Topul Rali's research while affiliated with ETH Zurich and other places

Publications (63)

Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
Fresh rhizome of Acorus calamus L. collected from Isan village in the Kabwum District of Morobe Province were subjected to exhaustive hydrodistillation to afford pale yellow coloured oil in 1.05 percent yield. Evaluation of the chemical composition in the volatile oil distillates indicated β-asarone to be the major constituent with a composition of...
Article
In an ongoing study to identify and document the different volatile chemical constituents in the diversity of endemic aromatic plants, we present herein a comparative analysis of the chemical constituents from different aromatic plant species found in Papua New Guinea. In this study, the barks, heartwood, fruits and leaves of different plant specie...
Article
Two prenylated benzophenones, guttiferones O (1) and P (2), were isolated from the stem bark of the Papua New Guinean plant Garcina solomonensis. The structures of these compounds and their relative configurations were determined by spectroscopic methods. Both compounds inhibited the phosphorylation of the synthetic biotinylated peptide substrate K...
Article
Full-text available
Fresh aerial parts of three species of basil, Ocimum basilicum, O. tacilium and O. canum were subjected to exhaustive hydrodistillation to afford pale yellow coloured oils in 1.0, 0.7 and 0.01 percent yields respectively. Detailed chemical evaluation by GC and GC/MS revealed O. basilicum to be composed of a total of eleven components representing 1...
Article
Abstract The methanol and hexane extracts of Halimeda tuna, Enhalus acoroides, Turbinaria ornata, Hormo-physa articulata, Padina sp., Liaqura sp. and Sargassum sp. were tested against Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae. Most of the methanol and hexane extracts exhibited antibacterial activity...
Article
Bioassay-guided fractionation of an organic extract from the leaves of Cupaniopsis macropetala resulted in the isolation of a new alkaloid, galloyl tyramine ( 1), together with the known flavonoid glycoside quercitrin ( 2). The structure of 1 was determined following 1D and 2D NMR, IR, UV, and MS data analysis. Compounds 1 and 2 displayed IC 50 val...
Article
The aerial parts of Hyptis suaveolens L. Poit (Lamiaceae) were exhaustively hydro-distilled to afford a colourless oil of 0.3 percent yield. Detailed chemical analysis using GC and GC-MS method showed a total of 21 components, accounting for 91.4 percent of the total identified chemical constituents. The main monoterpenes identified were sabinene (...
Article
The aerial parts of Hyptis suaveolens L. Poit (Lamiaceae) were exhaustively hydro-distilled to afford a colourless oil of 0.3 percent yield. Detailed chemical analysis using GC and GC-MS method showed a total of 21 components, accounting for 91.4 percent of the total identified chemical constituents. The main monoterpenes identified were sabinene (...
Article
Hydrodistillation of the steam volatile constituents in the fruit kernel of Galbulimima belgraveana (F. Muell.) Sprague afforded colorless oil in 0.9 percent yield. Detailed chemical investigation using GC-MS analysis revealed the distillate to be composed of 31 identified compounds and the major constituents were monoterpenes. The main components...
Article
In the first chemical investigation of the Papua New Guinean plant Elaeocarpus fuscoides, one new indolizidine alkaloid, elaeocarpenine (1), and three known alkaloids, isoelaeocarpicine (2), isoelaeocarpine (3), and elaeocarpine (4), were isolated from the leaves. Their structures were determined by 1D and 2D NMR spectroscopy. Since treatment of el...
Article
The first phytochemical investigation of the Papua New Guinean plant Elaeocarpus habbemensis resulted in the isolation of two new pyrrolidine alkaloids, habbemines A (2) and B (3), as a 1:1 mixture of inseparable diastereomers. The structures of these compounds and their relative configurations were determined by spectroscopic means. An equimolar m...
Article
Full-text available
Exhaustive hydro-distillation of the leaves of Piper aduncum and fruits of Piper gibbilimbum (Piperaceae) afforded colorless and pale orange colored oils in 0.35 and 0.30 % yields, respectively. Detailed chemical analysis by GC/MS indicated the volatile constituents of Piper aduncum to be composed of dill apiole (43.3%), beta-caryophyllene (8.2%),...
Article
Full-text available
Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-...
Article
As part of our search for natural products active against the JNK3 kinase, two novel, charged benzylisoquinolines, latifolian A (1) and latifolian B (2), were isolated from the stem bark of the Papua New Guinean vine Gnetum latifolium. The planar structures were determined through detailed 2D NMR analysis. The relative configurations were assigned...
Article
Two new triterpenes, 3 beta,6 beta,23-trihydroxyolean-12-en-28-oic acid [1] and 3 beta,6 beta,19 alpha,23-tetrahydroxyolean-12-en-28 acid [2], have been isolated from the leaves of Timonius timon (Rubiaceae) with other known compounds: 3 beta,6 beta,19,23-tetrahydroxyurs-12-en-8 -oic acid, 3-0-[beta-D-quinovopyranosyl]quinovic acid, 3-0-[alpha-L-ar...
Article
From the petroleum-ether extract of the dried aerial parts of Hypericum papuanum, three new prenylated tricyclic and four new bicyclic acylphloroglucinol derivatives were isolated by bioactivity-guided fractionation. The structures of the bicyclic compounds enaimeone A, B, and C (1/1a, 2/2a, and 3/3a, resp.) were elucidated as rel-(1R,5R,6S)-4-hydr...
Article
A new cytotoxic 1,7-dioxa-dispiro[5.1.5.2]pentadeca-9,12-dien-11-one derivative, aculeatin D, and a new alkenone, 5-hydroxy-hexacos-1-en-3-one, have been isolated as minor compounds from the rhizomes of Amomum aculeatum. Their structures have been determined mainly by NMR spectroscopy and mass spectrometry. Aculeatin D showed high cytotoxicity agai...
Article
Five new prenylated tricyclic and three new bicyclic acylphloroglucinol derivatives have been isolated by bioactivity-guided fractionation of the petroleum ether extract of the dried aerial parts of Hypericum papuanum. The tricyclic compounds (1--5) were named papuaforins A--E. The bicyclic compounds were isolated together with their corresponding...
Article
Eight new tirucallane-type triterpenes, dyvariabilins A-H (1-8), three known tirucallanes, niloticin (9), dihydroniloticin (10), and tirucalla-7,24-diene-3 beta,23-diol (11), and two known sesquiterpenes, 1-(1-hydroxy-2-methylpropyl)-3a-methyl-7-methyleneoctahydroinden-4-ol and (+)-aphanamol I, were isolated from the stem bark of Dysoxylum variabil...
Article
Eight new tirucallane-type triterpenes, dyvariabilins A-H (1-8), three known tirucallanes, niloticin (9), dihydroniloticin (10), and tirucalla-7,24-diene-3 beta ,23-diol (11), and two known sesquiterpenes, 1-(1-hydroxy-2-methylpropyl)-3a-methyl-7-methyleneoetahydroinden-4-ol and (+)-aphanamol I, were isolated from the stem bark of Dysoxylum variabi...
Article
Three new coumarin derivatives, compounds 1-3, three new furanocoumarins, compounds 4-6, and a novel dioxocane derivative, compound 7, were isolated from the fern Cyclosorus interruptus (Willd.) H. Itô. Based on spectrometric and spectroscopic analysis (FAB or El mass spectrometry as well as 1D and 2D NMR experiments) their structures were characte...
Article
Cytotoxicity against the KB cancer cell line as a lead bioactivity-guided fractionation of the petroleum ether extract of rhizomes of Amomum aculeatumRoxb. led to the isolation of three novel dioxadispiro[5.1.5.2]pentadeca-9,12-dien-11-one derivatives. The structures of aculeatin A (1), aculeatin B (2), and aculeatin C (3) were established as rel-(...
Article
Full-text available
Bioactivity-guided fractionation of the petroleum ether extract of the aerial parts of Hypericum papuanum led to the isolation of five new tricyclic phloroglucinol derivatives. On the basis of extensive 1D and 2D NMR experiments as well as MS studies, their structures were elucidated as the C-3 epimers of 8-hydroxy-4,4, 7-trimethyl-9-(2-methylpropi...
Article
From the leaves of Stenochlaena palustris five new O-acylated flavonol glycosides, stenopalustrosides A-E (1-5), have been isolated along with five known compounds, kaempferol 3-O-(3' '-O-E-p-coumaroyl)-(6' '-O-E-feruloyl)-beta-D-glucopyranoside (6), kaempferol 3-O-(3' ',6' '-di-O-E-p-coumaroyl)-beta-D-glucopyranoside (7), kaempferol 3-O-(3' '-O-E-...
Article
A novel glycoside, (4S*,5R*)-4-[(9Z)-2,13-di-(O-β-d-glucopyranosyl)-5,9,10-trimethyl-8-oxo-9-tetradecene-5-yl]-3,3,5-trimethylcyclohexanone, namely stenopaluside, and a new cerebroside, 1-O-β-d-glucopyranosyl-(2S*,3R*,4E,8Z)-2-N-[(2R)-hydroxytetracosanoyl]octadecasphinga-4,8-dienine, were isolated from the leaves of Stenochlaena palustris, along wi...
Article
Fractionation of the petroleum ether extract from the leaves of Piper gibbilimbum collected in Papua New Guinea afforded four new alkenylphenols, gibbilimbols A-D (1-4). The structures of the isolates were elucidated by spectroscopic methods, mainly 1D- and 2D-NMR spectroscopy. Gibbilimbols A-D were found to be toxic to brine shrimp with an LC50 of...
Article
A new lupane type triterpene, 3β,20,25-trihydroxy lupane, was isolated from the petrol extract of the leaves of Rhus taitensis together with the known compounds 3,20-dihydroxylupane, 20-hydroxylupane-3-one, 20,28-dihydroxylupane-3-one, 3,16-dihydroxy lup-20(29)-ene and 28-hydroxy-β-amyrone. Their structures were determined by means of spectral meth...
Article
Two new dammarane triterpenoids, trans-securinegin [(20S)-24-methylidenedammarane-3alpha-yl(2E)-3-(4-hydroxyphenyl)-2-propenate (1)] and cis-securinegin [(20S)-24-methylidenedammarane-3alpha-yl(2Z)-3-(4-hydroxyphenyl)-2-propenate (2)], were isolated from the leaves of Securinega melanthesoides, along with the known compound bergenin. The structures...
Article
Two new oleanene-type triterpenoids, dillenic acids D and E, have been isolated from the leaves and stems of Dillenia papuana together with the new natural product 3-oxoolean-12-en-30-oic acid. Together with these compounds, the known compound, betulinic acid (3 beta-hydroxy-20(29)-lupen-28-oic acid) was isolated as the major component of the fract...
Article
Based on ethnopharmacological literature, 17 species of medicinal plants used in the traditional medicine in Papua New Guinea were collected. Extracts of different polarities were tested in a preliminary biological screening for their antimicrobial (Escherichia coli, Bacillus subtilis, Micrococcus luteus and Penicillium oxalicum) and molluscicidal...
Article
From the dichloromethane extract of leaves of Macaranga pleiostemona, four antibacterial prenylated flavanones were isolated. Their structures were elucidated by analysis of their spectral data. One, macarangaflavanone A, is a new compound, the remaining three are previously reported natural products. Macarangaflavanone B is clearly shown not to be...
Article
Three new oleanene-type triterpenoids, dillenic acids A [1], B [2], and C [3], and two known compounds, 3-oxoolean-1,12-dien-30-oic acid [4] (a new natural product) and the lupene derivative betulinaldehyde, have been isolated from the Papua New Guinean medicinal plant Dillenia papuana. The structures of the new compounds were elucidated as 2 alpha...
Article
Bioactivity-guided fractionation of a CH2Cl2 extract from the leaves of Piper aduncum afforded three new dihydrochalcones, piperaduncins A [3], B [4], and C [5], as well as two known dihydrochalcones, 2',6'-dihydroxy-4'-methoxydihydrochalcone [1] and 2',6',4-trihydroxy-4'-methoxydihydrochalcone [2] (asebogenin), together with sakuranetin, anodendro...
Article
Five new prenylated benzoic acid derivatives, methyl 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxybenzoate (1), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-hydroxybenzoate (2), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (3), methyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (4)...
Article
1.1. The lipid content and fatty acid composition of flesh and liver of 19 different species of PNG fish were studied.2.2. The total lipids were extracted with chloroform-methanol (2:1, v/v) and lipid content was determined gravimetrically.3.3. The total lipids transesterified with 7% BF3-MeoH and the distribution of fatty acid profiles were determ...
Article
In addition to stigmasterol, piperiton, methyl 2,2-dimethyl-2H-chromene-6-carboxylate, methyl 3-(2-hydroxy-3-methyl-3-butenyl)-4-hydroxy-benzoate and methyl (6S)-2-trans-6-hydroxy-2,6-dimethyl-2,7-octadienoate, three new natural products were isolated from Piper aduncum and characterized as methyl 8-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylate, 2...
Article
Five New unusual monoterpene-substituted dihydrochalcones, the adunctins A–E (1″S)-1-{2′-hydroxy-4′-methoxy-6′-[4″-methyl-1″-(1‴-methylethyl)cyclohex-3″ -en-1″ -yloxy]phenyl}-3-phenylpropan-1-one (1), (5aR*,8R*,9aR*)-3-phenyl-1-[5′,8′,9′,9′a-tetrahydro-3′-hydroxy-1′-methoxy-8′-(1″-methylethyl)-5′-a-methyldibenzo-[b,d]furan-4′-yl]propan-1-one (2), (...
Article
Bioactivity-guided fractionation of a methylene chloride extract from the leaves of Piper aduncum afforded a new amide, aduncamide. In addition, the light petrol extract yielded the sesquiterpenes viridiflorol, cubebol, spathulenol and caryophyllenol-II. For cubebol the C-NMR data are fully assigned. Aduncamide displayed antibacterial and cytotoxic...
Article
Three new compounds, 6'-O-coumaroyl-1'-O-[2-(4-hydroxyphenyl)ethyl]-beta-D-glucopyra nos ide [1] (eutigoside A), 6'-O-coumaroyl-1'-O-[2-(1-hydroxy-4-oxo-2,5-cyclohexadien-1- yl)ethyl]-beta-D-glucopyranoside [2] (eutigoside B), and 6'-O-cinnamoyl-1'-O-[2-(1-hydroxy-4-oxo-2,5-cyclohexadien-1-yl)eth yl]- beta-D-glucopyranoside [3] (eutigoside C) have...
Article
Nine angustine-type alkaloids were isolated from ammoniacal extracts of Nauclea orientalis L. (Rubiaceae). Three of them, 10-hydroxyangustine and the two diastereoisomeric 3,14-dihydroangustolines, have not been described in the literature thus far. The structures of the isolates were determined with spectroscopic methods, mainly 1D- and 2D-NMR spe...
Article
Two new indole alkaloid glycosides, 10-hydroxystrictosamide and 6'-O-acetylstrictosamide, as well as the known alkaloids strictosamide and vincosamide were isolated from the leaves of Nauclea orientalis L. The structures of the isolated compounds were determined using spectroscopic methods, mainly 1D- and 2D-NMR spectroscopy.
Article
A methanolic extract ofFicus septica leaves displayed intense antibacterial and antifungal activities. Bioactivity-guided fractionation with TLC bioautography led to the isolation of two indolizidine alkaloids, the novel ficuseptine, 4,6-bis-(4-methoxyphenyl)- 1,2,3-trihydroindolizidinium chloride, and antofine. The structure of ficuseptine was det...

Citations

... One of the distinctive features of plasma NEFA (and tissue fatty acid composition) in temperate marine teleosts is a high ratio of n-3/n-6 fatty acids (4.7 to 14.4) due to elevated levels of DHA and EPA, which are common in cold-water food chains and have important roles in the function of cold-adapted membranes in fishes (Henderson and Tocher, 1987; Hazel and Williams, 1990; Ballantyne et al., 1993). The tissue lipids of tropical marine teleosts, on the other hand, contain less DHA and more AA and its elongation product docosatetraenoic acid (22:4n-6), resulting in lower n-3/n-6 ratios (Sinclair et al., 1983; Gibson et al., 1984; Hansel et al., 1993). In fact, Sinclair et al. (1984) demonstrated that the relative n-6 fatty acid content in fishes increased as sampling occurred closer to the equator. ...
... To the best of our knowledge, this is the first report of the antifungal activity of compounds 1 to 14 against the three phytopathogenic fungi studied. In addition, no reports have been found in the literature of antifungal activity against other phytopathogenic fungi for compounds 1 to 3, 8 to 10 and 12 to 14, while antifungal activity has been reported against C. cladosporoides and C. sphaerospermum for 4 [44], and Penicillium oxalicum for 11 [46]. The maximum concentration evaluated was 200 µg/mL. ...
... After a 75-day study, it was shown that the provision of durian seed flour and Kelakai leaf flour had a very significant effect on the growth in length and weight of Nile tilapia reared. Treatment B, providing feed formulation of peeled with durian seed flour and Kelakai leaf flour as much as 5% of body weight per day resulted in the highest growth in length and weight of fish (Amid & Mirhosseini, 2012;Liu et al., 1998;Sifa et al., 2002). Thus the treatment of provision feed formulations of peeled durian seed flour and Kelakai leaf flour made a positive contribution to the growth of the length and weight of Nile tilapia. ...
... Compared with 3,20-dihydroxylupane, the downfield of H-3 (+1.34), C-3 (+2.4) and upfield of C-2 (-3.9) of 1 indicated that the fatty acid was esterified with 3-OH [19,20], which was confirmed by the correlation of H 4.54 (H-3) and C 172.7 (C-1') in the HMBC spectrum ( Figure 3). Thus, the structure of compound 1 was elucidated and named as lupan-20-ol-3()-yl 3-hydroxyoctadecanoate. ...
... Among the other Ficus species, F. septica extract showed strong antibacterial activity against E. coli, both ethyl acetate (leaves), and methanol (leaves and stem) extracts. A similar study reported that the methanol extract of F. septica leaves displayed antimicrobial activity, this extract contains two indolizidine alkaloids, the novel ficuseptine 4,6-bis-(4-methoxyphenyl)-1,2,3-trihydrolndolizidinium chloride, and antofine [26]. A study performed by Vital et al. [27] showed the presence of alkaloids, quaternary base, tannin, 2-deoxysugars, and benzopyrone nucleus in leaves of F. septica extract, and this extract revealed antimicrobial activity inhibiting the growth of S. aureus, E. coli, and Candida albicans with inhibition zone diameter of 13.83±4.01, ...
... Diuretic drugs are clinically used to the treatment of oedema, hypertension, urolithiasis and others diseases (Orjala et al., 1992;Pietrow and Karellas, 2006;Rose, 1991;Wright et al., 2007). Urolithiasis is a disturbance that affects kidney, which is considered a systemic disorder associated with bone loss and fractures, chronic kidney disease, hypertension, increased risk of coronary artery disease, metabolic syndrome, and type-2 diabetes mellitus (Sakhaee et al., 2012). ...
... In this regard, antofine and other related natural or synthetic alkaloids have been the focus of several studies due to their ability to exhibit a large spectrum of interesting biological properties. Antofine and its natural derivatives were found to be distributed mainly in the Asclepiadaceae family plants Apocynaceae (Staerk et al. 2002), Lauraceae (Othman et al. 2017), and Moraceae (Damu et al. 2009;Baumgartner et al. 1989). These alkaloids were largely studied not only for their anticancer activity (Staerk et al. 2002;Chemler 2009;Gao et al. 2007a;Bour, et al. 2014), but also for their anti-inflammatory action (Yang et al. 2007), antifungal effect (Dhiman et al. 2012), and antiviral activity (Wu et al. 2013;Wang et al. 2014). ...
... Studies of the chemical composition of P. aduncum have focused mainly on the volatile compounds of the leaves [9][10][11]. In this paper, as a continuation of our studies on the essential oil compositions of Cuban aromatic species, we report the chemical composition of P. aduncum subsp. ...
... O xidative dearomatization reactions are found in the biosynthesis of many biologically active compounds in nature. 1 In chemical synthesis, many oxidative methods mediated by mainly transition metal or hypervalent iodine compounds have been developed for the dearomatization of arenols. 2 In this context, dearomative spirolactonization of arenols tethered to a carboxyl group as an intramolecular nucleophile have been developed using iodine-based catalysis (Scheme 1a). 3 Compared with spirolactonization, oxidative spiroetherification of arenols tethered to a hydroxy group and spiroamination of arenols tethered to a secondary amido group have been less explored, 2,4 despite their usefulness for the synthesis of core structures of many biologically important compounds. 5 Conventionally, these reactions were best performed using hypervalent iodine compounds as stoichiometric oxidants under acidic conditions. 4 Recently, the oxidative cyclization of arenols under stoichiometric (R 4 N + [Br 3 ] − /K 2 CO 3 ) 6 or catalytic (10 mol % RuCl 3 / KBrO 3 ) 7 conditions has also been reported. ...
... Phytochemical research of the alcoholic extract of M. tenuiflora green propolis led to the isolation of six compounds 1-6 ( Figure 1). Their NMR spectroscopic data (Figures S1-S12) match well with previous reports, including two flavones quercetin 3methyl ether (1) and 3,3'-O-dimethylquercetin (2), and four flavanones eriodictyol 5-O-methyl ether (3), 5,4'-dihydroxy-6,7dimethoxyflavanone (4), licoflavanone (5), and macarangaflavanone B (6). [6][7][8][9][10][11] From previous studies, propolis from Asian and European regions contained a significant concentration of flavonoids, while Brazilian propolis was only accompanied by terpenoids and prenylated coumaric acids. [12] Our current result can be seen as new evidence for the presence of flavonoids in Brazilian propolis. ...