Publications by authors named "Ateeque Ahmad"

40 Publications

Detection of natural inhibitors against human liver cancer cell lines through QSAR, Molecular Docking, and ADMET studies.

Curr Top Med Chem 2020 Dec 4. Epub 2020 Dec 4.

Metabolic & Structural Biology Department, CSIR-Central Institute of Medicinal & Aromatic Plants, Lucknow 226015 (Uttar Pradesh). India.

Background: Liver cancer is ranked as the fifth most prevalent and third most lethal cancer worldwide. The incidence rates of this cancer are on the rise, and only limited treatment options are available.

Methods: To identify and optimize the inhibitors of liver cancer cell-lines, a QSAR model was developed by using multiple linear regression methods. The robustness of the model was validated through statistical methods and wet-lab experiments.

Results: The developed QSAR models yielded high activity descriptor relationship accuracy of 91%, referred by regression coefficient (r2= 0.91), and a high activity prediction accuracy of 89%. The external predicted (pred_r2 ) ability of the model was 90%.

Conclusion: The QSAR study indicates that chemical descriptors such as to measure of electronegative atom count (Epsilon3), atom type count descriptors (MMFF_10), number of a carbon atom connected with four single bonds (SssssCEindex), molecular weight and, number of oxygen atom connected with two aromatic bonds (SaaOE-index) are significantly correlated with anticancer activity. The model, which was validated statistically and through wet-lab experiments, was further used in virtual screening of potential inhibitors against the liver cancer cell line WRL68. ADMET risk screening, synthetic accessibility, and Lipinski's rule of five are used to filter false positive hits. Afterward, to achieve a set of aligned ligand poses and rank the predicted active compounds, docking studies were carried out. The studied compounds and their metabolites were also analyzed for different pharmacokinetics parameters. Finally, a series of compounds were proposed as anticancer agents.
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http://dx.doi.org/10.2174/1568026620666201204155830DOI Listing
December 2020

Sanitary landfill site selection by integrating AHP and FTOPSIS with GIS: a case study of Memari Municipality, India.

Environ Sci Pollut Res Int 2021 Feb 9;28(6):7528-7550. Epub 2020 Oct 9.

Ho Chi Minh City University of Technology (HUTECH), 475A Dien Bien Phu Street, Binh Thanh District, Ho Chi Minh City, Vietnam.

Sanitary landfill is still considered as one of the most significant and least expensive methods of waste disposal. It is essential to consider environmental impacts while selecting a suitable landfill site. Thus, the site selection for sanitary landfill is a complex and time-consuming task needing an assessment of multiple criteria. In the present study, a decision support system (DSS) was prepared for selecting a landfill site in a growing urban region. This study involved two steps of analysis. The first step of analysis involved the application of spatial data to prepare the thematic maps and derive their weight. The second step employed a fuzzy multicriteria decision-making (FMCDM) technique for prioritizing the identified landfill sites. Thus, initially, the analytic hierarchy process (AHP) was used for weighting the selected criteria, while the fuzzy technique for order of preference by similarity to ideal solution (FTOPSIS) was applied for addressing the uncertainty associated with decision-making and prioritizing the most suitable site. A case study was conducted in the city of Memari Municipality. The main goal of this study was the initial evaluation and acquisition of landfill candidate sites by utilizing GIS and the following decision criteria: (1) environmental criteria consisting of surface water, groundwater, land elevation, land use land cover, distance from urban residence and buildup, and distance from sensitive places; and (2) socioeconomic criteria including distance from the road, population density, and land value. For preparing the final suitability map, the integration of GIS layers and AHP was used. On output, 7 suitable landfill sites were identified which were further ranked using FTOPSIS based on expert's views. Finally, candidate site-7 and site-2 were selected as the most suitable for proposing new landfill sites in Memari Municipality. The results from this study showed that the integration of GIS with the MCDM technique can be highly applied for site suitability. The present study will be helpful to local planners and municipal authorities for proposing a planning protocol and suitable sites for sanitary landfill in the near future.
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http://dx.doi.org/10.1007/s11356-020-11004-7DOI Listing
February 2021

New Chemical Constituents from the Bark of Leveille and their Evaluation of Antioxidant Activities.

Molecules 2019 Nov 1;24(21). Epub 2019 Nov 1.

Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.

Four new constituents, as c-6-oxogeran-4-enyl-10-oxy--β-arabinopyranosyl-4'--β-arabinopyranosyl-2''-octadec-9''',12''',15'''-trienoate (), geran-3(10)-enyl-1-oxy--β-arabinopyranosyl-4'--β-arabinopyranosyl-2''-octadec-9''',12''',15'''-trienoate (), geranilan-8-oxy---d-xylopyranosyl-2'--octadec-9'',12'',15''-trienoate (), 1-cyclohex-2', 5'-dienyl 1-cyclohexylethanol--β-d-xylopyranoside (), along with six known constituents, guaiacol--β-d-arabinopyaranoside (), -tetradecanyl oleate (), oleyl-β-d-xyloside (), -octadec-9,12-dienoyl--β-d-arabinopyranoside (), linolenyl--β-d-arabinofuranoside () andglyceryl-1,3-dipalmito-2-olein (), were isolated and identified from the bark. The new structures were established by one-and two-dimensional NMR (and in combination with IR, FAB-MSand HR-ESI-FTMS. The comparative evaluation of antioxidant potential by phosphomolybdenum, DPPH, FRAP and the NO assay of four different compounds (-), we have found that the compounds 1 and 2 have power as a natural antioxidant, whereas the compound and exhibited mild activity in comparison to compounds and .
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http://dx.doi.org/10.3390/molecules24213967DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6865017PMC
November 2019

New chemical constituent from the stem of Roxb. and its biological activities.

Nat Prod Res 2019 Oct 3:1-4. Epub 2019 Oct 3.

Process Chemistry and Technology Department, Central Institute of Medicinal and Aromatic Plants , Lucknow , India.

Chemical investigations on the stem of Roxb. (Convolvulaceae) led to the isolation of one new compound characterised as 3',4'-dimethoxy-1-phenyl-1α, 2-ethanediol (), along with eight known compounds as tridecanyl palmitate, palmitic acid, n-pentatriacontane, -triacont-21, 27-dien-1-ol, kaempherol, chlorogenic acid, 5,7-dimethoxyapigenin and quercitin. The chemical structures were established with the help of physical, chemical and spectroscopic methods. The antimicrobial potential of the new compound () was evaluated against three bacterial and three fungal pathogenic strain and showed significant activities.
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http://dx.doi.org/10.1080/14786419.2019.1669033DOI Listing
October 2019

Contribution of momilactones A and B to diabetes inhibitory potential of rice bran: Evidence from in vitro assays.

Saudi Pharm J 2019 Jul 15;27(5):643-649. Epub 2019 Mar 15.

Khai Xuan International Co. Ltd., Ha Dong District, Duong Noi Ward, LK20A-20B, Khai Xuan Building, Hanoi 152611, Viet Nam.

This study was the first to detect the presence of the two compounds momilactone A (MA) and momilactone B (MB) in rice bran using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS). By in vitro assays, both MA and MB exhibited potent inhibitory activities on pancreatic α-amylase and α-glucosidase which were significantly higher than γ-oryzanol, a well-known diabetes inhibitor. Remarkably, MA and MB indicated an effective inhibition on trypsin with the IC values of 921.55 and 884.03 µg/mL, respectively. By high-performance liquid chromatography (HPLC), quantities of MA (6.65 µg/g dry weight) and MB (6.24 µg/g dry weight) in rice bran were determined. Findings of this study revealed the α-amylase, α-glucosidase and trypsin inhibitors MA and MB contributed an active role to the diabetes inhibitory potential of rice bran.
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http://dx.doi.org/10.1016/j.jsps.2019.03.006DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598221PMC
July 2019

Isolation and Purification of Bioactive Compounds from the Stem Bark of .

Molecules 2019 Mar 3;24(5). Epub 2019 Mar 3.

Chemical Engineering, CSIR, CIMAP, Kukrail Picnic Spot Road, Lucknow 226016, India.

This paper reports the successive isolation and purification of bioactive compounds from the stem bark of , a widely known medicinal plant. The ethyl acetate extract of the stem bark exhibited the strongest antioxidant activity assessed by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, and ferric reducing antioxidant power (FRAP) assays (IC = 46.7, 66.0, and 492.6, respectively). By column chromatography (CC) with elution of hexane and ethyl acetate at 8:2, 7:3, and 6:4 ratios, the isolation of this active extract yielded five fractions (⁻). Chemical structures of the constituents included in ⁻ were elucidated by gas chromatography-mass spectrometry (GC-MS), electrospray ionization-mass spectrometry (ESI-MS), and nuclear magnetic resonance (NMR) and resolved as methyl gallate (, , , ), gallic acid (, ), fraxetin (, , , ), and tomentin (). Mixture (IC DPPH and ABTS = 2.5 µg/mL) and (IC FRAP = 381 µg/mL) showed the highest antioxidant properties. Among the isolated fractions, was the most potential agent in growth inhibition of six bacterial strains including , , , and (MIC = 5, 20, 30, 20, 25, and 20 mg/mL, respectively). All identified constituents exerted an inhibitory activity on the growth of , of which the mixture performed the maximal inhibition on shoot (IC = 49.4 µg/mL) and root (IC = 47.1 µg/mL) growth. Findings of this study suggest that gallic acid, methyl gallate, fraxetin, and tomentin isolated from possessed antioxidant, antibacterial, and growth inhibitory potentials.
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http://dx.doi.org/10.3390/molecules24050889DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429288PMC
March 2019

Anti-ageing and anti-Parkinsonian effects of natural flavonol, tambulin from Zanthoxyllum aramatum promotes longevity in Caenorhabditis elegans.

Exp Gerontol 2019 06 28;120:50-61. Epub 2019 Feb 28.

Ageing Biology Lab, Microbial Technology and Nematology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India. Electronic address:

Ageing is a progressive deterioration in functional and structural well-being of the body, accompanied with age-associated neurological disorders such as Parkinson's disease (PD), Alzheimer's disease and Huntington's disease. PD is marked with motor function decline, progressive neurodegeneration due to aggregation of insoluble α-synuclein in the dopaminergic neuron. Here we investigated the effect of tambulin (3,5-dihydroxy-7,8-dimethoxy-2-(4-methoxyphenyl) chromen-4-one), a hydroxy substituted flavanol isolated from fruits of Zanthoxyllum armatum DC (Family-Rutaceae) for its longevity promoting and neuromodulatory activities using Caenorhabditis elegans model system. Our results show that tambulin treatment significantly enhance lifespan and stress tolerance in worms, along with mitigation of ageing biomarkers like lipofuscin and protein carbonyl. In line with the alleviated ROS levels, tambulin treatment led to upregulated mRNA expression of ROS scavenging genes viz., sod-1, sod-3, and ctl-2. Upregulation in daf-16 gene indicates the involvement of insulin signaling pathway in tambulin mediated longevity. Tambulin treatment exhibited curtailed PD manifestations in terms of reduced α-synuclein levels, lipid accumulation, improved locomotary behavior and dopamine levels. Altogether, our data suggest that tambulin mediated alleviation of PD manifestations possibly involved PD counter protective machinery as evident through upregulated mRNA expression of lagr-1, ymel-1, pdr-1, ubc-12, and lrk-1. Our studies present tambulin as a potential molecule for its properties against ageing and Parkinson's disease. Further studies are speculated to realize the mechanistic and pharmacological aspects of tambulin.
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http://dx.doi.org/10.1016/j.exger.2019.02.016DOI Listing
June 2019

Momilactones A and B Are α-Amylase and α-Glucosidase Inhibitors.

Molecules 2019 Jan 29;24(3). Epub 2019 Jan 29.

Department of Internal Medicine II, Division of Gastroenterology and Hepatology, Klinikum Hanau, 63450 Hanau, Germany.

Momilactones A (MA) and B (MB) are the active phytoalexins and allelochemicals in rice. In this study, MA and MB were purified from rice husk of cv. Koshihikari by column chromatography, and purification was confirmed by high-performance liquid chromatography, thin-layer chromatography, gas chromatography-mass spectrometry, liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS), and ¹H and C nuclear magnetic resonance analyses. By in vitro assays, both MA and MB exerted potent inhibition on α-amylase and α-glucosidase activities. The inhibitory effect of MB on these two key enzymes was greater than that of MA. Both MA and MB exerted greater α-glucosidase suppression as compared to that of the commercial diabetic inhibitor acarbose. Quantities of MA and MB in rice grain were 2.07 ± 0.01 and 1.06 ± 0.01 µg/dry weight (DW), respectively. This study was the first to confirm the presence of MA and MB in refined rice grain and reported the α-amylase and α-glucosidase inhibitory activity of the two compounds. The improved protocol of LC-ESI-MS in this research was simple and effective to detect and isolate MA and MB in rice organs.
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http://dx.doi.org/10.3390/molecules24030482DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385104PMC
January 2019

Comparative extraction and simple isolation improvement techniques of active constituents' momilactone A and B from rice husks of by HPLC analysis and column chromatography.

Saudi Pharm J 2019 Jan 20;27(1):17-24. Epub 2018 Jul 20.

Graduate School for International Development and Cooperation, Hiroshima University, Higashi-Hiroshima City, Hiroshima 739-8259, Japan.

This paper reports comparative extraction efficiencies and enhancement methods for natural herbicidal (growth inhibitors) compounds, momilactone A and B, respectively from the dried husks of using different extraction techniques and different solvent systems. Four different extraction techniques . percolation, agitation with heat, sonication and soxhlet using five solvent systems as ethyl acetate, acetone, acetonitrile, methanol and methanol:water (8:2) were evaluated. In these studies, it was observed that maximum extract yield was obtained using in methanol and methanol/water mixture as extracting solvent by soxhlet technique although the content of total momilactones A and B was higher in the methanol/water mixture in comparison to other extractions. The successive and simple isolation enrichment technique for momilactones A and B were achieved by solid-matrix partitioning after the treatment of methanolic extract with charcoal and using ethyl acetate as extracting solvent for momilactones A and B. The quantitative analysis of the extraction and enrichment development protocol was validated by a simple, accurate, reproducible RP-HPLC-UV-VIS method using a binary gradient elution comprising of acetonitrile and water (70:30). The separation was achieved on a waters Spherisorb S10 ODS 2 column (250 × 4.6 mm, I.D., 10 µm) that achieved a greater degree of linearity within an overall concentration of extracts and momilactones A and B, 1 mg mL and higher degree of correlation (0.9928 ≤ r ≤ 0.9936) for momilactones A and B. So far, comparative extraction of momilactones A and B and HPLC of these compounds has not been reported. Standards of momilactones A () and B () were isolated along with other two compounds as orizaterpenoid () and 7-ketostigmaterol () from ethyl acetate extract of rice hulls of and checked purity by HPLC-PDA-MS and identification of these isolated compounds (-) by complete spectroscopic techniques as IR, H NMR, C NMR, 2D NMR and HR-MS. The qualitative analysis of momilactone A and B separation technique by thin layer chromatography was also developed.
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http://dx.doi.org/10.1016/j.jsps.2018.07.014DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6323130PMC
January 2019

Analysis of Selected Phenolic Compounds in Organic, Pesticide-Free, Conventional Rice ( L.) Using LC-ESI-MS/MS.

Molecules 2018 Dec 25;24(1). Epub 2018 Dec 25.

Department of Crop Science, College of Sanghuh Life Science, Konkuk University, Seoul 05029, Korea.

Rice ( L.) contains generous amounts of carbohydrates, proteins, vitamins, and dietary fibers, in addition to secondary metabolites such as phenols and flavonoids that act as antioxidants. The phenolic compounds detected in rice (organic rice (OR), conventional rice (CR), and pesticide-free rice (PFR)), namely, protocatechuic, gentisic, -hydroxybenzoic, -coumaric, ferulic, salicylic, and caffeic acids, are notable free radical scavengers. The sum of these phenolic compounds was found to be higher in PFR, followed by CR and OR ( < 0.0001), when the rice types were classified based on the farming system employed. In addition, significant differences were observed in the -hydroxybenzoic acid levels for the OR and CR groups compared with the PFR groups ( < 0.01). Furthermore, greater quantities of -coumaric acid were found in CR-08 and OR-02, although these groups contained overall higher and lower sums of phenolic compounds, respectively. Moreover, significance was observed in the sum of the phenolic compounds, although only small quantities were found in polished rice. Further research is thus required to provide a clearer picture regarding the phenolic profiles of different rice brands.
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http://dx.doi.org/10.3390/molecules24010067DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6337394PMC
December 2018

Synthesis of eugenol derivatives and its anti-inflammatory activity against skin inflammation.

Nat Prod Res 2020 Jan 22;34(2):251-260. Epub 2018 Dec 22.

Molecular Bioprospection Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, India.

Eugenol is a phytochemical present in aromatic plants has generated considerable interest in the pharmaceutical industries mainly in cosmetics. A series of eugenol esters (ST1-ST7) and chloro eugenol () have been synthesized. The structures of newly synthesized compounds were confirmed by H and C NMR and mass spectrometry. In an effort to evaluate the pharmacological activity of eugenol derivatives, we explored its anti-inflammatory potential against skin inflammation using and bioassay. Synthesized derivatives significantly inhibited the production of pro-inflammatory cytokines against LPS-induced inflammation in macrophages. Among all derivatives, [Chloroeugenol (6-chloro, 2-methoxy-4-(prop-2-en-1-yl)-phenol)] exhibited most potent anti-inflammatory activity without any cytotoxic effect. We have further evaluated the efficacy and safety in in-vivo condition. exhibited significant anti-inflammatory activity against TPA-induced skin inflammation without any skin irritation effect on experimental animals. These findings suggested that may be a useful therapeutic candidate for the treatment of skin inflammation.
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http://dx.doi.org/10.1080/14786419.2018.1528585DOI Listing
January 2020

Changes in Soybean ( L.) Flour Fatty-Acid Content Based on Storage Temperature and Duration.

Molecules 2018 Oct 21;23(10). Epub 2018 Oct 21.

Department of Crop Science, College of Sanghuh Life Science, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

Soybeans are low in saturated fat and a rich source of protein, dietary fiber, and isoflavone; however, their nutritional shelf life is yet to be established. This study evaluated the change in the stability and quality of fatty acids in raw and roasted soybean flour under different storage temperatures and durations. In both types of soybean flour, the fatty-acid content was the highest in the order of linoleic acid (18-carbon chain with two double bonds; C18:2), oleic acid (C18:1), palmitic acid (C16:0), linolenic acid (18:3), and stearic acid (C18:0), which represented 47%, 26%, 12%, 9%, and 4% of the total fatty-acid content, respectively. The major unsaturated fatty acids of raw soybean flour-oleic acid, linoleic acid, and linolenic acid-decreased by 30.0%, 94.4%, and 97.7%, and 38.0%, 94.8%, and 98.0% when stored in polyethylene and polypropylene film, respectively, after 48 weeks of storage under high-temperature conditions. These values were later increased due to hydrolysis. This study presents the changes in composition and content of two soybean flour types and the changes in quality and stability of fatty acids in response to storage temperature and duration. This study shows the influence of storage conditions and temperature on the nutritional quality which is least affected by packing material.
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http://dx.doi.org/10.3390/molecules23102713DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222662PMC
October 2018

Standardization and xanthine oxidase inhibitory potential of Zanthoxylum armatum fruits.

J Ethnopharmacol 2019 Feb 19;230:1-8. Epub 2018 Oct 19.

Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants (CIMAP), Lucknow 226015, India.

Ethnopharmacological Relevance: Tejovati (Zanthoxylum armatum DC; Family- Rutaceae) popularly known as toothache tree is widely distributed in sub-tropical Himalaya region. Traditionally, The Southeast Asian population of Indo-Nepal origin uses it to treat asthma, gout, pain, and inflammation. The Ayurvedic action of the plant includes the balancing of Vata-Kapha in the body. Which lead to various ailments related to the circulation of blood and water, digestion, immunity, and skin. Therefore, in-vitro xanthine oxidase (XO) inhibition potential of the extract could be worth to explore prospect in the prevention/treatment of gouty affections of the joints and other diseases.

Aim Of Study: Anti-inflammatory and antioxidant potential of Z. armatum fruit (ZAF) has been reported. To date, no scientific study to validate the claim for gout treatment/management has been attempted so far. The present study deals with the xanthine oxidase inhibitory potential of a various extract of ZAF and marker-based high-performance liquid chromatography (HPLC) standardization of most active fraction.

Materials And Methods: Liquid-liquid partioning of crude methanol extract of the ZAF followed by repeated column chromatography of most active fraction has resulted in the isolation of seven compounds. Five distinct groups of compounds were isolated, purified, and identified. We have investigated the therapeutic action of ZAF in the management of gout through in-vitro assay of XO, a key enzyme involved in gout pathogenesis.

Results: Phytochemical investigation of ZAF has resulted in the isolation of seven compounds of diverse nature. It is noteworthy to mention that out of seven, five compounds have shown the xanthine oxidase inhibitory action. The ethyl acetate fraction was most potent to inhibit XO. The XO inhibitory activity (IC values) of isolated marker chemical was ranging from 5.62 to 41.21 µM. Three compounds viz. acetyl phenyl acetate (ZA-2), prudomestin (ZA-6), and tambulin (ZA-7) showed the most potent XO inhibitory activity (IC ≈ 6 µM) comparable with a positive control (Allopurinol, IC, 3.38 µM). This is the first validated HPLC-PDA method for simultaneous analysis and accurate quantification of seven compounds (phenolic acid, acetyl phenyl acetate, xylopyranoside, diphenyl ether and three flavones) in ZAF as well as their distribution in other tissues of the plant.

Conclusion: Most potent three chemicals (ZA-2, 6 and 7) could be considered as bioactive to ensure the robust quality of the enriched fraction of ZAF with defined XO inhibition potential. Therefore, either single purified component or their enriched fraction could be a better choice for the management of gout than the crude extract of ZAF. Developed HPLC method is suitable for quality assurance analysis and process control of ZAF derived product intended for gout management. XO inhibitory potential exhibited by the characterized compounds validate the traditional use of this ZAF for the treatment of gout. Further, a detailed study is required to assess the effect of ZAF chemicals on serum uric acid and mechanism of XO inhibition.
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http://dx.doi.org/10.1016/j.jep.2018.10.018DOI Listing
February 2019

Characterization of New Polyphenolic Glycosidic Constituents and Evaluation of Cytotoxicity on a Macrophage Cell Line and Allelopathic Activities of .

Molecules 2018 Aug 2;23(8). Epub 2018 Aug 2.

Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.

Four new constituents, as 5, 7-dihydroxy-4'-methoxyflavonol-3---d-arabinopyranosyl-(2''→1''')---d-arabinopyrnosyl-2'''--3'''', 7''''-dimethylnonan-1''''-oate (), 5-hydroxy-7, 4'-dimethoxyflavone-5---d-arabinopyranosyl-(2"→1''')---d-arabinopyranosyl-2'''--3'''', 7''''-dimethylnonan-1''''-oate (), 5-hydroxy-7, 4'-dimethoxyflavone-5---d-arabinofuranosyl-(2"→1''')---d-arabinopyranosyl-2'''--lanost-5-ene () and 4',4''-diferuloxy feruloyl---d-arabinopyranosyl-(2a→1b)---d-arabinopyranosyl-(2b→1c)---d-arabinopyranosyl-(2c→1d)---d-arabinopyranosyl-(2d→1e)---d-arabinopyranosyl-2e-3''', 7'''-dimethylnonan-1'''-oate (), along with three known compounds (⁻) were isolated from leaves and straw. The structures of new and known compounds were elucidated by 1D (¹H and C NMR) and 2D NMR spectral methods, : COSY, HMBC, and HSQC aided by mass techniques and IR spectroscopy. The cytotoxicity of these constituents was assessed by using (RAW 264.7) mouse macrophage cell line, and allelopathic effects of compounds (⁻) on the germination and seedling growth characteristics such as seedling length and root length of barnyardgrass () were evaluated. Significant inhibitory activity was exhibited by compounds comprising flavone derivatives such as (⁻) on all of seed germination characteristics. The allelopathic effect of flavone derivatives were more pronounced on seedling length and root length than the germination characteristics. The higher concentration of flavone derivatives showed stronger inhibitory effects, whereas the lower concentrations showed stimulatory effects in some cases.
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http://dx.doi.org/10.3390/molecules23081933DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222760PMC
August 2018

Flavonoid glycosides from leaves and straw of and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination.

Saudi Pharm J 2018 Mar 12;26(3):375-387. Epub 2018 Jan 12.

Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.

Five new flavonoids namely, 5-hydroxy-6-isoprenyl-7,4'-dimethoxyflavonol-3---d-arabinofuranoside (), 5,7-dihydroxy-4'-methoxyflavone-7---d-arabinopyranosyl-2''--decan-1'''-oate (), 3-butanoyl-5,6,8-trihydroxy-7,4'-dimethoxyflavonol--5---d-glucopyranoside (), 7, 4'-dimethoxy-5-hydroxyflavone-5---d-arabinopyranosyl-(2'' → 1''')---d-arabinopyranoside (), and 5,6-dihydroxy-7, 4'-dimethoxyflavone-5---d-glucopyranoside (), together with two known compounds, were isolated from the methanol extract of leaves and straw. Their structures of new compounds were elucidated by 1D and 2D NMR spectral methods, viz: COSY, HMBC and HSQC aided by mass techniques and IR spectroscopy. The cytotoxicity of these compounds (- were assessed by using (RAW 264.7) mouse macrophages cell line, and allelopathic effects of compounds (- on the germination characteristics of barnyardgrass () and pigweed ( L.) were also evaluated. The compounds , and showed cytotoxicity and compounds - exhibited significant inhibitory activity on the seed germination of two weed species.
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http://dx.doi.org/10.1016/j.jsps.2018.01.003DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5856946PMC
March 2018

Weed Suppressing Potential and Isolation of Potent Plant Growth Inhibitors from Castanea crenata Sieb. et Zucc.

Molecules 2018 Feb 7;23(2). Epub 2018 Feb 7.

Department of Genetic Engineering, Agricultural Genetics Institute, Pham Van Dong Street, Hanoi 122300, Vietnam.

This study isolated, determined, and quantified plant growth inhibitors in Japanese chestnut ( Sieb. et Zucc), a deciduous species native to Japan and Korea. In laboratory assays, leaves showed strong inhibition on germination and seedling growth of (barnyardgrass), (lettuce), and (radish). Laboratory and greenhouse trials showed that leaves of appeared as a promising material to manage weeds, especially the dicot weeds. By GC-MS and HPLC analyses, gallic, protocatechuic, -hydroxybenzoic, caffeic, ferulic, ellagic, and cinnamic acids were identified and quantified, of which ellagic acid was present in the highest quantity (2.36 mg/g dried leaves). By column chromatography and spectral data (¹H- and C-NMR, IR, and LC-MS) analysis, a compound identified as 2α,3β,7β,23-tetrahydroxyurs-12-ene-28-oic acid () was purified from the methanolic leaf extract of (0.93 mg/g dried leaves). This constituent showed potent inhibition on growth of , a problematic weed in agricultural practice. The inhibition of the compound (IC = 2.62 and 0.41 mM) was >5 fold greater than that of -hydroxybenzoic acid (IC = 15.33 and 2.11 mM) on shoot and root growth of , respectively. Results suggest that the isolated the compound has potential to develop natural herbicides to manage . This study is the first to isolate and identify 2α,3β,7β,23-tetrahydroxyurs-12-ene-28-oic acid in a plant and report its plant growth inhibitory potential.
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http://dx.doi.org/10.3390/molecules23020345DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017574PMC
February 2018

New chemical constituents from the fruits of Zanthoxylum armatum and its in vitro anti-inflammatory profile.

Nat Prod Res 2019 Mar 22;33(5):665-672. Epub 2017 Nov 22.

a Process Chemistry and Technology Department , Central Institute of Medicinal and Aromatic Plants , Lucknow , India.

Chemical investigations on the fruits of Zanthoxylum armatum Roxb. (Rutaceae) led to the isolation of two new constituents characterised as 2α-methyl-2β-ethylene-3β-isopropyl-cyclohexan-1β, 3α-diol (1) and phenol-O-β-D-arabinopyranosyl-4'-(3″, 7″, 11″, 15″-tetramethyl)-hexadecan-1″-oate (2) along with known compounds m-methoxy palmityloxy benzene (3), acetyl phenyl acetate (4), linoleiyl-O-α-D-xylopyranoside (5), m-hydroxyphenoxy benzene (6) and palmitic acid (7). The chemical structures were established with the help of physical, chemical and spectroscopic methods. The anti-inflammatory potential of isolated compounds 1 and 2 was evaluated using in vitro target-based anti-inflammatory activity in LPS-stimulated primary peritoneal macrophages isolated from mice. Production of pro-inflammatory cytokines (TNF-α and IL-6) was significantly inhibited by the treatment of isolated compounds 1 and 2 in a dose-dependent manner.
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http://dx.doi.org/10.1080/14786419.2017.1405404DOI Listing
March 2019

New constituents triterpene ester and sugar derivatives from Meyer and their evaluation of antioxidant activities.

Saudi Pharm J 2017 Jul 24;25(5):801-812. Epub 2016 Dec 24.

Process Chemistry and Technology Department, Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.

C. A. Meyer (Araliaceae), is a well-known herb and used in the old established system of Oriental remedy, especially in Japan, China and Korea. Four new compounds characterized as ()- 7β,11α,19,21-tetra-O-decanoyl-18, 22β-dihydroxy-dammar-1-en-3-one (), 3β,4α,12β-trihydroxystigmast-5-en-21-yl octadecan-9',12'-dienoate (), dammar-12, 24-dien-3α, 6β, 15α-triol-3α-D-arabinopyranosyl-6β-L-arabinopyranoside () and dammar-24-en-3α, 6β, 16α, 20β-tetraol-3α-D-arabinopyranosyl-6β-D-arabinopyranoside () were isolated and established from the ethyl acetate and butanol extracts of the roots of . Their structures were established on the basis of spectral data and chemical reactions. Natural compounds indicative a great reservoir of materials and compounds with evolved biological activity, including antioxidant. Compounds - were investigated for antioxidant potential using ferric reducing antioxidant power (FRAP), the Nitric oxide (NO) scavenging activity, reducing power, phosphomolybdenum and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging actions, and the decision showed the compounds and have probablyessential antioxidant properties than the compounds and presented weak activity.
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http://dx.doi.org/10.1016/j.jsps.2016.12.002DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5506737PMC
July 2017

A Review on Phytoconstituents and Biological activities of Cuscuta species.

Biomed Pharmacother 2017 Aug 4;92:772-795. Epub 2017 Jun 4.

Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, 226015, Uttar Pradesh, India. Electronic address:

The genus Cuscuta belonging to the Cuscutaceae family comprises of about 100-170 species spread around the world. Although several species have been studied for their phytochemical characterization and biological activities but still many species are yet unexplored till date. Cuscuta are parasitic plants generally of yellow, orange, red or rarely green color. The Cuscuta species were reported rich in flavonoid and glycosidic constituents along with alkaloids, fatty acids, fixed oil, minerals, essential oil and others phytomolecules also etc. Flavonoids and other molecules of Cuscuta species were reported for different types of biological activities such as antiproliferative activity, antioxidant activity, anti-inflammatory, hepatoprotective, antimicrobial and anxiolytic activity, while some other flavonoids have exhibited potential antiviral and anticancer especially in ovarian and breast cancer activities. This review is an attempt to compile all the available data for the 24 different of Cuscuta species on the basis of different types of phytochemical constituents and biological studies as above.
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http://dx.doi.org/10.1016/j.biopha.2017.05.124DOI Listing
August 2017

Antiproliferative and antimicrobial efficacy of the compounds isolated from the roots of Oenothera biennis L.

J Pharm Pharmacol 2017 Sep 29;69(9):1230-1243. Epub 2017 May 29.

Molecular Bioprospection Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, Uttar Pradesh, India.

Background: Oenothera biennis L., commonly known as evening primrose, harbours the flavonoids, steroids, tannins, fatty acids and terpenoids responsible for a diverse range of biological activity, such as antitumour, anti-arthritic and anti-inflammatory effects. In addition to the previous reports from aerial parts of this plant, studies related to antiproliferative or antimicrobial activity from the roots are warranted.

Objective: To investigate antiproliferative and antimicrobial activity of compounds/mixture (1-8) isolated and characterized from the roots of O. biennis L. A possible mechanism of antiproliferative activity was also studied by targeting ornithine decarboxylase (ODC) and cathepsin D (CATD).

Study Design: Antiproliferative efficacy of the compounds/mixture was examined in selected cancer cell lines along with their probable mechanism of action. The antimicrobial activity was also studied against selected microbes (bacteria and fungi).

Methods: Antiproliferative potential was evaluated by MTT assay against selected cell lines. The mechanism of action was studied spectrophotometrically by targeting ODC and CATD using both an in-vitro and an in-silico approach. The antimicrobial efficiency was analysed using the disc diffusion and broth dilution methods.

Key Findings: Oenotheralanosterol B (3) and the mixture of oenotheralanosterol A and oenotheralanosterol B (4) exhibited antiproliferative activity against breast, hepatic, prostate and leukaemia cancer cell lines as well as in mouse macrophages (IC 8.35-49.69 μg/ml). Oenotheralanosterol B (3) and the mixture of oenotheralanosterol A and oenotheralanosterol B (4) displayed a strong molecular interaction with succinate dehydrogenase (binding energy -6.23 and -6.84 kcal/mol and Ki 27.03 and 9.6 μm, respectively). Oenotheralanosterol A (1), oenotheralanosterol B (3) and mixture of oenotheralanosterol A and oenotheralanosterol B (4) potently inhibited the ODC activity with IC ranging from 4.65 ± 0.35 to 19.06 ± 4.16 μg/ml and also showed a strong interaction with ODC (BE -4.17 to -4.46 kcal/mol). Oenotheralanosterol A (1), cetoleilyl diglucoside (2), oenotheralanosterol B (3), dihydroxyprenylxanthone acetylated (6) and dihydroxyprenylxanthone (7) inhibited CATD activity (IC 3.95 ± 0.49 to 24.35 ± 2.89 μg/ml). The in-silico molecular interaction analysis of compounds with CATD revealed the non-specific interaction. A moderate antimicrobial activity was observed against selected microbes with a growth inhibition ranging from 6 to 14 mm and minimum inhibitory concentration between 125 and 500 μg/ml. Oenotheralanosterol B (3) and dihydroxyprenylxanthone acetylated (6) exhibited better antimicrobial activity with an MIC range from 62.50 to 500 μg/ml.

Conclusion: Oenotheralanosterol B (3) exhibited stronger antiproliferative and antimicrobial potential with respect to the other compounds tested, whereas oenotheralanosterol A (1) was a potent inhibitor of ODC and CATD. Hence, it is suggested that these in-vitro findings could be studied further in vivo for biological activity, safety evaluation and derivatization to enhance potency and efficacy.
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http://dx.doi.org/10.1111/jphp.12753DOI Listing
September 2017

Phenolic Compositions and Antioxidant Properties in Bark, Flower, Inner Skin, Kernel and Leaf Extracts of Castanea crenata Sieb. et Zucc.

Antioxidants (Basel) 2017 May 5;6(2). Epub 2017 May 5.

Graduate School for International Development and Cooperation, Hiroshima University, Higashi-Hiroshima city, Hiroshima 739-8529, Japan.

In this study, different plant parts (barks, flowers, inner skins, kernels and leaves) of (Japanese chestnut) were analyzed for total phenolic, flavonoid, and tannin contents. Antioxidant properties were evaluated by using 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), reducing power, and β-carotene bleaching methods. The highest total phenolic and tannin contents were found in the inner skins (1034 ± 7.21 mg gallic acid equivalent/g extract and 253.89 ± 5.59 mg catechin equivalent/g extract, respectively). The maximum total flavonoid content was observed in the flowers (147.41 ± 1.61 mg rutin equivalent/g extract). The inner skins showed the strongest antioxidant activities in all evaluated assays. Thirteen phenolic acids and eight flavonoids were detected and quantified for the first time. Major phenolic acids were gallic, ellagic, sinapic, and -coumaric acids, while the principal flavonoids were myricetin and isoquercitrin. The inner skin extract was further fractionated by column chromatography to yield four fractions, of which fraction F3 exhibited the most remarkable DPPH scavenging capacity. These results suggest that provides promising antioxidant capacities, and is a potential natural preservative agent in food and pharmaceutical industries.
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http://dx.doi.org/10.3390/antiox6020031DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5488011PMC
May 2017

Characterization and evaluation of bioactive polyphenolic constituents from Zanthoxylum armatum DC., a traditionally used plant.

Biomed Pharmacother 2017 May 27;89:366-375. Epub 2017 Feb 27.

Molecular Bioprospection Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, Uttar Pradesh, India. Electronic address:

Zanthoxylum armatum or Timoor has been used in different traditional system of medicine due to its aromatic properties and also in the treatment of cancer, diarrhea and cholera. In the present investigation, four chemically distinct compounds namely Tambulin (6), Prudomestin (7), Ombuin (8) and 3, 4, 5, 3', 4', 5'-hexahydroxydiphenyl ether (9) have been isolated and quantified from the fruits. To explore the biological activities, we have further studied the antiproliferative, antimicrobial and antioxidant efficacy. Tambulin which was also found in maximum amount (0.125%) in fruits revealed significant antiproliferative activity (IC 37.96±0.36 to 48.7±0.21μg/mL) against breast, liver, colon and skin cancer cell lines corroborated by resilient binding interaction with SDH (-6.76Kcal/mol) and inhibition constant (Ki: 11.02μM). Hexane and ethyl acetate fraction exhibited moderate antibacterial efficacy (MIC: 250-1000μg/mL) against selected pathogenic microbes while Ombuin displayed broad spectrum antibacterial effect with MIC ranges from 125 to 500μg/mL. Total phenolic content (5.27±0.06 to 46.12±0.40mg/g of gallic acid equivalents), total flavonoids content (6.05±0.24 to 14.46±0.73mg/g of quercetin equivalents), ferric reducing power (42.35±0.85 to 62.52±0.66mg/g of ferrous sulfate equivalents) and percent free radical scavenging activity (59.56±0.38 to 64.85±1.78) were also estimated. Our findings infer that Tambulin exhibited significant antiproliferative activity whereas Ombuin was found to display broad spectrum antibacterial activity which adds one more positive attribute to its traditional usage.
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http://dx.doi.org/10.1016/j.biopha.2017.02.040DOI Listing
May 2017

Synthesis of 3,5-dihydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)benzopyran-4-one derivatives as anticancer agents.

Bioorg Med Chem Lett 2016 11 15;26(21):5322-5327. Epub 2016 Sep 15.

Medicinal Chemistry Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India. Electronic address:

Different alkyl amide (15a-l) and alkyl amine (16a-e) derivatives of 7,8-dimethoxy-3-hydroxy-2-(4-methoxyphenyl)benzopyran-4-one were synthesized and evaluated for their anticancer activity against five different cancer cell lines using SRB assay. Compounds 15e, 15i, 15j and 16a-e showed significant anticancer activity within the range of IC 2.58-34.86μM. The most promising molecule, 16c, was further analyzed for its effect on cell cycle and apoptosis of estrogen receptor positive cancer cells (MCF-7 cells) which showed that 16c triggered apoptosis in MCF-7 cells and arrested cells population at sub-G (apoptotic) and GM phase. In tubulin polymerization assay, 16c interfered with kinetics of tubulin polymerization.
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http://dx.doi.org/10.1016/j.bmcl.2016.09.036DOI Listing
November 2016

In silico assay development for screening of tetracyclic triterpenoids as anticancer agents against human breast cancer cell line MCF7.

PLoS One 2014 3;9(11):e111049. Epub 2014 Nov 3.

Metabolic and Structural Biology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, Uttar Pradesh, India.

Experimental activity of a compound on cancer cell line/target is mostly analyzed in the form of percentage inhibition at different concentration gradient and time of incubation. In this study a statistical model has been developed referred as in silico assay using support vector regression model, which can act with change in concentration gradient and time of incubation. This model is a function of concentration gradient, treatment hour and independent components; which calculate the percentage inhibition in combination of above three components. This model is designed to screen tetracyclic triterpenoids active against human breast cancer cell line MCF7. The model has been statistically validated, checked for applicability domain and predicted results were reconfirmed by MTT assay, for example Oenotheranstrol derivatives, OenA & B. Computational SAR, target and docking studies were performed to understand the cytotoxic mechanism of action of Oenotheranstrol compounds. The proposed in silico assay model will work for specific chemical family for which it will be optimized. This model can be used to analyze growth kinetics pattern on different human cancer cell lines for designed compounds.
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http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0111049PLOS
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4218838PMC
August 2015

Triterpene glycosides from red ginseng marc and their anti-inflammatory activities.

Bioorg Med Chem Lett 2014 Sep 22;24(17):4203-8. Epub 2014 Jul 22.

Department of Applied Bioscience, College of Life and Environmental Sciences, Konkuk University, Seoul 143-701, South Korea. Electronic address:

Three new triterpene glycosides ursan-3β,19α,22β-triol-3-O-β-D-glucopyranosyl (2'→1″)-β-D-glucopyranoside (1), ursan-3α,11β-diol-3-O-α-D-glucopyranosyl-(6'→1″)-α-D-glucopyranosyl-(6″→1‴)-α-D-glucopyranosyl-(6‴→1‴')-α-D-glucopyranoside (2) and lanost-5,24-dien-3β-ol-3-O-β-D-glucopyranosyl-(6'→1″)-β-D-glucopyranosyl-(6″→1‴)-β-D-glucopyranoside (3), together with one known compound were isolated and identified from the marc of red ginseng. Their structures were elucidated by spectroscopic data analysis. Compounds (1-3) were investigated for anti-inflammatory effects using the RAW 264.7 macrophage cell line. In the cell proliferation assay, lipopolysaccharide stimulation decreased cell proliferation of RAW 264.7 macrophage cells, but the suppression of cell proliferation was significantly protected by treatment with compounds 2 and 3. Compounds 2 and 3 had a suppressive effect on the production of nitric oxide (NO), and they inhibited mRNA expression of proinflammatory mediators such as inducible nitric oxide synthase, and cyclooxygenase-2, and proinflammatory cytokines such as two interleukins and tumor necrosis factor-α. These findings suggest that compounds 2 and 3 have potential anti-inflammatory activities.
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http://dx.doi.org/10.1016/j.bmcl.2014.07.042DOI Listing
September 2014

New polyglucopyranosyl and polyarabinopyranosyl of fatty acid derivatives from the fruits of Lycium chinense and its antioxidant activity.

Food Chem 2014 May 18;151:435-43. Epub 2013 Nov 18.

Department of Applied Bioscience, College of Life and Environmental Sciences, Konkuk University, Seoul 143 701, South Korea. Electronic address:

Four new compounds 3,4-dihydroxy benzoic acid 3-octadecanoyl-4-O-α-L-arabinopyranosyl (2a→1b)-2a-O-α-L-arabinopyranosyl-(2b→1c)-2b-O-α-L-arabinopyranoside (1), 2,6,10-trimethyl-n-dodec-2-en-1-oyl-1-O-α-L-arabinopyranosyl-(2a→1b)-2a-O-α-L-arabinopyranosyl-(2b→1c)-2b-O-α-L-arabinopyranosyl-(2c→1d)-2c-O-α-L-arabinopyranosyl-(2d→1e)-2d-O-α-L-arabinopyranosyl-(2e→1f)-2e-O-α-L-arabinopyranosyl-(2f→1g)-2f-O-α-L-arabinopyranoside (2), n-docos-9,12-dienoyl-α-D-glucopyranosyl-(2a→1b)-2a-O-α-D-glucopyranosyl-(2b→1c)-2b-O-α-D-glucopyranosyl-(2c→1d)-2c-O-α-D-glucopyranosyl-(2d→1e)-2d-O-α-D-glucopyranosyl-(2e→1f)-2e-O-α-D-glucopyranoside (3), β-D-glucopyranosyl-(2a→1b)-2a-O-β-L-arabinopyranosyl-(2b→1c)-2b-O-β-L-arabinopyranosyl-(2c→1d)-2c-O-β-L-arabinopyranosyl-(2d→1e)-2d-O-β-L-arabinopyranosyl-(2e→1f)-2e-O-β-L-arabinopyranoside (4) along with some know compounds, were isolated and identified from a methanol extract Lycium chinense fruits. Their structures were determined of the new compounds using one- and two-dimensional NMR spectroscopies in combination by IR, FAB/MS and HR-FAB/MS. The compounds 1-4 were investigated for the antioxidant potential using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity, reducing power and the phosphomolybdenum activity and the results demonstrate that the compounds (2 and 3) has potential as a natural antioxidant whereas the compound (4) exhibited moderate activity and the compound (1) exhibited weak antioxidant activity.
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http://dx.doi.org/10.1016/j.foodchem.2013.11.061DOI Listing
May 2014

Structure-activity relationships of monoterpenes and acetyl derivatives against Aedes aegypti (Diptera: Culicidae) larvae.

Pest Manag Sci 2013 Nov 21;69(11):1235-8. Epub 2013 Mar 21.

Plant Protection Division, Central Institute of Medicinal and Aromatic Plants, Lucknow, India.

Background: Dengue fever virus transmitted by Aedes aegypti causes lethal mortalities of human beings, and, because of the lack of any vaccine, management of this vector, especially with phytochemicals, is essential. In the present investigation, the structure-activity relationship of monoterpenes and their acetyl derivatives was studied to identify structural features that are responsible for mosquitocidal activity.

Results: Derivatization of monoterpenes (eugenol, geraniol, linalool, L-menthol and terpeniole) followed by structure-activity relationship studies identified all five acetyl derivatives as having enhanced mosquitocidal activity against fourth-instar larvae of Aedes aegypti. Acetylation of the hydroxyl group in general increased activity in comparison with hydroxyl compounds. Based on LC50 values (ppm), the activities could be placed in the following order: eugenyl acetate (50.2) > linalyl acetate (119.7) > terpinyl acetate (287.1) > menthyl acetate (308.4) > geranyl acetate (325.5), as compared with monoterpenoids: eugenol (82.8) > linalool (242.6) > terpineol (331.7) > L-menthol (365.8) > geraniol (415.0). In eugenyl acetate, the presence of an aromatic ring and a side chain with an allylic double bond makes it most effective.

Conclusion: Bioactive functional groups identified in the study may contribute to the understanding of larvicidal activity of acetyl derivatives and may help in the development of ecofriendly mosquito larvicidal compounds.
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http://dx.doi.org/10.1002/ps.3488DOI Listing
November 2013

New chemical constituents from Oryza sativa straw and their algicidal activities against blue-green algae.

J Agric Food Chem 2013 Aug 14;61(34):8039-48. Epub 2013 Aug 14.

Department of Applied BioScience, College of Life and Environmental Sciences, Konkuk University, Seoul 143-701, South Korea.

Five new constituents, 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-β-D-xylopyranosyl-(2a→1b)-2a-O-β-D-xylopyranosyl-(2b→1c)-2b-O-β-D-xylopyranosyl-2c-octadecanoate (1), 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-2d-octadecanoate (2), kaempferol-3-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-2d-hexadecanoate (3), methyl salicylate-2-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-(2d→1e)-2d-O-α-D-xylopyranosyl-(2e→1f)-2e-O-α-D-xylopyranosyl-(2f→1g)-2f-O-α-D-xylopyranosyl-(2g→1h)-2g-O-α-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate (4), and oleioyl-β-D-arabinoside (5), along with eight known compounds, were isolated from a methanol extract of Oryza sativa straw. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopies in combination with IR, ESI/MS, and HR-ESI/FTMS. In bioassays with blue-green algae, the efficacies of the algicidal activities of the five new compounds (1-5) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound 5 had the highest growth inhibition (92.6 ± 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound 5 has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.
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http://dx.doi.org/10.1021/jf402145uDOI Listing
August 2013

New tetraterpene glycosides from the fruits of Lycium chinense.

J Asian Nat Prod Res 2013 17;15(2):136-44. Epub 2013 Jan 17.

Department of Applied Life Science, Konkuk University, Seoul 143-701, South Korea.

Two new compounds lyciumtetraterpenic hexaarabinoside (1) and tetraterpenyl hexaarabinoside (2), along with two known compounds, were isolated from the methanol extract of the fruits of Lycium chinense Miller (Solanaceae), and their structures have been elucidated as 6-(1,1,5-trimethyl-5α-hydroxycyclohexanyl)-6'-(1',1',5'-trimethyl-2'β-hydroxycyclohexanyl)-9,13,9',13'-tetramethyloctadec-7,9,11,13,15,7',9',11',13'-nonene-5α-D-arabinopyranosyl(2a → 1b)-β-D-arabinopyranosyl-(2b → 1c)-β-D-arabinopyranosyl-2'-β-D-arabinopyranosyl-(2d → 1e)-α-D-arabinopyranosyl-(2e → 1f)-α-D-arabinopyranoside (1) and 1(6),11(12),13(14),1'(6'),11'(12'),13'(14')-dodecahydro-β-caroten-4β,4'β-diol-4β-L-arabinopyranosyl-(2a → 1b)-β-L-arabinopyranosyl-(2b → 1c)-β-D-arabinopyranosido-4'β-L-arabinopyranosyl-(2d → 1e)-β-L-arabinopyranosyl-(2e → 1f)-β-D-arabinopyranoside (2) on the basis of spectral data analysis and chemical reactions.
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http://dx.doi.org/10.1080/10286020.2012.756315DOI Listing
April 2013

HILIC quantification of oenotheralanosterol A and B from Oenothera biennis and their suppression of IL-6 and TNF-α expression in mouse macrophages.

J Ethnopharmacol 2012 May 5;141(1):357-62. Epub 2012 Mar 5.

Analytical Chemistry Department, Central Institute of Medicinal and Aromatic Plants (CSIR-CIMAP), Lucknow, India.

Ethnopharmacological Relevance: Evening primrose (Oenothera biennis L.) is a wild medicinal herb of Central American origin that is now globally widespread. Its traditional uses include treatment of rheumatoid arthritis and premenopausal pain both of which have an inflammatory component. The present study demonstrates the in vitro anti-inflammatory activity of three Oenothera biennis compounds.

Materials And Methods: Oenotheralanosterol A and B (Oen-A & Oen-B) along with gallic acid (GA) were isolated and characterized using column chromatography and NMR. The compounds were tested with LPS stimulated peritoneal mouse macrophages assaying for suppression of IL-6, TNF-α and NO synthesis. An HILIC method for the simultaneous quantitation of GA, Oen-A, and Oen-B in Oenothera biennis plant material was also developed as a means of monitoring quality of plant material.

Results: Significant inhibition of TNF-α and IL-6 by GA, Oen-A and Oen-B was observed (p<0.05). Inhibition was concentration dependent and no synergistic or antagonistic effect on pro-inflammatory cytokines was found when used in combination (1:1) (p>0.05). The HILIC analysis method was validated using Oenothera biennis root.

Conclusion: The study demonstrates the anti-inflammatory activity of Oenothera biennis root compounds and supports its traditional use in arthritis management. Active anti-inflammatory compounds were identified and quantified by the HILIC method.
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http://dx.doi.org/10.1016/j.jep.2012.02.046DOI Listing
May 2012