DOCSLIB.ORG

Salicylic Acid and Methyl Gallate from the Roots of Conyza Canedensis

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Salicylic Acid and Methyl Gallate from the Roots of Conyza Canedensis Salicylic acid and Methyl gallate from the roots of Conyza canedensis Javid A Banday*1, FA Mir2, Saleem Farooq3, Mushtaq A Qurishi1, Surrinder Koul3 and TK Razdan4 1Department of Chemistry, University of Kashmir, Hazratbal, Srinagar-190006, J&K, India 2University Science Instrumentation Centre (USIC), University of Kashmir, Srinagar-190006, J&K, India 3Bio-organic Division, Indian Institute of Integrative Medicine(CSIR), Canal Road, Jammu, J&K, India 4Department of Chemistry, University of Jammu, Ambedkar Road, Jammu, J&K, India From the root part of Conyza canedensis (Astereacea), Salicylic acid (2-Hydroxybenzoic acid) (1) and Methyl gallate (Methyl- 3,4,5-trihydroxybenzoate) (2) were isolated for the first time, along with five known compounds (3-7). The structures of all these compounds were elucidated on the basis of their spectral data. Keywords: Conyza canedensis, Astereacea, Salicylic acid, Methyl gallate. INTRODUCTION Genus Conyza (Family Astereaceae), consists of more than 70 Plant Material: The root part of Conyza canedensis (5.4 Kg) species and is an annual or perennial plant. The plants are were collected from Hazratbal, Srinagar (J&K, India) ) in June mainly distributed in tropical and sub-tropical regions. The 2007. The specimen was identified by Akhtar H. Malik, species Conyza canedensis Linn. is native to North America Curator, Centre for Biodiversity & Taxanomy, University of and is distributed in almost all parts of the world. In India, Kashmir (Specimen deposited under accession No. 33214 and Conyza canedensis is widespread in northern areas. The whole Collection No. 1202- Javid, Kash). plant is locally used for the treatment of edema, hematuria, hepatitis and cholecystitis[1]. Extraction and isolation: The air dried, finely powdered root material (1Kg) was extracted for 72 hours sequentially with Earlier, aerial parts of Conyza canedensis have been shown to petroleum ether (60-80oC), ethyl acetate and methanol in a possess sphingolipids[2,3], phenolic acids[3], steroids and soxhlet apparatus to afford the respective extracts, which triterpenoids[3,4], acetylenes, 16β,20β-dihydroxytaraxastane-3- were concentrated under reduced pressure. The methanol β-O-palmitate, 8R,9R-dihydroxymatricarine methyl ester [4], extract (06 g) was charged on silica gel (60-120 mesh) column phenyl esters[5], β-sitosterol, α-spinasterol[6], stigmasterol[7], and eluted with a gradient of ethyl acetate and methanol matricarine methyl ester, matricane lactone[8], friedelin[9] (19:1, 9:1, 4:1, 7:3). Four major fractions were collected. and friedelinol[10], etc. Since, the chemistry of the roots of the plant seemed not to have been worked out, the present The ethyl acetate-methanol fraction (19:1, 0.1g) showed one investigation was undertaken to determine the components of major spot on TLC with some impurities in traces. It was the roots of the plant. In this paper we report the isolation and purified with column chromatography using silica gel (60- structural elucidation, by extensive spectral methods, of two 120 mesh) as adsorbent and eluted with chloroform-methanol aromatic compounds, Salicylic acid (1) and Methyl gallate (2) (11.5:1) to give compound (3) (13 mg). The ethyl acetate- (figure 1), (already reported in other species of the genus) [11], methanol fraction (9:1, 0.3g) on silica gel column for the first time, in addition to five known compounds: 3β- chromatography (60-120 mesh), with chloroform-methanol Erythrodiol (3), 3,5-Dimethoxybenzoic acid (4), 4- (4:1) as eluent, gave compound (4) (12 mg) and a mixture (71 hydroxybenzoic acid (5), 3,5-Dihydroxybenzoic acid (6), mg). The mixture was subjected to silica gel column 3β-Hydroxyolean-12-en-28-oic acid (7) from the methanol chromatography (100-200 mesh) and eluted with chloroform- extract of the root part of the plant. methanol (17:3) to yield the compounds (1) (11 mg) and (5) (10 mg). The ethyl acetate-methanol fraction (4:1, 0.2g) was MATERIALS AND METHODS subjected to silica gel column chromatography (60-120 mesh), with chloroform-methanol (3:1) as eluent, to give more of the General: Melting points were determined in centigrade scale compound (5) (4 mg) and (6) (07 mg). The ethyl acetate- in one end open capillary on Buchii 570 melting point methanol fraction (7:3, 0.09g) gave three major spots on TLC. apparatus and are uncorrected. IR spectrum was recorded It was separated by silica gel column chromatography (60-120 using KBr discs on Perkin-Elmer Paragon-1000 mesh), using chloroform-methanol (3:1) as eluent to give spectrophotometer, Esquire 3000 spectrometer. 1H and 13C- more of the compound (6) (5 mg) and a mixture (64 mg). The NMR spectra were recorded by a Bruker 500 and 125 MHz mixture was subjected to silica gel column chromatography instruements, respectively, using TMS as internal standard (100-200 mesh) and eluted with chloroform-methanol (7:3) to yield the compounds (2) (14 mg) and (7) (09 mg). and CDCl3 and CD3OD as solvent. The chemical shift values are reported in ppm (δ) units and the coupling constants (J) are in Hz. Column chromatography was carried out with Salicylic acid (2-Hydroxybenzoic acid) (1): o Merk silica gel (60-120 mesh and 100-200 mesh). Aluminium Colourless crystals, m.p.160.5 C, UV (MeOH) λmax. nm 302, -1 sheets, precoated with silica gel 60 F254 (20x20 cm, 0.2 mm 234, 208. IR (KBr) νmax : 3237(OH), 1662(C=O), 1609, 2856, 1 thick; E-Merck) were used for TLC to check the purity of the 2991, 1440, 1292, 1246, 1154, 892. H-NMR (CD3OD, 500 MHz) compounds and were visualized under UV light (254 and 366 δ: 7.89 (1H, d, J = 7.3 Hz, H-6), 7.48 (1H, t, J = 7.4 Hz, H-4)), 7.1 nm) followed by cerric sulfate as spraying reagent. (1H, d, J = 8.1 Hz, H-3) , 6.96 (1H, t, J = 7.3 Hz, H-5)), 12.1 (1H, 13 s, COOH). C-NMR (CD3OD, 125 MHz) δ: 174.2(C=O), 162.0 Corresponding Author: Javid A Banday, Department of Chemistry, University of Kashmir, Hazratbal, Srinagar-190006, J&K, India (C-2), 136.4(C-4), 130.5(C-6), 119.4(C-5), 117.3(C-3), 111.5(C-1). 3,5-Dihydroxybenzoic acid (6): o MS: m/z at (rel.int.) 138.0314(calculated for C7H6O3, 138.0316) Colourless crystals, m.p.236-238 C, UV (MeOH) λmax. nm 218, -1 (M+) (54), 120(100), 107(86), 92(99), 77(33). 250, 299. IR (KBr) νmax : 3515(O-H), 1710(C=O), 1 1630(Aromatic). H-NMR (CD3OD, 500 MHz) δ: 7.11 (2H, d, From these results, the structure of the compound (1) was J= 1.8Hz, H-2/H-6), 6.65(1H, d, J= 1.8Hz, H-4). 13C- NMR identified as Salicylic acid, which was confirmed by (CD3OD, 125 MHz) δ: 169.4(C=O), 159.0(C-3/C-5), 139.8(C-1), comparison of its spectral data with the data values reported 109.0(C-2/C-6), 108.3(C-4). MS: m/z at (rel. int.) 155.0259 + in literature [11,12]. (calculated for C7H7O4, 155.0266) (M+), 136(M-H2O) , 121(90), 72(14), 71(46). Methyl gallate (Methyl-3,4,5-trihydroxybenzoate) (2): o Colourless amorphous solid, m.p.203 C, UV (MeOH) λmax. The spectral data were in complete agreement with that -1 [17,18] nm 330, 260 , 236. IR (KBr) νmax : 3597, 2963, 1742, 1697, 1237, reported in literature. 1 1016. H-NMR (CD3OD, 500 MHz) δ : 3.79 (3H s,-OCH3), 7.1 13 (2H, s, H-2/H-6). C- NMR (CD3OD, 125 MHz) δ: 170(C=O), 3β-Hydroxyolean-12-en-28-oic acid (7): o -1 145.3(C-3/C-5), 139.8(C-4), 121(C-1), 110.4(C-2/C-6), Colourless crystals, m.p.305-306 C. IR (KBr) νmax : 3400-2640, 1 51.8(OCH3). MS: m/z at (rel. int.) 184.0971(calculated for 1700, 1660, 820. H-NMR (CD3OD, 500 MHz) δ : 5.24 (2H,t, J= C8H8O5, 184.0968) (M+) (38), 154(100), 126(32), 107(10), 79(23), 3.45Hz, H-12), 3.60(1H,dd,J= 4.1, 9.9Hz, H-3), 1.12, 1.03, 0.98, 13 69(07), 53(21), 51(22). 0.97, 0.91, 0.90, 0.89 (3H each, s, CH3) ; C- NMR (CD3OD, 125 MHz) δ :183.4(C-28), 143.6(C-13),122.7(C-12),79.0(C-3),55.2(C- From these results, the structure of the compound (2) was 5),47.6(C-9), 46.5(C-17), 45.9(C-19), 41.6(C-14), 41.0(C-18), identified as Methyl gallate, which was confirmed by 39.1(C-8), 38.7(C-4), 38.4(C-1), 37.1(C-10), 33.8(C-21), 33.0(C- comparison of its spectral data with the data values reported 29), 32.6(C-7), 32.4(C-22), 30.6(C-20), 28.1(C-23), 27.7(C-15), in literature.[11,13,14] 27.2(C-2), 25.9(C-27), 23.5(C-30), 23.4(C-11), 23.4(C-16), 18.3(C- 6), 17.1(C-26), 15.6(C-24), 15.3(C-25). MS: m/z at (rel. int.) 3β-Erythrodiol (3): 456.3610 (calculated for C8H8O5, 456.3603) 456(M+) (4), o -1 Colourless crystals, m.p.229 C, IR (KBr) νmax : 3580, 3430(O- 248(98), 208(12), 203(60), 133(53). 1 H), 1610(C=C). H-NMR (CD3Cl3, 500 MHz) δ : 5.70 (1H, t, J =3.6Hz, H-12), 3.12 (1H, d, Jaa=11.2 Hz, Jae=4.5 Hz,H-12), The spectral data were in complete agreement with that 1.15(3H,s, H-27), 0.98(3H,s,H-23), 0.93(3H,s,H-26), reported in literature.
Load more

Recommended publications
  • Hplc∓Dad∓ESI-MS/MS Screening of Bioactive Components
    Food Chemistry 166 (2015) 179–191 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits ⇑ Ibrahim M. Abu-Reidah a,b,c, Mohammed S. Ali-Shtayeh a, , Rana M. Jamous a, David Arráez-Román b,c, ⇑ Antonio Segura-Carretero b,c, a Biodiversity & Environmental Research Center (BERC), Til, Nablus POB 696, Palestine b Department of Analytical Chemistry, Faculty of Sciences, University of Granada, Avda. Fuentenueva, 18071 Granada, Spain c Functional Food Research and Development Centre (CIDAF), PTS Granada, Avda. del Conocimiento, Edificio Bioregión, 18016 Granada, Spain article info abstract Article history: Rhus coriaria L. (sumac) is an important crop widely used in the Mediterranean basin as a food spice, and Received 25 March 2014 also in folk medicine, due to its health-promoting properties. Phytochemicals present in plant foods are in Received in revised form 29 May 2014 part responsible for these consequent health benefits. Nevertheless, detailed information on these Accepted 3 June 2014 bioactive compounds is still scarce. Therefore, the present work was aimed at investigating the Available online 12 June 2014 phytochemical components of sumac fruit epicarp using HPLC–DAD–ESI-MS/MS in two different ionisation modes. The proposed method provided tentative identification of 211 phenolic and other Keywords: phyto-constituents, most of which have not been described so far in R. coriaria fruits. More than 180 Palestinian sumac phytochemicals (tannins, (iso)flavonoids, terpenoids, etc.) are reported herein in sumac fruits for the first Anacardiaceae Hydrolysable tannins time.
    [Show full text]
  • Molecular Docking Study on Several Benzoic Acid Derivatives Against SARS-Cov-2
    molecules Article Molecular Docking Study on Several Benzoic Acid Derivatives against SARS-CoV-2 Amalia Stefaniu *, Lucia Pirvu * , Bujor Albu and Lucia Pintilie National Institute for Chemical-Pharmaceutical Research and Development, 112 Vitan Av., 031299 Bucharest, Romania; [email protected] (B.A.); [email protected] (L.P.) * Correspondence: [email protected] (A.S.); [email protected] (L.P.) Academic Editors: Giovanni Ribaudo and Laura Orian Received: 15 November 2020; Accepted: 1 December 2020; Published: 10 December 2020 Abstract: Several derivatives of benzoic acid and semisynthetic alkyl gallates were investigated by an in silico approach to evaluate their potential antiviral activity against SARS-CoV-2 main protease. Molecular docking studies were used to predict their binding affinity and interactions with amino acids residues from the active binding site of SARS-CoV-2 main protease, compared to boceprevir. Deep structural insights and quantum chemical reactivity analysis according to Koopmans’ theorem, as a result of density functional theory (DFT) computations, are reported. Additionally, drug-likeness assessment in terms of Lipinski’s and Weber’s rules for pharmaceutical candidates, is provided. The outcomes of docking and key molecular descriptors and properties were forward analyzed by the statistical approach of principal component analysis (PCA) to identify the degree of their correlation. The obtained results suggest two promising candidates for future drug development to fight against the coronavirus infection. Keywords: SARS-CoV-2; benzoic acid derivatives; gallic acid; molecular docking; reactivity parameters 1. Introduction Severe acute respiratory syndrome coronavirus 2 is an international health matter. Previously unheard research efforts to discover specific treatments are in progress worldwide.
    [Show full text]
  • Evolution of 49 Phenolic Compounds in Shortly-Aged Red Wines Made from Cabernet Gernischt (Vitis Vinifera L
    Food Sci. Biotechnol. Vol. 18, No. 4, pp. 1001 ~ 1012 (2009) ⓒ The Korean Society of Food Science and Technology Evolution of 49 Phenolic Compounds in Shortly-aged Red Wines Made from Cabernet Gernischt (Vitis vinifera L. cv.) Zheng Li, Qiu-Hong Pan, Zan-Min Jin, Jian-Jun He, Na-Na Liang, and Chang-Qing Duan* Center for Viticulture and Enology, College of Food Science and Nutritional Engineering, China Agricultural University, Beijing 100083, PR China Abstract A total of 49 phenolic compounds were identified from the aged red wines made from Cabernet Gernischt (Vitis vinifera L. cv.) grapes, a Chinese characteristic variety, including 13 anthocyanins, 4 pryanocyanins, 4 flavan-3-ol monomers, 6 flavan-3-ol polymers, 7 flavonols, 6 hydroxybenzoic acids, 5 hydroxycinnamic acids, 3 stilbenes, and 1 polymeric pigment. Evolution of these compounds was investigated in wines aged 1 to 13 months. Variance analysis showed that the levels of most phenolics existed significant difference in between wines aged 3 and 9 months. Cluster analysis indicated that 2 groups could be distinguished, one corresponding to wines aged 1 to 3 months and the other to wines aged 4 to 13 months. It was thus suggested that there were 2 key-stages for the development of fine wine quality, at the aged 3 and 9 months, respectively. This work would provide some helpful information for quality control in wine production. Keywords: Cabernet Gernischt, aged wine, phenolic compound, evolution, high performance liquid chromatography coupled with tandem mass spectrometry Introduction 3-ols in red wine and correlation with wine age (12), the evolutions of low molecular weight phenolic compounds Phenolic compounds in red wines mainly contain such as gallic acids and caffeic acids (13,14), as well as the anthocyanins, flavonols, flavan-3-ols, phenolic acids effects of oak barrel compounds and sorption behaviors on (including hydroxybenzoic acids and hydroxycinnamic evolution of phenolic compounds (15), have been reported.
    [Show full text]
  • Antioxidant, Cytotoxic, and Antimicrobial Activities of Glycyrrhiza Glabra L., Paeonia Lactiflora Pall., and Eriobotrya Japonica (Thunb.) Lindl
    Medicines 2019, 6, 43; doi:10.3390/medicines6020043 S1 of S35 Supplementary Materials: Antioxidant, Cytotoxic, and Antimicrobial Activities of Glycyrrhiza glabra L., Paeonia lactiflora Pall., and Eriobotrya japonica (Thunb.) Lindl. Extracts Jun-Xian Zhou, Markus Santhosh Braun, Pille Wetterauer, Bernhard Wetterauer and Michael Wink T r o lo x G a llic a c id F e S O 0 .6 4 1 .5 2 .0 e e c c 0 .4 1 .5 1 .0 e n n c a a n b b a r r b o o r 1 .0 s s o b b 0 .2 s 0 .5 b A A A 0 .5 0 .0 0 .0 0 .0 0 5 1 0 1 5 2 0 2 5 0 5 0 1 0 0 1 5 0 2 0 0 0 1 0 2 0 3 0 4 0 5 0 C o n c e n tr a tio n ( M ) C o n c e n tr a tio n ( M ) C o n c e n tr a tio n ( g /m l) Figure S1. The standard curves in the TEAC, FRAP and Folin-Ciocateu assays shown as absorption vs. concentration. Results are expressed as the mean ± SD from at least three independent experiments. Table S1. Secondary metabolites in Glycyrrhiza glabra. Part Class Plant Secondary Metabolites References Root Glycyrrhizic acid 1-6 Glabric acid 7 Liquoric acid 8 Betulinic acid 9 18α-Glycyrrhetinic acid 2,3,5,10-12 Triterpenes 18β-Glycyrrhetinic acid Ammonium glycyrrhinate 10 Isoglabrolide 13 21α-Hydroxyisoglabrolide 13 Glabrolide 13 11-Deoxyglabrolide 13 Deoxyglabrolide 13 Glycyrrhetol 13 24-Hydroxyliquiritic acid 13 Liquiridiolic acid 13 28-Hydroxygiycyrrhetinic acid 13 18α-Hydroxyglycyrrhetinic acid 13 Olean-11,13(18)-dien-3β-ol-30-oic acid and 3β-acetoxy-30-methyl ester 13 Liquiritic acid 13 Olean-12-en-3β-ol-30-oic acid 13 24-Hydroxyglycyrrhetinic acid 13 11-Deoxyglycyrrhetinic acid 5,13 24-Hydroxy-11-deoxyglycyirhetinic
    [Show full text]
  • Rhamnus Prinoides Plant Extracts and Pure Compounds Inhibit Microbial Growth and Biofilm Ormationf
    Georgia State University ScholarWorks @ Georgia State University Biology Dissertations Department of Biology 12-15-2020 Rhamnus prinoides Plant Extracts and Pure Compounds Inhibit Microbial Growth and Biofilm ormationF Mariya Campbell Follow this and additional works at: https://scholarworks.gsu.edu/biology_diss Recommended Citation Campbell, Mariya, "Rhamnus prinoides Plant Extracts and Pure Compounds Inhibit Microbial Growth and Biofilm ormation.F " Dissertation, Georgia State University, 2020. https://scholarworks.gsu.edu/biology_diss/246 This Dissertation is brought to you for free and open access by the Department of Biology at ScholarWorks @ Georgia State University. It has been accepted for inclusion in Biology Dissertations by an authorized administrator of ScholarWorks @ Georgia State University. For more information, please contact [email protected]. RHAMNUS PRINOIDES PLANT EXTRACTS AND PURE COMPOUNDS INHIBIT MICROBIAL GROWTH AND BIOFILM FORMATION by MARIYA M. CAMPBELL Under the Direction of Eric Gilbert, PhD ABSTRACT The increased prevalence of antibiotic resistance threatens to render all of our current antibiotics ineffective in the fight against microbial infections. Biofilms, or microbial communities attached to biotic or abiotic surfaces, have enhanced antibiotic resistance and are associated with chronic infections including periodontitis, endocarditis and osteomyelitis. The “biofilm lifestyle” confers survival advantages against both physical and chemical threats, making biofilm eradication a major challenge. A need exists for anti-biofilm treatments that are “anti-pathogenic”, meaning they act against microbial virulence in a non-biocidal way, leading to reduced drug resistance. A potential source of anti-biofilm, anti-pathogenic agents is plants used in traditional medicine for treating biofilm-associated conditions. My dissertation describes the anti-pathogenic, anti-biofilm activity of Rhamnus prinoides (gesho) extracts and specific chemicals derived from them.
    [Show full text]
  • G166766A Agilent Fiehn GC/MS Metabolomics RTL Library: List of Compounds
    G166766A Agilent Fiehn GC/MS Metabolomics RTL Library: List of Compounds Data Sheet 800 Metabolite library for more compound identification The Agilent Fiehn GC/MS metabolomics RTL Library is the most comprehensive commercially available GC/MS library of metabolite spectra. This expanding library currently contains over 1,400 entries for approximately 800 common metabolites, including spectra corresponding to partial derivatization of metabolites under the recommended conditions. In this list, each entry includes the name, CAS, and PubChem numbers of the native molecule for easier compound recognition and subsequent literature, software, and pathway searching.
    [Show full text]
  • Streptococcus Gallolyticus Natalia Jiménez, Inés Reverón, María Esteban-Torres, Félix López De Felipe, Blanca De Las Rivas and Rosario Muñoz*
    Jiménez et al. Microbial Cell Factories 2014, 13:154 http://www.microbialcellfactories.com/content/13/1/154 RESEARCH Open Access Genetic and biochemical approaches towards unravelling the degradation of gallotannins by Streptococcus gallolyticus Natalia Jiménez, Inés Reverón, María Esteban-Torres, Félix López de Felipe, Blanca de las Rivas and Rosario Muñoz* Abstract Background: Herbivores have developed mechanisms to overcome adverse effects of dietary tannins through the presence of tannin-resistant bacteria. Tannin degradation is an unusual characteristic among bacteria. Streptococcus gallolyticus is a common tannin-degrader inhabitant of the gut of herbivores where plant tannins are abundant. The biochemical pathway for tannin degradation followed by S. gallolyticus implies the action of tannase and gallate decarboxylase enzymes to produce pyrogallol, as final product. From these proteins, only a tannase (TanBSg) has been characterized so far, remaining still unknown relevant proteins involved in the degradation of tannins. Results: In addition to TanBSg, genome analysis of S. gallolyticus subsp. gallolyticus strains revealed the presence of an additional protein similar to tannases, TanASg (GALLO_0933). Interestingly, this analysis also indicated that only S. gallolyticus strains belonging to the subspecies “gallolyticus” possessed tannase copies. This observation was confirmed by PCR on representative strains from different subspecies. In S. gallolyticus subsp. gallolyticus the genes encoding gallate decarboxylase are clustered together and close to TanBSg, however, TanASg is not located in the vicinity of other genes involved in tannin metabolism. The expression of the genes enconding gallate decarboxylase and the two tannases was induced upon methyl gallate exposure. As TanBSg has been previously characterized, in this work the tannase activity of TanASg was demonstrated in presence of phenolic acid esters.
    [Show full text]
  • Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus Altissima
    molecules Article Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima Jian-Cheng Ni 1 ID , Jian-Ting Shi 1, Qing-Wei Tan 1,2,* and Qi-Jian Chen 1,2,* 1 Key Laboratory of Bio-Pesticide and Chemistry-Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China; [email protected] (J.-C.N.); [email protected] (J.-T.S.) 2 Key Laboratory of Plant Virology of Fujian Province, Institute of Plant Virology, Fujian Agriculture and Forestry University, Fuzhou 350002, China * Correspondence: [email protected] (Q.-W.T.); [email protected] (Q.-J.C.); Tel.: +86-591-837-893-65 (Q.-W.T.); +86-591-837-894-69 (Q.-J.C.) Received: 2 November 2017; Accepted: 29 November 2017; Published: 4 December 2017 Abstract: Four novel compounds—two phenylpropionamides, one piperidine, and one phenolic derivatives—were isolated and identified from the fruit of a medicinal plant, Ailanthus altissima (Mill.) Swingle (Simaroubaceae), together with one known phenylpropionamide, 13 known phenols, and 10 flavonoids. The structures of the new compounds were elucidated as 2-hydroxy-N-[(2-O-β-D-glucopyranosyl)phenyl]propionamide (1), 2-hydroxy-N-[(2-O-β-D-glucopyranosyl-(1!6)-β-D-glucopyranosyl)phenyl]propionamide (2), 2β-carboxyl- piperidine-4β-acetic acid methyl ester (4), and 4-hydroxyphenyl-1-O-[6-(hydrogen- 3-hydroxy-3-methylpentanedioate)]-β-D-glucopyranoside (5) based on spectroscopic analysis. All the isolated compounds were evaluated for their inhibitory activity against Tobacco mosaic virus (TMV) using the leaf-disc method. Among the compounds isolated, arbutin (6), β-D-glucopyranosyl-(1!6)-arbutin (7), 4-methoxyphenylacetic acid (10), and corilagin (18) showed moderate inhibition against TMV with IC50 values of 0.49, 0.51, 0.27, and 0.45 mM, respectively.
    [Show full text]
  • Crystal Engineering of Molecular and Ionic Cocrystals by Tien Teng Ong
    Crystal Engineering of Molecular and Ionic Cocrystals by Tien Teng Ong A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy Department of Chemistry College of Arts and Sciences University of South Florida Major Professor: Michael J. Zaworotko, Ph.D. Ning Shan, Ph.D. Örn Almarsson, Ph.D. Shengqian Ma, Ph.D. Date of Approval: March 25, 2011 Keywords: Aqueous Solubility, Ellagic Acid, Lithium Salts, Amino Acids, Lithium Diamondoid Metal-Organic Materials © Copyright 2011, Tien Teng Ong Dedication To my dearest parents and esteemed mentor who is apt to judge and appraise this artefact Acknowledgements First and foremost, I will seize this opportunity to express my deepest gratitude to my Ph.D. mentor, Dr. Michael J. Zaworotko, for providing me with the physical and mental space to nucleate and crystallize into who I am today. I must thank the members of my graduate committee: Dr. Ning Shan, Dr. Örn Almarsson, Dr. Shengqian Ma, for their scientific inputs, guidance and support throughout my doctoral research, and Dr. R. Douglas Shytle for kindly agreeing to serve as the chairperson of my examination committee. I thank all past and present members in the research groups of Dr. Zaworotko and Dr. Eddaoudi for their informative discussions, especially the cocrystal team whose earlier work highlighted the trials that lie ahead of me. I especially like to acknowledge and thank Dr. Kapildev K. Arora, Dr. Łukasz Wojtas and Jason A. Perman for imparting their knowledge in the practice of single crystal X-ray crystallography as an indispensable tool in my doctoral research.
    [Show full text]
  • E. R. E. E.O.E. the Present Invention Provides Novel Compounds with Hypot
    US0093.76369B2 (12) United States Patent (10) Patent No.: US 9,376,369 B2 Chatterjee (45) Date of Patent: Jun. 28, 2016 (54) ANTI-CHOLESTEROLEMIC COMPOUNDS OTHER PUBLICATIONS AND METHODS OF USE Muruganandam et al. Indian Journal of Experimental Biology, vol. 40, Oct. 2002, pp. 1151-1160.* (71) Applicant: Subroto Chatterjee, Columbia, MD Wang et al..Journal of Ethnopharmacology 96 (2005) 483-487, pub (US) lished online Nov. 11, 2004.* Conner et al. Nutrition 12:274-277, 1996.* (72) Inventor: Subroto Chatterjee, Columbia, MD Definition of Inflammation by Medical dictionary, http://medical (US) dictionary.thefreedictionary.com/Inflammation, internet article downloaded Sep. 22, 2015.* - r Chae, Hypertension, 2001; 38:399-403.* (*) Notice: Subject to any disclaimer the term of this Abe I et al. "Potent and selective inhibition of squalene epoxidase by past list: G adjusted under 35 synthetic galloyl esters.” Biochem Biophys Res Commun. Apr. 2, M YW- y U days. 2000:270(1): 137-40. Alzheimer's Disease—downloaded Jun. 2011 from PubMed Health. (21)21) AppAppl. No.: 13/946,5589 American Heart Association, Cholesterol Abnormalities & Dis ease—downloaded Jun. 2011. (22) Filed: Jul.19, 2013 Baker, State University of New York at Buffalo Reporter, vol. 28, No. 35: Jul 24, 1997. O O Crespy Vetal. "A review of the health effects of green tea catechins (65) Prior Publication Data in in vivo animal models.” JNutr. Dec. 2004;134(12 Suppl):3431S US 2014/0031304 A1 Jan. 30, 2014 344OS. s Definition of food—dlownloaded from biology-online.org <http:// biology-online.org>, Jun. 2011. O O Merck Manuals Online: Stroke—downloaded Jun.
    [Show full text]
  • Inflammation and Oxidative Stress in an Obese State and the Protective
    nutrients Review Inflammation and Oxidative Stress in an Obese State and the Protective Effects of Gallic Acid Phiwayinkosi V. Dludla 1,2,* , Bongani B. Nkambule 3, Babalwa Jack 2, Zibusiso Mkandla 3, Tinashe Mutize 3, Sonia Silvestri 1, Patrick Orlando 1, Luca Tiano 1, Johan Louw 2,4 and Sithandiwe E. Mazibuko-Mbeje 2,5 1 Department of Life and Environmental Sciences, Polytechnic University of Marche, 60131 Ancona, Italy; [email protected] (S.S.); [email protected] (P.O.); [email protected] (L.T.) 2 Biomedical Research and Innovation Platform, South African Medical Research Council, Tygerberg 7505, South Africa; [email protected] (B.J.); [email protected] (J.L.); [email protected] (S.E.M.-M.) 3 School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4000, South Africa; [email protected] (B.B.N.); [email protected] (Z.M.); [email protected] (T.M.) 4 Department of Biochemistry and Microbiology, University of Zululand, KwaDlangezwa 3886, South Africa 5 Division of Medical Physiology, Faculty of Health Sciences, Stellenbosch University, Tygerberg 7505, South Africa * Correspondence: [email protected]; Tel.: +27-021-938-0333 Received: 15 October 2018; Accepted: 17 November 2018; Published: 21 December 2018 Abstract: Metabolic complications in an obese state can be aggravated by an abnormal inflammatory response and enhanced production of reactive oxygen species. Pro-inflammatory response is known to be associated with the formation of toxic reactive oxygen species and subsequent generation of oxidative stress.
    [Show full text]
  • Supplementary Information Aggregating Behavior of Phenolic Compounds: a Source of False Bioassay Results?
    Supplementary Information Aggregating behavior of Phenolic Compounds: A Source of False Bioassay Results? Table S1. List of the phenolic compounds used in the study and their bioactivity summary data in PubChem BioAssays database. (PubChem search). ratio Chemical name MW Supplier active total (actuve/total) Acacetin 284.3 Carl Roth GmbH, Germany 41 520 0.079 Alphanaphthoflavone 272.9 Acros, USA 31 135 0.230 Apigenin 270.2 Fluka, Switzerland 146 1062 0.137 L-ascorbic acid 176.1 Sigma, Germany 67 780 0.086 Benzoic acid 122.1 Merck, Germany 24 429 0.056 3-Benzoylbenzo(F)coumarin 300.3 Acros, USA N/A N/A 3-(2-Benzoxazolyl)umbelliferone 279.2 Fluka, Switzerland 8 73 0.110 Bergapten 216.2 Carl Roth GmbH, Germany 21 590 0.036 Butylated hydroxyanisole 180.2 Sigma, Germany N/A N/A Caffeic acid 180.2 Sigma, USA 101 1101 0.092 (+)-Catechin 290.3 Sigma, USA 9 305 0.030 Catechol 110.1 Sigma, Germany 70 639 0.110 Chrysin 254.3 Extrasynthese, France 84 791 0.106 o-Coumaric acid 164.2 Sigma, USA 6 35 0.171 Coumarin 102 255.3 Acros, USA 0 2 0.000 Coumarin 30 347.4 ICN, USA 127 761 0.167 Coumarin 7 333.4 Acros, USA 158 796 0.198 Coumarin 146.2 Merck, Germany 38 916 0.041 Cyanidin chloride 322.7 Carl Roth GmbH, Germany 5 11 0.455 Daidzein 254.3 Extrasynthese, France 61 785 0.078 Daphnetin 178.2 Extrasynthese, France 27 240 0.113 7-Diethylamino-3-thenoylcoumarin 327.4 Acros, USA 13 82 0.159 2,3-Dihydroxybenzoic acid 154.1 Fluka, Switzerland 5 327 0.015 2,5-Dihydroxybenzoic acid 154.1 Fluka, Switzerland 5 223 0.022 2,6-Dihydroxybenzoic acid 154.1 Fluka, Switzerland
    [Show full text]