, Jose and Silva, Mario and Burgos, Viviana and Heydenreich, Matthias and Schmidt, Bernd and Thu Tran, and Vetter, Irina}, title = {(-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia tupa with Agonist Activity at Nicotinic Acetylcholine Receptor}, series = {Natural product communications : an international journal for communications and reviews}, volume = {10}, journal = {Natural product communications : an international journal for communications and reviews}, number = {8}, publisher = {NPC}, address = {Westerville}, issn = {1934-578X}, pages = {1355 -- 1357}, year = {2015}, abstract = {Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at alpha 3 beta 2/alpha 3 beta 4 nAChR and alpha 7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR}, language = {en} } @article{ShainyanSuslovaTranDinhPhienetal.2019, author = {Shainyan, Bagrat A. and Suslova, Elena N. and Tran Dinh Phien, and Shlykov, Sergey A. and Heydenreich, Matthias and Kleinpeter, Erich}, title = {1-Methylthio-1-phenyl-1-silacyclohexane: Synthesis, conformational preferences in gas and solution by GED, NMR and theoretical calculations}, series = {Tetrahedron}, volume = {75}, journal = {Tetrahedron}, number = {46}, publisher = {Elsevier}, address = {Oxford}, issn = {0040-4020}, doi = {10.1016/j.tet.2019.130677}, pages = {9}, year = {2019}, abstract = {1-Methylthio-1-phenyl-1-silacyclohexane 1, the first silacyclohexane with the sulfur atom at silicon, was synthesized and its molecular structure and conformational preferences studied by gas-phase electron diffraction (GED) and low temperature C-13 and Si-29 NMR spectroscopy (LT NMR). Quantum-chemical calculations were carried out both for the isolated species and solvate complexes in gas and in polar medium. The predominance of the 1-MeSaxPheq conformer in gas phase (1-Ph-eq :1-Ph-ax = 55:45, Delta G degrees = 0.13 kcal/mol) determined from GED is consistent with that measured in the freon solution by LT NMR (1-Ph-eq:1-Ph-ax = 65:35, Delta G degrees = 0.12 kcal/mol), the experimentally measured ratios being close to that estimated by quantum chemical calculations at both the DFT and MP2 levels of theory. (C) 2019 Elsevier Ltd. All rights reserved.}, language = {en} } @article{PoleschnerHeydenreich1995, author = {Poleschner, Helmut and Heydenreich, Matthias}, title = {13C NMR chemical shifts of unbranched 2-Alkyn-1-ols, w-Alkyn-1-ols and "internal" Alkyn-1-ols}, year = {1995}, language = {en} } @article{PoleschnerHeydenreichSchilde2000, author = {Poleschner, Helmut and Heydenreich, Matthias and Schilde, Uwe}, title = {13C, 19F and 77Se NMR study of vicinal (E)-fluoro(organylseleno)olefins and [(E)- fluoroalkenyl]diorganylselenonium salts}, year = {2000}, abstract = {Selenides of the type R1Se-EMe3 (E = Si, Ge, Sn, Pb) react with xenon difluoride by cleavage of the Se-E bond to yield the R1Se-F intermediate and the fluorides Me3E-F, whereas the Se-C bond in PhSe-tBu (E = C) is stable against XeF2. The presence of R1Se-F intermediates is confirmed by addition to acetylenes (4-octyne, 3-hexyne). Thus, the fluoroselenenylation of acetylenes gives fluoro(organylseleno)olefins in preparative yields. In the cases of E = Si, Ge, Sn, and Pb, aryl and n-alkyl groups are suitable as the substituent R1. The X-ray crystal structural analysis of (E)-3- (p-carboxyphenylseleno)-4-fluorohex-3-ene - the first example of an uncharged fluoroselenoolefin synthesized from p- EtO2C-C6H4-Se-SnMe3, XeF2, and 3-hexyne followed by an ester hydrolysis - shows that the addition of the selenenylfluoride intermediate to the acetylene proceeds via a trans-addition, as is known for the R2Se2-XeF2 reagents.}, language = {en} } @article{PoleschnerHeydenreich1997, author = {Poleschner, Helmut and Heydenreich, Matthias}, title = {1H and 13C NMR Spectra and One-Bond 13C,13C Coupling Constants of 2-Alken-4-yn-1-ols, (E)-2-Alken-4-yn-1-yl Acetates and (E)-2-Alken-4-yn-1-als}, year = {1997}, language = {en} } @article{MutaiHeydenreichThoithietal.2013, author = {Mutai, Peggoty and Heydenreich, Matthias and Thoithi, Grace and Mugumbate, Grace and Chibale, Kelly and Yenesew, Abiy}, title = {3-Hydroxyisoflavanones from the stem bark of dalbergia melanoxylon - isolation, antimycobacterial evaluation and molecular docking studies}, series = {Phytochemistry letters}, volume = {6}, journal = {Phytochemistry letters}, number = {4}, publisher = {Elsevier}, address = {Amsterdam}, issn = {1874-3900}, doi = {10.1016/j.phytol.2013.08.018}, pages = {671 -- 675}, year = {2013}, abstract = {Two new 3-hydroxyisoflavanones, (S)-3,4',5-trihydroxy-2',7-dimethoxy-3'-prenylisoflavanone (trivial name kenusanone F 7-methyl ether) and (S)-3,5-dihydroxy-2',7-dimethoxy-2 '',2 ''-dimethylpyrano[5 '',6 '':3',4']isoflavanone (trivial name sophoronol-7-methyl ether) along with two known compounds (dalbergin and formononetin) were isolated from the stem bark of Dalbergia melanoxylon. The structures were elucidated using spectroscopic techniques. Kenusanone F 7-methyl ether showed activity against Mycobacterium tuberculosis, whereas both of the new compounds were inactive against the malaria parasite Plasmodium falciparum at 10 mu g/ml. Docking studies showed that the new compounds kenusanone F 7-methyl ether and sophoronol-7-methyl ether have high affinity for the M. tuberculosis drug target INHA.}, language = {en} } @article{AtilawHeydenreichNdakalaetal.2014, author = {Atilaw, Yoseph and Heydenreich, Matthias and Ndakala, Albert and Akala, Hoseah M. and Kamau, Edwin and Yenesew, Abiy}, title = {3-Oxo-14 alpha, 15 alpha-epoxyschizozygine: A new schizozygane indoline alkaloid from Schizozygia coffaeoides}, series = {Phytochemistry letters}, volume = {10}, journal = {Phytochemistry letters}, publisher = {Elsevier}, address = {Amsterdam}, issn = {1874-3900}, doi = {10.1016/j.phytol.2014.07.003}, pages = {28 -- 31}, year = {2014}, abstract = {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.}, language = {en} } @article{DereseBarasaAkalaetal.2014, author = {Derese, Solomon and Barasa, Leonard and Akala, Hoseah M. and Yusuf, Amir O. and Kamau, Edwin and Heydenreich, Matthias and Yenesew, Abiy}, title = {4 '-Prenyloxyderrone from the stem bark of Millettia oblata ssp teitensis and the antiplasmodial activities of isoflavones from some Millettia species}, series = {Phytochemistry letters}, volume = {8}, journal = {Phytochemistry letters}, publisher = {Elsevier}, address = {Amsterdam}, issn = {1874-3900}, doi = {10.1016/j.phytol.2014.02.001}, pages = {69 -- 72}, year = {2014}, abstract = {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).}, language = {en} } @article{MuivaMutisyaMachariaHeydenreichetal.2014, author = {Muiva-Mutisya, Lois and Macharia, Bernard and Heydenreich, Matthias and Koch, Andreas and Akala, Hoseah M. and Derese, Solomon and Omosa, Leonidah K. and Yusuf, Amir O. and Kamau, Edwin and Yenesew, Abiy}, title = {6 alpha-Hydroxy-alpha-toxicarol and (+)-tephrodin with antiplasmodial activities from Tephrosia species}, series = {Phytochemistry letters}, volume = {10}, journal = {Phytochemistry letters}, publisher = {Elsevier}, address = {Amsterdam}, issn = {1874-3900}, doi = {10.1016/j.phytol.2014.09.002}, pages = {179 -- 183}, year = {2014}, abstract = {The CH2Cl2/MeOH (1: 1) extract of the roots of Tephrosia villosa showed good antiplasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 3.1 +/- 0.4 and 1.3 +/- 0.3 mu g/mL, respectively. Chromatographic separation of the extract yielded a new rotenoid, 6 alpha-hydroxy-alpha-toxicarol, along with five known rotenoids, (rotenone, deguelin, sumatrol, 12 alpha-hydroxy-alpha-toxicarol and villosinol). Similar treatment of the extract of the stem of Tephrosia purpurea (IC50 = 4.1 +/- 0.4 and 1.9 +/- 0.2 mu g/mL against D6 and W2 strains of P. falciparum, respectively) yielded a new flavone having a unique substituent at C-7/C-8 [trivial name (+)-tephrodin], along with the known flavonoids tachrosin, obovatin methyl ether and derrone. The relative configuration and the most stable conformation in (+)-tephrodin was determined by NMR and theoretical energy calculations. The rotenoids and flavones tested showed good to moderate antiplasmodial activities (IC50 = 9 +/- 23 mu M). Whereas the cytotoxicity of rotenoids is known, the flavones (+)-tephrodin and tachrosin did not show significant cytotoxicity (IC50 > 100 mu M;) against mammalian African monkey kidney (vero) and human larynx carcinoma (HEp2) cell lines. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.}, language = {en} }