@article{YenesewMidiwoMeisneretal.1998, author = {Yenesew, Abiy and Midiwo, Jacob O. and Meisner, M. and Heydenreich, Matthias and Peter, Martin G.}, title = {Two prenylated flavanones from stem bark of erythrina burttii}, year = {1998}, language = {en} } @article{YenesewMidiwoHeydenreichetal.1998, author = {Yenesew, Abiy and Midiwo, Jacob O. and Heydenreich, Matthias and Peter, Martin G.}, title = {Four isoflavanones from stem bark of erythrina sacleuxii}, year = {1998}, language = {en} } @article{YenesewMidiwoHeydenreichetal.2000, author = {Yenesew, Abiy and Midiwo, Jacob O. and Heydenreich, Matthias and Schanzenbach, Dirk and Peter, Martin G.}, title = {Two Isoflavanones from the Stem Bark of Erythrina sacleuxii}, year = {2000}, abstract = {From the stem bark of Erythrina sacleuxii two new isoflavanones, (R)-5,7-dihydroxy-2',4',5'- trimethoxyisoflavanone (trivial name, (R)-2,3-dihydro-7-demethylrobustigenin) and (R)-5-hydroxy- 2',4',5'-trimethoxy-2'',2''- dimethylpyrano[5'',6'':6,7]isoflavanone (trivial name, (R)-saclenone) were isolated. In addition the known compounds shinpterocarpin, 2,3-dehydrokievitone, abyssinone V, abyssinone V-4'-methyl ether, erythrinasinate and 4'-O-methylsigmoidin B were isolated. The structures were determined on the basis of spectroscopic evidence.}, language = {en} } @article{YenesewMidiwoGuchuetal.2002, author = {Yenesew, Abiy and Midiwo, Jacob O. and Guchu, S. M. and Heydenreich, Matthias and Peter, Martin G.}, title = {Three iosoflav-3-enes and a 2-arylbenzofuran from the root bark of Erythrina burttii}, year = {2002}, abstract = {From the root bark of Erythrina burttii three new isoflav-3-enes, 7,4'-dihydroxy-2'-methoxy-6- (1'',1''-dimethylallyl)isoflav-3-ene (trivial name, burttinol-A), 4'-hydroxy-2'- methoxy-(2'',2''-dimethylpyrano[5'',6'':8,7]isoflav-3-ene (trivial name, burttinol-B), 7,4'-dihydroxy-2'-methoxy-8-(3'',3''-dimethylallyl)isoflav-3-ene (trivial name, burttinol-C), and a new 2-arylbenzofuran, 6,4'-dihydroxy-2'-methoxy-5- (1'',1''-dimethylallyl)-2-arylbenzofuran (trivial name, burttinol-D) were isolated. In addition, the known compounds, abyssinone V-4'-methyl ether, bidwillol A, calopocarpin, erybraedin A, erythrabyssin II, isobavachalcone, phaseollidin and phaseollin were identified. The structures were determined on the basis of spectroscopic evidence.}, language = {en} } @article{YenesewIrunguDereseetal.2003, author = {Yenesew, Abiy and Irungu, Beatrice and Derese, Solomon and Midiwo, Jacob O. and Heydenreich, Matthias and Peter, Martin G.}, title = {Two prenylated flavonoids from the stem bark of Erythrina burttii}, year = {2003}, abstract = {From the stem bark of Erythrina burttii, a new isoflavone, 5,2',4'-trihydroxy-7-methoxy-6-(3- methylbut-2-enyl)isoflavone (trivial name, 7-O-methylluteone) and a new flavanone, 5,7-dihydroxy-4'-methoxy- 3'-(3-methylbutadienyl)-5'-(3-methylbut-2-enyl)flavanone (trivial name, burttinonedehydrate) along with three known isoflavonoids (8-prenylluteone, 3-O-methylcalopocarpin and genistein) were isolated. The structures were detd. on the basis of spectroscopic evidence.}, language = {en} } @phdthesis{DereseYenesewMidiwoetal.2003, author = {Derese, Solomon and Yenesew, Abiy and Midiwo, Jacob O. and Heydenreich, Matthias and Peter, Martin G.}, title = {A new isoflavone from stem bark of Millettia dura}, issn = {1011-3924}, year = {2003}, language = {en} } @article{YenesewInduliDereseetal.2004, author = {Yenesew, Abiy and Induli, M. and Derese, Solomon and Midiwo, Jacob O. and Heydenreich, Matthias and Peter, Martin G. and Akala, Hoseah M. and Wangui, Julia and Liyala, Pamela and Waters, Norman C.}, title = {Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica}, issn = {0031-9422}, year = {2004}, abstract = {The ethyl acetate extract of the stem bark of Erythrina abyssinica showed anti-plasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 7.9 +/- 1.1 and 5.3 +/- 0.7 mug/ml, respectively. From this extract, a new chalcone, 2,3,4,4'-tetrahydroxy-5- prenylchalcone (trivial name 5-prenylbutein) and a new flavanone, 4',7-dihydroxy-3'-methoxy-5'- prenylflavanone (trivial name, 5-deoxyabyssinin II) along with known flavonoids have been isolated as the anti- plasmodial principles. The structures were determined on the basis of spectroscopic evidence. (C) 2004 Elsevier Ltd. All rights reserved}, language = {en} } @article{WanjohiYenesewMidiwoetal.2005, author = {Wanjohi, John M. and Yenesew, Abiy and Midiwo, Jacob O. and Heydenreich, Matthias and Peter, Martin G. and Dreyer, M. and Reichert, M. and Bringmann, Gerhard}, title = {Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica}, issn = {0040-4020}, year = {2005}, abstract = {From the fruits of Bulbine abyssinica three new dimeric anthracene derivatives, (P)-8,9,1',8'- tetrahydroxy-3,3'-dimethyl[10,7'-bianthracene]-1,4,9',10'- tetraone (trivial name abyquinone A), (10R)-1,4,8,1',8-pentahydroxy-3,3'-dimethyl-[10,7'-bianthracene]9,9',10' (10H)-trione (trivial name abyquinone B), and (10R)-3,4'-dihydro-1,4,8,3',8',9'-hexahydroxy-3,3'- dimethyl-[10,7'-biant hracene]9,1'(10H,2'H)-dione (trivial name abyquinone Q were isolated. Despite their structural differences, these three compounds are connected to each other by the apparently biomimetic conversion of abyquinone C (a preanthraquinonylanthrone with two stereogenic centers) into B (an anthraquinonylanthrone with one stereogenic center) and finally into A (an axially chiral bianthraquinone) under mild conditions, involving a highly efficient center-to-axis chirality transfer. In addition, the known anthraquinones islandicin and chrysophanol were identified. The structures were determined on the basis of spectroscopical evidences, chemical transformations, and quantum chemical CD calculations. (C) 2005 Elsevier Ltd. All rights reserved}, language = {en} } @article{YenesewMushibeIndulietal.2005, author = {Yenesew, Abiy and Mushibe, E. K. and Induli, M. and Derese, Solomon and Midiwo, Jacob O. and Kabaru, Jacques M. and Heydenreich, Matthias and Koch, Andreas and Peter, Martin G.}, title = {7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoloata}, issn = {0031-9422}, year = {2005}, abstract = {From the acetone extract of the roots of Derris trifoliata an isollavonoid derivative, named 7a-O- methyldeguelol, a modified rotenoid with an open ring-C, representing a new sub-class of isollavonoids (the sub-class is here named as rotenoloid), was isolated and characterised. In addition, the known rotenoids, rotenone, deguelin and alpha-toxicarol, were identified. The structures were determined on the basis of spectroscopic evidence. Rotenone and deguelin were identified as the larvicidal principles of the acetone extract of the roots of Derris trifoliata. (c) 2005 Elsevier Ltd. All rights reserved}, language = {en} } @article{YenesewDereseMidiwoetal.2005, author = {Yenesew, Abiy and Derese, Solomon and Midiwo, Jacob O. and Bii, Christine C. and Heydenreich, Matthias and Peter, Martin G.}, title = {Antimicrobial flavonoids from the stem bark of Erythrina burttii}, issn = {0367-326X}, year = {2005}, abstract = {The chloroform extract of the stem bark of Erythrina burttii showed antifungal and antibacterial activities using the disk diffusion method. Flavonoids were identified as the active principles. Activities were observed against fungi and Gram(+) bacteria, but the Gram(-) bacteria Escherichia coli was resistant. (c) 2005 Elsevier B.V. All rights reserved}, language = {en} } @article{YenesewKiplagatDereseetal.2006, author = {Yenesew, Abiy and Kiplagat, John T. and Derese, Solomon and Midiwo, Jacob O. and Kabaru, Jacques M. and Heydenreich, Matthias and Peter, Martin G.}, title = {Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata}, doi = {10.1016/j.phytochem.2006.01.002}, year = {2006}, abstract = {The crude methanol extract of the seeds of Derris trifoliata showed potent and dose dependent larvicidal activity against the 2nd instar larvae of Aedes aegypti. From this extract two unusual rotenoid derivatives, a rotenoloid (named 7a-O-methyl-12a-hydroxydeguelol) and a spirohomooxarotenoid (named spiro-13-homo-13-oxaelliptone), were isolated and characterised. In addition a rare natural chromanone (6,7-dimethoxy-4-chromanone) and the known rotenoids rotenone, tephrosin and dehydrodeguelin were identified. The structures were assigned on the basis of spectroscopic evidence. The larvicidal activity of the crude extract is mainly due to rotenone. (c) 2006 Elsevier Ltd. All rights reserved}, language = {en} } @article{AndayiYenesewDereseetal.2006, author = {Andayi, Andrew W. and Yenesew, Abiy and Derese, Solomon and Midiwo, Jacob O. and Gitu, Peter M. and Jondiko, Ogoche J. I. and Akala, Hoseah M. and Liyala, Pamela and Wangui, Julia and Waters, Norman C. and Heydenreich, Matthias and Peter, Martin G.}, title = {Antiplasmodial flavonoids from Erythrina sacleuxii}, issn = {0032-0943}, doi = {10.1055/s-2005-873200}, year = {2006}, abstract = {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}, language = {en} } @misc{BringmannMutanyattaComarMaksimenkaetal.2008, author = {Bringmann, Gerhard and Mutanyatta-Comar, Joan and Maksimenka, Katja and Wanjohi, John M. and Heydenreich, Matthias and Brun, Reto and M{\"u}ller, Werner E. G. and Peter, Martin and Midiwo, Jacob O. and Yenesew, Abiy}, title = {Joziknipholones A and B : the First Dimeric Phenylanthraquinones, from the Roots of Bulbine frutescens}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus-42638}, year = {2008}, abstract = {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.}, language = {en} } @article{BringmannMutanyattaComarMaksimenkaetal.2008, author = {Bringmann, Gerhard and Mutanyatta-Comar, Joan and Maksimenka, Katja and Wanjohi, John M. and Heydenreich, Matthias and Brun, Reto and M{\"u}ller, Werner E. G. and Peter, Martin G. and Midiwo, Jacob O. and Yenesew, Abiy}, title = {Joziknipholones A and B : the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens}, issn = {0947-6539}, year = {2008}, abstract = {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.}, language = {en} } @article{YenesewTwinomuhweziKiremireetal.2009, author = {Yenesew, Abiy and Twinomuhwezi, Hannington and Kiremire, Bernard T. and Mbugua, Martin N. and Gitu, Peter M. and Heydenreich, Matthias and Peter, Martin G.}, title = {8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica}, issn = {1011-3924}, year = {2009}, abstract = {A new pterocarpan (named 8-methoxyneorautenol) was isolated from the acetone ext. of the root bark of Erythrina abyssinica. In addn., the known isoflavonoid derivs. eryvarin L, erycristagallin and shinpterocarpin were identified for the first time from the roots of this plant. The structures were detd. on the basis of spectroscopic evidence. The new compd. showed selective antimicrobial activity against Trichophyton mentagrophytes. The acetone ext. of the root bark of E. abyssinica showed radical scavenging activity towards 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). The pterocarpenes, 3-hydroxy-9-methoxy-10-(3,3-dimethylallyl)pterocarpene and erycristagallin, were the most active constituents of the roots of this plant and showing dose-dependent activities similar to that of the std. quercetin. [on SciFinder (R)]}, language = {en} } @misc{PeterYenesewTwinomuhwezietal.2009, author = {Peter, Martin G. and Yenesew, Abiy and Twinomuhwezi, Hannington and Kabaru, Jacques M. and Akala, Hoseah M. and Kiremire, Bernard T. and Heydenreich, Matthias and Eyase, Fredrick and Waters, Norman C. and Walsh, Douglas S.}, title = {Antiplasmodial and larvicidal flavonoids from Derris trifoliata}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus-44614}, year = {2009}, abstract = {From the dichloromethane-methanol (1:1) extract of the seed pods of Derris trifoliata, a new flavanone derivative (S)-lupinifolin 4´-methyl ether was isolated. In addition, the known flavonoids lupinifolin and rotenone were identified. The structures were determined on the basis of spectroscopic evidence. Lupinfolin showed moderate in vitro antiplasmodial activity against the D6 (chloroquine-sensitive) and W2 (chloroquineresistant) strains of Plasmodium falciparum. The different parts of this plant showed larvicidal activities against Aedes aegypti and rotenoids were identified as the active principles.}, language = {en} } @misc{PeterMuivaYenesewetal.2009, author = {Peter, Martin G. and Muiva, Lois M. and Yenesew, Abiy and Derese, Solomon and Heydenreich, Matthias and Akala, Hoseah M. and Eyase, Fredrick and Waters, Norman C. and Mutai, Charles and Keriko, Joseph M. and Walsh, Douglas S.}, title = {Antiplasmodial β-hydroxydihydrochalcone from seedpods of Tephrosia elata}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus-44437}, year = {2009}, abstract = {From the seedpods of Tephrosia elata, a new β-hydroxydihydrochalcone named (S)-elatadihydrochalcone was isolated. In addition, the known flavonoids obovatachalcone, obovatin, obovatin methyl ether and deguelin were identified. The structures were determined on the basis of spectroscopic evidence. The crude extract and the flavonoids obtained from the seedpods of this plant showed antiplasmodial activities. The literature NMR data on β-hydroxydihydrochalcones is reviewed and the identity of some of the compounds assigned β-hydroxydihydrochalcone skeleton is questioned.}, language = {en} } @article{JumaAkalaEyaseetal.2011, author = {Juma, Wanyama P. and Akala, Hoseah M. and Eyase, Fredrick L. and Muiva, Lois M. and Heydenreich, Matthias and Okalebo, Faith A. and Gitu, Peter M. and Peter, Martin G. and Walsh, Douglas S. and Imbuga, Mabel and Yenesew, Abiy}, title = {Terpurinflavone an antiplasmodial flavone from the stem of Tephrosia Purpurea}, series = {Phytochemistry letters}, volume = {4}, journal = {Phytochemistry letters}, number = {2}, publisher = {Elsevier}, address = {Amsterdam}, issn = {1874-3900}, doi = {10.1016/j.phytol.2011.02.010}, pages = {176 -- 178}, year = {2011}, abstract = {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.}, language = {en} } @article{MachumiYenesewMidiwoetal.2012, author = {Machumi, Francis and Yenesew, Abiy and Midiwo, Jacob O. and Heydenreich, Matthias and Kleinpeter, Erich and Tekwani, Babu L. and Khan, Shabana I. and Walker, Larry A. and Muhammad, Ilias}, title = {Antiparasitic and anticancer carvotacetone derivatives of Sphaeranthus bullatus}, series = {Natural product communications : an international journal for communications and reviews}, volume = {7}, journal = {Natural product communications : an international journal for communications and reviews}, number = {9}, publisher = {NPC}, address = {Westerville}, issn = {1934-578X}, pages = {1123 -- 1126}, year = {2012}, abstract = {The CH2Cl2-MeOH (1:1) extract of the aerial parts of Sphaeranthus bullatus, an annual herb native to tropical East Africa, showed activity against chloroquine sensitive D6 (IC50 9.7 mu g/mL) and chloroquine resistant W2 (IC50 15.0 mu g/mL) strains of Plasmodium falciparum. Seventeen secondary metabolites were isolated from the extract through conventional chromatographic techniques and identified using various spectroscopic methods. The compounds were evaluated for their in vitro antiplasmodial, antileishmanial and anticancer activities revealing activity of four carvotacetone derivatives, namely 3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone (1) 3,7-dihydroxy-5-tigloyloxycarvotacetone (2), 3-acetoxy-5,7-dihydroxycarvotacetone (3) and 3,5,7-trihydroxycarvotacetone (4); with antiplasmodial IC50 values of 1.40, 0.79, 0.60 and 3.40 mu g/mL, respectively, against chloroquine sensitive D6 strains of P. falciparum; antiplasmodial activity of IC50 2.00, 0.90, 0.68 and 2.80 mu g/mL respectively, against chloroquine resistant W2 strains of P. falciparum, antileishmanial IC50, values of 0.70, 3.00, 0.70 and 17.00 mu g/mL, respectively, against the parasite L. donovanii promastigotes, and anticancer activity against human SK-MEL, KB, BT-549 and SK-OV-3 tumor cells, with IC50 values between <1.1 - 5.3 mu g/mL, for 1-3. In addition, cytotoxic effects of the active compounds were evaluated against monkey kidney fibroblasts (VERO) and pig kidney epithelial cells (LLC-PK11). The structures of carvotacetone derivatives were determined by ID and 2D NMR spectroscopy; the absolute stereochemical configuration of 3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone (I) was determined as 3R, 4R, 5S by circular dichroism, specific rotation, H-1 NMR and 2D NMR ROESY and NOESY experiments.}, language = {en} } @article{InduliChelotiWasunaetal.2012, author = {Induli, Martha and Cheloti, Michael and Wasuna, Antonina and Wekesa, Ingrid and Wanjohi, John M. and Byamukama, Robert and Heydenrich, Matthias and Makayoto, Moses and Yenesew, Abiy}, title = {Naphthoquinones from the roots of Aloe secundiflora}, series = {Phytochemistry letters}, volume = {5}, journal = {Phytochemistry letters}, number = {3}, publisher = {Elsevier}, address = {Amsterdam}, issn = {1874-3900}, doi = {10.1016/j.phytol.2012.04.014}, pages = {506 -- 509}, year = {2012}, abstract = {Two new naphthoquinones, 5-hydroxy-3,6-dimethoxy-2-methylnaphthalene-1,4-dione and 5,8-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione, were isolated from the roots of Aloe secundiflora together with the known compounds chrysophanol, helminthosporin, isoxanthorin, ancistroquinone C, aloesaponarins I and II, aloesaponols I and II, laccaic acid D methyl ester and asphodelin. The structures were elucidated based on spectroscopic evidence. This appears to be the first report on the occurrence of naphthoquinones in the genus Aloe. Aloesaponarin I and 5-hydroxy-3,6-dimethoxy-2-methylnaphthalene-1,4-dione showed anti-bacterial activity against Mycobacterium tuberculosis with MIC values of 21-23 mu g/mL in the Microplate Alamar Blue Assay (MABA) and Low Oxygen Recovery Assay (LORA); 5-hydroxy-3,6-dimethoxy-2-methylnaphthalene-1,4-dione also showed cytotoxicity against the Vero cell line (IC50 = 10.2 mu g/mL).}, language = {en} }