Showing papers in "Planta Medica in 1983"
TL;DR: An extract of the crude drug “ukon”, the rhizomes of CURCUMA LONGA, exhibited intense preventive activity against carbon tetrachloride-induced liver injury in primary cultured rat hepatocytes and curcuminoids were shown to possess significant antihepatotoxic action.
Abstract: An extract of the crude drug “ukon”, the rhizomes of CURCUMA LONGA, exhibited intense preventive activity against carbon tetrachloride-induced liver injury IN VIVO and IN VITRO. The extract was subjected to fractionation by monitoring the activity by the IN VITRO assay methods employing carbon tetrachloride- and galactosamine-produced cytotoxicity in primary cultured rat hepatocytes. Curcuminoids were shown to possess significant antihepatotoxic action. The liver protective effects of some analogues of ferulic acid and p-coumaric acid, probable metabolites of the curcuminoids, were also evaluated.
220 citations
TL;DR: The results suggest that magnolol causes a depression of the ascending activating systems as well as of the spinal cord.
Abstract: The pharmacological properties of magnolol and honokiol, neolignane derivatives, extracted from MAGNOLIA OFFICINALIS, used in Chinese and Japanese traditional medicine, for neurosis and gastrointestinal complaints, were investigated. Magnolol and honokiol produced sedation, ataxia, muscle relaxation and a loss of the righting reflex with an increase in dose of 50 to 500 mg/kg i.p. Magnolol and honokiol at a dose of 50 mg/kg suppressed spinal reflexes in young chicks in a similar manner, but with a much longer duration of action than mephenesin. Pretreatment of mice with magnolol 100 mg/kg inhibited tonic extensor convulsions and death produced by an intracerebroventricular injection of penicillin G potassium 50 μg. In rats, after an intraventricular injection of penicillin G 400 μg, magnolol suppressed the incidence of spike discharge, but not seizure discharge. Magnolol produced spindle discharges in sensory and motor cortex electroencephalograms and inhibited mid brain reticular formation- and hypothalamus-stimulated responses in the neo- and palaeo-cortex electroencephalograms, respectively. These results suggest that magnolol causes a depression of the ascending activating systems as well as of the spinal cord.
157 citations
TL;DR: During the course of experiments on the metabolism of Chinese crude drugs by human intestinal flora, glycyrrhizin, an active component of liquorice, was shown to be hydrolyzed to the aglycone, 18-β-glycyRRhetic acid, which was then transformed to a new compound, 3-epi-18β- glycyrrhetic acid.
Abstract: During the course of experiments on the metabolism of Chinese crude drugs by human intestinal flora, glycyrrhizin, an active component of liquorice, was shown to be hydrolyzed to the aglycone, 18-β-glycyrrhetic acid, which was then transformed to a new compound, 3-epi-18β-glycyrrhetic acid. The epimerization of 18β-glycyrrhetic acid to 3-epi-18β-glycyrrhetic acid was also shown to be reversible VIA a metabolic intermediate, 3-dehydro-18β-glycyrrhetic acid.
107 citations
TL;DR: Resveratrol, piceid and 2,3,5,4′-tetrahydroxy stilbene-2-O-D-glucoside were found to inhibit lipid peroxidation induced by ADP and NADPH in rat liver microsomes.
Abstract: The effects of POLYGONUM CUSPIDATUM S IEB. et Z UCC. (“Kojo-kon” or “Itadori-kon” in Japanese) of POLYGONUM MULTIFLORUM (“Kashuwu” or “Tsurudo-kudami-kon” in Japanese) roots and their stilbene components (piceid and 2,3,5,4′-tetrahydroxy stilbene-2-O-D-glucoside) on liver injury caused in rats by feeding peroxidized oil were investigated. Piceid and 2,3,5,4′-tetrahydroxy stilbene-2-O-D-glucoside were found to partly inhibit the deposition of lipid peroxides in the liver of those rats. The stilbene glucosides reduced the elevation of GOT and GPT levels in the serum of the rats. Furthermore, resveratrol, piceid and 2,3,5,4′-tetrahydroxy stilbene-2-O-D-glucoside were found to inhibit lipid peroxidation induced by ADP and NADPH in rat liver microsomes.
105 citations
TL;DR: Data support the assumption that the pathway leading to lupanine is the basic pathway of quinolizidine alkaloid biosynthesis and that the other alkaloids are derived from l upanine.
Abstract: The patterns of quinolizidine alkaloids in cell cultures of 10 species of Fabaceae were analyzed by high-resolution GLC and GLC-MS and compared with the alkaloids present in the leaves of the respective plants. Lupanine was produced in all 10 cell suspension cultures as the main alkaloid. It was accompanied by sparteine, tetrahydrorhombifoline, 17-oxosparteine, 13-hydroxylupanine, 4-hydroxylupanine, 17-oxolupanine, and 13-hydroxylupanine esters as minor alkaloids in some species. The alkaloid patterns of the plants differed markedly in that alpha-pyridone alkaloids were the major alkaloids in the genera Cytisus, Genista, Laburnum and Sophora but were not accumulated in the cell cultures. These data further support the assumption that the pathway leading to lupanine is the basic pathway of quinolizidine alkaloids biosynthesis and that the other alkaloids are derived from lupanine.
90 citations
85 citations
TL;DR: The differentiation of alkaloid storage cells depends both on the cell line and the growth conditions and seems to be a prerequisite for the accumulation of alk alkaloids in cell suspension cultures of CATHARANTHUS ROSEUS.
Abstract: The localization and storage of alkaloids were investigated in a low producing cell suspension culture of CATHARANTHUS ROSEUS(L.) G. Don. (Apocynaceae). Fluorescence microscopy and electron microscopy indicate alkaloid accumulation to occur inside the vacuoles of particular cells. These alkaloid storage cells exhibit a vacuolar pH of 3, while "normal" cells of a suspension culture have a vacuolar pH of about 5. Alkaloids are taken up in their unprotonated forms, trapped by protonation inside the vacuole and are accumulated there. The differentiation of alkaloid storage cells depends both on the cell line and the growth conditions and seems to be a prerequisite for the accumulation of alkaloids in cell suspension cultures of CATHARANTHUS ROSEUS.
84 citations
TL;DR: An efficient separation by HPLC of isoflavone aglycones and glucosides on reversed - phase columns is described.
Abstract: An efficient separation by HPLC of isoflavone aglycones and glucosides on reversed - phase columns is described. The main isoflavone constituents of CICER ARIETINUM L., various TRIFOLIUM species, BAPTISIA AUSTRALIS L. and ONONIS SPINOSA L. are formononetin 7-O-glucoside 6''-malonate and biochanin A 7-O-glucoside 6''-malonate.
81 citations
TL;DR: The occurrence of quaternary alkaloids in TINOSPORA (and PARABAENA) species (Menispermaceae) has been studied and only magnoflorine was detected in the ParaBAENA material examined.
Abstract: The occurrence of quaternary alkaloids in TINOSPORA (and PARABAENA) species (Menispermaceae) has been studied. The main components were generally the protoberberine bases berberine and palmatine, with jatrorrhizine an occasional minor constituent, and the aporphine base magnoflorine. Choline was also often present. Only magnoflorine was detected in the PARABAENA material examined.
81 citations
79 citations
TL;DR: Scarcely any of the scopolamine added to the medium was converted to hyoscyamine by either culture, and the alkaloids were detected in the medium as well as in the cells.
Abstract: Adventitious roots were induced from 2-year-old, hyoscyamine rich suspension cultures of Hyoscyamus niger L. The cultured roots grew well in Linsmaier-Skoog medium containing 10 (-8)M 6-benzyladenine with 3% sucrose and produced much more scopolamine (0.12-0.30% dW) than hyoscyamine (0.04-0.08% dW). The alkaloids were detected in the medium as well as in the cells. Ten to twenty percent of the hyoscyamine added to the medium was converted to scopolamine within 24 days by the root cultures, but only 1 to 3% was converted by the suspension cultures. Scarcely any of the scopolamine added to the medium was converted to hyoscyamine by either culture.
TL;DR: The rapid development of natural product chemistry has led to the isolation of a wide range of secondary metabolites, which, in many cases, was shown to be of glycosidic nature, and the largest group, the C-glycosyl flavonoids, has been intensively studied by many authors and was the subject of two recent review articles.
Abstract: The rapid development of natural product chemistry has led to the isolation of a wide varieLty of secondary metabolites, which, in many cases, was shown to be of glycosidic nature. In particular our knowledge of the chemistry, occurrence and biogenesis of glycosides has grown substantially during the last two decades [1, 2]. Most of this effort has been directed toward the large group of the 0-glycosides as well as the Sand N-glycosides. Far less effort has been given to the C-glycosides due to analytical difficulties. C-Glycosides are a special type of glycoside since the aglycone is directly attached to carbon 1 of a pyranose ring of a sugar while 0-glycosides possess a hemiacetal linkage. It is more correct to regard them as C-glycosyls or anhydropolyols as proposed by BANDYUKOVA and YUGIN [3]. Since the original term C-glycoside is well established, it should be maintained. One of the main characteristics of C-glycosides is resistance towards acid hydrolysis. Even after prolonged acid treatment the sugar residue, which is attached by a carbon-carbon-bond, remains attached to the aglycone. Cleavage of the C-C-linkage is achieved only under drastic conditions. When oxidizing reagents are used partial degradation of the sugar residue is likely [4]. Classification of C-glycosides is usually based on the aglycone [5, 6]. Five aromatic ring systems are known to occur C-glycosylated (Fig. 1). The largest group, the C-glycosyl flavonoids, has been intensively studied by many authors and was the subject of two recent review articles [3, 7]. Xanthone C-glycosides appear to be biogenetically related to C-glycosyl flavonoid compounds. Another group, C-glycosylated chromone derivatives, are relatively rare. Aromatic three-ring systems, notably the anthrones, are C-linked to glucose. C-Glycosyl derivatives of gallic acid Fig. 1. Basic structures of C-glycoside aglycones.
TL;DR: It was shown that the growth in rotary shaking cultures was 1.8 times higher than in reciprocal cultures, while the saponin production was almost the same, and the most effective hormonal condition was the combination of indole-3-butyric acid with kinetin.
Abstract: Two high saponin-producing cell lines were selected from the original callus induced in 1967 and maintained in good state. For saponin production and growth in two cell lines, the comparison of static and suspension cultures, static cultures in the dark or in the light and rotary or reciprocal shaking cultures were made in detail. It was shown that the growth in rotary shaking cultures were 1.8 times higher than in reciprocal cultures, while the saponin production was almost the same, and the most effective hormonal condition was the combination of indole-3-butyric acid with kinetin. The saponin content per fresh weight was almost the same as that of the crude drug, whereas that per dry weight was 4 times higher.
TL;DR: An IN VITRO assay method for antihepatotoxic activity using carbon tetrachloride-induced lesion in primary cultured mouse and rat liver cells was established and good correlation of results obtained with those by IN VIVO assay methods was corroborated by screening of some natural products.
Abstract: Conditions were examined to devise an IN VITRO assay method for antihepatotoxic activity using carbon tetrachloride-induced lesion in primary cultured mouse and rat liver cells. Utilizing 24 hr-preincubated hepatocytes from rats, which give more cells and are more sensitive to the hepatotoxin than mice, a satisfactory assay procedure was established. A good correlation of results obtained by this IN VITRO assay method with those by IN VIVO assay methods was corroborated by screening of some natural products. This assay method offers many advantages: numerous samples disposed at one time at a low expense, small sample sizes required, and little variation and good reproducibility of results.
TL;DR: A new naphtoquinone and 9 known phenolic components were isolated from a Japanese drug the roots of POLYGONUM CUSPIDATUM and a new component was proved to be 2-methoxy-6-acetyl-7-methyljuglone.
Abstract: A new naphtoquinone and 9 known phenolic components were isolated from a Japanese drug the roots of POLYGONUM CUSPIDATUM. The new component was proved to be 2-methoxy-6-acetyl-7-methyljuglone.
TL;DR: It is speculated that scopoletin probably produces hypotension in laboratory animals through (a) its smooths muscle relaxant activity - by which means it presumably dilates blood vessels; and (b) by acting as a non-specific spasmolytic agent (like papaverine).
Abstract: The plausible mechanisms of the hypotensive effect of scopoletin, a coumarin isolated from the fruits of TETRAPLEURA TETRAPTERA T AUB (Mimosaceae), have been investigated IN VIVO and IN VITRO. The results obtained show that scopoletin inhibits the indirect electrical stimulation-evoked contractions of the cat nictitating membrane ( IN VIVO); and also the contractions of isolated perfused central ear artery of rabbit, induced by electrical stimulation or intraluminal noradrenaline administration. This coumarin, like papaverine, reduces the amplitude and frequency of the spontaneous, myogenic, rhythmic contractions, and exogenous noradrenaline-evoked contractions of the rat isolated portal vein. Scopoletin also inhibits the spontaneous, myogenic, pendular, rhythmic contractions of the rabbit isolated duodenum and attenuates the indirect electrical stimulation-provoked or exogenous noradrenaline-induced relaxations of the muscle preparation. It also depresses the electrical stimulation-evoked contractions of the chick isolated oesophagus. Scopoletin, on its own accord, relaxes all the smooth muscles examined and inhibits the spasmogenic activities of a wide variety of agonists on guinea-pig isolated ileum to approximately the same extent. It is therefore speculated that scopoletin probably produces hypotension in laboratory animals through (a) its smooths muscle relaxant activity - by which means it presumably dilates blood vessels; and (b) by acting as a non-specific spasmolytic agent (like papaverine).
TL;DR: In the presence of lycorine, a delay in virus production and a decrease in total amount of virus were observed, suggesting that this inhibitory effect is concentration dependent, it is due to a block of viral protein synthesis and not to an extracellular inactivation or inhibition of viral adsorption.
Abstract: Lycorine, one of the principal alkaloids of the Amaryllidaceae, exerts an antiviral effect on several RNA and DNA viruses. This effect on the growth pattern of different viruses has now been investigated. In the presence of lycorine, a delay in virus production and a decrease in total amount of virus were observed. This inhibitory effect is concentration dependent, it is due to a block of viral protein synthesis and not to an extracellular inactivation or inhibition of viral adsorption.
TL;DR: Three novel diterpenoids, pseudolaric acids A, B and C, were isolated from the root bark of Pseudolarix kaempferi Gorden used as an antifungal agent in folk medicine in China.
Abstract: Three novel diterpenoids, pseudolaric acids A, B and C, were isolated from the root bark of PSEUDOLARIX KAEMPFERI G ORDEN used as an antifungal agent in folk medicine in China. The structures of pseudolaric acids B and C were assigned as 1 and 6 by spectral and chemical evidence. Pseudolaric acids A, B and C possess antifungal activity and pseudolaric acid B possesses an antifertility effect.
Journal Article•
TL;DR: Hippadine, an alkaloid of the Amaryllidaceae, produced reversible inhibition of fertility in male rats, with decrease in the testicular weight and DNA content and increase in protein concentration indicating a fall in the relative proportion of freshly divided cells.
Abstract: Hippadine, an alkaloid of the Amaryllidaceae, produced reversible inhibition of fertility in male rats. A decrease in the testicular weight and DNA content and an increase in protein concentration indicated a fall in the relative proportion of freshly divided cells. The weights of accessory sex organs revealed continued production of androgens. A plausible mechanism for this biochemical function of hippadine is envisaged.
TL;DR: A methanol extract of the Oriental crude drug “chōtōkō”, UNCARIA hooks, elicited a strong and long-lasting hypotension on injection into rats, which differed considerably from the effects expected for the known constituents, rhynchophylline and its analogues.
Abstract: A methanol extract of the Oriental crude drug “chōtōkō”, UNCARIA hooks, elicited a strong and long-lasting hypotension on injection into rats. The activity differed considerably from the effects expected for the known constituents, rhynchophylline and its analogues, which elicit only weak transient hypotensive effects. Fractionation of the extract, along with the pharmacological assays, resulted in isolation of three indole alkaloid glucosides, cadambine ( 1), 3α-dihydrocadambine ( 2) and 3β-isodihydrocadambine ( 3). The former ( 1) was found inactive but the latter two ( 2 and 3) exhibited strong and long-lasting hypotensive actions similar to the extract. 3β-Dihydrocadambine ( 4), which was not detected in the extract, also showed a strong hypotensive activity.
TL;DR: From diverse parts of POLYALTHIA NITIDISSIMA, thirteen isoquinoline alkaloids have been isolated and identified and four of these dimers, namely N,N'-dimethyllindoldhamine, isodaurisoline, 7-O-methyllinderhamine and 7'-O-Methyllindlehamine are new natural products.
Abstract: From diverse parts of POLYALTHIA NITIDISSIMA, thirteen isoquinoline alkaloids have been isolated and identified. They belong to the structural types of benzylisoquinolines, aporphinoids, protoberberines and mainly bisbenzylisoquinolines. Four of these dimers, namely N,N'-dimethyllindoldhamine, isodaurisoline, 7-O-methyllindoldhamine and 7'-O-methyllindoldhamine, are new natural products.
TL;DR: By means of isoelectric focusing and disc-gel electrophoresis evidence was obtained for the existence of four norlaudanosoline synthase isoenzymes, none of which catalyses the reaction of dopamine with 3,4-dihydroxyphenylpyruvate, the key intermediate in the formation of isoquinoline alkaloids occurring in the plant kingdom.
Abstract: A new enzyme, (S)-norlaudanosoline synthase, which catalyses the synthesis of (S)-norlaudanosoline from dopamine and 3,4-dihydroxyphenylacetaldehyde was isolated from the soluble protein extract of ESCHSCHOLTZIA TENUIFOLIA cell suspension cultures and purified approximately 40-fold. The apparent molecular weight of the enzyme is 15 500 Dalton. The pH optimum is 7.8, temperature optimum 40 degrees C, apparent K (M) values for dopamine and dihydroxyphenyl-acetaldehyde are 1.5 mM and 0.7 mM respectively. The synthase shows high substrate specificity in that only the phenylacetaldehydes are transformed but not the phenylpyruvates. No apparent cofactor requirement could be demonstrated. By means of isoelectric focusing and disc-gel electrophoresis evidence was obtained for the existence of four norlaudanosoline synthase isoenzymes, none of which catalyses the reaction of dopamine with 3,4-dihydroxyphenylpyruvate. These enzymes are responsible for the synthesis of (S)-norlaudanosoline, the key intermediate in the formation of isoquinoline alkaloids occurring in the plant kingdom.
TL;DR: A new phenolic glucoside, named curculigoside (I), was isolated from the rhizomes of CURCULIGO ORCHIOIDES G AERTN and its structure was elucidated as 5-hydroxy-2-O-beta-D-glucopyranosylbenzyl 2,6-dimetoxybenzoate.
Abstract: A new phenolic glucoside, named curculigoside (I), was isolated from the rhizomes of CURCULIGO ORCHIOIDES G AERTN. and its structure was elucidated as 5-hydroxy-2-O-beta-D-glucopyranosylbenzyl 2,6-dimetoxybenzoate.
TL;DR: Leaves of Chrysanthemum cinerariaefolium at various stages of development were found to contain differing amounts of pyrethrins, the variation corresponds to the number of oil glands per unit area of leaf surface.
Abstract: Leaves of Chrysanthemum cinerariaefolium at various stages of development were found to contain differing amounts of pyrethrins. The variation corresponds to the number of oil glands per unit area of leaf surface. Leaf tissue was mechanically and enzymatically separated into lower and upper epidermis and mesophyll cells. Pyrethrins were found to be present in each layer, more pyrethrins were present in the epidermal layers of young leaves while the mesophyll cells were found to have higher pyrethrins in older, more mature cells.
TL;DR: Both saponins inhibit the spontaneous motility of mice, even at low doses (1 mg/ kg), they show an antagonistic effect on amphetamine and exert a synergistic activity on chlordiazepoxide.
Abstract: From the leaves of COLUBRINA ASIATICA B RONGEN (Rhamnaceae) two saponins have been isolated and structurally elucidated, mainly by (13)C-NMR-spectroscopic methods, as jujubogenin-3-O-[2-O-acetyl-3-O-(3-O-beta-D-xylopyranosyl-4-O-acetyl-beta-D-glucopyranosyl)-alpha-L-arabinoside] (colubrinoside) and jujubogenin-3-O- [2-O-acetyl -3-O- (2-O- beta -D- xylopyranosyl-beta-D-glucopyranosyl)-alpha-L-arabinoside] (colubrin) respectively. Both saponins inhibit the spontaneous motility of mice, even at low doses (1 mg/ kg), they show an antagonistic effect on amphetamine and exert a synergistic activity on chlordiazepoxide.
TL;DR: The capability to immobilize living plant cells within this synthetic chemically crosslinked gel system, combined with the favourable beads/ free-medium ratio of monoterpene distribution, point towards a potential development of a continuous biotransformation process carried out by plant-cells entrapped in this system.
Abstract: Plant cells were entrapped by mixing suspended MENTHA cells with linear, water soluble polyacrylamide-hydrazide chains followed by the stoichiometric addition of glyoxal as the cross linking agent (PAAH-G entrapment). In parallel, some cells were entrapped in calcium-alginate beads, as previously described. The capability of both immobilized cell systems to reduce monoterpenes was compared with freely suspended MENTHA cells. Entrapment by either alginate or PAAH-G did not impair cell vitality, as observed by fluorescein diacetate staining. Biotransformation of (-) menthone to (+) neomenthol by M-cells and of (+) pulegone to (+) isomenthone by P-cells indicated that the transformation efficiency of the cells entrapped in PAAH-G is as high as that of freely suspended cells. Moreover, the distribution of both precursor and product in the medium versus their content in the cells (or cells contained in gel-beads) showed that less monoterpenes were retained in cells entrapped in PAAH-G, as compared to the freely suspended cells. Thus prolonged incubation (e.g. 24 hr), which usually results in appreciable loss of monoterpenes from the chloroform extract of freely-suspended-cells, caused considerably less loss from the PAAH-G entrapped-cells. In a preliminary test it was shown that PAAH-G entrapped cells were capable to perform three, consecutive, batch-type monoterpene biotransformations, without significant decrease of transformation capability. The capability to immobilize living plant cells within this synthetic chemically crosslinked gel system, combined with the favourable beads/ free-medium ratio of monoterpene distribution, point towards a potential development of a continuous biotransformation process carried out by plant-cells entrapped in this system.
TL;DR: The pharmacological actions of scopoletin on the various organsystems examined were resistant to the actions of specific antagonists such as atropine and physostigmine.
Abstract: The cardiovascular and neuromuscular actions of scopoletin have been investigated in some laboratory animals. Pharmacological examination showed that it possessed depressor (hypotensive) effects in anaesthetized rats, produced negative chronotropic and inotropic responses on guinea-pig isolated atria, inhibited acetylcholine-induced contractures of the toad rectus abdominis muscle, and depressed or abolished electrically-evoked twitches of the chick isolated biventer-cervicis muscle or rat isolated phrenic-nerve hemidiaphragm muscle preparations. The pharmacological actions of scopoletin on the various organsystems examined were resistant to the actions of specific antagonists such as atropine and physostigmine. The pharmacological implications of these findings and plausible mechanism(s) of action of scopoletin are discussed.
TL;DR: The essential oils of MAJORANA SYRIACA, CORIDOTHYMUS CAPITATUS and SATUREJA THYMBRA plants growing wild in Israel were investigated by means of GLC and GLC-MS.
Abstract: The essential oils of MAJORANA SYRIACA, CORIDOTHYMUS CAPITATUS and SATUREJA THYMBRA plants growing wild in Israel were investigated by means of GLC and GLC-MS. 18 components were identified, the main ones being thymol, carvacrol, gamma-terpinene and p-cymene.
TL;DR: The extraction and Spectrophotometric assay procedure is described for analysis of ODAP in small samples, suitable for the assay of 3-4 seeds of most Lathyrus species, and has been used to screen a collection of Lath Cyrus accessions for use in a breeding program to develop agronomic strains with low toxicity.
Abstract: Lathyrus species have potential as feed crops, but many contain a neurotoxin, beta-N-oxalyl-L-alpha-beta-diaminopropionic acid (ODAP). An extraction and Spectrophotometric assay procedure are described for analysis of ODAP in small samples (0.5 g) of seed. The assay utilizes o-phthalaldehyde as a reagent, following hydrolysis of the ODAP. It is sensitive and specific, and suitable for the assay of 3-4 seeds of most Lathyrus species. The method has been used to screen a collection of Lathyrus accessions for use in a breeding program to develop agronomic strains with low toxicity.