DOCSLIB.ORG

Flavonoid Biosynthesis 21221.Pdf

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Flavonoid Biosynthesis 21221.Pdf Flavonoid Biosynthesis – https://www.kegg.jp/kegg-bin/highlight_pathway?scale=1.0&map=map00941&keyword=flavonoids Flavonoids are a major class of plant secondary metabolites that serves a multitude of functions including pigments and antioxidant activity. Flavonoids are synthesized from phenylpropanoid derivatives by condensation with malonyl- CoA. For example, condensation of p-coumaroyl-CoA (C6-C3) with three malonyl-CoA (C3) molecules results in naringenin chalcone with a diphenylpropane (C6-C3-C6) unit, which is converted to naringenin with the flavone (2-phenylchromen-4-one) backbone by conjugate ring closure. These and further modifications yield a variety of structural forms including chalcones, flavanones, dihyroflavonols, and flavans, anthocyanins, flavones and flavonols, and isoflavonoids. (Phenylpropanoid Biosynthesis) -> [1,2] 1) Cinnamoyl-CoA -> [1,2] 1) chalcone synthase -> Pinocembrin chalcone -> chalcone isomerase -> Pinocembrin -> [1,2,3] 1) Pinostrobin OR 2) flavone synthase I -> Chrysin OR 3) naringenin 3- dioxygenase -> Pinobanksin -> [1,2] 1) flavonol synthase -> Galangin OR 2) Pinobanksin 3-O- acetate OR 2) trans-cinnamate 4-monooxygenase -> p-Coumaroyl-CoA -> [1,2,3,4,5,6] 1) chalcone synthase -> isoliquiritigenin -> [1,2] 1) Butein -> chalcone isomerase -> Butin -> naringenin 3-dioxygenase -> Fustin -> bifunctional dihydroflavonol 4-reductase/flavanone 4- reductase <-> Fisetinidol-4beta-ol <-> Fustin OR 2) chalcone isomerase -> Liquiritgenin [1,2,3,4] 1) flavonoid 3’-monooxygenase -> Butin -> naringenin 3-dioxygenase -> Fustin -> bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase <-> Fisetinidol-4beta-ol <-> Fustin OR 2) flavone synthase I & II -> 7,4’-dihydroxyflavone OR 3) (Isoflavonoid Biosynthesis) OR 4) naringenin 3-dioxygenase -> Garbanzol -> [1,2] 1) bifunctional dihydroflavonol 4- reductase/flavanone 4-reductase -> 5-deoxyleucopelargonidin <-> garbanzol OR 2) flavonoid 3’- monooxygenase -> Fustin -> bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase <- > Fisetinidol-4beta-ol <-> Fustin OR 2) hydroxycinnamoyl-CoA reductase -> Dihydro-4- coumaroyl-CoA -> chalcone synthase -> Phloretin -> phlorizin synthase -> Phlorizin OR 3) chalcone synthase -> Naringenin chalcone -> [1,2,3,4] 1) chalcononaringenin 2’-O- glucosyltransferase -> Chalcone 2’-O-glucoside OR 2) chalcone 4’-O-glucosyltransferase -> 2’,4,4’,6’-Tetrahydroxychalcone 4’-O-glucoside -> aureusidin synthase -> Aureusidin 6-O- glucoside OR 3) desmethylxanthohumol -> desmethylxanthohumol 6’-O-methyltransferase -> xanthohumol 4’-O-methyltransferase -> 4-O-Methylxanthohumol OR 4) chalcone isomerase -> naringenin -> [1…10] 1) (Isoflavonoid Biosynthesis) OR 2) flavanone 7-O-beta-glucosyltransferase -> Prunin -> flavanone 7-O-glucoside 2’’-O-beta-L-rhamnosyltransferase -> Naringin OR 3) Hesperetin -> flavanone 7-O-beta-glucosyltransferase -> Hesperetin 7-O-glucoside -> flavanone 7-O-glucoside 2’’-O-beta-L-rhamnosyltransferase -> Neohesperidin OR 4) flavonoid 4’-O- methyltransferase -> Isosakuranetin OR 5) naringenin 3-dioxygenase -> Dihydrokaempferol -> [1,2,3] 1) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> cis-3,4- Leucopelargonidin -> [1,2,3] 1) anthocyanidin synthase -> Dihydrokaempferol (Feedback Loop) OR 2) leucoanthocyanidin reductase -> Afzelechin OR 3) anthocyanidin synthase -> Pelargonidin -> [1,2] 1) anthocyanidin reductase -> (-)-epiafzelechin OR 2) (Anthocyanin Biosynthesis) OR 2) flavonol synthase -> Kaempferol -> [1,2] 1) (flavone and flavonol biosynthesis) OR 2) flavonoid 3’,5’-hydroxylase & flavonoid 3’-monooxygenase -> Quercetin -> flavonoid 3’,5’hydroxylase -> Hansford Boutchyard IV www.phytpharma.com 2/24/21 Myricetin OR 3) flavonoid 3’,5’-hydroxylase & flavonoid 3’-monooxygenase -> Dihydroquercetin -> bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Leucocyanidin -> [1,2,3] 1) anthocyanidin synthase -> Dihydroquercetin (Feedback Loop) OR 2) leucoanthocyanidin reductase -> (+)-Catechin OR 3) anthocyanidin synthase -> Cyanidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epicatechin OR 3) flavonoid 3’,5’-hydroxylase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 6) naringenin 7-O-methyltransferase -> Sakuranetin OR 7) bifunctional dihydroflavonol 4- reductase/flavanone 4-reductase -> Apiforol OR 8) 8-C-Glucosylnaringenin -> Vitexin OR 9) flavone synthase I & II -> Apigenin -> [1,2,3] 1) Vitexin OR 2) (Flavone and Flavonol Biosynthesis) OR 3) flavonoid 3’,5’-hydroxylase & flavonoid 3’-monooxygenase -> Luteolin -> flavonoid 3’,5’- hydroxylase -> Tricetin -> flavone synthase I -> Dihydrotricetin -> naringenin 3-dioxygenase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 10) flavonoid 3’,5’- hydroxylase & flavonoid 3’-monooxygenase -> Eriodictyol -> [1,2,3,4,5] 1) naringenin 3- dioxygenase -> dihydroquercetin -> Dihydroquercetin -> bifunctional dihydroflavonol 4- reductase/flavanone 4-reductase -> Leucocyanidin -> [1,2,3] 1) anthocyanidin synthase -> Dihydroquercetin (Feedback Loop) OR 2) leucoanthocyanidin reductase -> (+)-Catechin OR 3) anthocyanidin synthase -> Cyanidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epicatechin OR 3) flavonoid 3’,5’-hydroxylase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4- reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 2) flavone synthase I & II -> Luteolin -> flavonoid 3’,5’-hydroxylase -> Tricetin -> flavone synthase I -> Dihydrotricetin -> naringenin 3- dioxygenase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 3) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Luteoforol OR 4) flavonoid 3’,5’-hydroxylase -> Dihydrotricetin -> naringenin 3-dioxygenase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4- reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 5) homoeriodictyol OR 4) shikimate O- hydroxycinnamoyltransferase -> p-Coumaroyl quinic acid -> 5-O-(4-coumaroyl)-D-quinate 3’- monooxygenase -> Caffeoyl quinic acid -> shikimate O-hydroxycinnamoyltransferase -> Caffeoyl- CoA -> [1,2] 1) caffeoyl-CoA O-methyltransferase -> Feruloyl-CoA -> chalcone synthase -> homoeriodictyol chalcone -> homoeriodictyol OR 2) chalcone synthase -> Eriodictyol chalcone -> [1,2,3] 1) homoeriodictyol chalcone -> homoeriodictyol OR 2) Eriodictyol -> [1,2,3,4,5] 1) Hansford Boutchyard IV www.phytpharma.com 2/24/21 naringenin 3-dioxygenase -> dihydroquercetin -> Dihydroquercetin -> bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Leucocyanidin -> [1,2,3] 1) anthocyanidin synthase -> Dihydroquercetin (Feedback Loop) OR 2) leucoanthocyanidin reductase -> (+)- Catechin OR 3) anthocyanidin synthase -> Cyanidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epicatechin OR 3) flavonoid 3’,5’-hydroxylase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4- reductase/flavanone 4-reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase - > (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 2) flavone synthase I & II - > Luteolin -> flavonoid 3’,5’-hydroxylase -> Tricetin -> flavone synthase I -> Dihydrotricetin -> naringenin 3-dioxygenase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin OR 3) bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase -> Luteoforol OR 4) flavonoid 3’,5’-hydroxylase -> Dihydrotricetin -> naringenin 3-dioxygenase -> Dihydromyricetin -> [1,2] 1) flavonol synthase -> Myricetin OR 2) bifunctional dihydroflavonol 4-reductase/flavanone 4- reductase -> Leucodelphinidin -> [1,2] 1) leucoanthocyanidin reductase -> (+)-Gallcatechin OR 2) anthocyanidin synthase -> Delphinidin -> [1,2] 1) (Anthocyanin Biosynthesis) OR 2) anthocyanidin reductase -> (-)-Epigallocatechin
Load more

Recommended publications
  • Chromanone-A Prerogative Therapeutic Scaffold: an Overview
    Arabian Journal for Science and Engineering https://doi.org/10.1007/s13369-021-05858-3 REVIEW-CHEMISTRY Chromanone‑A Prerogative Therapeutic Scafold: An Overview Sonia Kamboj1,2 · Randhir Singh1 Received: 28 September 2020 / Accepted: 9 June 2021 © King Fahd University of Petroleum & Minerals 2021 Abstract Chromanone or Chroman-4-one is the most important and interesting heterobicyclic compound and acts as a building block in medicinal chemistry for isolation, designing and synthesis of novel lead compounds. Structurally, absence of a double bond in chromanone between C-2 and C-3 shows a minor diference from chromone but exhibits signifcant variations in biological activities. In the present review, various studies published on synthesis, pharmacological evaluation on chroman- 4-one analogues are addressed to signify the importance of chromanone as a versatile scafold exhibiting a wide range of pharmacological activities. But, due to poor yield in the case of chemical synthesis and expensive isolation procedure from natural compounds, more studies are required to provide the most efective and cost-efective methods to synthesize novel chromanone analogs to give leads to chemistry community. Considering the versatility of chromanone, this review is designed to impart comprehensive, critical and authoritative information about chromanone template in drug designing and development. Keywords Chroman-4-one · Chromone · Pharmacological activity · Synthesis · Analogues 1 Introduction dihydropyran (ring B) which relates to chromane, chromene, chromone and chromenone, but the absence of C2-C3 dou- Chroman-4-one is one of the most important heterobicyclic ble bond of chroman-4-one skeleton makes a minor difer- moieties existing in natural compounds as polyphenols and ence (Table 1) from chromone and associated with diverse as synthetic compounds like Taxifolin, also known as chro- biological activities [1].
    [Show full text]
  • Flavonoid Glucodiversification with Engineered Sucrose-Active Enzymes Yannick Malbert
    Flavonoid glucodiversification with engineered sucrose-active enzymes Yannick Malbert To cite this version: Yannick Malbert. Flavonoid glucodiversification with engineered sucrose-active enzymes. Biotechnol- ogy. INSA de Toulouse, 2014. English. NNT : 2014ISAT0038. tel-01219406 HAL Id: tel-01219406 https://tel.archives-ouvertes.fr/tel-01219406 Submitted on 22 Oct 2015 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Last name: MALBERT First name: Yannick Title: Flavonoid glucodiversification with engineered sucrose-active enzymes Speciality: Ecological, Veterinary, Agronomic Sciences and Bioengineering, Field: Enzymatic and microbial engineering. Year: 2014 Number of pages: 257 Flavonoid glycosides are natural plant secondary metabolites exhibiting many physicochemical and biological properties. Glycosylation usually improves flavonoid solubility but access to flavonoid glycosides is limited by their low production levels in plants. In this thesis work, the focus was placed on the development of new glucodiversification routes of natural flavonoids by taking advantage of protein engineering. Two biochemically and structurally characterized recombinant transglucosylases, the amylosucrase from Neisseria polysaccharea and the α-(1→2) branching sucrase, a truncated form of the dextransucrase from L. Mesenteroides NRRL B-1299, were selected to attempt glucosylation of different flavonoids, synthesize new α-glucoside derivatives with original patterns of glucosylation and hopefully improved their water-solubility.
    [Show full text]
  • Their Antioxidant and Enzyme Inhibitory Activities
    antioxidants Article Semi-Continuous Subcritical Water Extraction of Flavonoids from Citrus unshiu Peel: Their Antioxidant and Enzyme Inhibitory Activities Dong-Shin Kim and Sang-Bin Lim * Department of Food Bioengineering, Jeju National University, Jeju 63243, Korea; [email protected] * Correspondence: [email protected] Received: 9 April 2020; Accepted: 24 April 2020; Published: 25 April 2020 Abstract: We extracted and hydrolyzed bioactive flavonoids from C. unshiu peel using subcritical water (SW) in a semi-continuous mode. The individual flavonoid yields, antioxidant and enzyme inhibitory activities of the SW extracts were analyzed. The extraction yields of hesperidin and narirutin increased with increasing temperature from 145 ◦C to 165 ◦C. Hydrothermal hydrolysis products (HHP), such as monoglucosides (hesperetin-7-O-glucoside and prunin) and aglycones (hesperetin and naringenin) were obtained in the SW extracts at temperatures above 160 ◦C. The sum of hesperidin and its HHP in the SW extracts was strongly correlated with antioxidant activities, whereas the contents of hesperetin and naringenin were strongly correlated with enzyme inhibitory activities. Hesperetin exhibited the highest antioxidant activities (2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, ferric-reducing antioxidant power, and oxygen radical absorbance capacity), whereas hesperetin-7-O-glucoside exhibited the highest enzyme inhibitory activities (angiotensin-I converting enzyme (ACE) and pancreatic lipase (PL)). Naringenin exhibited the highest enzyme inhibitory activities (xanthine oxidase and α-glucosidase). PMFs (sinensetin, nobiletin, and tangeretin) also exhibited relatively high inhibitory activities against ACE and PL. This study confirms the potential of SW for extracting and hydrolyzing bioactive flavonoids from C. unshiu peel using an environmentally friendly solvent (water) and a shorter extraction time.
    [Show full text]
  • Antifungal Activity of Natural and Enzymatically-Modified Flavonoids
    Food Chemistry 124 (2011) 1411–1415 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Antifungal activity of natural and enzymatically-modified flavonoids isolated from citrus species Maria Paula Salas a,b,*, Gustavo Céliz c, Hugo Geronazzo c, Mirta Daz c, Silvia Liliana Resnik b,d a Agencia Nacional de Promoción Científica y Tecnológica (ANCYPT), Argentina b Departamento de Industrias, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, 1428, Ciudad Autónoma de Buenos Aires, Argentina c Instituto de Investigaciones para la Industria Química (CONICET) and Facultad de Ciencias Exactas, Universidad Nacional de Salta, Avenida Bolivia 5150, Salta, Argentina d Comisión Científica de Investigaciones, Calle 526 entre 10 y 11, La Plata, Buenos Aires, Argentina article info abstract Article history: The antifungal activity of isolated flavonoids from Citrus species, such as naringin, hesperidin and neohes- Received 2 November 2009 peridin, and enzymatically-modified derivatives of these compounds, was studied on four fungi often Received in revised form 17 June 2010 found as food contaminants: Aspergillus parasiticus, Aspergillus flavus, Fusarium semitectum and Penicillium Accepted 27 July 2010 expansum. Although all the flavonoids showed antifungal activity, the intensity of this activity depended on the type of fungus and compound used. The hesperetin glucoside laurate strongly inhibited the myce- lial growth of P. expansum, while prunin decanoate was the most inhibiting flavonoid for A. flavus, A. par- Keywords: asiticus, and F. semitectum. Flavonoids The flavonoids naringin, hesperidin and neohesperidin, obtained as byproducts at low cost from the Mycelial growth Fungal growth residues of the citrus industries, present an interesting option for these industries.
    [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]
  • Chondroprotective Agents
    Europaisches Patentamt J European Patent Office © Publication number: 0 633 022 A2 Office europeen des brevets EUROPEAN PATENT APPLICATION © Application number: 94109872.5 © Int. CI.6: A61K 31/365, A61 K 31/70 @ Date of filing: 27.06.94 © Priority: 09.07.93 JP 194182/93 Saitama 350-02 (JP) Inventor: Niimura, Koichi @ Date of publication of application: Rune Warabi 1-718, 11.01.95 Bulletin 95/02 1-17-30, Chuo Warabi-shi, 0 Designated Contracting States: Saitama 335 (JP) CH DE FR GB IT LI SE Inventor: Umekawa, Kiyonori 5-4-309, Mihama © Applicant: KUREHA CHEMICAL INDUSTRY CO., Urayasu-shi, LTD. Chiba 279 (JP) 9-11, Horidome-cho, 1-chome Nihonbashi Chuo-ku © Representative: Minderop, Ralph H. Dr. rer.nat. Tokyo 103 (JP) et al Cohausz & Florack @ Inventor: Watanabe, Koju Patentanwalte 2-5-7, Tsurumai Bergiusstrasse 2 b Sakado-shi, D-30655 Hannover (DE) © Chondroprotective agents. © A chondroprotective agent comprising a flavonoid compound of the general formula (I): (I) CM < CM CM wherein R1 to R9 are, independently, a hydrogen atom, hydroxyl group, or methoxyl group and X is a single bond or a double bond, or a stereoisomer thereof, or a naturally occurring glycoside thereof is disclosed. The 00 00 above compound strongly inhibits proteoglycan depletion from the chondrocyte matrix and exhibits a function to (Q protect cartilage, and thus, is extremely effective for the treatment of arthropathy. Rank Xerox (UK) Business Services (3. 10/3.09/3.3.4) EP 0 633 022 A2 BACKGROUND OF THE INVENTION 1 . Field of the Invention 5 The present invention relates to an agent for protecting cartilage, i.e., a chondroprotective agent, more particularly, a chondroprotective agent containing a flavonoid compound or a stereoisomer thereof, or a naturally occurring glycoside thereof.
    [Show full text]
  • (Piper Nigrum L.) Products Based on LC-MS/MS Analysis
    molecules Article Nontargeted Metabolomics for Phenolic and Polyhydroxy Compounds Profile of Pepper (Piper nigrum L.) Products Based on LC-MS/MS Analysis Fenglin Gu 1,2,3,*, Guiping Wu 1,2,3, Yiming Fang 1,2,3 and Hongying Zhu 1,2,3,* 1 Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning 571533, China; [email protected] (G.W.); [email protected] (Y.F.) 2 National Center of Important Tropical Crops Engineering and Technology Research, Wanning 571533, China 3 Key Laboratory of Genetic Resources Utilization of Spice and Beverage Crops, Ministry of Agriculture, Wanning 571533, China * Correspondence: [email protected] (F.G.); [email protected] (H.Z.); Tel.: +86-898-6255-3687 (F.G.); +86-898-6255-6090 (H.Z.); Fax: +86-898-6256-1083 (F.G. & H.Z.) Received: 16 July 2018; Accepted: 7 August 2018; Published: 9 August 2018 Abstract: In the present study, nontargeted metabolomics was used to screen the phenolic and polyhydroxy compounds in pepper products. A total of 186 phenolic and polyhydroxy compounds, including anthocyanins, proanthocyanidins, catechin derivatives, flavanones, flavones, flavonols, isoflavones and 3-O-p-coumaroyl quinic acid O-hexoside, quinic acid (polyhydroxy compounds), etc. For the selected 50 types of phenolic compound, except malvidin 3,5-diglucoside (malvin), 0 L-epicatechin and 4 -hydroxy-5,7-dimethoxyflavanone, other compound contents were present in high contents in freeze-dried pepper berries, and pinocembrin was relatively abundant in two kinds of pepper products. The score plots of principal component analysis indicated that the pepper samples can be classified into four groups on the basis of the type pepper processing.
    [Show full text]
  • Survey of Phenolic Compounds Produced in Citrus
    USDA ??:-Z7 S rveyof Phenolic United States Department of Agriculture C mpounds Produced IliIIiI Agricultural Research In Citrus Service Technical Bulletin Number 1856 December 1998 United States Department of Agriculture Survey of Phenolic Compounds Agricultural Produced in Citrus Research Service Mark Berhow, Brent Tisserat, Katherine Kanes, and Carl Vandercook Technical Bulletin Number 1856 December 1998 This research project was conducted at USDA, Agricultural Research Service, Fruit and Vegetable Chem­ istry laboratory, Pasadena, California, where Berhow was a research chemist, TIsserat was a research geneticist, Kanes was a research associate, and Vandercook, now retired, was a research chemist. Berhow and Tisserat now work at the USDA-ARS National Center for AgriCUltural Utilization Research, Peoria, Illinois, where Berhow is a research chemist and Tisserat is a research geneticist. Abstract Berhow, M., B. Tisserat, K. Kanes, and C. Vandercook. 1998. Survey of Mention of trade names or companies in this publication is solely for the Phenolic Compounds Produced in Citrus. U.S. Department ofAgriculture, purpose of providing specific information and does not imply recommenda­ Agricultural Research Service, Technical Bulletin No. 1856, 158 pp. tion or endorsement by the U. S. Department ofAgriculture over others not mentioned. A survey of phenolic compounds, especially flavanones and flavone and flavonol compounds, using high pressure liquid chromatography was While supplies last, single copies of this publication may be obtained at no performed in Rutaceae, subfamily Aurantioideae, representing 5 genera, cost from- 35 species, and 114 cultivars. The average number of peaks, or phenolic USDA, ARS, National Center for Agricultural Utilization Research compounds, occurring in citrus leaf, flavedo, albedo, and juice vesicles 1815 North University Street were 21, 17, 15, and 9.3, respectively.
    [Show full text]
  • Studies on the Extraction and Characterization of Pectin and Bitter
    Copyright is owned by the Author of the thesis. Permission is given for a copy to be downloaded by an individual for the purpose of research and private study only. The thesis may not be reproduced elsewhere without the permission of the Author. STUDIES ON THE EXTRACTION AND CHARACTERIZATION OF' PECTIN AND BITTER PRINCIPLES FROM NEW ZEALAND GRAPEFRUIT AND PHILIPPINE CALAMANSI A thesis presented in partial fulfilment of the requirements for the d egr ee of Master of Technology in Food Technology at Massey University MYRNA ORDONA NISPEROS 1981 ii ABSTRACT A study was conducted to determine the presence of bitter components in NZ grapefruit and Philippine ca.lamansi; describe the effect of maturity on the bitter components and other chemical constituents of grapefruit; reduce the bitterness of grapefruit juice by adsorption on polyvinylpyrrolidone; and to extract and characterize pectin from grapefruit peel. Naringin (995 ppm), narirutin (187 ppm), and limonoids (7.9 ppm) were detected in NZ grapefruit juice concentrate (27° Brix). Naringin was not detected in the calamansi juice, and limonin was detected at the level of 10.5 ppm in juice containing 5% crushed seeds. Maturation of the grapefruit caused an increase in pH from J.00 to J.50, an increase in total soluble solids from 10.8 to 14.4 with a decline to 13.5° Brix later in the season, a steady fall in acidity from 2.50 to 1.31 g citric acid/100 mL, and a continuous rise in the Brix/acid ratio from 4.2 to 10.J. Juice yield fluctuated throughout the season.
    [Show full text]
  • The Role of Extractives in the Natural Durability of the Heartwood of Dicorynia Guianensis Amsh
    The role of extractives in the natural durability of the heartwood of Dicorynia guianensis Amsh: new insights in antioxydant and antifungal properties Jean-Baptiste Say Anouhe, Florence Bobelé Niamké, Milcard Faustin, David Virieux, Jean-Luc Pirat, Augustin Amissa Adima, Seraphin Kati-Coulibaly, Nadine Amusant To cite this version: Jean-Baptiste Say Anouhe, Florence Bobelé Niamké, Milcard Faustin, David Virieux, Jean-Luc Pirat, et al.. The role of extractives in the natural durability of the heartwood of Dicorynia guianensis Amsh: new insights in antioxydant and antifungal properties. Annals of Forest Science, Springer Nature (since 2011)/EDP Science (until 2010), 2018, 75 (1), pp.15. 10.1007/s13595-018-0691-0. hal-01779497 HAL Id: hal-01779497 https://hal.umontpellier.fr/hal-01779497 Submitted on 26 May 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Copyright Annals of Forest Science (2018) 75: 15 https://doi.org/10.1007/s13595-018-0691-0 ORIGINAL PAPER The role of extractives in the natural durability of the heartwood of Dicorynia guianensis
    [Show full text]
  • Evaluation of Anticancer Activities of Phenolic Compounds In
    EVALUATION OF ANTICANCER ACTIVITIES OF PHENOLIC COMPOUNDS IN BLUEBERRIES AND MUSCADINE GRAPES by WEIGUANG YI (Under the Direction of CASIMIR C. AKOH) ABSTRACT Research has shown that diets rich in phenolic compounds may be associated with lower risk of several chronic diseases including cancer. This study systematically evaluated the bioactivities of phenolic compounds in blueberries and muscadine grapes, and assessed their potential cell growth inhibition and apoptosis induction effects using two colon cancer cell lines (HT-29 and Caco-2), and one liver cancer cell line (HepG2). In addition, the absorption of blueberry anthocyanin extracts was evaluated using Caco-2 human intestinal cell monolayers. Polyphenols in three blueberry cultivars (Briteblue, Tifblue and Powderblue), and four cultivars of muscadine (Carlos, Ison, Noble, and Supreme) were extracted and freeze dried. The extracts were further separated into phenolic acids, tannins, flavonols, and anthocyanins using a HLB cartridge and LH20 column. In both blueberries and muscadine grapes, some individual phenolic acids and flavonoids were identified by HPLC with more than 90% purity in anthocyanin fractions. The dried extracts and fractions were added to the cell culture medium to test for cell growth inhibition and induction of apoptosis. Polyphenols from both blueberries and muscadine grapes had significant inhibitory effects on cancer cell growth. The phenolic acid fraction showed relatively lower bioactivities with 50% inhibition at 0.5-3 µg/mL. The intermediate bioactivities were observed in the flavonol and tannin fractions. The greatest inhibitory effect among all four fractions was from the anthocyanin fractions in the three cell lines. Cell growth was significantly inhibited more than 50% by the anthocyanin fractions at concentrations of 15-300 µg/mL.
    [Show full text]
  • Ep 2858641 B1
    (19) TZZ __T (11) EP 2 858 641 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 31/352 (2006.01) A61K 31/35 (2006.01) 06.09.2017 Bulletin 2017/36 A61P 17/00 (2006.01) A61Q 1/06 (2006.01) A61Q 1/14 (2006.01) A61K 8/49 (2006.01) (2006.01) (2006.01) (21) Application number: 13800034.4 A61K 8/60 A61Q 17/04 A61Q 19/08 (2006.01) A61K 8/86 (2006.01) A61Q 19/10 (2006.01) A61K 8/97 (2017.01) (22) Date of filing: 06.06.2013 A61K 8/99 (2017.01) A61Q 19/00 (2006.01) (86) International application number: PCT/US2013/044464 (87) International publication number: WO 2013/184884 (12.12.2013 Gazette 2013/50) (54) IMPROVED METHODS FOR BOTANICAL AND/OR ALGAE EXTRACTION VERBESSERTES VERFAHREN FÜR PFLANZEN- UND/ODER ALGENEXTRAKTION PROCÉDÉS AMÉLIORÉS POUR L’EXTRACTION DE VÉGÉTAUX ET/OU D’ALGUES (84) Designated Contracting States: • JUDD, Christopher AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Riverhead, NY 11901 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • RICHTER, Nicole Jeannine PL PT RO RS SE SI SK SM TR Port Jefferson, NY 11777 (US) (30) Priority: 06.06.2012 US 201261656221 P (74) Representative: Herzog, Fiesser & Partner Patentanwälte PartG mbB (43) Date of publication of application: Isartorplatz 1 15.04.2015 Bulletin 2015/16 80331 München (DE) (73) Proprietors: (56) References cited: • BASF Corporation WO-A1-2011/140655 KR-B1- 100 741 644 Florham Park, NJ 07932 (US) US-A1- 2006 078 633 US-A1- 2006 099 690 • BASF Beauty Care Solutions France SAS US-A1- 2011 190 175 69007 Lyon (FR) • MINUTH, T.
    [Show full text]