DOCSLIB.ORG

Flavonoid Pattern in the Pterid4ceae, III. Flavonoid Constituents in the Fronds of Dennstaedtia Quitf Ordii

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Flavonoid Pattern in the Pterid4ceae, III. Flavonoid Constituents in the Fronds of Dennstaedtia Quitf Ordii Bot. Meg. Tokyo 83: 263-269 (August 25, 1970) Flavonoid Pattern in the Pterid4ceae, III. Flavonoid Constituents in the Fronds of Dennstaedtia quitf ordii Yoko AKABORI* and Masao HASEGAWA* Received April 11, 1970 Abstract Flavonoid glycosides in the fronds of Dennstaedtia wilfordii were isolated to study the flavonoid pattern of the genus Dennstaedtia. The fronds contained pinocembrin 7-rhamnoglucoside (III), pinocembrin 7-glucoside (II), isoquercitrin (VII) and astragalin (V). Among them pinocembrin 7-rhamnoglucoside (III) was obtained as crystal and the sugar component was confirmed as neohesperidose (VIII) by NMR, enzymic hydrolysis and chromatographic behaviors. Other flavonoids were identified by paper and thin layer chromatography. The flavonoid pattern of D. wilfordii was different from that of the four species belonging to the genus Adiantum, which had been already reported. In the previous papers1'2' we reportedd the flavonoid patterns of four species of the genus Adiantum A. aethiopicum, A. monochlamys, A. capillus-veneris and A. cuneatum. They contained flavonol glycosides as the main flavonoids and their structural differences were observed in the glycosidec sugars. The genus Dennstaedtia is characterized3' by the presence of indisia, exteriorly opened indisia, undimidiated and uncuneif ormic ultimate pinnules and marginal son. While the genus Adiantum can be distinguished from Dennstaedtia by the presence of indisia consisting of the reflexed margin of the segment, scaly rhizomes and soni borne on the reflexed margin of the pinnules. The morphological differences are of great to taxonomy, so some taxonomists have elevated both genera to the rank of families4'5,s', i. e., Dennstaedtiaceae and Adiantaceae. So we deal with the flavonoid constituents of D. wilfordii concerning to taxo- nomical studies in this report. Experiments and. Results Isolation of flavonoids. Fronds of D. wilfordii were collected at Nippara on the west side of Tokyo in early November, and 290 g of fresh leaves were extracted as described in the previous papery. After addition of a small amount of ethanol to the ethyl acetate extract, it was allowed to stand for several days. White crystall mass appeared was gathered by filtration; yield, 0.5 g. This crude pinocembrin 7- rhamnoglucoside (III) was recrystallized from aqueous ethanol and from 99% ethanol to give colorless needles of m. p. 265-266°. * Department of Biology, Faculty of Science, Tokyo Metropolitan University, Setagaya Ku, Tokyo, Japan. 264 AKABORI,Y. and HASEGAWA,M. Vol. 83 Pinocembrin 7-glucoside (II) was isolated from the mother liquor of recrystalli- zation using thin layer and paper chromatography. Solvent systems were ECFW (TLC), BAW and 6% AA (abbreviations are in Table 1). After filtration of pinocembrin 7-rhamnoglucoside (III), the mother liquor was subjected to a large scale paper chromatography with the solvent systems of BAW and 6%AA. Two brown bands on the chromatogram under a UV lamp were ex- tracted with 50°o ethanol. Each extract was hydrolyzed with a mixture of 2 N HCl and ethanol (1:1)7'. On hydrolysis, the lower glycoside gave quercetin (VI) and glucose, while the aglycone of upper glycoside was not sufficiently determined be- cause of its minute amount. Rf values and absorption maxima of the two glycosides showed their identity with isoquercitrin (VII) and astragalin (V). Pinocembrin 7-rhamnoglucoside (III). An ethanolic solution gave a brown color- ation with ferric chloride and an aqueous solution gave a reddish brown coloration. In alcoholic solution it gave a yellow orange coloration with magnesium powder and conc. hydrochloric acid, but no coloration was given with zinc powder and conc. hydrochloric acid. Absorption : /ZM°H330 ma, 286 mp (log =4.10) Specific rotation : [a]D=-112.7° (2.9% in pyridine), [a]D=- 75.0° (0.4% in 80% aqueous acetone). Anal. Calc. for C27H32O132H2O:C, 56.53: H, 5.75 Found : C, 56.73: H, 5.43. Rf values and IR spectrum are shown in Table 1 and Fig. 2, respectively. The acetate was prepared as usual with pyridine and acetic anhydride, m. p. 121-122°. Hydrolysis of pinocembrin 7-rhamnoglucoside (III). The pinocembrin glycoside (69.8 mg) was hydrolyzed with 5% hydrochloric acid on a water bath, and 30.7 mg (43.9°0) of the aglycone was obtained. When it is posturated as pinocembrin 7- rhamnoglucoside (III) the theoretical yield of pinocembrin (I) will be 45.3%. The aglycone was recrystallized from aqueous ethanol to give colorless needles of m. p. 192-194°. After subliming at 165-175°/3 mm Hg, it gave a melting point of 195-196°. No depression was observed by admixture with authentic pinocembrin (I)$' obtained from Prunus verecunda. Table 1. Rf values x 100 of pinocembrin 7-rhamnoglucoside and its hydrolyzed products. August, 1970 Flavonoid Pattern in the Pteridaceae III 265 Fig. 1. Structures of flavonoids isolated from D. wilfordii and neohesperidose. The filtrate was treated with Amberlite IRA-410 and concentrated to a syrup. This was paperchromatographed, and glucose and rhamnose were identified by com- parison with authentic sugars. Quantitative analyses of sugars by wilson's method9j and of pinocembrin (I) by spectrophotometric method showed that the ratio of Fig. 2. IR spectra of pinocembrin and pinocembrin 7-rhamnoglucoside. (KBr) A = pinocembrin 7-rhamnoglucoside, B = authentic pinocembrin, C = pinocembrin 266 AK.ABORI,Y. and HASEGAWA,M. Vol. 83 pinocembrin, glucose and rhamnose was to be 1 : 1 : 1. Rf values of these three components are listed in Table 1. IR spectra of the authentic pinocembrin and the= aglycone obtained by hydrolysis are shown in Fig. 2. Structure of glycosidic sugar of Pinocembrin 7-rhamnoglucoside (III). a. Enzymic hydrolysis. Pinocembrin 7-rhamnoglucoside (III) was treated in the' same procedure as Okada10' with a mixture of naringinase and hesperidinase which was obtained from Aspergillus niger. This enzyme mixture split rhamnose from the glycoside. In parallel, naringin and hesperidin were also tested for comparison. The glycoside gave rhamnose and pinocembrin 7-glucoside (II) by hydrolysis with hesperidinase, which was prepared by acid treatment'0' from the mixture of both enzymes. Chromatographic behaviors of the hydrolyzed products are shownn diagramatically in Fig. 3. b. NMR spectrum of the glycoside acetate. Rosier et a111' reported that the flavonoids, rutinoside and neohesperidoside, were distinguished by NMR spectra of their acetates in CDC13. They have described that the ratio of integrated proton numbers in the region 4.5-5.5 ppm (int. TMS) and 3.4-4.4 ppm was 7 : 5 in the case of neohesperidoside, and 8:4 in the case of rutinoside. From the chart (see Fig. 4) of pinocembrin 7-rhamnoglucoside acetate, we could read a proton ratio between the above regions. It showed a ratio of 7: 5. c. Hydrolysis with acetic acid. Pinocembrin 7-rhamnoglucoside (III), naringin and hesperidin were hydrolyzed with 10% acetic acid for 14 hours12', respectively. On cooling, a solidified mass in each flask was filtered, and the filtrate was evapo- rated using a rotary evaporator. Each of the residue was paperchromatographed and then subjected to paper electr- ophoresis13' in 0.2 M borate buffer, pH 10. From hesperidin (hesperetin 7-rutinoside) glucose, rhamnose and rutinose were detected, but in the case of naringin and pinocembrin 7-rhamnoglucoside (III) gave glucose and rhamnose. From the results obtained above, we could think of this glycoside as pinocem- brin 7-neohesperidoside. Pinocembrin 7-glucoside (II). Pinocembrin monoglycoside was compared on paper chromatogram with pinocembrin 7-glucoside (II) obtained by partial hydrolysis of Fig. 3. Enzymic hydrolysis of pinocembrin 7-rhamnoglucoside and related compounds. Abbreviations : H = hesperidin, N = naringin, P = prunin, S = pinocembrin 7-rhamno- glucoside. H', N' and S' inicate reaction products of H, N and S, respectively. August, 1970 Flavonoid Pattern in the Pteridaceae III 267 Fig. 4. NMR spectrum of acetylated pinocembrin 7-rhamnoglucoside. -pinocembrin 7-rhamnoglucoside (III) with naringinase. Rf values of the aglycone, the glycoside and the sugar are summarized in Table 2. Astragalin (V) and isoquercitrin (VII). Rf values of astragalin (V) and iso- quercitrin (VII) and its aglycone and sugar were also shown in Table 2. Their absorption maxima were coincident with those of the authentic samples. Table 2. Rf values x 1.00 of pinocembrin 7-glucoside, isoquercitrin, astragalin and their hydrolyzed products. Discussion As for pinocembrin 7-rhamnoglucoside (III), Ribas et a114' isolated it from Sarothamnus commutatus and gave the name sarotanoside (sarantoside, Chem. Abst. 54. 2502 (1960)). Matas15' also isolated a pinocembrin rhamnoglucoside (III) from Cytisus commutatus, but he thought it was an isomer of sarotanoside by comparison of their melting points of acetates, specific rotations and color reactions with zinc 268 AKABORI, Y. and HASEFAWA, M. Vol. 83 and hydrochloric acid. But unfortunately, dissaccharide components of both glyco- sides have not been studied in detail. The glycoside obtained by us resembles closely to sarotanoside in melting point, but it differs in melting point of the acetate and specific rotation as shown in Table 3. A slight difference was also observed in melting point of the acetate and specificc rotation of an isomer described by Matas. Chopin and Dellamonica16' have synthesized pinocembrin 7-rhamnoglucoside,, pinocembrin 7-neohesperidoside, which has the melting point of 237° and the specific. rotation of-112° in pyridine. However, this compound is different from our glycoside in its melting point (cf., Table 3). Disagreements as such will be studied later in_n detail. Concerning the relationship between taste and structure of the glycosides Horowitz17j describes that neohesperidosides of flavanones have a bitter taste in general. Our glycoside has slightly bitter taste, so this fact suggests the glycosidicc sugar may be neohesperidose (VIII). The flavonoid pattern of D. wil f ordii is characterized by a large content of flavanone glycoside, especially pinocembrin 7-neohesperidoside, and a lesser amounts of flavonol glycosides. The flavonoid pattern of D.
Load more

Recommended publications
  • Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: a Review
    molecules Review Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: A Review Hanghang Lou 1,†, Lifei Hu 2,†, Hongyun Lu 1, Tianyu Wei 1 and Qihe Chen 1,* 1 Department of Food Science and Nutrition, Zhejiang University, Hangzhou 310058, China; [email protected] (H.L.); [email protected] (H.L.); [email protected] (T.W.) 2 Hubei Key Lab of Quality and Safety of Traditional Chinese Medicine & Health Food, Huangshi 435100, China; [email protected] * Correspondence: [email protected]; Tel.: +86-0571-8698-4316 † These authors are equally to this manuscript. Abstract: Flavonoids belong to a class of plant secondary metabolites that have a polyphenol structure. Flavonoids show extensive biological activity, such as antioxidative, anti-inflammatory, anti-mutagenic, anti-cancer, and antibacterial properties, so they are widely used in the food, phar- maceutical, and nutraceutical industries. However, traditional sources of flavonoids are no longer sufficient to meet current demands. In recent years, with the clarification of the biosynthetic pathway of flavonoids and the development of synthetic biology, it has become possible to use synthetic metabolic engineering methods with microorganisms as hosts to produce flavonoids. This article mainly reviews the biosynthetic pathways of flavonoids and the development of microbial expression systems for the production of flavonoids in order to provide a useful reference for further research on synthetic metabolic engineering of flavonoids. Meanwhile, the application of co-culture systems in the biosynthesis of flavonoids is emphasized in this review. Citation: Lou, H.; Hu, L.; Lu, H.; Wei, Keywords: flavonoids; metabolic engineering; co-culture system; biosynthesis; microbial cell factories T.; Chen, Q.
    [Show full text]
  • Interpreting Sources and Endocrine Active Components of Trace Organic Contaminant Mixtures in Minnesota Lakes
    INTERPRETING SOURCES AND ENDOCRINE ACTIVE COMPONENTS OF TRACE ORGANIC CONTAMINANT MIXTURES IN MINNESOTA LAKES by Meaghan E. Guyader © Copyright by Meaghan E. Guyader, 2018 All Rights Reserved A thesis submitted to the Faculty and the Board of Trustees of the Colorado School of Mines in partial fulfillment of the requirements for the degree of Doctor of Philosophy (Civil and Environmental Engineering). Golden, Colorado Date _____________________________ Signed: _____________________________ Meaghan E. Guyader Signed: _____________________________ Dr. Christopher P. Higgins Thesis Advisor Golden, Colorado Date _____________________________ Signed: _____________________________ Dr. Terri S. Hogue Professor and Department Head Department of Civil and Environmental Engineering ii ABSTRACT On-site wastewater treatment systems (OWTSs) are a suspected source of widespread trace organic contaminant (TOrC) occurrence in Minnesota lakes. TOrCs are a diverse set of synthetic and natural chemicals regularly used as cleaning agents, personal care products, medicinal substances, herbicides and pesticides, and foods or flavorings. Wastewater streams are known to concentrate TOrC discharges to the environment, particularly accumulating these chemicals at outfalls from centralized wastewater treatment plants. Fish inhabiting these effluent dominated environments are also known to display intersex qualities. Concurrent evidence of this phenomenon, known as endocrine disruption, in Minnesota lake fish drives hypotheses that OWTSs, the primary form of wastewater treatment in shoreline residences, may contribute to TOrC occurrence and the endocrine activity in these water bodies. The causative agents specific to fish in this region remain poorly understood. The objective of this dissertation was to investigate OWTSs as sources of TOrCs in Minnesota lakes, and TOrCs as potential causative agents for endocrine disruption in resident fish.
    [Show full text]
  • Combinatorial Biosynthesis of Non-Bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms Sueharu Horinouchi
    J. Antibiot. 61(12): 709–728, 2008 THE JOURNAL OF REVIEW ARTICLE ANTIBIOTICS Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms Sueharu Horinouchi Received: August 1, 2008 / Accepted: October 14, 2008 © Japan Antibiotics Research Association Abstract One of the approaches of combinatorial biosynthesis is combining genes from different organisms and designing a new set of gene clusters to produce bioactive compounds, leading to diversification of both chemical and natural product libraries. This makes efficient use of the potential of the host organisms, especially when microorganisms are used. An Escherichia coli system, in which artificial biosynthetic pathways for production of plant-specific medicinal polyketides, such as flavonoids, stilbenoids, isoflavonoids, and curcuminoids, are assembled, has been designed and expressed. Starting with amino acids tyrosine and phenylalanine as substrates, this system yields naringenin, resveratrol, genistein, and curcumin, for example, all of which are beneficial to human health because of their wide variety of biological activities. Supplementation of unnatural carboxylic acids to the recombinant E. coli cells carrying the artificial pathways by precursor-directed biosynthesis results in production of unnatural compounds. Addition of decorating or modification enzymes to the artificial pathway leads to production of natural and unnatural flavonols, flavones, and methylated resveratrols. This microbial system is promising for construction of larger libraries by employing other polyketide synthases and decorating enzymes of various origins. In addition, the concept of building and expressing artificial biosynthetic pathways for production of non-bacterial and unnatural compounds in microorganisms should be successfully applied to production of not only plant-specific polyketides but also many other useful compound classes.
    [Show full text]
  • Development and Optimization of a High Sensitivity LC-MS/MS Method for the Determination of Hesperidin and Naringenin in Rat Plasma: Pharmacokinetic Approach
    molecules Article Development and Optimization of a High Sensitivity LC-MS/MS Method for the Determination of Hesperidin and Naringenin in Rat Plasma: Pharmacokinetic Approach Jesús Alfredo Araujo-León 1,* , Rolffy Ortiz-Andrade 2, Rivelino Armando Vera-Sánchez 1, Julio Enrique Oney-Montalvo 1, Tania Isolina Coral-Martínez 1 and Zulema Cantillo-Ciau 3 1 Chromatography Laboratory, Chemistry Faculty, Autonomous University of Yucatan, Mérida 97069, Mexico; [email protected] (R.A.V.-S.); [email protected] (J.E.O.-M.); [email protected] (T.I.C.-M.) 2 Pharmacology Laboratory, Chemistry Faculty, Autonomous University of Yucatan, Mérida 97069, Mexico; rolff[email protected] 3 Medicinal Chemistry Laboratory, Chemistry Faculty, Autonomous University of Yucatan, Mérida 97069, Mexico; [email protected] * Correspondence: [email protected]; Tel.: +52-999-922-5708 Academic Editor: Derek J. McPhee Received: 6 August 2020; Accepted: 12 September 2020; Published: 16 September 2020 Abstract: The purpose of this study was to develop, optimize, and fully validate a high-sensitivity methodology using UHPLC-MS/MS to simultaneously quantify hesperidin and naringenin in microsamples (100 µL) of murine plasma after intragastric administration of single pure flavonoids and a mixture. The optimization process allowed for high sensitivity with detection limits of approximately picogram order using an electrospray ionization (ESI) source in negative mode and an experiment based on multiple reaction monitoring (MRM). The validation parameters showed excellent linearity and detection limits, with a precision of less than 8% and a recovery of over 90%. This methodology was applied to compare the pharmacokinetic parameters for the administration of hesperidin and naringenin in individual form or in the form of a mixture.
    [Show full text]
  • Cushnie TPT, Lamb AJ. Antimicrobial Activity of Flavonoids. International Journal of Antimicrobial Agents, 2005. 26(5):343-356
    Cushnie TPT, Lamb AJ. Antimicrobial activity of flavonoids. International Journal of Antimicrobial Agents, 2005. 26(5):343-356. PMID: 16323269 DOI: 10.1016/j.ijantimicag.2005.09.002 The journal article above is freely available from the publishers at: http://www.idpublications.com/journals/PDFs/IJAA/ANTAGE_MostCited_1.pdf and also... http://www.ijaaonline.com/article/S0924-8579(05)00255-4/fulltext Errata for the article (typesetting errors by Elsevier Ireland) are freely available from the publishers at: http://www.ijaaonline.com/article/S0924-8579(05)00352-3/fulltext and also... http://www.sciencedirect.com/science/article/pii/S0924857905003523 International Journal of Antimicrobial Agents 26 (2005) 343–356 Review Antimicrobial activity of flavonoids T.P. Tim Cushnie, Andrew J. Lamb ∗ School of Pharmacy, The Robert Gordon University, Schoolhill, Aberdeen AB10 1FR, UK Abstract Flavonoids are ubiquitous in photosynthesising cells and are commonly found in fruit, vegetables, nuts, seeds, stems, flowers, tea, wine, propolis and honey. For centuries, preparations containing these compounds as the principal physiologically active constituents have been used to treat human diseases. Increasingly, this class of natural products is becoming the subject of anti-infective research, and many groups have isolated and identified the structures of flavonoids possessing antifungal, antiviral and antibacterial activity. Moreover, several groups have demonstrated synergy between active flavonoids as well as between flavonoids and existing chemotherapeutics. Reports of activity in the field of antibacterial flavonoid research are widely conflicting, probably owing to inter- and intra-assay variation in susceptibility testing. However, several high-quality investigations have examined the relationship between flavonoid structure and antibacterial activity and these are in close agreement.
    [Show full text]
  • Expression and Functional Analysis of the Nobiletin Biosynthesis-Related
    www.nature.com/scientificreports OPEN Expression and functional analysis of the nobiletin biosynthesis‑related gene CitOMT in citrus fruit Mao Seoka1,4, Gang Ma1,2,4, Lancui Zhang2, Masaki Yahata1,2, Kazuki Yamawaki1,2, Toshiyuki Kan3 & Masaya Kato1,2* Nobiletin, a polymethoxy favone (PMF), is specifc to citrus and has been reported to exhibit important health-supporting properties. Nobiletin has six methoxy groups at the 3′,4′,5,6,7,8-positions, which are catalyzed by O-methyltransferases (OMTs). To date, researches on OMTs in citrus fruit are still limited. In the present study, a novel OMT gene (CitOMT) was isolated from two citrus varieties Satsuma mandarin (Citrus unshiu Marc.) and Ponkan mandarin (Citrus reticulata Blanco), and its function was characterized in vitro. The results showed that the expression of CitOMT in the favedo of Ponkan mandarin was much higher than that of Satsuma mandarin during maturation, which was consistent with the higher accumulation of nobiletin in Ponkan mandarin. In addition, functional analysis showed that the recombinant protein of CitOMT had methylation activity to transfer a methyl group to 3′-hydroxy group of favones in vitro. Because methylation at the 3′-position of favones is vital for the nobiletin biosynthesis, CitOMT may be a key gene responsible for nobiletin biosynthesis in citrus fruit. The results presented in this study will provide new strategies to enhance nobiletin accumulation and improve the nutritional qualities of citrus fruit. Flavonoids are a group of secondary metabolites that include more than 10,000 kinds of derivatives1. According to their structure, favonoids are divided into several subgroups, including favanones, favones, favonols, favanols, isofavones, and anthocyanidins2.
    [Show full text]
  • HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Ex
    H OH metabolites OH Article HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Extracts from Two Helichrysum italicum Species Katja Kramberger 1,2 , Darja Barliˇc-Maganja 1, Dunja Bandelj 3, Alenka Baruca Arbeiter 3, Kelly Peeters 4,5, Ana MiklavˇciˇcVišnjevec 3,* and Zala Jenko Pražnikar 1,* 1 Faculty of Health Sciences, University of Primorska, 6310 Izola, Slovenia; [email protected] (K.K.); [email protected] (D.B.-M.) 2 Faculty of Medicine, University of Ljubljana, 1000 Ljubljana, Slovenia 3 Faculty of Mathematics, Natural Sciences and Information Technologies, University of Primorska, 6000 Koper, Slovenia; [email protected] (D.B.); [email protected] (A.B.A.) 4 InnoRenew CoE, 6310 Izola, Slovenia; [email protected] 5 Andrej MarušiˇcInstitute, University of Primorska, 6000 Koper, Slovenia * Correspondence: [email protected] (A.M.V.); [email protected] (Z.J.P.); Tel.: +386-05-662-6469 (Z.J.P.) Received: 4 September 2020; Accepted: 8 October 2020; Published: 12 October 2020 Abstract: Mediterranean plant Helichrysum italicum represents a rich source of versatile bioactive compounds with potential benefits for human health. Despite extensive research on the plant’s active constituents, little attention has yet been paid to characterizing the relationship between its intra-specific genetic diversity and metabolite profile. The study aimed to determine metabolic profile of H. italicum ssp. italicum (HII) and ssp. tyrrhenicum (HIT) cultivated on the experimental plantation in Slovenia and to compare the chemical composition of extracts regarding the solvent extraction process. Extracts were prepared upon conventional extract preparation procedures: maceration with 50 % methanol or ethanol and cold or hot water infusion and analyzed using High Performance Liquid Chromatography-Diode Array Detection-Electrospray Ionization-Quadrupole Time-of-Flight-Mass Spectrometry (HPLC-DAD-ESI-QTOF-MS).
    [Show full text]
  • Assembly of a Novel Biosynthetic Pathway for Production of the Plant Flavonoid Fisetin in Escherichia Coli
    Downloaded from orbit.dtu.dk on: Oct 06, 2021 Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli Stahlhut, Steen Gustav; Siedler, Solvej; Malla, Sailesh; Harrison, Scott James; Maury, Jerome; Neves, Ana Rute; Förster, Jochen Published in: Metabolic Engineering Link to article, DOI: 10.1016/j.ymben.2015.07.002 Publication date: 2015 Document Version Publisher's PDF, also known as Version of record Link back to DTU Orbit Citation (APA): Stahlhut, S. G., Siedler, S., Malla, S., Harrison, S. J., Maury, J., Neves, A. R., & Förster, J. (2015). Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli. Metabolic Engineering, 31, 84-93. https://doi.org/10.1016/j.ymben.2015.07.002 General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. Users may download and print one copy of any publication from the public portal for the purpose of private study or research. You may not further distribute the material or use it for any profit-making activity or commercial gain You may freely distribute the URL identifying the publication in the public portal If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Metabolic Engineering 31 (2015) 84–93 Contents lists available at ScienceDirect Metabolic Engineering journal homepage: www.elsevier.com/locate/ymben Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli Steen G.
    [Show full text]
  • FDA Briefing Document Pharmacy Compounding Advisory Committee
    FDA Briefing Document Pharmacy Compounding Advisory Committee (PCAC) Meeting June 23, 2016 The attached package contains background information prepared by the Food and Drug Administration (FDA) for the panel members of the Pharmacy Compounding Advisory Committee (advisory committee). We are bringing certain compounding issues to this advisory committee to obtain the committee’s advice. The background package may not include all issues relevant to the final regulatory recommendation and instead is intended to focus on issues identified by the Agency for discussion by the advisory committee. The FDA background package often contains assessments and/or conclusions and recommendations written by individual FDA reviewers. Such conclusions and recommendations do not necessarily represent the final position of the individual reviewers, nor do they necessarily represent the final position of the Review Division or Office. The FDA does not intend to issue a final determination on the issues at hand until input from the advisory committee process has been considered, all reviews have been finalized, consultation with the United States Pharmacopeia has occurred, and public comment has been considered through notice and comment rulemaking. The final determination may be affected by issues not discussed at the advisory committee meeting. Table of Contents I. Introduction ................................................................................................................... 3 A. Bulk Drug Substances That Can Be Used by Compounders under
    [Show full text]
  • USDA Database for the Flavonoid Content of Selected Foods
    USDA Database for the Flavonoid Content of Selected Foods Release 3.1 Prepared by Seema Bhagwat, David B. Haytowitz, and Joanne M. Holden (ret.) Nutrient Data Laboratory Beltsville Human Nutrition Research Center Agricultural Research Service U.S. Department of Agriculture December 2013 U.S. Department of Agriculture Agricultural Research Service Beltsville Human Nutrition Research Center Nutrient Data Laboratory 10300 Baltimore Avenue Building 005, Room 107, BARC-West Beltsville, Maryland 20705 Tel. 301-504-0630, FAX: 301-504-0632 E-Mail: [email protected] Web site: http://www.ars.usda.gov/nutrientdata Table of Contents Release History ............................................................................................. i Suggested Citation: ...................................................................................... ii Documentation .............................................................................................1 Subclasses of flavonoids and selected compounds .................................2 Methods and Procedures used to generate the database ........................2 Data Evaluation ........................................................................................4 Flavonoid Individual Data Table ...............................................................5 Sources of Data ...........................................................................................6 Format of the Tables ....................................................................................7 Food Description
    [Show full text]
  • Naringin: Biosynthesis and Pharmaceutical Applications
    Review Article Naringin: Biosynthesis and Pharmaceutical Applications PRIYA SHARMA, V. KUMAR1 AND P. GULERIA* Plant Biotechnology & Genetic Engineering Lab, Dept of Biotechnology, DAV University, Jalandhar, Punjab-144 012, 1Department of Biotechnology, School of Bioengineering and Biosciences, Lovely Professional University, Phagwara, Punjab-141 114, India Sharma et al.: Biosynthesis and Pharmaceutical Applications of naringin Naringin is a plant flavonoid of huge medicinal importance. It is synthesized by the phenylpropanoid pathway via seven enzyme catalysed steps from phenylalanine to prunin. The genes encoding the enzymes of phenylpropanoid pathway have been cloned and characterized. Naringin has been known to possess antioxidant, antiinflammatory and antitumer potential. Exposure to naringinin vivo and in vitro in several test animals and cell lines has been reported to demonstrate activities that could treat asthma, hyperlipidaemia, diabetes, tumour, hyperthyroidism and osteoclastogenesis. Based on the reported research of naringin on test animals, naringin could be regarded as an efficient natural remedy for the treatment of human metabolic disorders. However, detailed exploration of naringin exposure on humans needs to be studied. Key words: Naringin, phenylpropanoid pathway, medical applications, health, nutrition Naringin is a plant flavonoid of great human value. isoflavonoids, medicarpin 3-O-glucoside-6-O- Flavonoids are ubiquitous polyphenolic secondary malonate, formononetin 7-O-glucoside-6″-O-malonate metabolites isolated from vascular plants[1]. They have a and coumestrol glycosides[14]. The Betula pendula and general structure of 15-carbon skeleton that contains two B. resinifera plants originating from Finland, Germany phenyl rings A, B and a heterocyclic ring C[2]. Flavonols and Alaska have also been reported to accumulate are the most important flavonoids participating in flavonoids, condensed tannins and hydroxycinnamic the stress responses of plants[3].
    [Show full text]
  • Enhancing Flavonoid Production by Promiscuous Activity Of
    Enhancing flavonoid production by promiscuous activity of prenyltransferase, BrPT2 from Boesenbergia rotunda Yvonne Jing Mei Liew1, Yean Kee Lee2, Norzulaani Khalid1,3, Noorsaadah Abd Rahman2 and Boon Chin Tan3 1 Institute of Biological Sciences, Faculty of Science, University of Malaya, Kuala Lumpur, Malaysia 2 Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur, Malaysia 3 Center for Research in Biotechnology for Agriculture, University of Malaya, Kuala Lumpur, Malaysia ABSTRACT Flavonoids and prenylated flavonoids are active components in medicinal plant extracts which exhibit beneficial effects on human health. Prenylated flavonoids consist of a flavonoid core with a prenyl group attached to it. This prenylation process is catalyzed by prenyltranferases (PTs). At present, only a few flavonoid-related PT genes have been identified. In this study, we aimed to investigate the roles of PT in flavonoid production. We isolated a putative PT gene (designated as BrPT2) from a medicinal ginger, Boesenbergia rotunda. The deduced protein sequence shared highest gene sequence homology (81%) with the predicted homogentisate phytyltransferase 2 chloroplastic isoform X1 from Musa acuminata subsp. Malaccensis. We then cloned the BrPT2 into pRI vector and expressed in B. rotunda cell suspension cultures via Agrobacterium-mediated transformation. The BrPT2-expressing cells were fed with substrate, pinostrobin chalcone, and their products were analyzed by liquid chromatography mass spectrometry. We found that the amount of flavonoids,
    [Show full text]