Records of Natural Products Articles
Issue: 6 November-December
Records of Natural Products
Year: 2018 Volume: 12 Issue:6 November-December
1) Antioxidant and Anti-inflammatory Activities of Marantodes pumilum (Blume) Kuntze and Their Relationship with the Phytochemical Content
Marantodes pumilum is a herbaceous plant that has widely recognized for its medicinal use. The plant used widely has led to many studies on its phytochemical identification, pharmacological and toxicological activities. Phytoconstituents found in the Marantodes pumilum extracts showed high antioxidant and anti-inflammatory properties which are essential for many pharmacological effects. The aim of the systematic review is to provide the information of antioxidant and anti-inflammatory properties found in Marantodes pumilum. A critical literature search from three electronic databases such as SCOPUS, EBSCOhost and Ovid Medline was conducted for related studies published from the years 1946 to November 2017. The research studies published in English and related with the antioxidant and anti-inflammatory effects of Marantodes pumilum were the main inclusion criteria in this review. A total 512 relevant articles was identified, whereby 21 articles met the inclusion criteria. Twelve chemical assay studies, five animal studies, two in vitro cell culture study, one combined in vivo animal and chemical study and one combined chemical assay and in vitro cell culture study included in this review. All of the studies reported moderate to noticeable positive effects of Marantodes pumilum against oxidation and inflammation. This systematic review highlights the antioxidant and anti-inflammatory effects and their relation with phytoconstituents of Marantodes pumilum extracts.DOI http://doi.org/10.25135/rnp.220.127.116.11 Keywords Marantodes pumilum Primulaceae antioxidant anti-inflammatory phytoconstituents DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
2) Medicinal Components and Pharmacological Effects of Rosa rugosa
Rosa rugosa is a widespread ornamental plant and generally utilized for food and medicinal purposes. The previous studies focused on the potent ingredients extracted from R. rugosa, such as essential oils, flavonoids, polyphenols, polysaccharides, pigments, vitamins and so on. Moreover, sufficient evidences and research data revealed that pharmacological effects of R. rugosa on various diseases were associated with these functional components. 19α-Hydroxyursane-type triterpenoids, such as euscaphic acid (EA) and tormentic acid (TA), are responsible for the anti-inflammatory action. Antioxidants such as flavonoids and polyphenols play a critical role against tumors and diabetes. Sesquiterpene and hydrolyzable tannins are essential for antimicrobial ability. Rosamultin reduces hepatotoxicity through enhancing the epoxide hydrolase activity. These studies suggest that R. rugosa has prospects of curing many diseases or assisting in traditional chemosynthetic drugs treatment.DOI http://doi.org/10.25135/rnp.18.104.22.168 Keywords Rosa rugosa Thunb medicines secondary metabolites pharmacological effects DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
3) Structure Elucidation of A N ew I ridoid from Artemisia integrifolia
The ether extract of Artemisia integrifoliawas separated by chromatography and afforded a new iridoid, arteintegin A (6), together with five known compounds, namely chamazulene (1) , acetylenes (E)-2, (E)-3, (Z)-4, eugenol (5). The structure elucidation of the new compound was carried out by 1D ( 1H NMR and 13C NMR) and 2D-NMR (COSY, HSQC and NOESY) spectral analysis .DOI http://doi.org/10.25135/rnp.63.18.01.202 Keywords Iridoid Artemisia integrifolia NMR HR-ESI-MS DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
4) Biological Activity and Chemical Composition of the Endophytic fungus Fusarium sp. TP-G1 obtained from the Root of Dendrobium officinale Kimura et Migo
Dendrobium officinable Kimura et Migo is a famous traditional herb medicine and is wildly used in folk as a tonic herb. Its endophytic fungi play prominent part in the function of D. officinable Kimura et Migo. In this study we first report the co-production of trichosetin (1), beauvericin (2), beauvericin A (3), enniatin B (4), enniatin H (5), enniatin I (6), enniatin MK1688 (7), fusaric acid (8) and dehydrofusaric acid (9) by the endophytic fungus Fusarium sp. TP-G1 deriving from the root of D. officinable kimura et Migo. These isolates’ reported bioactivities and the tested biological activities in this paper consisted with the functions of D. officinable Kimura et Migo. We found the MICs value of compounds 1−7 against Staphylococcus aureus and MRSA showed nearly no difference, while compounds 8−9 were first found to have the antimicrobial activities against Acinetobacter baumannii with a MIC value of 64 μg/mL and 128 μg/mL respectively. Compounds 2, 4, 5 and 6 were first found to show moderate anti-tumor activities against BL16F10; and compounds 4 and 5 were first found to show moderate anti-tumor activities against MCF-7. Furthermore, we report first here the isoleucine (Ile) replacement in beauvericin and enniatin will influence their antibacterial and brine shrimp lethality activities.DOI http://doi.org/10.25135/rnp.22.214.171.124 Keywords Endophytic fungi D . officinable Kimura et Migo beauvericin trichosetin enniatin fusaric acid DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
5) Investigation of Pesticidal Activities of Essential Oil of Eucalyptus camaldulensis Dehnh
In this study, chemical compositions of the volatile oil extracted from Eucalyptus camaldulensis Dehnh. were analyzed by using GC and GC-MS. The oxygenated sesquiterpenes, monoterpene hydrocarbons, s esquiterpene hydrocarbons and oxygenated monoterpenes compositions were detected in the sample studied. Pesticidal effects of this oil were investigated on storage insect pests like Rhizopertha dominica F. (Col.: Bostrychidae), Sitophilus granarius L. (Col.: Curculionidae), Tribolium confusum Duv. (Col.: Tenebrionidae), Callosobruchus maculatus F. and Acanthoscelides obtectus Say. (Col.: Bruchidae) . The essential oil was tested on some fungal pathogens and weeds. As fungal pathogens, Verticillium dahliae Kleb,Fusarium oxyporum Schl., Phytium debaryanum Auct. non R. Hesse, Sclerotinia sclerotiorum (Lib.) de Barry and Rhizoctania solani Kühn. were used while tests on the weeds were performed on Convolvulus arvensis L., Melilotus officinalis L. andAmaranthus retroflexus L. in invitro conditions. E. camaldulensis essential oil was found to be effective at 10 and 20 µL against all the tested insect pests. Our results also showed that growth of fungal mycelial as well as weed stems and roots were significantly affected by essential oil. In 10 and 20 µL, V. dahliae, P. debaryanum, F. oxyporum and S. sclerotiorum mycelial growth were inhibited in 7 days, while no effect was observed on R. solani mycelial growth in this duration. On the other hand, the applications of the oil to the weeds showed different results for each species examined. Although at 5, 10 and 20 µL concentrations of E. camaldulensis essential oil did not affect the root and stem growth of C. arvensis , the stem and root growth ofM. officinalis and A. retroflexus were reduced by the tested essential oil at the same concentration and time. The research results suggest that E. camaldulensis essential oil might have potential to be used as a natural pesticide as well as fungicide.DOI http://doi.org/10.25135/rnp.64.18.02.088 Keywords Eucalyptus camaldulensis Dehnh. essential oil pesticidal effect DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
6) Chemical Characterization of 64 Propolis Samples from Hakkari, Turkey
Propolis is a resinous substance produced by honey bees from various plants they visit. Sixty-four propolis samples were collected from different localities of four districts (Merkez, Yüksekova, Şemdinli, and Çukurca) in Hakkari territory. Ethanol extracts of the propolis samples were prepared, and their chemical contents were determined by gas chromatography–mass spectroscopy (GC–MS). Flavonoids were generally found in a high concentration in Şemdinli samples of Turkey. Twenty-seven coumarins were identified in the 28 propolis samples among studied 64 ones. Except suberosin, the coumarins were never reported before in any propolis sample with Turkish origin. The propolis samples belonging to Yüksekova were found to be richer in coumarins than the others, and the most richest one among the Yüksekova apiaries, was found to be Akocak sample (Y2) with 41.99% total yield, followed by Akçalı sample (Y5) (30.86%). This is a first comprehensive and original report about the chemical profile of propolis samples from Hakkari. The propolis samples from Hakkari exhibited a chemical content rich in flavonoids including coumarins and furocoumarins.DOI http://doi.org/10.25135/rnp.126.96.36.1995 Keywords Chemical analysis coumarin flavonoid Hakkari propolis DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
7) Mode of Action: Synergistic Interaction of Peppermint (Mentha x piperita L. Carl) Essential Oil and Meropenem Against Plasmid-Mediated Resistant E. coli
This study investigated the bactericidal mechanism of peppermint essential oil (PEO) when used singly and in combination with meropenem against multidrug resistant Escherichia coli.Chemical compositions of PEO were identified via GC-MS, followed by time-kill analysis which was performed to evaluate the antibacterial activities of PEO and meropenem. Furthermore, outer membrane permeability test, zeta potential measurement and scanning electron microscopy were performed to evaluate the ability of PEO in bacterial membrane disruption. Next, anti-quorum sensing assay was performed to assess the ability of PEO in quorum sensing inhibition.A complete killing activity was observed within five minutes of treatment with PEO and meropenem at sub-lethal concentrations. In addition, the outer membrane permeability test and zeta potential measurement performed indicated increase in the membrane permeability and membrane disruption which can be observed in the scanning electron micrograph. Furthermore, significant decrease in the light production of E. coli pSB1075 treated by PEO indicates the presence of quorum sensing inhibitors within PEO.The findings suggest that PEO has the ability to disrupt the bacterial outer membrane which increases membrane permeability, in addition to the possible inhibition of bacterial quorum sensing ability in multidrug resistant E. coli, aiding in the reversal of antibiotic resistance.DOI http://doi.org/10.25135/rnp.59.17.12.078 Keywords Escherichia coli essential oil membrane permeability Mentha x piperita L. Carl quorum sensing synergism DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
8) Evaluating Antiinflammatory and Antiandrogenic Effects of Garden Cress (Lepidium sativum L.) in HaCaT cells
Lepidium sativum L. (Brassicaceae) (Ls), garden cress, is an edible herb that is botanically related to watercress and mustard, sharing their peppery, tangy flavor and aroma. The various parts of the plant have been traditionally used for many respiratory, rheumatologic, cardiovasculary, metabolic, and gastrointestinal disorders. Several studies were performed showing its antiinflammatory, anticarcinogenic, antiproliferative as well as tissue protective effects. In all of these studies the positive effects of Ls were concluded as the result of its antioxidant features due to the polyphenols and organosulphur compounds. In this study, we investigated the molecular basis of antiinflammatory, antiproliferative, antimitotic and antiandrogenic effects of Ls leaf extract in HaCaT cells. The gene expression levels of vascular endothelial growth factor (VEGF), tumor necrosis factor-alpha (TNF-α), interleukin 1-alpha (IL-1α), and 5 alpha-reductase type II (SRD5A2) were studied. Gene expressions were determined by RT-qPCR analysis. Fold change results of the gene expression analyses showed that the plant extract caused statistically significant downregulation of VEGF (0.2167, p<0.0001), TNF-α (0.4133, p = 0.0262), and SRD5A2 (0.0567, p<0.0001). The fold change for IL-1α was 0.6900 and this result was not statistically significant (p = 0.1522). These preliminary results may partially explain the clinical success of Ls in the traditional medicine. Considering these results, topical application of Lepidium sativum extract may be beneficial for inflammatory, androgen dependent disorders of the skin.DOI http://doi.org/10.25135/rnp.79.18.01.204 Keywords Lepidium sativum garden cress SRD5A2 TNFα VEGF DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
9) The Protective Effect and MoA of Panax notoginseng Saponins Combined with Aminoguanidine on Kidney in Diabetic Nephropathy Rats
This study was conducted to explore the protecting effect and treatment mechanism of Panax notoginseng saponins (PNS) in combination with aminoguanidine (AG) on kidney functions in diabetic nephropathy (DN) rats. Rats were divided into 5 groups (A, P, P+A, D and N) and diabetes was induced by streptozotocin (STZ). After 8 weeks, all rats were sacrificed and the renal functions as well as 24 hrs urinary proteins were examined quantitatively. Periodic acid-Schiff stain (PAS) was used to observe the pathological changes of renal tissue. Immune-nephelometry, immunoradiometric assay, Immunohistochemical and real-time fluorescence were used for blood C-reactive protein, tumor necrosis factor-α (TNF-α), surface specific marker antigen (ED-1) and determination of transforming growth factor- β1 (TGF-β1) in kidney tissue. There was a significant reduction in renal pathological changes of rats in group P, A, and P+A when compared with group D, while the changes were most obvious in group P+A. Blood glucose, glomerular volume (V), serum creatinine, 24 hrs urinary protein, blood CRP and TNF- in groups P, A and P+A were significantly (P<0.05) lower than group D with lowest in group P+A. Immunohistochemical staining showed, only a few ED-1 positive staining (macrophages) in group N glomeruli and the renal tubules. The staining of ED-1 group D was higher while in groups P, A and P+A was significantly reduced. There was a basic quantity of TGF-β1 mRNA expression in group N rats while the expression of TGF-β1 mRNA in group D was significantly increased when compared with control group. In group P, A and P+A, the expression level of TGF-β1 mRNA was significantly (P<0.05) decreased. The protective effect of combined use of these two PNS and AG on the kidney is superior to the single drug treatment. The mechanism of PNS combined with AG in the treatment of DN may be closely related to the reduction of urinary protein, anti-inflammatory response, and inhibition of the expression of TGF-β1.DOI http://doi.org/10.25135/rnp.54.18.01.203 Keywords Diabetic nephropathy TGF-β1 Panax notoginseng DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
10) Alkaloids of Papaver libanoticum and their Cytotoxic Activity
Papaver libanoticum (family Papaveraceae) is an endemic Lebanese plant that has not been investigated before. The plant extract was found to possess a potent opioid analgesic activity with characteristic profile that suggest its potential use for the treatment of opioid abuse and withdrawal symptoms. The present study aims at exploring the cytotoxic activities of the plant extract and the isolated alkaloidal compounds. Chromatographic separation of Papaver libanoticum extract resulted in the isolation of; dehydroremerine (1), roemerine (2), berberine (3), alborine (4), remrefidine (5), and mecambrine (6). Their chemical structures were determined based on different recorded spectroscopic data in addition to comparison with those published in literature. The cytotoxic activity of the plant extract and its alkaloids (2-5) were determined by MTT assay on human breast cancer (MCF7) and human colon cancer cells (HCT116). The results indicated that berberine exhibited the highest inhibitory effect against both cell lines with IC 50 of 22 and 106 µM on MCF7 and HCT116 cells, respectively. Other compounds (including the crude extract) showed different dose-dependent inhibitory effects on the two cell lines indicating cell type specificity and suggesting different cell-alkaloid interactions. Further studies are needed to explore the structure-activity relationships (SAR) of alkaloids derived from P. libanoticum .DOI http://doi.org/10.25135/rnp.188.8.131.52 Keywords Cytotoxic activity Papaver libanoticum aporphine alkaloids spectroscopic analysis DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
11) Herbicidal and Fungicidal Effects of Cuminum cyminum, Mentha longifolia and Allium sativum Essential Oils on Some Weeds and Fungi
In this study, chemical compositions of essential oil extracted from Cuminum cyminum L., Mentha longifolia L. and Allium sativum L. were analysed using GC and GC-MS methods. T he herbicidal effects of the essential oils on seed germination, root and shoot growth of Rumex crispus L. and Convolvulus arvensis L. were investigated. Meanwhile their effects regarding the mycelial development inVerticilium dahliaKleb. and Fusarium oxysporumSchl. were also evaluated. Only the highest three concentrations; 10, 15, 20 μ g/cm 2 of A. sativum L. were 100% inhibited the seed germination, root and shoot growth of R. crispus L.; C. cyminum L. and M. longifolia L were affected at a rate of 100% by the four concentrations. All the three essential oils showed significant effect (100%) in the parameters examined against C. arvensis L. The essential oils obtained from C. cyminum L., M. longifolia L. and A. sativum L. were found to be 100% effective on V. dahlia Kleb. mycelium growth in all concentrations examined. However, C. cyminum L. and M. longifolia L. essential oils were found to be 30.0-36.6% effective at the concentration of 5 μ g/cm 2 on mycelium development of F. oxysporum Schl.; and the other 3 concentrations totally inhibited the growth of the fungi. The essential oil of A. sativum L. was the most effective; and 100% inhibition of the mycelial growth of F. oxysporum was detected in all concentrations. The oils used in the study have the potential of being used as herbicides and fungicides.DOI http://doi.org/10.25135/rnp.80.18.05.106 Keywords Cuminum cyminum L. Mentha longifolia L. Allium sativum L. essential oil weed fungi DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
12) Chemical Composition and Antioxidant Activity of the Seeds Oil of Vitex kwangsiensis C. Pei
The chemical co nstitution of the seeds essential oil of Vitex kwangsiensis C. Pei and in vitro antioxidant activity ha ve been investigated. The essential oil was isolated by hydrodistillation method then analyzed by GC-MS. Fifty-six compounds were identified, representing 9 3.1 % of the oil. The main components identified were methyl linoleate (11. 2 %), caryophyllene oxide(10. 3 %), β-eudesmol (9. 1 %) and methyl palmitate (8. 1 %). The antioxidant activity was tested by DPPH method and it showed weak antioxidant activity. The composition and bioactivity of Vitex kwangsiensis seeds oil are described for the first time.DOI http://doi.org/10.25135/rnp.55.17.11.072 Keywords Vitex kwangsiensis essential oil antioxidant activity DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
13) Quinolone Alkaloids Along with Other Constituents from Zanthoxylum rhetsa and their Chemotaxonomic Significance
A total of eight compounds were isolated from thepetroleum ether and chloroform extracts of the root bark of Zanthoxylum rhetsa (Roxb.) (D.C). These are a coumarin xanthyletin (1), five quinolone alkaloids zanthodioline (2), arnottianamide (3), skimmianine (4), fagaridine (5), oxynitidine (7), a lignan pluviatilol (6), and a triterpene lupeol (8) were identified. Structures of the isolates were characterized by extensive 1D and 2D NMR analyses and by comparing their spectral data with the published values. The compounds, zanthodioline (2), oxynitidine (7), fagaridine (5), and pluviatilol (6) are the first record from this plant.DOI http://doi.org/10.25135/rnp.184.108.40.206 Keywords Zanthoxylum rhetsa quinolone alkaloids lignan triterpene NMR spectroscopy DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
14) Comparisons of Chemical and Biological Studies of Essential Oils of Stem, Leaves and Seeds of Zanthoxylum alatum Roxb growing wild in the State of Azad Jammu and Kashmir, Pakistan
The fresh plant material of stem, leaves and seeds of Zanthoxylum alatum Roxb (Rutaceae) collected at high altitude of District Kotli, the State of Azad Jammu & Kashmir and subjected to Clevenger type hydro distillation for the extraction of essential oils. The essential oils were characterized by using gas chromatography-mass spectrometry (GC-MS) technique. Twenty five components have been identified from the stem yielded about 95.8 % of the total essential oils, the major constituents were Terpinen-4-ol (30.47%), β -Terpenene (16.16%), eighteen components identified from the leaves which yields about 89.08 % of the oil, Tridecanone (25%), Isohexane (21.4%), Eucalyptol (8.5%) and Linalool (7.21%) were the major constituents. From the seeds of Z. alatum twenty components have been identified which yielded about 98.5 % of the oil; major components were Linalool (45%), Isohexnae (38%), Methyl-10-octadecanoate (6.25%). The essential oils show significant antioxidant, antimicrobial activities. The essential oils of Z. alatum are expected to be used as traditional herbal system of medicine.DOI http://doi.org/10.25135/rnp.56.17.11.073 Keywords Zanthoxylum alatum Roxb essential oil antioxidant and antimicrobial DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.
15) Cytotoxic Sesterterpenoids from Bornean Sponge Spongia sp.
Four scalarane sesterterpenoids, scalarolide acetate (1), scalarolide (2), 12-O-deacetyl-12-epi-19-O-methylscalarin (3) and methyl 18-hydroxy-19-norscalar-16-en-20-carboxylate (4) were isolated from the Bornean sponge Spongia sp. The distinction between 12 a -OAc and 12 b -OAc, and 19-olide and 20-olide in sesterterpenes were revealed as well as previously not assigned relative configuration at 18-OH of 4 is reported herein for the first time. In addition, compounds 1-3 showed strong cytotoxic activities against adult T-cell leukemia (ATL), S1T cells. This is the first record of scalarane sesterterpenes from the Bornean sponge.DOI http://doi.org/10.25135/rnp.69.18.01.209 Keywords Borneo sponge sesterterpenes adult T-cell leukemia S1T DETAILS PDF OF ARTICLE © 2018 ACG Publications. All rights reserved.