Crude Alkaloid Fraction Research Articles

Toxicity and growth inhibitory activities of methanol extract and the β-carboline alkaloids of Peganum harmala L. against two coleopteran stored-grain pests

Methanol extract and the β-carboline alkaloids were extracted from the seeds of Peganum harmala (Zygophyllaceae). Their toxicity, growth inhibitory and effects on the progeny production of Tribolium castaneum and Rhyzopertha dominica was studied. To assess any additive effects among the extracted β-carbolines, they were tested as binary mixtures (1:1) or as a crude alkaloid fraction. All extracts exhibited a considerable adulticidal effect with increasing activities in response to increased exposure period. Using the contact toxicity bioassay, the crude β-carboline fraction was the most effective (LC 50’s were 20.1 and 36.7) μg/cm 2, 48 h post-treatment against R. dominica and T. castaneum, respectively. LC 50’s of (harmaline + harmine), (harmaline + harmane), and methanol extract were (31.2, 39.4), (33.7, 47.2), and (39.8, 65.2) μg/cm 2, 24 h post-treatment against R. dominica and T. castaneum, respectively. At 48 h post-treatment, LC 50 of (harmaline + harmine) reached 22.4 μg/cm 2 against R. dominica. When mixed with the insect’s diets, toxicity of all extracts were increased with the crude alkaloidal fraction the most toxic (LC 50’s were 7.8 and 14.7) mg/kg grains, 48 h post exposure against R. dominica and T. castaneum, respectively. When the 2nd instar larvae were fed sub-lethal doses-treated grains, development and F1 progeny of both insects were significantly affected ( P ≤ 0.001). At 3.5 mg/kg grains of the crude alkaloidal extract, percentages of malformed larvae and pupae of T. castaneum were 19.7 and 33.4%, respectively. In this case, a total life span of 81.3 days was recorded for the treated individuals compared to 44.2 for the control. A reduction in the adult progeny of 56.9, 44.0 and 43.6% was obtained with 3.5 mg/kg of the crude alkaloids, (harmaline + harmine) and methanol extract, respectively. Meanwhile, the reduction in adult progeny of R. dominica reached 79.2% with the same concentration of the crude alkaloid extract.

The novel antihyperglycaemic action of hunteria umbellata seed fractions mediated via intestinal glucose uptake inhibition

The present study evaluated the antihyperglycaemic effect and mechanism of action of fractions of the aqueous seed extract of Hunteria umbellata (K. Schum.) Hallier f. ( HU ) in normal and alloxan-induced hyperglycaemic rats. HU was partitioned in chloroform, acetyl acetate and butan-1-ol to give chloroform fraction ( HU c), ethyl acetate fraction ( HU e), butanol fraction ( HU b) and the “residue” ( HU m), respectively. 200 mg/kg of each of these fraction dissolved in 5% Tween 20 in distilled water was investigated for its acute oral hypoglycaemic effects in normal rats over 6 hours while its repeated dose antihyperglycaemic effect was evaluated in alloxan-induced hyperglycaemic rats over 5 days. In addition, 50 mg/kg of the crude alkaloid fraction ( HU Af) extracted from HU was evaluated for its possible antihyperglycaemic activity in alloxaninduced hyperglycaemic rats using oral glucose tolerance test (OGTT) over 6 hours. Using the solvent system, distilled water-butanol-ammonium hydroxide (2:15:1, v/v/v), HU b was chromatographed and stained with Dragendorff’s reagent for confirmatory qualitative analysis for alkaloids. Results showed that oral pre-treatment with 200 mg/kg of HU e, HU b and HU m resulted in a significant (p<0.05, p<0.001) time dependent hypoglycaemic effect, with the butan-1-ol fraction HU causing the most significant (p<0.001) hypoglycaemic effect. In the alloxan-induced hyperglycaemic rats, repeated oral treatment with 200 mg/kg of same HU fractions for 5 days resulted in significant (p<0.05) decreases in the fasting blood glucose concentrations with the most significant (p<0.01) antihyperglycaemic effect also recorded for HU b. Similarly, oral pretreatment with 50 mg/kg of HU Af significantly (p<0.05, p<0.01 and p<0.001) attenuated an increase in the post-absorptive glucose concentration at 1st -6th h in the alloxan-induced hyperglycaemic OGTT model. In addition, alkaloid was present in most of the separated spots on the TLC plate. In conclusion, results of this study showed that HU contains a relative high amount of alkaloids which could have accounted for the antihyperglycaemic action of HU that was mediated via intestinal glucose uptake inhibition. Key words: Hunteria umbellata aqueous seed extract, Alkaloid fraction, Intestinal glucose uptake inhibition, Normal and alloxan-induced hyperglycaemic rats

Hasubanan type alkaloids in Stephania hernandifolia

To study the hasubanan type alkaloids in Stephania hernandifolia. The dried herbs of S. hernandifolia. were extracted with 95% ethanol. After removal of the solvent, the residue was first partitioned between acid water and petroleum ether, then the aqueous layer was basified and extracted with chloroform to obtain crude alkaloids. Column chromatograghic methods with on silica gel, Rp-18, MCI CHP 20P, Sephadex LH-20 were applied for the isolation and purification of the crude alkaloid fraction. The structures were elucidated by their physicochemical properties and spectral data. Nine hasubanan type alkaloids were obtained and identified as aknadinine(1), longanone(2), stephasunoline (3), N-methylstephuline(4), epistephamiersine(5), prostephabyssine(6), aknadilactam(7), dihydroepistephamiersine(8), hasubanonine(9). Compounds 2-8 were isolated from this plant for the first time.

Antiplasmodial activity of atisinium chloride from the Bhutanese medicinal plant, Aconitum orochryseum

Ethnopharmacological relevance The plant Aconitum orochryseum Stapf. (Ranunculaceae) is employed together with other plants in Bhutanese traditional medicine and is indicated for malaria-associated fever. Aim of the study To study the in vitro antiplasmodial activity of atisinium chloride, the major alkaloid from Aconitum orochryseum. Materials and methods Atisinium chloride was extracted and purified from aerial parts of Aconitum orochryseum and its structure and absolute configuration confirmed by single crystal X-ray crystallography. The crude methanol extract, crude alkaloid fraction, and atisinium chloride were tested for in vitro antiplasmodial activity against the malarial Plasmodium falciparum strains TM4/8.2 (TM4; wild type) and K1CB1 (K1; chloroquine and antifolate resistant). Results The diterpenoid alkaloid atisinium chloride was shown to have moderate antiplasmodial activities with IC 50 values of 4 μM and 3.6 μM, respectively against the TM4 strain and the K1 strain of Plasmodium falciparum. Conclusions Our studies provide the first evidence in support of one of the indicated treatments with Aconitum orochryseum in Bhutanese traditional medicine. This alkaloid also represents a potential new antimalarial structural lead.

Evaluation of Analgesic Potential of Solanum trilobatum Roots

In the present work, the antinociceptive action was assayed in several experimental models in mice: writhing, formalin and hot plate tests. The crude alkaloid fraction (25, 50, 100 mg/

Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD

The metabolism of the phenolic 1-benzyltetrahydroisoquinoline alkaloids was studied in cell cultures of Macleaya and Corydalis species. The crude alkaloid fraction obtained from feeding experiments was investigated by application of the combined LC/NMR and LC/APCI-MS (/MS) techniques. Several metabolites were detected, and their structures (6 and 8-14) were identified. Bioconversion of the phenolic 1-benzyltetrahydroisoquinoline (2) into the pseudoprotoberberine (8) was demonstrated for the first time. LC/APCI-MS and LC/CD experiments carried out on a chiral column permitted the deduction of the major enantiomeric form of the chiral metabolites. Thus, the combination of NMR, MS, and CD data permitted the structural elucidation and stereochemical analysis of the metabolites in the extract matrix solution, without isolation and sample purification prior to the coupling experiments.

Antioxidant Activity of Crude Extract, Alkaloid Fraction, and Flavonoid Fraction from Boldo (Peumus boldus Molina) Leaves

ABSTRACT: Boldo is an endemic plant from Chile widely used in folk medicine, whose biological (mainly antioxidant) activity has been attributed to the presence of the alkaloid boldine. The aim of this study was to determine the contribution of the flavonoid and other crude fractions from boldo leaves to the antioxidant activity of extracts. The main constituent in the flavonoid fraction was also isolated. The antioxidant activity and reducing power of crude boldo extract and fractions were measured and compared with natural and synthetic antioxidants. The antioxidant activity of boldo leaf extracts came mainly from the flavonoid fraction (44.1%) followed by the alkaloid fraction (15.6%), with catechin and boldine being the main contributors of the antioxidant activity of these 2 fractions (60.9% and 35.6% of the total activity, respectively). On the basis of these results, we propose to use catechin and boldine as markers for the antioxidant activity of boldo leaves. Tailor‐made antioxidants to be used in foods can be prepared by enriching these 2 fractions.

Pharmacological effect and toxicity of alkaloids from Gelsemium elegans Benth.

Gelsemium elegans Benth. (Loganiaceae), a toxic plant indigenous to southeastern Asia, is well known among hilltribes as an effective means for committing suicide. A crude alkaloidal fraction from its leaves was isolated by conventional acid–base extraction. Tests in animals showed that the alkaloids exerted analgesic and anti-inflammatory effects. At a lethal dose, the alkaloids produced violent clonic convulsions that led to respiratory failure. Since the convulsions could be prevented by pentobarbital or diazepam and potentiated by reserpine, it is postulated that the alkaloids act centrally against GABA action.

Anti-inflammatory, antipyretic and antinociceptive activities of Tabernaemontana pandacaqui Poir

Studies on carrageenin-induced rat paw edema, yeast-induced hyperthermia in rat and writhing response induced by acetic acid in mice showed that the alcoholic extract of stems of Tabernaemontana pandacaqui ( T. pandacaqui) has significant anti-inflammatory, antipyretic and antinociceptive activities. These activities are due to alkaloidal components since they were also observed when the crude alkaloidal (CA) fraction separated from alcoholic extract was tested in the same models.

Alkaloid Production in Diploid and Autotetraploid Plants of Datura stramonium

A comparative investigation of alkaloid production and accumulation in the roots and leaves of diploid (2n = 24), and C 4 generation of induced autotetraploid (4n = 48) Datura stramonium L. plants was performed. Fifteen alkaloids have been determined in the roots and two in the leaves, at a level of 1% or more of the crude alkaloid fractions in both ploidy levels. Two 3-tigloyloxy-6-isovaleryloxy-7- hydroxytropane isomers were detected for the first time in genus Datura. In the conditions of the prolonged photoperiod, hyoscyamine was the main alkaloid in the roots whereas scopolamine was the main alkaloid in the leaves of both ploid forms. In comparison to diploids, the roots and leaves of tetraploids had a higher alkaloid content and scopolamine/hyoscyamine ratio.

An evaluation of toxicity of Taxus baccata Linn. (Talispatra) in experimental animals

A toxicological study was performed in albino mice and rat with methanolic extract and isolated alkaloid of Taxus baccata Linn. (family: Taxaceae). LD 50 study showed the higher toxic activity in stem (TXA-1,2,3) as compared with leaf (TXB-1,2,3) extract. As the extract were further fractionated into crude alkaloids and purified by chromatography the toxicity of these fractions were found to be in increasing order as follows: methanolic extract (1)<crude alkaloidal fraction (2)<purified alkaloidal fraction (3). The effects of leaf and stem extract of T. baccata were studied on certain biochemical and haematological parameters of mice and rat after 10, 20 and 30 days of exposure. Among the parameters examined, the exposed animal exhibited significant decrease in total leukocyte count (TLC), lymphocytes and cholesterol level (mg/dl), whereas increase was observed in serum transminases (SGOT, SGPT) and alkaline phosphatase (AP) of TXA-1 and TXB-1 treated groups indicating toxic conditions associated due to liver involvement.

Antiproliferative effects of alkaloids from Sedum sarmentosum on murine and human hepatoma cell lines

The whole plant of Sedum sarmentosum (SS) has been traditionally used for the treatment of chronic viral hepatitis in China and South Korea. Certain hepatitis virus causes acute and chronic hepatitis and induces hepatocellular carcinoma (HC). In the present study, we examined whether the crude alkaloid fraction (CAF) of SS had any anticancer effects on hepatoma cell lines. Murine hepatoma (BNL CL.2) and human hepatoma (HepG2) cell lines were cultured in the presence of CAF of SS at various doses (50–150 μg/ml) for 24 or 48 h. CAF caused a dose-dependent inhibition of cell proliferation without necrosis or apoptosis. Antiproliferative effects of CAF of SS were associated with an increase in the number of cells in the G1 phase of cell cycle. This study suggests that SS may improve survival of hepatoma patients via the inhibition of excessive growth of tumor cells.

Droplet counter-current chromatography of indole alkaloids from Tabernaemontana hilariana

This paper reports the separation of the indole alkaloids from the benzene extract of the root barks of Tabernaemontana hilariana (Apocynaceae). The crude alkaloid fraction was fractionated by droplet counter-current chromatography using a low polarity mixture (hexane:ethyl acetate:ethanol:water). Nine indole alkaloids (3-hydroxycoronaridine, coronaridine, voacangine, 3-(2-oxopropyl) coronaridine, voacangine hydroxyindolenine, ibogamine, voacangine pseudoindoxyl, coronaridine pseudoindoxyl and tabernanthine) were identified using thin layer chromatography, gas chromatography coupled with mass spectrometry and nuclear magnetic resonance spectroscopy. Copyright © 1999 John Wiley & Sons, Ltd.

Neuropharmacological activities of the crude alkaloidal fraction from stems of Tabernaemontana pandacaqui Poir.

The crude alkaloidal (CA) fraction from the stem of Tabernaemontana pandacaqui Poir. was studied for its pharmacological activity on the central nervous system (CNS) of animals. The CA fraction was found to produce symptoms of CNS depression in conscious rats and mice, viz. reduction in spontaneous motility, potentiation of pentobarbital sleeping time, prolongation of latency of convulsions induced by pentylenetetrazole and antinociception. However, the fraction could not antagonize oxotremorine-induced tremor. The observations suggest that the CA fraction possesses a CNS depressant activity.

Inhibition of cytochrome P450-dependent monooxygenases by an alkaloid fraction from Helietta apiculata markedly potentiate the hypnotic action of pentobarbital

Crude alkaloid fraction (CAF) isolated from the leaves of Helietta apiculata showed the presence of furoquinolines. The extract was investigated to determine if it can enhance the sensitivity of the central nervous system (CNS) to the hypnotic action of pentobarbital. Administration of CAF to mice in a dose range of 300–500 mg/kg prior to an injection of pentobarbital (40 mg/kg, i.p.) was associated with a statistically significant decrease of sleep latency and prolongation of pentobarbital-induced sleeping time. Pretreatment of rats with the same alkaloid extract (150 mg/kg, i.p. for 4 days) prior to administration of pentobarbital (40 mg/kg, i.p.) caused not only significant reduction of the levels of microsomal proteins, total cytochrome P450 enzymes and a decrease of aminopyrin- N-demethylation and 3,4-benz(a)pyrene hydroxylation but also changed the pattern of cytochrome P450. It is concluded that the CAF isolated from H. apiculata can potentiate the CNS depressant effect of pentobarbital due to alteration of barbiturate metabolism through inhibition, mainly, of cytochrome P450-dependent enzymes.

Cardiovascular activity of the crude alkaloidal fraction from Tabernaemontana pandacaqui in the rat

The effects of a crude alkaloidal (CA) fraction from the stem of Tabernaemontana pandacaqui Poir. on the blood pressure and heart rate were investigated in conscious as well as anesthetized rats. The CA fraction exerted a hypotensive activity in both experimental models. In pentobarbital anesthetized rats, an intravenous administration of the CA fraction caused two consecutive hypotensive and bradycardiac responses. In order to investigate the mechanism of the responses, the effect of the CA fraction on the blood pressure and the heart rate was tested in various experimental animals such as pithed rats, reserpinized rats under pentobarbital anesthesia and atropine- or chlorpheniramine-treated rats under pentobarbital anesthesia. The results obtained suggest that the hypotensive and bradycardiac responses of the first phase might involve cholinergic and central mechanisms, whereas those of the second phase involve mechanisms which are mediated by central, biogenic amines, acetylcholine and histamine.

Gas chromatographic analysis of indole alkaloids from Tabernaemontana hilariana

A fast and efficient procedure was elaborated to identify the alkaloid constituents from Tabernaemontana hilariana (Apocynaceae). The strategy based on fractioning of the crude alkaloid fraction in small cartridges followed by thin-layer chromatography (TLC), capillary gas chromatography-flame ionization detection as well as high-resolution gas chromatography-mass spectrometry afforded voacangine, coronaridine, ibogamine pseudoindoxyl, voacangine hydroxyindolenine, 3-hydroxycoronaridine and 3-(2-oxopropyl)coronaridine.

A New Basic Taxoid from Taxus cuspidata

The new basic taxoid 2‘-hydroxytaxine II (1) was isolated from the needles of Taxus cuspidata as the major component of the crude alkaloid fraction. An HPLC method for the analysis and separation of the alkaloid fraction was developed. The structure of 1 was determined mainly by spectroscopic analysis.

Influence of alkaloid concentration on acceptability of tall larkspur (Delphinium spp.) to cattle and sheep

Tall larkspur (Delphinium spp.) is a serious toxic plant problem on western U.S. ranges. The major toxins in tall larkspur are methyllycaconitine (MLA) and 14-deacetylnudicauline (14-DAN); the sum of both is termed the toxic alkaloid concentration. Toxic alkaloids comprise about 20-50% of the total alkaloid concentration in tall larkspur. Toxic and total alkaloid concentration generally declines with maturity, whereas cattle and sheep consumption of larkspur typically increases with plant maturity. We hypothesized that cattle and sheep consumption of tall larkspur was negatively related to higher concentrations of total or toxic alkaloid. We compared consumption of several collections of dried, ground larkspur and fresh larkspur in a series of trials. In another trial, a crude alkaloid fraction was extracted with ethanol, added to alfalfa hay, and consumption compared to untreated alfalfa hay, alcohol-treated hay, and the essentially alkaloid-free plant residue. In all cases we correlated amounts eaten with total and toxic alkaloid concentration. A grazing trial was also conducted to relate larkspur consumption over time to alkaloid concentrations. Total alkaloid concentrations in dried, whole-plant collections ranged from 9.3 to 38.8 mg/g of dry weight, whereas toxic alkaloid concentrations varied from 0.0 to 7.1 mg/g. In one pen trial, cattle preferred a larkspur collection (P<0.01) that contained no toxic alkaloids but had a high total alkaloid concentration (39 mg/g). There was no correlation (P>0.05), however, between concentrations of total or toxic alkaloids and amount of dry plant consumed in this or any other trial. Conversely, sheep consumption tended to be negatively influenced by total and toxic alkaloid concentration (P≤0.08). In the trials with extract, cattle preferred the alcohol-treated hay and rejected the alkaloid-free residue (P<0.01), whereas the alkaloid-treated hay was of intermediate acceptability. Cattle preferred the alkaloid-treated hay over the alkaloid-free residue, indicating that alkaloids did not deter consumption. Conversely, the alkaloid-treated hay was less preferred than either untreated or alcohol-treated hay, suggesting a negative effect on acceptability. There was no correlation between alkaloid concentration and amount of treated feed eaten. In field trials, the amount of composited, fresh leaves or flowers eaten by cattle was influenced by plant part (P=0.04), but was not related (P>0.05) to alkaloid concentration. Cattle preferred leaves over flowers when offered individual plants differing in phenological stage and/or amount of shade, but alkaloid concentration was not related to consumption. We conclude that knowledge of the concentration of total or toxic alkaloid in tall larkspur will give little or no indication of plant acceptability to cattle. Even though accurate predictions can be made about the potential toxicity of larkspur based on the concentration of toxic alkaloids, predictions about consumption must be based primarily on plant phenology.

Effect ofIpomoea intrapilosa Methanol Extract on the Serotonergic Response in Rat Uterus

A methanol extract (MEII) obtained from the seeds of Ipomoea intrapilosa and its isolated crude alkaloid fraction (ALKII) were tested as possible blockers of the serotonergic response in the rat uterus in vitro. The results obtained showed an unsurmountable non-selective inhibition of the contractile response induced by serotonin on isolated uterine smooth muscle.