Interactive Effects of Wide-Spectrum Monochromatic Lights On

Total Page:16

File Type:pdf, Size:1020Kb

Interactive Effects of Wide-Spectrum Monochromatic Lights On molecules Article Interactive Effects of Wide-Spectrum Monochromatic Lights on Phytochemical Production, Antioxidant and Biological Activities of Solanum xanthocarpum Callus Cultures Hazrat Usman 1, Muhammad Asad Ullah 1 , Hasnain Jan 1, Aisha Siddiquah 1, Samantha Drouet 2,3, Sumaira Anjum 4 , Nathalie Giglioli-Guviarc’h 5, Christophe Hano 2,3,* and Bilal Haider Abbasi 1,* 1 Department of Biotechnology, Quaid-i-Azam University, Islamabad 45320, Pakistan; [email protected] (H.U.); [email protected] (M.A.U.); [email protected] (H.J.); [email protected] (A.S.) 2 Laboratoire de Biologie des Ligneux et des Grandes Cultures (LBLGC), INRA USC1328 Unversité d’, CEDEX 2, 45067 Orléans, France; [email protected] 3 COSMACTIFS, Bioactifs et Cosmétiques, CNRS GDR3711, CEDEX 2, 4506 Orléans, France 4 Department of Biotechnology, Kinnaird College for Women, Lahore 54000, Pakistan; [email protected] 5 EA2106 Biomolecules et Biotechnologies Vegetales, Universite de Tours, 37000 Tours, France; [email protected] * Correspondence: [email protected] (B.H.A.); [email protected] (C.H.); Tel.: +92-51-90644121 or +92-300-5125822 (B.H.A.); +33-2-37-30-97-53 (C.H.); Fax: +92-51-90644121 (B.H.A.) Academic Editors: Hosam O. Elansary and Vincenzo De Feo Received: 28 January 2020; Accepted: 31 March 2020; Published: 8 May 2020 Abstract: Solanum xanthocarpum is considered an important traditional medicinal herb because of its unique antioxidant, and anti-diabetic, anti-aging, and anti-inflammatory potential. Because of the over exploitation linked to its medicinal properties as well as destruction of its natural habitat, S. xanthocarpum is now becoming endangered and its supply is limited. Plant in vitro culture and elicitation are attractive alternative strategies to produce biomass and stimulate biosynthesis of medicinally important phytochemicals. Here, we investigated the potential influence of seven different monochromatic light treatments on biomass and secondary metabolites accumulation in callus culture of S. xanthocarpum as well as associated biological activities of the corresponding extracts. Among different light treatments, highest biomass accumulation was observed in white light-treated callus culture. Optimum accumulation of total flavonoid contents (TFC) and total phenolic contents (TPC) were observed in callus culture kept under continuous white and blue light respectively than control. Quantification of phytochemicals through HPLC revealed that optimum production of caffeic acid (0.57 0.06 mg/g DW), methyl-caffeate (17.19 mg/g 1.79 DW), scopoletin ± ± (2.28 0.13 mg/g DW), and esculetin (0.68 0.07 mg/g DW) was observed under blue light callus ± ± cultures. Compared to the classic photoperiod condition, caffeic acid, methyl-caffeate, scopoletin, and esculetin were accumulated 1.7, 2.5, 1.1, and 1.09-folds higher, respectively. Moreover, high in vitro cell free antioxidant, anti-diabetic, anti-aging, and anti-inflammatory activities were closely associated with the production of these secondary metabolites. These results clearly showed the interest to apply multispectral light as elicitor of in vitro callus cultures S. xanthocarpum to promote the production of important phytochemicals, and allow us to propose this system as an alternative for the collection of this endangered species from the wild. Keywords: Solanum xanthocarpum; elicitation; multispectral lights; caffeic acid; coumarins; anti-diabetic; anti-inflammatory Molecules 2020, 25, 2201; doi:10.3390/molecules25092201 www.mdpi.com/journal/molecules Molecules 2020, 25, x FOR PEER REVIEW 2 of 25 Molecules 2020, 25, 2201 2 of 25 1. Introduction 1. Introduction Medicinal plants are used by mankind as a source of primary health care for thousands of years, in an Medicinalattempt to plants cure diseases are used because by mankind of their as wide a source pharmaceutical of primary health and therapeutic care for thousands applications of years, [1]. Medicinalin an attempt plants to cure are diseasesused widely because in both of their developed wide pharmaceutical and developing and countries. therapeutic According applications to the [1]. WHOMedicinal report plants on aretraditional used widely medicine in both strategy developed 2014 and–2023, developing 70% population countries. Accordingof the world to the rely WHO on traditionalreport on traditional medicines, medicine mostly of strategy plant origin 2014–2023,, whereas 70% 80% population population of of the developing world rely countries on traditional uses medicinalmedicines, plants mostly for of treatment plant origin, of diseases whereas [1] 80%. With population a paradigm of developing shift in the countries20th century uses to medicinalward the useplants of synthetic for treatment chemicals, of diseases reputed [1 to]. be With more a paradigmeffective and shift safer in to the combat 20th century diseases, toward the interest the use in medicinalof synthetic plants chemicals, has temporarily reputed tofailed be more and some effective studies and reported safer to combatthat the diseases,use of medicinal the interest plants in wasmedicinal reduced plants by one has- temporarilyfourth during failed thatand period some [2,3] studies. However, reported numerous that the usestudies of medicinal show that plants the excessivewas reduced use of by synthetic one-fourth drugs during could that have period side [effects2,3]. However, and considerably numerous increase studies the show incidence that theof someexcessive diseases use of[3] synthetic. With the drugs development could have of side modern effects approaches and considerably, such as increase biotechnological the incidence plant of sourcing,some diseases analyt [ical3]. Withtools for the compounds development identification of modern,approaches, and isolation such or molecular as biotechnological investigation plant of biologicalsourcing, analyticalactivity mechanism tools for compoundss, herbal medicine identification, is back in and the isolation spotlights or molecular[4]. Solanum investigation xanthocarpum of Schrad.biological and activity Wendl mechanisms,(Solanaceae; aka herbal Solanum medicine virginianum is back L. in or the Solanum spotlights mairei [4 ].H.Solanum Lév.) is a xanthocarpum wild annual herb.Schrad. The and plant Wendl is also (Solanaceae known under; aka Solanum the vernacular virginianum namesL. of or KantakariSolanum maireior Bhatkatiya.H. Lév.) isIts a fruits, wild annualedible yellowherb. Theberries plant surrounded is also known by enlarged under thecalyx, vernacular are largely names used as of traditional Kantakari medicine or Bhatkatiya. to cure Its various fruits, ailments.edible yellow Several berries biological surrounded activities by enlarged relevant calyx, with are their largely traditional used as traditionaluses have medicinebeen reported to cure, includingvarious ailments. antioxidant Several [5–7] biological, anti-diabetic activities [8,9] relevant, anti-inflammatory with their traditional [10,11], as uses well have as effects been reported, on skin appearanceincluding antioxidant [12]. Phytochemical [5–7], anti-diabetic profiling of [8 S.,9 ],xanthocarpum anti-inflammatory extracts [ 10revealed,11], as the well presence as effects of ondiverse skin classesappearance of bioactive [12]. Phytochemical secondary metabolite profilings ofincludingS. xanthocarpum alkaloidextracts glycoside revealeds [13,14] the, saponin presences [15,16] of diverse, but alsoclasses of ofhigh bioactive levels secondaryof coumarins metabolites [17], in particular including alkaloidof scopoletin glycosides and esculetin [13,14], saponins (Figure [1).15 ,From16], but a biosyntheticalso of high levelspoint of coumarinsview, these [ 17coumarins], in particular derived of scopoletinfrom the phenylpropanoid and esculetin (Figure pathway,1). From more a preciselybiosynthetic from point trans of- view,cinnamic these acid, coumarins rather derivedvia umbelliferone from the phenylpropanoid than through lactonization pathway, more reaction precisely of thefrom caffeictrans -cinnamicacid derivative, acid, rather2’-hydroxy via umbelliferone-caffeic acid lead than to through esculetin lactonization formation [18] reaction. Scopoletin of the is ca ffalsoeic producedacid derivative, from 2’-hydroxy-catrans-cinnamicffeic acid acid but lead via to esculetincaffeic acid formation ester [18derivatives]. Scopoletin (Figure is also 1) produced [18,19]. Alternatively,from trans-cinnamic caffeic acidacid but is stored via caff ineic its acid methylated ester derivatives form, i.e. (Figure, methyl1)[-caffeate18,19]. Alternatively,, in S. xanthocarpum caffeic (Figureacid isstored 1) [20] in. its methylated form, i.e., methyl-caffeate, in S. xanthocarpum (Figure1)[20]. O OH NH2 L-Phenylanine FLAVONOIDS PAL O O O HO HO OH OH OCH3 HO HO trans-cinnamic acid caffeic acid methyl-caffeate HO HO H3C O HO O O HO O O HO O O umbelliferone esculetin scopoletin Figure 1. SchematicSchematic view view of of the the phenylpropanoid phenylpropanoid pathway pathway leading leading to to the the production production of of flavonoids, flavonoids, phenolics (in (in particular, particular, caffeic caffeic acid acid and and methyl methyl-ca-caffeateffeate)) and and coumarins coumarins (in particular, (in particular, esculetin esculetin and and scopoletin). PAL: l-phenylalanine ammonia-lyse. Adapted from Bourgaud et al. [18] and Karamat et al. [19]. Molecules 2020, 25, 2201 3 of 25 Because of the over exploitation linked to its medicinal properties as
Recommended publications
  • The Bioactive Compounds in Agricultural Products and Their Roles in Health Promoting Functions
    Louisiana State University LSU Digital Commons LSU Doctoral Dissertations Graduate School 2015 The ioB active Compounds in Agricultural Products and Their Roles in Health Promoting Functions Yixiao Shen Louisiana State University and Agricultural and Mechanical College, [email protected] Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_dissertations Part of the Life Sciences Commons Recommended Citation Shen, Yixiao, "The ioB active Compounds in Agricultural Products and Their Roles in Health Promoting Functions" (2015). LSU Doctoral Dissertations. 2791. https://digitalcommons.lsu.edu/gradschool_dissertations/2791 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Doctoral Dissertations by an authorized graduate school editor of LSU Digital Commons. For more information, please [email protected]. THE BIOACTIVE COMPOUNDS IN AGRICULTURAL PRODUCTS AND THEIR ROLES IN HEALTH PROMOTING FUNCTIONS A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The School of Nutrition and Food Sciences by Yixiao Shen B.S., Shenyang Agricultural University, 2010 M.S., Shenyang Agricultural University, 2012 December 2015 ACKNOWLEDGEMENTS This dissertation is a lively description of my whole Ph.D. life which is full of love from the ones who played an integral role in the completion of this degree. It is with my deepest gratitude to express my appreciation to those helping me realize my dream. To Dr. Zhimin Xu, thank you so much for offering me the opportunity to pursue my doctoral degree under your mentorship.
    [Show full text]
  • Review Article Caffeates and Caffeamides: Synthetic Methodologies and Their Antioxidant Properties
    Hindawi International Journal of Medicinal Chemistry Volume 2019, Article ID 2592609, 15 pages https://doi.org/10.1155/2019/2592609 Review Article Caffeates and Caffeamides: Synthetic Methodologies and Their Antioxidant Properties Merly de Armas-Ricard ,1 Enrique Ruiz-Reyes,2 and Oney Ramírez-Rodríguez 1 1Laboratory of Chemistry and Biochemistry, Campus Lillo, University of Aysén, Eusebio Lillo 667, Coyhaique 5951537, Aysén, Chile 2Department of Chemistry, Basic Sciences Institute, Technical University of Manabí (Universidad Técnica de Manabí), Av Urbina y Che Guevara, Portoviejo, Manabí, Ecuador Correspondence should be addressed to Merly de Armas-Ricard; [email protected] and Oney Ramírez-Rodríguez; [email protected] Received 29 April 2019; Accepted 25 July 2019; Published 11 November 2019 Academic Editor: Rosaria Volpini Copyright © 2019 Merly de Armas-Ricard et al. ­is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Polyphenols are secondary metabolites of plants and include a variety of chemical structures, from simple molecules such as phenolic acids to condensed tannins and highly polymerized compounds. Caeic acid (3,4-dihydroxycinnamic acid) is one of the hydroxycinnamate metabolites more widely distributed in plant tissues. It is present in many food sources, including coee drinks, blueberries, apples, and cider, and also in several medications of popular use, mainly those based on propolis. Its derivatives are also known to possess anti-inammatory, antioxidant, antitumor, and antibacterial activities, and can contribute to the prevention of atherosclerosis and other cardiovascular diseases. ­is review is an overview of the available information about the chemical synthesis and antioxidant activity of caeic acid derivatives.
    [Show full text]
  • Thesis P.Murciano Martinez 29 February 2016
    Alkaline pretreatments of lignin-rich by-products and their implications for enzymatic degradation Patricia Murciano Martínez Thesis committee Promotor Prof. Dr H. Gruppen Professor of Food Chemistry Wagenigen University Co-promotor Dr M. A. Kabel Assistant Professor, Laboratory of Food Chemistry Wageningen University Other members Prof. Dr G. Zeeman, Wageningen University Prof. Dr C. Felby, University of Copenhagen Dr R. J. A. Gosselink, Wageningen UR Food & Biobased Research Dr J. Wery, Corbion-Purac Biochem, Gorinchem This research was conducted under the auspices of the Graduate School VLAG (Advanced studies in Food Technology, Agrobiotechnology, Nutrition and Health Sciences). Alkaline pretreatments of lignin-rich by-products and their implications for enzymatic degradation Patricia Murciano Martínez Thesis Submitted in fulfilment of the requirements for the degree of doctor at Wageningen University by the authority of the Rector Magnificus Prof. Dr A.P.J. Mol, in the presence of the Thesis Committee appointed by the Academic Board to be defended in public on Friday 1 April 2016 at 4 p.m. in the Aula. Patricia Murciano Martínez Alkaline pretreatments of lignin-rich by-products and their implications for enzymatic degradation 162 pages. PhD thesis, Wageningen University, Wageningen, NL (2016) With references, with summary in English ISBN: 978-94-6257-662-9 Table of contents Chapter 1 General introduction 1 Chapter 2 Delignification outperforms alkaline extraction as 25 pretreatment for enzymatic fingerprinting of xylan from oil palm
    [Show full text]
  • The Phytochemistry of Cherokee Aromatic Medicinal Plants
    medicines Review The Phytochemistry of Cherokee Aromatic Medicinal Plants William N. Setzer 1,2 1 Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA; [email protected]; Tel.: +1-256-824-6519 2 Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA Received: 25 October 2018; Accepted: 8 November 2018; Published: 12 November 2018 Abstract: Background: Native Americans have had a rich ethnobotanical heritage for treating diseases, ailments, and injuries. Cherokee traditional medicine has provided numerous aromatic and medicinal plants that not only were used by the Cherokee people, but were also adopted for use by European settlers in North America. Methods: The aim of this review was to examine the Cherokee ethnobotanical literature and the published phytochemical investigations on Cherokee medicinal plants and to correlate phytochemical constituents with traditional uses and biological activities. Results: Several Cherokee medicinal plants are still in use today as herbal medicines, including, for example, yarrow (Achillea millefolium), black cohosh (Cimicifuga racemosa), American ginseng (Panax quinquefolius), and blue skullcap (Scutellaria lateriflora). This review presents a summary of the traditional uses, phytochemical constituents, and biological activities of Cherokee aromatic and medicinal plants. Conclusions: The list is not complete, however, as there is still much work needed in phytochemical investigation and pharmacological evaluation of many traditional herbal medicines. Keywords: Cherokee; Native American; traditional herbal medicine; chemical constituents; pharmacology 1. Introduction Natural products have been an important source of medicinal agents throughout history and modern medicine continues to rely on traditional knowledge for treatment of human maladies [1]. Traditional medicines such as Traditional Chinese Medicine [2], Ayurvedic [3], and medicinal plants from Latin America [4] have proven to be rich resources of biologically active compounds and potential new drugs.
    [Show full text]
  • Enzymatic Synthesis and Hydrolysis of Linear Alkyl and Steryl Hydroxycinnamic Acid Esters
    Research Collection Doctoral Thesis Enzymatic Synthesis and Hydrolysis of Linear Alkyl and Steryl Hydroxycinnamic Acid Esters Author(s): Schär, Aline Lea Publication Date: 2016 Permanent Link: https://doi.org/10.3929/ethz-a-010670414 Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library DISS. ETH NO. 23265 Enzymatic Synthesis and Hydrolysis of Linear Alkyl and Steryl Hydroxycinnamic Acid Esters A thesis submitted to attain the degree of DOCTOR OF SCIENCES of ETH ZURICH (Dr. sc. ETH Zurich) presented by Aline Lea Schär MSc ETH in Food Science, ETH Zurich born on 24.01.1987 citizen of Madiswil (BE) accepted on the recommendation of Prof. Dr. Laura Nyström, examiner Dr. Pierre Villeneuve, co-examiner Prof. Dr. Evangelos Topakas, co-examiner 2016 Wir treten auf. Wir spielen. Wir treten ab. Moritz Leuenberger Abstract Phenolic acids are natural antioxidants found widely in the plant kingdom in various forms. In the focus of this thesis were hydroxycinnamic acids, namely ferulic acid, caffeic acid, sinapic acid and p-coumaric acid. In multiphase food systems, the polarity of the phenolic antioxidant is a crucial property, which can be adjusted through esterification. Nowadays, an enzymatic procedure is often preferred for this purpose over a chemically catalyzed reaction. However, a phenolic hydroxyl group in para-position in combination with an unsaturated side chain makes enzymatic esterification of hydroxycinnamic acids by lipases challenging. Since this is the case for the hydroxycinnamic acids mentioned above, it is of interest to find efficient ways to enzymatically esterify them.
    [Show full text]
  • Hydrolysis of Phenolic Acid Esters by Esterase Enzymes from Caco-2 Cells and Rat Intestinal Tissue
    MSc project, School of Food Science and Nutrition, University of Leeds, 2012 “Submitted in partial fulfilment of the requirements for the Degree of Master of Science” Hydrolysis of phenolic acid esters by esterase enzymes from Caco-2 cells and rat intestinal tissue. Name Surname 29 August 2012 Abstract Regular consumption of coffee has been associated with a number of health benefits including a reduced risk of type 2 diabetes, and cholorgenic acids and their hydroxycinnamic acid metabolites are thought to be important mediators. However their effectiveness is dependent on their hydrolysis, metabolism and absorption from the gastrointestinal tract. Previous research has shown that hydrolysis occurs in the stomach and large intestine, however little is known about the fate of chlorogenic acids in the small intestine. Chlorogenic acid isomers and phenolic acid methyl esters were incubated with Caco-2 cells and rat intestinal tissue extract to determine if esterase enzymes from these models could hydrolyse the ester link in the compounds. Results of the 2 hour incubations showed that methyl ferulate (19.8% hydrolysis) and methyl caffeate (11.4% hydrolysis) were better hydrolysed than 5-O-caffeoylquinic acid (0.02% hydrolysis) and 3-O- caffeoylquinic acid (0.18% hydrolysis). There was also evidence that hydrolysis occurs via a predominantly intracellular mechanism, as during the 24 hour incubation, 57.1% of methyl ferulate incubated directly with Caco-2 cells was hydrolysed to ferulic acid, compared with 0.25% that was hydrolysed when incubated in medium that had been pre-incubated with Caco-2 cells to test for extracellular esterase activity. Incubation with rat intestine extract showed ability to hydrolyse methyl ferulate but not 5-O-caffeoylquinic acid.
    [Show full text]
  • Characterization of Cell Wall Degrading Enzymes from Chrysosporium Lucknowense C1 and Their Use to Degrade Sugar Beet Pulp
    Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp Stefan Kühnel Thesis committee Thesis supervisor Prof. dr. ir. H. Gruppen Professor of Food Chemistry Wageningen University Thesis co-supervisor Dr. H. A. Schols Associate Professor, Laboratory of Food Chemistry Wageningen University Other members Dr. E. Bonnin Institut National de la Recherche Agronomique (INRA), Nantes, France Prof. dr. J. van der Oost Wageningen University Prof. dr. J. G. M. Sanders Wageningen University Dr. J. A. M. de Bont C5 Yeast Company B. V., Bergen op Zoom This research was conducted under the auspices of the Graduate School VLAG (Graduate School of Nutrition, Food Technology, Agrobiotechnology and Health Sciences) Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp Stefan Kühnel Thesis submitted in fulfilment of the requirements for the degree of doctor at Wageningen University by the authority of the Rector Magnificus Prof. dr. M. J. Kropff, in the presence of the Thesis Committee appointed by the Academic Board to be defended in public on Friday 9 September 2011 at 4 p.m. in the Aula. Stefan Kühnel Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp 192 pages PhD thesis Wageningen University, NL (2011) With references, with summaries in English, Dutch and German ISBN: 978-90-8585-978-9 Abstract Kühnel, S Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp Ph.D. thesis Wageningen University, The Netherlands, 2011 Key words Pectin, arabinan, biorefinery, mode of action, branched arabinose oligomers, ferulic acid esterase, arabinohydrolase, pretreatment Sugar beet pulp is the cellulose and pectin-rich debris remaining after sugar extrac- tion from sugar beets.
    [Show full text]
  • Identifying New Lignin Bioengineering Targets: 1. Monolignol-Substitute Impacts on Lignin Formation and Cell Wall Fermentability
    Grabber et al. BMC Plant Biology 2010, 10:114 http://www.biomedcentral.com/1471-2229/10/114 RESEARCH ARTICLE Open Access IdentifyingResearch article new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability John H Grabber*1, Paul F Schatz1, Hoon Kim2, Fachuang Lu2 and John Ralph2 Abstract Background: Recent discoveries highlighting the metabolic malleability of plant lignification indicate that lignin can be engineered to dramatically alter its composition and properties. Current plant biotechnology efforts are primarily aimed at manipulating the biosynthesis of normal monolignols, but in the future apoplastic targeting of phenolics from other metabolic pathways may provide new approaches for designing lignins that are less inhibitory toward the enzymatic hydrolysis of structural polysaccharides, both with and without biomass pretreatment. To identify promising new avenues for lignin bioengineering, we artificially lignified cell walls from maize cell suspensions with various combinations of normal monolignols (coniferyl and sinapyl alcohols) plus a variety of phenolic monolignol substitutes. Cell walls were then incubated in vitro with anaerobic rumen microflora to assess the potential impact of lignin modifications on the enzymatic degradability of fibrous crops used for ruminant livestock or biofuel production. Results: In the absence of anatomical constraints to digestion, lignification with normal monolignols hindered both the rate and extent of cell wall hydrolysis by rumen microflora. Inclusion of methyl caffeate, caffeoylquinic acid, or feruloylquinic acid with monolignols considerably depressed lignin formation and strikingly improved the degradability of cell walls. In contrast, dihydroconiferyl alcohol, guaiacyl glycerol, epicatechin, epigallocatechin, and epigallocatechin gallate readily formed copolymer-lignins with normal monolignols; cell wall degradability was moderately enhanced by greater hydroxylation or 1,2,3-triol functionality.
    [Show full text]
  • Antiproliferative Constituents in the Plants 7. Leaves of Clerodendron Bungei and Leaves and Bark of C
    1338 Notes Biol. Pharm. Bull. 24(11) 1338—1341 (2001) Vol. 24, No. 11 Antiproliferative Constituents in the Plants 7. Leaves of Clerodendron bungei and Leaves and Bark of C. trichotomum1) Tsuneatsu NAGAO, Fumiko ABE, and Hikaru OKABE* Faculty of Pharmaceutical Sciences, Fukuoka University, 8–19–1 Nanakuma, Jonan-ku, Fukuoka 814–0180, Japan. Received May 2, 2001; accepted August 3, 2001 The constituents of the leaves of Clerodendron bungei STEUD. (Verbenaceae) and leaves and bark of C. tri- chotomum THUNB. were investigated guided by the antiproliferative activity against three tumor cell lines (MK-1: human gastric adenocarcinoma, HeLa: human uterus carcinoma, and B16F10: murine melanoma). Two phenylethanoid glycoside caffeic acid esters, acteoside and isoacteoside, were isolated as the constituents which selectively inhibit the growth of B16F10 cells. The antiproliferative activities against B16F10 cells of acteoside (GI50: 8 mM), isoacteoside (8 mM) and their methanolysis products, methyl caffeate (26 mM), 3,4-dihydroxyphenethyl alcohol (8 mM), 3,4-dihydroxyphenethyl glucoside (10 mM), desrhamnosyl acteoside (6 mM), and desrhamnosyl isoacteoside (6 mM) suggested that the 3,4- dihydroxyphenethyl alcohol group might be more responsible for the activities of acteoside and isoacteoside than the caffeoyl group. The activities of chlorogenic acid, 3,4-dihydroxyphenylacetic acid, 3-(3,4-dihydroxyphenyl) alanine, 3,4-dihydroxy-phenethylamine hydrochloride, ferulic acid, sinapic acid, and five dihydroxybenzoic acids were also determined and compared with those of the above compounds. Key words Clerodendron; antiproliferative activity; acteoside; isoacteoside; caffeic acid ester; 3,4-dihydroxyphenethyl alcohol Clerodendron bungei STEUD. (Verbenaceae) is a shrub in- benzoic acids and 3,4-dihydroxyphenylacetic acid (Wako digenous to China and it has been cultivated in Japan as a Pure Chemical Industry Ltd., Osaka, Japan), caffeic acid garden plant.
    [Show full text]
  • 2.3.4 Efficient Biomass Conversion: Delineating the Best Lignin
    Efficient Biomass Conversion: Delineating the Best Lignin Monomer-Substitutes Investigators John Ralph, Professor, Biochemistry; Xuejun Pan, Professor, Biological Systems Engineering; Sara Patterson, Professor, Horticulture; Dino Ress, Postdoctoral Researcher; Yuki Tobimatsu, Postdoctoral Researcher; Martina Opietnik, Postdoctoral Researcher; Sasikumar Elumalai, Postdoctoral Researcher; Jenny Bolivar, Graduate Researcher; Christy Davidson, Technician, U. Wisconsin-Madison. Involved coworkers (unfunded): Hoon Kim and Fachuang Lu, Research Scientists, U. Wisconsin-Madison. Collaborators: John Grabber, Research Scientist, and Paul Schatz, Technician, US Dairy Forage Research Center, USDA-ARS. [This project has now completed its first full year] Abstract The three year plan is to delineate a set of approaches for successfully altering lignin structure, in a way that allows plant cell wall breakdown to produce biofuels in a more energy-efficient manner, by providing alternative plant-compatible monomers to the lignification process. The approach is to synthesize and test various classes of novel plant compatible monomer-substitutes for their abilities to incorporate into lignins, and then to determine how such incorporation affects biomass processing in biomimetic cell wall systems. The ability of a chosen monomer to incorporate into lignins (copolymerizing with the traditional monomers) is determined by in vitro biomimetic lignification involving the phenolic radical coupling reactions that typify the lignification process.Those that successfully make co-polymers are polymerized into a suspension-cultured cell wall system to further delineate their polymerization efficacy and to provide biomimetic cell wall material for preliminary testing of conversion efficiency following selected pretreatments and in a variety of processes. The most promising monomer-substitutes will be revealed to other GCEP researchers so that the process of understanding the pathways that produce the monomers and obtaining the required genes can proceed most expediently.
    [Show full text]
  • 12.2% 118000 130M Top 1% 154 4400
    We are IntechOpen, the world’s leading publisher of Open Access books Built by scientists, for scientists 4,400 118,000 130M Open access books available International authors and editors Downloads Our authors are among the 154 TOP 1% 12.2% Countries delivered to most cited scientists Contributors from top 500 universities Selection of our books indexed in the Book Citation Index in Web of Science™ Core Collection (BKCI) Interested in publishing with us? Contact [email protected] Numbers displayed above are based on latest data collected. For more information visit www.intechopen.com Chapter Enzymatic Synthesis of Functional Structured Lipids from Glycerol and Naturally Phenolic Antioxidants Jun Wang, Linlin Zhu, Jinzheng Wang, Yan Hu and Shulin Chen Abstract Glycerol is a valuable by-product in biodiesel production by transesterification, hydrolysis reaction, and soap manufacturing by saponification. The conversion of glycerol into value-added products has attracted growing interest due to the dramatic growth of the biodiesel industry in recent years. Especially, phenolic structured lipids have been widely studied due to their influence on food quality, which have antioxidant properties for the lipid food preservation. Actually, they are triacylglycerols that have been modified with phenolic acids to change their positional distribution in glycerol backbone by enzymatically catalyzed reactions. Due to lipases’ fatty acid selectivity and regiospecificity, lipase-catalyzed reactions have been promoted for offering the advantage of greater control over the positional distribution of fatty acids in glycerol backbone. Moreover, microreactors were applied in a wide range of enzymatic applications. Nowadays, phenolic structured lipids have attracted attention for their applications in cosmetic, pharmaceutical, and food industries, which definitely provide attributes that consumers will find valuable.
    [Show full text]
  • Fermentation Products of Solvent Tolerant Marine Bacterium Moraxella Spp
    Fermentation Products of Solvent Tolerant Marine Bacterium Moraxella spp. MB1 and Its Biotechnological Applications in Salicylic Acid Bioconversion Solimabi Wahidullah*, Deepak N. Naik, Prabha Devi Bioorganic Chemistry Lab, Chemical Oceanography Division, CSIR- National Institute of Oceanography, Dona Paula, Goa, India Abstract As part of a proactive approach to environmental protection, emerging issues with potential impact on the environment is the subject of ongoing investigation. One emerging area of environmental research concerns pharmaceuticals like salicylic acid, which is the main metabolite of various analgesics including aspirin. It is a common component of sewage effluent and also an intermediate in the degradation pathway of various aromatic compounds which are introduced in the marine environment as pollutants. In this study, biotransformation products of salicylic acid by seaweed, Bryopsis plumosa, associated marine bacterium, Moraxella spp. MB1, have been investigated. Phenol, conjugates of phenol and hydroxy cinnamic acid derivatives (coumaroyl, caffeoyl, feruloyl and trihydroxy cinnamyl) with salicylic acid (3–8) were identified as the bioconversion products by electrospray ionization mass spectrometry. These results show that the microorganism do not degrade phenolic acid but catalyses oxygen dependent transformations without ring cleavage. The degradation of salicylic acid is known to proceed either via gentisic acid pathway or catechol pathway but this is the first report of biotransformation of salicylic acid into cinnamates, without ring cleavage. Besides cinnamic acid derivatives (9–12), metabolites produced by the bacterium include antimicrobial indole (13) and b-carbolines, norharman (14), harman (15) and methyl derivative (16), which are beneficial to the host and the environment. Citation: Wahidullah S, Naik DN, Devi P (2013) Fermentation Products of Solvent Tolerant Marine Bacterium Moraxella spp.
    [Show full text]