Isolation Of Alkaloids Research Articles

Two New Indole Alkaloids from Emmenopterys henryi

AbstractTwo new indole alkaloids, 5‐oxodolichantoside (1) and deglycocadambine (2), were isolated from the twigs and leaves of Emmenopterys henryi, together with four known indole alkaloids and five known iridoids. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and confirmed by single‐crystal X‐ray diffraction studies. This is the first report on the isolation of indole alkaloids from this species. The indole alkaloids were evaluated for their cytotoxic activities against five human cancer lines.

Isolation, characterization, and NMR spectroscopic data of indole and oxindole alkaloids from Mitragyna speciosa

A new indole alkaloid, 7β-hydroxy-7H-mitraciliatine (1) and a new oxindole alkaloid, isospeciofoleine (2) together with nine known alkaloids were isolated from Mitragyna speciosa and characterized by NMR, CD, and MS spectroscopic data analyses. The 1H and 13C NMR spectroscopic data of isospeciofoline (3), isorotundifoline (4), paynantheine (5), and 3-isopaynantheine (6) were also reported for the first time.

Investigation of flavonoids from Siparuna sarmentosa Perkins

Siparuna sarmentosa Perkins (Siparunaceae), known as 'Limão-bravo' is an herbaceous plant of an important medicinal genus from Brazilian Amazon. There are reports of medicinal uses of several species of Siparuna by indigenous and local communities. Literature reports the isolation of flavonoids, alkaloids and terpenoids from this genus but there are no reports on the chemistry of the species Siparuna sarmentosa (Ss). Previous work on S. guianensis by HPLC-DAD-ESI-MS/MS [Negri,2012] reports the presence of C-glycosylated flavonoids, never before reported for Siparuna. In this way, this study aims to evaluate the chemical profile of Ss by TLC, HPLC-DAD and HR-ESI-MS and to isolate the flavonoid derivatives by CCC in order to confirm the C-glycosyl pattern. Leaves of Ss, collected in the National Park Adolpho Ducke (Manaus, Brazil) were extracted with methanol and the crude extract obtained (SsEM) was subjected to clean-up by SPE. The clean-up performed by SPE was carried out in reversed phase (RP18) and the yielded fractions were analyzed by HR-ESI-MS. The error for each suggested molecular formula was calculated in ppm. The presence of lucenin-2 (1.5 ppm) and vicenin-2 (0.3 ppm), vitexin (4.6 ppm), quercitrin (2.9 ppm) and vanillic acid (0.4 ppm) [Negri,2012] is suggested. In order to obtain an enriched flavonoid fraction for further isolation of the proposed C-glycosyl flavonoids, high-speed countercurrent chromatography (HSCCC) of SsEM was performed with the biphasic solvent system hexane-ethyl acetate-methanol-water 3:6:6:5, in reversed phase mode, affording the flavonoid fraction SsFF. In this process a flavonoid aglycone and a terpenoid derivative were recovered from the organic stationary phase of the HSCCC fractionation. Their structure is under elucidation.

Isolation and quantification of alkaloids from Tetrapterys mucronata - a plant used in the ayahuasca preparation

Isolation and quantification of alkaloids from Tetrapterys mucronata - a plant used in the ayahuasca preparation

Studies on antioxidant potential and active compounds of Scutellaria salviifolia Bentham

The genus Scutellaria (Lamiaceae), includes about 350 species, is widespread in all over the world1. There are 15 Scutellaria L. species in Turkish flora and 3 of which are endemic2. Infusions of most of the species are used as tonic, antidiarrheaic, hemostatic, for wound healing, in gastric disorders, nausea and allergies3, 4. Scutellaria species and their active principles possess antitumor, anti-angiogenesis, hepatoprotective, antioxidant, anticonvulsant, antibacterial, and antiviral activities. Investigations on Scutellaria were resulted isolation of flavonoids, iridoid glucosides, phenylethanoid glycosides, diterpenes, triterpenoids, alkaloids and essential oils1. In the present study, aqueous extract of endemic S. salviifolia, collected from Ankara, Turkey; was tested for its radical scavenging activities against DPPH, SO, NO and ABTS radicals spectroscopically2. The extract showed concentration dependent radical scavenging ability. Its gallic acid equivalent total phenolic content was found as 72,3 mg/g dry extract using Folin-Ciocalteau reagent. On the other hand, the aqueous extract of the endemic S. salviifolia was subjected to polyamide column chromatography for the fractionation. Eluted fractions were tested for their radical scavenging activities. The most active phenylethanoid-rich fraction eluted with %50 MeOH from polyamide column was applied to HPLC-DAD system. The comparison of this fraction with previously isolated phenylethanoid glycosides showed the presence of acteoside, leucosceptoside A, martynoside and teucrioside as major phenylethanoid glycosides. Isolation studies have still been continuing on the titled plant.

ChemInform Abstract: Lycopodium Alkaloids — Synthetic Highlights and Recent Developments

AbstractReview: 284 refs.

Phytochemical Study of the Alkaloidal Fractions of Unonopsis duckei R. E. Fr. Guided by Electrospray Ionisation Ion‐trap Tandem Mass Spectrometry

The Unonopsis genus is a promising source of aporphinoid alkaloids, substances with great biological potential. These alkaloids have a well-defined mass spectrometry fragmentation pattern that, together with previous phytochemical knowledge, can guide the isolation of alkaloids not yet described for the genus. Isolate substances not yet described in the Unonopsis genus, guided by alkaloidal profile analyses of stem barks, twigs and leaves of Unonopsis duckei using electrospray ionisation ion-trap tandem mass spectrometry (ESI-IT/MS(n) ). Methanolic extracts from stem barks, twigs and leaves were submitted to a liquid-liquid, acid-base partitioning treatment to obtain the alkaloidal fractions. These fractions were analysed by direct infusion into an ESI-IT/MS(n) system. The major alkaloids observed for each fraction were submitted to fragmentation analysis. The MS fragmentation patterns revealed the presence of alkaloids previously reported for Annonaceae, including nornuciferine, anonaine, asimilobine, liriodenine and lysicamine, known for the Unonopsis genus, as well as others that were not yet described for this genus. In this way, the proaporphine alkaloid glaziovine was isolated, as well as a mixture of the aporphine alkaloids glaucine and norglaucine, all described for the first time in the Unonopsis genus. Mass spectrometry monitoring was fundamental to prioritise the isolation of substances not yet identified for the Unonopsis genus, dismissing known compounds and simplifying the phytochemical study.

ChemInform Abstract: Isolation and Structure Elucidation of Alkaloids from Pinellia ternata

Abstractincluding the new compound alkterlactone (I)

Isolation, characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia

Two new alkaloids, named stenine A (1) and stenine B (2), along with the known compounds neostenine (3), stenine (4) and neotuberostemonine (5), were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1D- and 2D-NMR spectra and X-ray single-crystal diffraction experiment. Anti-acetylcholinesterase (AChE) activity of compounds 1–5 were also tested. Compounds 2 and 4 showed significant anti-acetylcholinesterase activities, with IC50 values of 2.1±0.2μM and 19.8±2.5μM, resp. The mode of AChE inhibition by Compound 2 (the most potential AChE inhibitor) was reversible and competitive. In addition, molecular modeling was performed to explore the binding mode of compound 2 with AChE.

In Vitro Anti-Staphylococcal Activity of Alkaloids from the Leaves of Callestimone Rigidus R.Br

Multidrug resistant Staphylococcus aureus poses a severe global threat worldwide due to their prevalence, genomic plasticity and limited therapeutic options being refractory to most antibiotic classes. This necessitates the discovery of new anti-staphylococcal interventions. Callistemon rigidus R.Br. (Myrtaceae) has been found to possess antibacterial potential against clinical isolates. Thied me study was a isolate and evaluate the antibacterial alkaloids from the leaves of Callistemon rigidus and assess their in vitro anti-staphylococcal potential. Alkaloid isolation was carried out by modiied method for plant alkaloid extraction. The in vitro anti-staphylococcal potential of the alkaloid bioactive fraction was assessed by using micro broth dilution and plate count assay methods. Pus and wound isolates had MIC of 80 µg/mL and 50 IC of 27.22 µg/mL respectively. Burn isolates showed MIC of 320 µg/mL and 50 50 13.57 µg/mL respectively. Urine and vaginal isolates exhibited a MIC of 80 µg/mL 50 and IC of 13.15 µg/mL respectively. Ceixime had MIC values was 320 µg/mL, 160 50 50 µg/mL and 160 µg/mL for pus and wound, burn, urine and vaginal isolates indicating the refractory behaviour when compared to alkaloid bioactive fraction from the leaves of Callistemon. The alkaloid bioactive fraction exhibits immense activity compared to standard antibiotic Ceixime. This work is the irst report of alkaloids and their antimicrobial activity from Callistemon rigidus leaves. The results suggest further isolation of individual alkaloids from alkaloid bioactive fraction and assessment their anti-staphylococcal activity as leads for development of anti-staphylococcal drugs.

Alkaloids from Papaver setigerum

The genus Papaver, which belongs to the family Papaveraceae, consists of approximately 110 annual, biennial, and perennial plants distributed in central and south-western Asia, central and southern Europe, and northern Africa. A variety of structurally diverse alkaloids such as benzylisioquinoline, morphinane, aporphine, protopine, and phthalideisoquinoline has been isolated from species of Papaveraceae. Of the genus Papaver, only the opium poppy (P. somniferum L.) and P. setigerum D. C. are able to produce the narcotic substances such as morphine, codeine and thebaine as their secondary metabolites. Although morphine is the most powerful pain-killer, it also has very strong addictive properties. For this reason, P. setigerum and P. somniferum are controlled as illegal opium poppy in Korea. In our previous study on unknown poppy from Jeju Island, it was identified as P. setigerum using by metabolite profiling and genetic methods. P. setigerum has been reported to contain various benzylisoquinoline, morphinane, and phthalideisoquinoline alkaloids. In this work, we have investigated the chemical constituents of the whole plants of P. setigerum. The present paper describes the isolation and structural characterization of a new rearranged phthalideisoquinoline alkaloid along with two known benzylisoquiline and a known phthalideisoquinoline alkaloids. The EtOAc-soluble fraction of the whole plants of P. setigerum was successively subjected to silica gel, C18, and semipreparative HPLC on ODS yielded a new alkaloid 1 together with three known compounds, papaverine (2), papaveraldine (3), and α-noscapine (4). Compound 1, tentatively named setigerumine I, was obtained as a light yellow amorphous powder and the UV absorption was appeared at 290 nm. The positive HRESIMS of 1 gave a [M+H] at m/z 428.1356 (calcd 428.1345), corresponding to the molecular formula C22H21NO8. The HNMR spectrum of 1 displayed a singlet aromatic proton (δH 6.41, ring A), a pair of ortho-coupled aromatic protons (δH 7.48 and 7.42, ring B), a -CH-CH-CH2group (δH 4.62, 3.86, 3.05, and 2.88), a methylenedioxy group (δH 5.87), three mothoxy groups (δH 4.05, 3.98, 3.66), and a N-methyl group (δH 2.86). The Cand DEPT NMR spectra of 1 yielded 22 carbon signals including those corresponding to a carbonyl carbon (δC 166.3), and a spiroketal carbon (δC 108.9). These H-, C, and DEPT NMR data indicated that 1 was closely similar with a rearranged phthalideisoquinoline alkaloid, dactylicapnosinine except for an additional methoxy group. The skeleton of rearranged phthalideisoquinoline alkaloid, consists of unique ring C, D with C-N-O-C, moieties, and the lactone ring E, was further clarified with H-H COSY and HMBC experiments. The five membered ring C was confirmed by -CH-CH-CH2correlation with HH COSY data. Moreover, the A-E ring system was assigned by the observed HMBC correlations from H-1 (δH 3.05, 2.88) to C-2, C-7, C-3a and C-7a, from H-3 (δH 4.62) to C3a and C-6', and from H-1' (δH 7.42) to C-α. The position of methoxy groups were established by HMBC correlations from three methoxy groups (δH 4.05, 3.98, 3.66) to C-4', C3', and C-4, respectively. Furthermore, methylenedioxy group (δH 5.87) was correlated with C-5, and C-6. The relative configuration of 1 was determined on the basis of coupling constant and NOESY experiment. The H-2 and H-3 was confirmed as cisand axial orientations by a comparison of coupling constant between H-2 and H-3 (J = 8.5 Hz), and the observed NOE correlations. In the NOESY spectrum, the cross peak was detected between H-3 and H-1', which is clearly indicated the relative configuration of C-α as shown in Figure 3. However, the optical rotation showed a zero value, it may be a racemate. This rearranged phthalideisoquinoline alkaloid is reported for the first time in the genus Papaveraceae.

Crude Drug Analysis, Antimicrobial and Larvicidal Screening of the Methanolic Leaf Extract of Cestrum nocturnum L. (Fam. Solanaceae)

Crude leaves of Cestrum nocturnum L. (Fam. Solanacease) were analyzed for their total extractives, ash and moisture content to characterize its physicochemical properties. Phytochemical analysis of the crude C. nocturnum resulted in the isolation of tannins, glycosides, alkaloids, steroidal saponins, sapogenins and flavonoids. Further separation of the methanolic leaf extract was done through liquid-liquid fractionation using five solvents with varying polarity namely, hexane, chloroform, ethyl acetate, butanol and water [1]. Thin layer chromatography and phytochemical screening were conducted to identify the secondary metabolites present in each fraction and subsequently, antimicrobial assay through paper disk diffusion method was tested against Staphylococcus aureus and Escherichia coli. The ethyl acetate fraction showed marked antimicrobial activity against the two bacterial strains with zones of inhibition ranged from 11 mm to 22 mm. This fraction was subjected to bioautography using chloroform:diethyl ether (2:1) identified as the optimum solvent system which was able to separate 8 distinct spots for both trials under different detection methods. The result showed no measurable zones of inhibition observed in any of the separated bands. The methanolic leaf extract was screened for its larvicidal activity according to WHO Communicable Disease Control Prevention and Eradication-WHO Pesticide Evaluation Scheme. All replicates of the sample from highest concentration (1 g/140mL; 100%) to lowest concentration (250 mg/140mL; 25%) had caused 100% mortality against third instar larvae of Aedes aegypti in 24 hours [2]. It is recommended to dilute the concentration of the sample to lower than 250 mg/140mL to determine the LC50 of the methanolic extract of C. nocturnum.

Preparation and Application of Reversed Phase ChromatorotorTM for the Isolation of Natural Products by Centrifugal Preparative Chromatography

A method of preparation of rotors with a reversed phase (RP) solid silica gel sorbent layer has been developed for centrifugal preparative chromatography (CPC), also known as rotational planar chromatography (RPC). The rotors consist of binder free RP solid SiO2 layers of different thicknesses packed between two supported circular glass discs and can be used in any appropriate device for centrifugal chromatography, like Chromatotron and CycloGraph. Polar and /or semi-polar compounds with close R(f) values, as well as extracts and column fractions were separated and/or purified in a preparative and/or semi-preparative scale using the RP rotors, eluted with mixtures of aqueous-based solvents. We herein report three examples of its application, using RP Chromatorotors, for the isolation of the diastereoisomeric alkaloids banistenosides I and II from Banisteriopsis caapi, saponins III and IV from Fagonia cretica, and the sesquiterpenes artemisinin (V) and artemisinic acid (VI) from Artemisia annua.

A New Saponin from the Seeds of Zizyphus jujuba var. spinosa

Sour jujube (Zizyphus jujuba Miller var. spinosa Hu ex H. F. Chou) is a thorny, rhamnaceous deciduous plant distributed widely throughout tropical and subtropical regions. The dried seeds are named sanjoin (Zizyphi Spinosi Semen) in Korean and have a thousand-year history of use in traditional medicine as a sedative for treating mild anxiety, nervousness and sleep-related problems. Previous phytochemical investigations on the seeds of this plant have resulted in the isolation of saponins, flavone C-glycosides, cyclopeptide alkaloids, triterpenoids, and others. These compounds exhibit multiple activities, such as hypnotic, histamine-release inhibitory, anti-inflammatory and sedative, inhibition of foam cell formation, adjuvant, and cardiotonic effects. Our previous studies focused on isolating the flavonoid-C-glycosides and the sedative activities of these flavonoids. In the continuing search for new chemicals and biomarkers from Z. jujuba var. spinosa for quality control studies of related herbal medicines, 8 flavonoids, along with 3 other known components, were isolated. In the present investigation, we report the isolation and structural elucidation of a new saponin, named jujuboside A2 (1), together with three known saponins, zizyphus saponin III (2), jujuboside B (3), jujuboside A (4), and a known sesquiterpene glucoside, dihydrophaseic acid 3-O-β-D-glucopyranoside (5), from the seeds of Z. jujuba var. spinosa. Compound 1 was obtained as a colorless amorphous powder. Its molecular formula was established as C58H94O26 from the [M−H] peak at m/z 1205.5961 (Calcd for C58H93O26: 1205.5955) in the HR-FAB-MS. The IR absorption bands at 3414, 1647, and 1043 cm implied the presence of hydroxyl, double bond, and glycosidic C-O functionalities. Acid hydrolysis of compound 1 with 5% HCl afforded a mixture of ebelin lactone and 17(Z)-ebelin lactone as the aglycon and D-glucose, 6-deoxy-L-talose, D-xylose, and L-arabinose as the sugar components identified on GLC analysis of the thiazolidine derivatives. The Hand C-NMR spectra of 1 suggested the presence of a jujubogenin moiety [δH 0.72, 0.97, 1.09, 1.10, 1.38, 1.67, and 1.70 (all s, CH3-19, CH3-29, CH3-18, CH3-28, CH3-21, CH3-26, and CH3-27), 3.18 (dd, J = 4.0, 11.7 Hz, H-3), 5.20 (br t, J = 9.5 Hz, H-23), and 5.53 (br d, J = 7.9 Hz, H-24)] and five monosaccharide units through easily identifiable signals for anomeric protons and carbons [δH 4.86 (d, J = 5.2 Hz), 4.90 (d, J = 7.7 Hz), 5.00 (d, J = 7.6 Hz), 5.43 (d, J = 7.3 Hz), and 6.11 (br s); δC 104.4, 105.2, 103.6, 106.0, and 101.7)]. The (−)-FAB-MS showed an [M−H] ion at m/z 1205, which was consistent with a pentasaccharide glycoside carrying two glucose, one 6-deoxyL-talose, two pentose (xylose and arabinose) units, and an aglycon with a molecular mass of 472. The presence of other

Isolation and identification of alkaloids and anthocyanins from flower and bulb of Lycoris radiata using HPLC and LC-ESI-MS

Three anthocyanins (cyanidin 3-diglucoside, cyanidin 3-sambubioside and cyanidin 3-glucoside) together with eleven known alkaloids (lycoricidine, hipppeastrine,O-Demethyllycoramin, lycoricidinol, galanthine, lycorine, lycorenine, lycoramine, galanthamine, homolycorine and pretazettine) were identified in the flower and bulb of Lycoris radiata using high-performance liquid chromatography coupled with UV detection and electrospray ionization mass spectrometry. Anthocyanins play a major role in protecting plant’s DNA from the UV spectrum of sunlight and also in attracting insects for the purpose of pollination. Thus, knowledge on the contents and types of anthocyanins of L. radiata will help to evaluate the adaptive evolution of flowers and provide useful information for the ornamental breeding.

Isolation and Structure Elucidation of Alkaloids from Pinellia ternata

Isolation and Structure Elucidation of Alkaloids from Pinellia ternata

Gelsochalotine, a novel indole ring-degraded monoterpenoid indole alkaloid from Gelsemium elegans

A phytochemical investigation of Gelsemium elegans Benth. led to the isolation of a novel alkaloid, gelsochalotine (1), as the first example of an indole ring-degraded monoterpenoid indole alkaloid from the family Loganiaceae. The structure of 1 was elucidated by spectroscopic analysis, and confirmed by single crystal X-ray diffraction. Studies on the biogenetic derivation of 1 were performed and its cytotoxic activities against human cancer cell lines, BEL-7420 and MDA-MD-435 cell, were evaluated with the MTT assay.

Phenolic alkaloids from the aerial parts of Dracocephalum heterophyllum

Chemical examination of aerial parts of Dracocephalum heterophyllum resulted in isolation of phenolic alkaloids, including two flavonoidal alkaloids, drahebephins A and B, one imidazole alkaloid with a phenolic substituent, drahebenine, together with 15 other known compounds. Their structures were established by extensive spectroscopic data analyses. Due to the stereogenic center in the pyrrolidin-2-one ring, the flavonoidal alkaloids are chiral, although they were isolated as racemates. The enantiomers were separated by HPLC using a chiral phase and stereochemically characterized by circular dichroism (CD) spectroscopy. The structure of compound drahebenine was established by X-ray crystallography.

Isolation, structure elucidation and antiplasmodial activity of novel bisindole alkaloids from Gonioma malagasy

Isolation, structure elucidation and antiplasmodial activity of novel bisindole alkaloids from Gonioma malagasy

Isolation of Geissospermum laeve alkaloids by pH-zone refining centrifugal partition chromatography for metal corrosion studies

Control of metal corrosion is of technical, economical, environmental, and aesthetical importance. The use of corrosion inhibitors is one of the best options to protect metals and alloys from corrosion. The environmental toxicity of synthetic inhibitors has prompted the search for green compounds. Plant extracts have become important as an environmentally acceptable, readily available and renewable source for a wide range of biodegradable, heavy metals-free inhibitors. Among natural compounds, alkaloids have very high corrosion inhibition efficiency. An alkaloidic extract of Geissospermum laeve (Apocynaceae) has been fractionated by centrifugal partition chromatography using the pH-zone refining mode in order to investigate the effect of isolated alkaloids on C38 steel corrosion in HCl 1M. Indole alkaloids were identified by LC-MS, 1H and 13C NMR.