Showing papers in "Planta Medica in 1982"
TL;DR: Screening results with seed extracts of 41 species of Euphorbiaceae were compared with 9KB and 9PS cytotoxicities and the method is rapid, reliable, inexpensive, and convenient as an in-house general bioassay tool.
Abstract: A method, utilizing brine shrimp (Artemia salina Leach), is proposed as a simple bioassay for natural product research. The procedure determines LC (50) values in microg/ml of active compounds and extracts in the brine medium. Activities of a broad range of known active compounds are manifested as toxicity to the shrimp. Screening results with seed extracts of 41 species of Euphorbiaceae were compared with 9KB and 9PS cytotoxicities. The method is rapid, reliable, inexpensive, and convenient as an in-house general bioassay tool.
3,617 citations
TL;DR: The structures of the prosapogenins were investigated by (13)C-NMR spectroscopy and Rg (1)-prosapogenin II was shown to be a mixture of ginsenoside Rh (1), and its C-20 epimer, produced by hydrolysis followed by epimerization at C- 20.
Abstract: Ginseng saponins, ginsenosides Rg (1), Re and Rb (1), decomposed under mild acidic conditions to yield prosapogenins. The structures of the prosapogenins were investigated by (13)C-NMR spectroscopy and Rg (1)-prosapogenin II was shown to be a mixture of ginsenoside Rh (1), and its C-20 epimer, produced by hydrolysis followed by epimerization at C-20. Rg (1)-prosapogenin III, the other prosapogenin derived from ginsenoside Rg (1); was a C-25,26 hydrated derivative of Rg (1)-prosapogenin II. Re-prosapogenin II was identified as a mixture of ginsenoside Rg (2) and its C-20 epimer, and Re-prosapogenine III as a C-25,26 hydrated derivative of Re-prosapogenin II.
174 citations
TL;DR: A series of 24 different saponins isolated from various medicinal plants have been tested against Biomphalaria glabrata, one of the snail vectors of schistosomiasis (bilharziasis).
Abstract: A series of 24 different saponins isolated from various medicinal plants have been tested against Biomphalaria glabrata, one of the snail vectors of schistosomiasis (bilharziasis). In general, monodesmosidic triterpenoid saponins exhibit strong molluscicidal activity whereas bidesmosidic saponins as well as the aglycones are fully inactive. Some dammarane glycosides and alkaloidal saponins have also been tested.
114 citations
TL;DR: The present paper is a continuation of the study on the Chinese traditional herb Artemisia annua, describing several additional constituents: quinghaosu IV and V (V, VII), quinghao acid (VIII) and a paraffinic alcohol; V, VII and VIII are compounds with unreported structures.
Abstract: The present paper is a continuation of our study on the Chinese traditional herb Artemisia annua L. [1-5], describing several additional constituents: quinghaosu IV and V (V, VII), quinghao acid (VIII) [6], chrysosplenol (VIa) [7] and a paraffinic alcohol; V, VII and VIII are compounds with unreported structures.
112 citations
TL;DR: A tentative structure for kolanone has been proposed based on a comparison of its spectral data with that published for other compounds of this class.
Abstract: Kolanone, a novel polyisoprenyl benzophenone, has been isolated from the fruit pulp of GARCINIA KOLA H EKKEL. A tentative structure for kolanone has been proposed based on a comparison of its spectral data with that published for other compounds of this class. Kolanone has been shown to exhibit significant antimicrobial activity against a range of organisms.
107 citations
TL;DR: The ether and methanol extracts of MAGNOLIAE CORTEX had potent antibacterial action against a cariogenic bacterium, STREPTOCOCCUS MATUANS, and the active principles of the extracts were identified to be magnolol and honokiol, which were bactericidal in the minimal inhibitory concentration.
Abstract: The ether and methanol extracts of MAGNOLIAE CORTEX (barks of MAGNOLIA OBOVATA T HUNB. or M. OFFICINALIS R HED. et W ILS.) had potent antibacterial action against a cariogenic bacterium, STREPTOCOCCUS MATUANS. The active principles of the extracts were identified to be magnolol and honokiol, which were bactericidal in the minimal inhibitory concentration (MIC) of 6.3 μg/ml against S. MUTANS. The antibacterial action of both compounds was stronger than that of berberine, a typical antibacterial alkaloid (MIC: 50 μg/ml), Magnolol and honokiol, however, did not inhibit glucosyltransferase (EC 2.4. 1.5) activity obtained from S. MUTANS and adherence of the heat-treated cells to glass or smooth tooth surfaces in the presence of glucosyltransferase and sucrose IN VITRO.
89 citations
TL;DR: A bicyclic sesquiterpene dialdehyde “Polygodial” has been isolated from leaves of the New Zealand tree PSEUDOWINTERA COLORATA and shown to possess strong antibiotic activity against the yeast CANDIDA ALBICANS.
Abstract: A bicyclic sesquiterpene dialdehyde “Polygodial” has been isolated from leaves of the New Zealand tree PSEUDOWINTERA COLORATA and shown to possess strong antibiotic activity against the yeast CANDIDA ALBICANS. Polygodial was also found in DRIMYS WINTERI but was absent from P. AXILLARIS and P. TRAVERSII.
78 citations
TL;DR: Strictosidine synthase was partially purified from Catharanthus roseus cell suspension cultures and immobilized on CNBr-activated Sepharose and catalyses exclusively the formation of the 3alpha(S)-isomer, strictosidine.
Abstract: Strictosidine synthase was partially purified from Catharanthus roseus cell suspension cultures and immobilized on CNBr-activated Sepharose. The immobilized enzyme exhibits a thermostability increased 300 fold over that of the soluble enzyme and catalyses exclusively the formation of the 3alpha(S)-isomer, strictosidine. Gram quantities of this biologically active glucoalkaloid, which hitherto had been difficult to synthesize and purify, were prepared.
75 citations
TL;DR: The isolation of acteoside and coniferin from Paulownia tomentosa bark along with the previously reported phenolic glucoside syringin is described.
Abstract: The isolation of acteoside and coniferin from Paulownia tomentosa bark along with the previously reported phenolic glucoside syringin is described. The structure of both, acteoside and coniferin, have been assigned by (1)H- and (13)C-NMR spectroscopy.
68 citations
TL;DR: Fagaramide dose-dependently inhibited prostaglandin synthesis in VITRO but had no effect on PGE 1 - induced potentiation of carrageenan oedema in indomethacin treated rats, suggesting that at least part of the anti-inflammatory activity of fagaramide is mediated via inhibition of prostaglandsin synthesis.
Abstract: The anti-inflammatory activity of piperonyl-4-acrylicisobutyl-amide (fagaramide) has been studied. Fagaramide was effective against carrageenan paw oedema in rats and was approximately twenty times less potent than indomethacin, a non-steroidal anti-inflammatory agent. Fagaramide was effective against the prostaglandin phase of an acute experimental inflammatory reaction. It dose-dependently inhibited prostaglandin synthesis IN VITRO but had no effect on PGE 1 - induced potentiation of carrageenan oedema in indomethacin treated rats. It is thus suggested that at least part of the anti-inflammatory activity of fagaramide is mediated via inhibition of prostaglandin synthesis.
TL;DR: The isolation of quinoline alkaloid, indole alkaloids and anthraquinones present in callus cultures initiated from different parts of Cinchona ledgeriana plants is described and a new minor alkaloidal was isolated and identified as 10-methoxycinchonamine.
Abstract: The isolation of quinoline alkaloids, indole alkaloids and anthraquinones present in callus cultures initiated from different parts of Cinchona ledgeriana plants is described. From leaves of C. ledgeriana a new minor alkaloid was isolated and identified as 10-methoxycinchonamine.
TL;DR: The essential oil of Origanum majorana L. plants, wild growing in Turkey, was investigated by means of LSC and GLC and contained about 65% carvacrol and 4% thymol.
Abstract: The essential oil of Origanum majorana L. plants, wild growing in Turkey, was investigated by means of LSC and GLC. The oil contained about 65% carvacrol and 4% thymol.
TL;DR: The structure of mulberrofuran C was shown to be VIII on the basis of spectral data and it was regarded biogenetically as a Diels-Alder adduct of a chalcone derivative and a dehydroprenyl 2-arylbenzofuran derivative.
Abstract: In addition to mulberrofuran C, a new 2-arylbenzofuran derivative, six flavonoid derivatives, cyclomorusin, morusin, kuwanon C, E, G and H, as well as a known 2-arylbenzofuran derivative, chalcomoracin, were isolated from extracts of root bark of the cultivated mulberry tree (a variety of Morus bombycis K OIDZUMI). The structure of mulberrofuran C was shown to be VIII on the basis of spectral data. It is regarded biogenetically as a Diels-Alder adduct of a chalcone derivative and a dehydroprenyl 2-arylbenzofuran derivative. Intravenous injection of mulberrofuran C produced significant hypotension in rabbit.
TL;DR: Successive fractionation of a crude methanolic extract of cultured PICRALIMA NITIDA cells accompanied by opiate receptor binding studies led to the detection and isolation of two compounds with opioid activity.
Abstract: Successive fractionation of a crude methanolic extract of cultured PICRALIMA NITIDA cells accompanied by opiate receptor binding studies led to the detection and isolation of two compounds with opioid activity. The substances were identified as the indole alkaloids pericalline and pericine, the latter, as yet, not described. Half-maximal inhibition (IC 50 ) by the alkaloids was 2.3 μMol/l for pericalline and 0.6 μMol/l for pericine, values which lie within the micromolar range of the weak analgetic codeine (IC 50 : 3.6 μMol/l).
TL;DR: Nobiletin, irigenin and pentamethyl quercetin showed inhibitory effect on barium sulphate transport in the small intestine of mice and further pharmacological investigations have revealed that these flavonoids have cholinergic activity.
Abstract: Nobiletin and irigenin were identified as inhibitors of cyclic AMP phosphodiesterase, which were contained in peels of immature fruits of CITRUS RETICULATA B LANCO (Japanese name “Seihi”) and in rhizomes of IRIS FLORENTINA L. The structure activity relationships of 33 flavonoids were studied and polymethoxy flavonoids were generally more inhibitory against cAMP phosphodiesterase than corresponding polyhydroxy flavonoids. Nobiletin, irigenin and pentamethyl quercetin showed inhibitory effect on barium sulphate transport in the small intestine of mice. Further pharmacological investigations have revealed that these flavonoids have cholinergic activity.
TL;DR: The structures of the two new secamine type alkaloids, 16-hydroxytetrahydrosecamine and 16-Hydroxy,16-demethoxycarbonyltetrahYDro Secamine were determined by means of their spectral data.
Abstract: From ASPIDOSPERMA EXCELSUM, rootbark, which has previously been shown to exhibit antimicrobial activity, 6 antimicrobial active alkaloids were isolated and identified: 11-methoxytubotaiwine, ochrolifuanine A, tetrahydrosecamine, 16-demethoxycarbonyltetrahydrosecamine, 16-hydroxytetrahydrosecamine and 16-hydroxy, 16-demethoxycarbonyltetrahydrosecamine. The minimum inhibitory concentration was determined for some of the alkaloids, using BACILLUS SUBTILIS as test organism. Didemethoxycarbonyltetrahydrosecamine was also shown to exhibit antimicrobial activity. No activity against gram negative bacteria could be found for the alkaloids by means of biograms. The site of demethoxycarbonylation in demethoxycarbonyltetrahydrosecamine was established as C-16. The structures of the two new secamine type alkaloids, 16-hydroxytetrahydrosecamine and 16-hydroxy,16-demethoxycarbonyltetrahydrosecamine were determined by means of their spectral data. During the isolation of the antimicrobially active alkaloids some inactive alkaloids were also isolated: compactinervine, N a -acetylaspidospermidine, O-dimethylaspidospermine, aricine, yohimbine and O-acetylyohimbine.
TL;DR: The composition of the phthalide mixture of the essential oil from roots of Levisticum officinale Koch was investigated and isosenkyunolide and propylidenephthalide were tentatively identified.
Abstract: The composition of the phthalide mixture of the essential oil from roots of LEVISTICUM OFFICINALE K OCH was investigated. The phthalide mixture was analyzed by combining separation methods - GLC, LSC and TLC - and subsequently using spectroscopic methods - IR, MS and NMR. E- and Z-butylidenephthalide, E- and Z-ligustilide, senkyunolide and validene-4,5-dihydrophthalide were found to be present; ISOsenkyunolide and propylidenephthalide were tentatively identified. The influence of the isolation procedure on the composition of the phthalide mixture was tentatively studied by comparison of mixtures isolated by solvent extraction and hydrodistillation respectively.
TL;DR: Since decarboxylated anacardic acid (cardanol) and salicylic acid do not kill snails at concentrations up to 5 ppm, it appears that both, carboxyl group and unsaturated side chain are absolutely required for molluscicidal activity.
Abstract: The components of anacardic acid, (a mixture of 6-n-C (15) alkylsalicylic acids whose side chains vary in degrees of unsaturation) have been isolated by high pressure liquid chromatography from a crude extract of cashew nut shell, Anacardium occidentale, and tested for toxicity to fresh water snails, Biomphalaria glabrata. The triene component is the most toxic form (LC (50) 0.35 ppm), the diene and monoene components are less toxic (LC (50) 0.9 and 1.4 ppm), and the saturated component is relatively nontoxic (LC (50) > 5 ppm). Since decarboxylated anacardic acid (cardanol) and salicylic acid do not kill snails at concentrations up to 5 ppm, it appears that both, carboxyl group and unsaturated side chain are absolutely required for molluscicidal activity. The mechanism of toxicity of anacardic acid to snails is unknown.
TL;DR: The fingerprint of the capillary gas-chromatogramm permitted differentiation of the essential oil of Melissa officinalis, Cymbopogon winterianus and Nepeta cataria var.
Abstract: Different oil-samples of Melissa officinalis L. were analysed by capillary GC/MS, using fused silica columns and E.I.-Mass-spectrometry. Comparing the observed mass-spectra with those of a spectral collection, 70 compounds of the oil were identified. Geranial, neral, 6-methyl-5-hepten-2-one, citronellal, geranyl-acetate, beta-caryophyllene, and beta-caryophyllene-oxide comprise about 96%. The fingerprint of the capillary gas-chromatogramm permitted differentiation of the essential oil of Melissa officinalis, Cymbopogon winterianus and Nepeta cataria var. citriodora., as well as a standardisation of pharmaceutical preparations containing Melissa oil.
TL;DR: Falcarindiol has been isolated in high yield from leaves of the N. Z. plant SCHEFFLERA DIGITATA but was not detected in other species of Araliaceae.
Abstract: Falcarindiol [(9Z)-heptadeca-1,9-diene-4,6-diyn-3,8-diol] has been isolated in high yield from leaves of the N. Z. plant SCHEFFLERA DIGITATA but was not detected in other, closely-related, species of Araliaceae. Low concentrations of falcarindiol were found to inhibit the germination of spores of most common dermatophyte fungi.
TL;DR: The results of the present study show that the hypotensive and bradycardiac effects of T. ARJUNA are mainly of central origin.
Abstract: TERMINALIA ARJUNA (Hindi name Arjuna, Family Combretacae) has been used in the treatment of cardiovascular disorders by Ayurvedic physicians. However, its properties have not been scientifically evaluated so far. Therefore, the present study was carried out to examine the underlying mechanism of the cardiovascular effects of aqueous solution of TERMINALIA ARJUNA extract. Intravenous (I. V.) administration of the extract was found to induce dose dependent decrease in blood pressure (B. P.) and heart rate (H. R.). These extracts also inhibited carotid occlusion response, without affecting the pressor responses, induced by intravenous injection of norepinephrine and by electrical stimulation of preganglionic fibres of the abdominal splanchnic nerve. Hypotension and bradycardia were also observed following the injection of the extract into the lateral cerebral ventricle and vertebral artery. The results of the present study show that the hypotensive and bradycardiac effects of T. ARJUNA are mainly of central origin.
Journal Article•
TL;DR: The alkaloids produced by leaf organ, root organ and root suspensions of two varieties of Cinchona ledgeriana have been determined quantitatively by HPLC, in contrast to previous findings.
Abstract: The alkaloids produced by leaf organ, root organ and root suspensions of two varieties of Cinchona ledgeriana have been determined quantitatively by HPLC. In contrast to previous findings, the root organs and root suspensions yielded quinine and quinidine. The root cells release alkaloids into the suspension medium.
TL;DR: I, a strong irritant, prepared by partial synthesis from ingenol (I) proved to be a weak tumor promoter as well and the antileukemic ingenol-3,20-dibenzoate (IX) was not found in the plant material investigated here.
Abstract: An ethyl acetate fraction of aerial parts of E. ESULA L. collected in Germany was shown to exhibit irritant and weak tumor promoting but not solitary carcinogenic activity. The diterpene moiety of the irritants and tumor promotors contained in E. esula was identified to be ingenol (I). From aerial parts the irritant 3-0-(2E,4Z)-decadienoylingenol (III, Euphorbia factor E 1 ) and a mixture E M of irritant Euphorbia factors shown to contain Euphorbia factor E 1 , 3-0-(2,4,6)-decatrienoylingenol (V, Euphorbia factor E 2 ) and 3-0-(2,4,6,8)-dodecatetraenoylingenol (VI, Euphorbia factor E 3 ) were isolated. The antileukemic ingenol-3,20-dibenzoate (IX) was not found in the plant material investigated here. IX, a strong irritant, prepared by partial synthesis from ingenol (I) proved to be a weak tumor promoter as well.
TL;DR: From the essential oil of myrrh, Commiphora abyssimica (Berg) Engler (Burseraceae) have been isolated: nine sesquiterpenoid hydrocarbons and the furanosesquiter penoids furanodiene, furanodienone, isofuranogermacrene, curzerenone and lindestrene.
Abstract: From the essential oil of myrrh, Commiphora abyssimica (Berg) Engler (Burseraceae) have been isolated: nine sesquiterpenoid hydrocarbons, the sesquiterpene alcohol elemol and the furanosesquiterpenoids furanodiene, furanodienone, isofuranogermacrene, curzerenone and lindestrene.
TL;DR: From the leaves and flowers of Crataegus monogyna and C. Pentagyna six new flavonoid-C- and O-glycosides respectively have been isolated and identified as 2''-O-rhamnosyl-orientin, 2''.
Abstract: From the leaves and flowers of Crataegus monogyna and C. Pentagyna six new flavonoid-C- and O-glycosides respectively have been isolated and identified as 2''-O-rhamnosyl-orientin, 2''-O-rhamnosyl-isoorientin, 2''-O-rhamnosyl-isovitexin, rutin, spiraeosid, 8-methoxy-kampferol and 8-methoxy-kampferol-3-O-glucoside. The structure of O-rhamnosyl-vitexin and O-acetyl-O-rhamnosyl-vitexin isolated previously, have been elucidated unambigiously mainly by NMR- and MS-spectroscopy.