[Show abstract][Hide abstract] ABSTRACT: isolation, structure elucidation and leishmanicidal activity of two new triterpenes, lantaninilic acid (I) and lantoic acid (II) along with six known triterpenes
[Show abstract][Hide abstract] ABSTRACT: Two new natural triterpenes, lantaninilic acid and lantoic acid, along with the known triterpenes lantadene A, and oleanolic, ursolic, betulinic, lantanolic, and camaric acid, were obtained from the aerial parts of Lantana camara through bioassay-guided isolation, monitoring the in vitro antileishmanial activity against promastigotes of Leishmania major. Oleanolic acid (3), ursolic acid (4), lantadene A (5), and lantanilic acid (7) showed significant leishmanicidal activities with IC50 values of 53.0, 12.4, 20.4, and 21.3 μM, respectively. The IC50 value of ursolic acid (4; 12.4 μM) was found to be comparable with that of the standard drugs, pentamidine (IC50 15.0 μM) and amphotericin B (IC50 0.31 μM). The in vitro activities of L. camara and its constituents against promastigotes of Leishmania major are reported here for the first time.
[Show abstract][Hide abstract] ABSTRACT: Carissa carandas Linn. commonly known as "Karaunda" (Apocynaceae) is a popular medicinal herb widely distributed in different parts of Pakistan. In addition to other medicinal uses, C. carandas is popular in indigenous system of medicine for its medicinal use in gut motility disorders like, constipation and diarrhea.
This study was planned to provide pharmacological basis to the medicinal use of C. carandas in constipation and diarrhea.
The crude extract of the leaves of C. carandas (Cc.Cr) was prepared in methanol and its fractionation was carried out with ethylacetate, petroleum ether and n-butanol. In-vivo studies were conducted on mice, while isolated rabbit jejunum and guinea-pig ileum preparations were used for the in-vitro experiments. The spasmogenic and spasmolytic responses of gut tissues were recorded using isotonic transducers coupled with PowerLab data acquisition system.
Cc.Cr was tested positive for steroids, triterpenoids, flavonoids and phenols, while the HPLC fingerprints of Cc.Cr, its petroleum (Cc.Pef), ethylacetate (Cc.Eaf) and n-butanol (Cc.Baf) fractions showed the presence of oleanolic acid, ursolic acid, stigmasterol and β-sitosterol. Oral administration of Cc.Cr to mice increased fecal output at lower doses (30 and 50mg/kg), while it showed protection against castor oil-induced diarrhea at higher doses (300 and 600mg/kg). In isolated guinea-pig ileum and rabbit jejunum, Cc.Cr and Cc.Baf exhibited stimulatory effect at 0.003-3mg/ml, which was partially sensitive to atropine or pyrillamine or partially/fully sensitive to atropine+pyrillamine, followed by relaxation at higher tested concentrations, being more potent in rabbit tissues. The ethylacetate fraction (0.1-5mg/ml) exhibited fully atropine-sensitive contractions in both guinea-pig and rabbit tissues, being more potent in guinea-pig while more efficacious in rabbit tissues. However, the petroleum fraction (0.003-1.0mg/ml) showed only spasmolytic activity in spontaneously contracting rabbit tissues, similar to nifedipine. In guinea-tissue, Cc.Pef did not cause any stimulant effect. When studied against high K(+) (80mM)-induced contraction, the crude extract and its fractions caused a dose-dependent inhibition, with the following order of potency: Cc.Pef>Cc.Eaf>Cc.Cr≥Cc.Baf, similar to nifedipine indicating Ca(++) channel antagonist like activity, which was further confirmed when the plant extract displaced Ca(++) curves to the right with suppression of maximum effect similar to that of nifedipine.
This study demonstrates that the crude extract of C. carandas possesses a gut-stimulatory effect mediated primarily through the activation of muscarinic and histaminergic receptors while its spasmolytic effect was mediated possibly through Ca(++) antagonist pathway. Thus, this study provides a clear evidence for the dual effectiveness of C. carandas in constipation and diarrhea, thus validating its medicinal use.
Journal of ethnopharmacology 02/2014; · 2.32 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: The present study was carried out to investigate the antioxidant effect of the methanolic extract, its alkaloidal and non-alkaloidal fractions along with petroleum ether soluble, ether soluble and ethyl acetate soluble sub-fractions of non-alkaloidal part of the bark of Holarrhena pubescens. The pure compound conessine was also tested. The activity was determined by using DPPH free radical scavenging assay at 500 μg/mL for the extract and the fractions, and at 200 μg/mL for conessine and the standard (ascorbic acid). The non-alkaloidal fraction was found to be more active (63% inhibition; EC 50 = 250 μg / mL) than the alkaloidal fraction (16% inhibition) and its polar ethyl acetate soluble fraction was found to be most active (70% inhibition; EC 50 = 250 μg / mL). Conessine was non-active at the concentration used.
[Show abstract][Hide abstract] ABSTRACT: The in vitro antioxidant activities of the methanol extract of fresh leaves of Psidium guajava cultivated in Pakistan and its different fractions were evaluated using 1,1-diphenyl-2- picrylhydrazyl (DPPH) free radical scavenging assay. The methanol extract, main ethyl acetate fraction and its polar sub fraction showed high free radical scavenging activity with EC50 11.72, 11.72 and 46.8 µg/mL respectively. The first two values are comparable with that of reference compound ascorbic acid (EC50 9.4 µg/mL). The known antioxidants gallic acid (1), methyl ferulate (2) and methyl p-E-coumarate (3) were isolated from the ethyl acetate insoluble fraction. Their structures were identified by mass, 1H- and 13C-NMR spectroscopy. Compounds 2 and 3 are reported for the first time from the genus Psidium.
Journal- Chemical Society of Pakistan 02/2014; 36(1):119. · 1.38 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: The antibacterial and antifungal activity of methanolic extract, its different fractions and pure compounds oleanolic acid (1) and 3, 4, 3′-tri-O-methylellagic acid (2) was evaluated against various Gram positive and Gram negative bacteria and fungi. The methanolic extract, its ether soluble and ethyl acetate soluble fractions exhibited strong activity against Bacillus subtilis with MIC = 62.5 µg/disc. Ethyl acetate soluble fraction also showed strong activity against Micrococcus luteus ATCC 9341 with MIC=62.5 µg/disc. Acetone soluble fraction demonstrated activity against Shigella dysenteriae (MIC= 62.5 µg/disc). The petroleum ether soluble fraction was found to be active against fungi Aspergullus flavus, Aspergullus niger and Trichophyton rubrum with MIC 250 µg/disc. Compounds 1 and 2 were found inactive against the microorganisms tested.
[Show abstract][Hide abstract] ABSTRACT: The genus Morinda is pan tropical in its distribution with about 80 species. This genus includes trees, shrubs and vines. In the Western Pacific region, vines are most common while the trees are only a few, including Morinda citrifolia which typically have "vine-like" characteristics of their branches and stems [1,2]. The tree belongs to the family Rubiaceae. It has different local names in various geographical locations. Some commonly used names include noni in Hawaii, nono in Tahiti, Indian Mulberry in India, Ba ji tian in China and cheese fruit in Australia . Morinda citrifolia has been used by humankind both as food and medicine for millennia [4-6]. Due to its traditional and current use, a number of biological and chemical studies have been performed on this species dating back more than 100 years. Literature survey however reveals that the leaves have the most prevalent traditional use and were usually used topically. On the other hand, in the current practice the fruit juice and less commonly the leaves or other parts are used and these are primarily given orally [3,7]. Hence in the present preliminary studies three parts namely fruits, leaves and stem were separately evaluated for different biological activities namely, anti-leishmanial, spasmolytic and spasmogenic, antioxidant and antimicrobial activities. It may be noted that in earlier studies the parts of the plant mainly used for these activities were roots , fruits and roots [9,10] and fruit juice . The present results provide a direction regarding the selection of particular part for studying any specific biological activity referred to above in future.
[Show abstract][Hide abstract] ABSTRACT: Brain-derived neurotrophic factor (BDNF) and c-Fos are shown to promote epileptogenesis and are taken as a marker of neuronal activity. The present study investigated the expression of BDNF and c-Fos in mice brain with pentylenetetrazol- (PTZ-) induced generalized seizure and evaluated the effect of novel tryptamine derivative HHL-6 on the expression of these two markers. The subconvulsive dose of PTZ (50 mg/kg) was administered on alternate days in the experimental groups until the seizure scores 4-5 developed in the PTZ-control group. At the end of each experiment, animals were sacrificed, brain samples were collected and cryosectioned, and immunohistochemical analysis of BDNF and c-Fos protein was performed. Data obtained from two sections per mouse (n = 12 animals/group) is presented as means ± S.E.M. The test compound HHL-6 demonstrated a potent anticonvulsant activity in the PTZ-induced seizure in mice. Significant reduction in the BDNF (P < 0.003) and c-Fos (P < 0.01) protein expression was observed in the HHL-6 treated group. Based on these results we suggest that one of the possible mechanisms of HHL-6 to inhibit epileptogenesis might be due to its controlling effect on the cellular and molecular expression of the factors that contribute to the development of epileptogenic plasticity in the CNS.
BioMed research international. 01/2014; 2014:876712.
[Show abstract][Hide abstract] ABSTRACT: The antituberculosis activity of six constituents including three triterpenoids, lawsowaseem, lawsonic acid, lawsonin; a dihydrobenzofuran derivative, lawsonicin; a naphthoquinone derivative, lawsonadeem, and vomifoliol isolated from the aerial parts of Lawsonia alba Lam was investigated. Compounds were identified using spectroscopic analysis. All the compounds were tested for their antitubercular activity against Mycobacterium tuberculosis strain H37 Rv and showed growth inhibition from 0 to 60 % at 6.25 µg/mL. Two acetyl derivatives were also assayed and caused 100 and 72 % growth inhibition of Mycobacterium tuberculosis strain H37 Rv respectively at MIC 6.25 µg/mL in the primary screen.
[Show abstract][Hide abstract] ABSTRACT: Lawsonia is a monotypic genus represented by Lawsonia alba (syn. Lawsonia inermis Linn.). In this review a comprehensive data of its chemical constituents and biological activities of its various extracts, fractions and pure compounds are presented. Studies on this important medicinal plant have resulted in the isolation and structure elucidation of more than 80 compounds up to 2011 and evaluation of biological activities of some of them. Different types of biological activities attributed to L. alba as well as the diverse structural entities isolated from this source offer a valuable source of information to carry out further studies on this plant in future.
[Show abstract][Hide abstract] ABSTRACT: Six bioactive compounds were isolated from the seeds extract of Piper nigrum Linn. following a larvicidal activity guided isolation against 4th instar larvae of Aedes aegypti L., a Dengue vector mosquito and a carrier of yellow fever. Their structures were elucidated using spectroscopic methods including HR-EI-MS, FAB-MS, 1H and 13C NMR (Broad Bond Decoupled, & DEPT), and 2D-NMR techniques (1H–1H COSY, NOESY, HMQC, HMBC, & 2D-J-resolved). These include three new constituents namely pipilyasine (1), pipzubedine (2) and pipyaqubine (3), and three known constituents pellitorine (4), pipericine (5) and piperine (6). The larvicidal activity was determined by WHO method.
[Show abstract][Hide abstract] ABSTRACT: In search of new anti-mycobacterial agents seven acyl and one benzyl derivatives of coniferyl alcohol were synthesized and evaluated along with coniferyl alcohol for antitubercular activity against Mycobacterium tuberculosis H37Rv (Mtb) in vitro. Four compounds (3-6) showed greater activity than the parent compound and inhibited MTB with IC90 9.11, 8.92, 4.28 and 3.01 µg/mL respectively. Compound 6, the most potent compound in vitro exhibited CC50 10.216 µg/mL in VERO cells with selectivity index 3.394. Reference compounds used were rifampin and isoniazid and had IC 90 0.0031 and 0.063 µg/mL respectively.
Journal- Chemical Society of Pakistan 02/2013; 35(3):886-889. · 1.38 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: A new triterpene carandinol (1) was isolated from the leaves of Carissa carandas L., along with five known compounds, betulinic acid (2), β-sitosterol-3-O-β-d-glucopyranoside (3), oleanolic acid (4), ursolic acid (5) and 4-hydroxybenzoic acid (6). The structure of compound 1 was deduced as 3β,21α-dihydroxyisohopane by exhaustive spectroscopic analyses. The known compounds 2–6 were identified by comparison with the reported spectral data. Compound 1 was evaluated for cytotoxicity, immunomodulatory, antiglycation, antioxidant and enzyme inhibition activity. It exhibited significant in vitro cytotoxicity to every cell line tested (HeLa, PC-3 and 3T3) and was relatively more toxic to human cervical cancer (HeLa) cell line. This is the first report of the isolation of an isohopane triterpene from the genus Carissa. Carandinol also represents the first example of a cytotoxic isohopane.
[Show abstract][Hide abstract] ABSTRACT: Seven constituents were isolated from the stems of Lawsonia alba Lam., following an activity-guided isolation, which include two new constituents, namely lawsorosemarinol (1) and lawsofructose (2), one known compound 2-(β-D-glucopyranosyloxy)-1, 4-naphthoquinone (3) and four compounds, 4-hydroxy coumarine (4), 3-(4-hyroxyphenyl)-triacontyl-(Z)-propenoate (5), 3-(4-hydroxy-3-methoxyphenyl)-triacontyl-(Z)-propenoate (6) and 7-hydroxy-4-methyl coumarin (7) first time isolated from Lawsonia alba. Their structure elucidation was based on spectroscopic data analyses. Compounds 3 and 7 showed a moderate inhibition of urease activity, while rest of them showed less than 50% inhibition. These compounds did not show any significant inhibition against α-chymotrypsin.
[Show abstract][Hide abstract] ABSTRACT: Ethnopharmacological relevance: Ocimum basilicum belongs to the genus Ocimum (Lamiaceae). Many species of this genus including O. basilicum have been traditionally used for the treatment of a variety of diseases including respiratory diseases and symptoms of tuberculosis.
The aim of the study was to evaluate the activity of pure constituents of O. basilicum, a plant used in traditional medicine to treat respiratory diseases including symptoms of tuberculosis, against Mycobacterium tuberculosis H37Rv.
The crude methanolic extract from the aerial parts (leaves, fruits and flowers) of the plant was separated into EtOAc and water subextracts and the EtOAc subextract was further divided into acidic and neutral fractions. Each of these was subjected to fractionation through column chromatography followed by prep. TLC. Several pure compounds were thus isolated and their activity was determined against M. tuberculosis H37Rv using MABA assay.
Nine compounds were assayed for antituberculosis activity which exhibited upto 49% inhibition of M. tuberculosis H37Rv at 6.25μg/mL. These include one new compound bacilicin, the structure of which was elucidated based on 2D-NMR (HSQC, HMBC, COSY and NOESY) and Ms spectral analysis. The known compounds were identified on the basis of comparison of their spectral data with those reported earlier.
Inhibition of M. tuberculosis by pure compounds from O. basilicum supports the use of this plant in ethnomedicine as a remedy for symptoms of tuberculosis. The results also suggest that the activity of the plant may be due to a synergistic effect of active compounds including those investigated in the present studies, and hence this plant is a potential candidate for obtaining further new antituberculosis natural products.
Journal of ethnopharmacology 08/2012; 144(1):220-2. · 2.32 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: In view of the attributed medicinal properties of reserpine, a number of acyl reserpine derivatives were prepared and tested for antimycobacterial activity against Mycobacterium tuberculosis, strain H(37)Rv and antioxidant activities. The results indicated that in the case of antimycobacterial activity, 10 out of 18 derivatives caused more inhibition than that caused by reserpine itself. The results of antioxidant activity revealed that acylation in benzene ring of reserpine decreases the percentage inhibition of DPPH in all the derivatives compared to the parent compound (1).
Natural product research 01/2012; 26(22):2084-8. · 1.01 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: A pentacyclic triterpene, oleanderocioic acid, two flavonoidal glycosides, quercetin-5-O-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside and kaempferol-5-O-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside, and a cardenolide, oleandigoside, together with 11 known compounds, were isolated from the leaves of Nerium oleander. Their structures were elucidated on the basis of spectroscopic analysis. The growth inhibitory and cytotoxic activities of eight compounds were evaluated against the MCF-7 human breast cancer cell line using a sulforhodamine B assay. Three compounds, oleandrin, odoroside A and B were further assayed using a panel of 57 human cancer cell lines.