Gas Chromatographic-Mass Spectrometric Investigation of Seep
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Molecular Biogeochemistry, Lecture 8
12.158 Lecture Pigment-derived Biomarkers (1) Colour, structure, distribution and function (2) Biosynthesis (3) Nomenclature (4) Aromatic carotenoids ● Biomarkers for phototrophic sulfur bacteria ● Alternative biological sources (5) Porphyrins and maleimides Many of the figures in this lecture were kindly provided by Jochen Brocks, RSES ANU 1 Carotenoid pigments ● Carotenoids are usually yellow, orange or red coloured pigments lutein β-carotene 17 18 19 2' 2 4 6 8 3 7 9 16 1 5 lycopenelycopene 2 Structural diversity ● More than 600 different natural structures are known, ● They are derived from the C40 carotenoid lycopene by varied hydrogenation, dehydrogenation, cyclization and oxidation reaction 17 18 19 2' 2 4 6 8 3 7 9 16 1 5 lycopene neurosporene α-carotene γ -carotene spirilloxanthin siphonaxanthin canthaxanthin spheroidenone 3 Structural diversity Purple non-sulfur bacteria peridinin 7,8-didehydroastaxanthin okenone fucoxanthin Biological distribution ● Carotenoids are biosynthesized de novo by all phototrophic bacteria, eukaryotes and halophilic archaea ● They are additionally synthesized by a large variety of non-phototrophs ● Vertebrates and invertebrates have to incorporate carotenoids through the diet, but have often the capacity to structurally modifiy them 4 Carotenoid function (1) Accessory pigments in Light Harvesting Complex (LHC) (annual production by marine phytoplancton alone: 4 million tons) e.g. LH-II Red and blue: protein complex Green: chlorophyll Yellow: lycopene (2) Photoprotection (3) photoreceptors for phototropism -
New Structural Insights Into the Extracellular Matrix And
NEW STRUCTURAL INSIGHTS INTO THE EXTRACELLULAR MATRIX AND HYDROCARBON DIVERSITY OF Botryococcus Braunii RACE B A Dissertation by MEHMET TATLI Submitted to the Office of Graduate and Professional Studies of Texas A&M University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Chair of Committee, Timothy P. Devarenne Committee Members, Jaan Laane Vladislav M. Panin Paul A. Lindahl Head of Department, Gregory D. Reinhart May 2018 Major Subject: Biochemistry Copyright 2018 Mehmet Tatli ABSTRACT Botryococcus braunii is a colonial green microalga that can produce large amounts of liquid isoprenoid hydrocarbons known as botryococcenes, which can be easily converted into conventional combustion engine fuels. B. braunii colony cells are held together by a complex extracellular matrix (ECM). ECM serves as a storage unit for liquid hydrocarbons, and contains a retaining wall and a polysaccharide fibrillar sheath. Analysis of “shells” revealed a single protein. Here we use peptide mass fingerprinting and bioinformatics to identify this protein called polysaccharide associated protein (PSAP). PSAP does not show similarity to any protein in databases, and contains several hydroxyproline domains and a predicted sugar binding domain. Staining studies confirm PSAP as a glycoprotein, and mass spectrometry analysis identified ten N-linked glycosylation sites comprising seven different glycans containing mostly mannose and N- acetylglucosamine with fucose and arabinose. Additionally, four hydroxyproline residues have short O-linked glycans of mainly arabinose and galactose, with 6-deoxyhexose. PSAP secretion and localization to shell material is confirmed using western blot analysis and microscopy. These studies indicate PSAP contains unique glycans and suggest its involvement in ECM polysaccharide fiber biosynthesis. -
Biosynthesis of New Alpha-Bisabolol Derivatives Through a Synthetic Biology Approach Arthur Sarrade-Loucheur
Biosynthesis of new alpha-bisabolol derivatives through a synthetic biology approach Arthur Sarrade-Loucheur To cite this version: Arthur Sarrade-Loucheur. Biosynthesis of new alpha-bisabolol derivatives through a synthetic biology approach. Biochemistry, Molecular Biology. INSA de Toulouse, 2020. English. NNT : 2020ISAT0003. tel-02976811 HAL Id: tel-02976811 https://tel.archives-ouvertes.fr/tel-02976811 Submitted on 23 Oct 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. THÈSE En vue de l’obtention du DOCTORAT DE L’UNIVERSITÉ DE TOULOUSE Délivré par l'Institut National des Sciences Appliquées de Toulouse Présentée et soutenue par Arthur SARRADE-LOUCHEUR Le 30 juin 2020 Biosynthèse de nouveaux dérivés de l'α-bisabolol par une approche de biologie synthèse Ecole doctorale : SEVAB - Sciences Ecologiques, Vétérinaires, Agronomiques et Bioingenieries Spécialité : Ingénieries microbienne et enzymatique Unité de recherche : TBI - Toulouse Biotechnology Institute, Bio & Chemical Engineering Thèse dirigée par Gilles TRUAN et Magali REMAUD-SIMEON Jury -
Application of CSIA of Light Oils and Utility of Carotenoid Biomarkers in Resource Plays of North America J
Application of CSIA of Light Oils and Utility of Carotenoid Biomarkers in Resource Plays of North America J. E. Zumberge1, C. D. Barrie1, J. B. Curtis*1, R. E. Summons2; 1. GeoMark Research, Ltd., Houston, TX, USA; 2. Massachusetts Institute of Technology, Cambridge, MA, USA. Abstract Here we examine the value in crude oil correlations and source rock depositional environment predictions based on non-standard compound-specific isotope analysis and carotenoid biomarker data. Results from various unconventional plays (e.g., Late Devonian Bakken and Woodford Fms from the Williston and Anadarko Basins; Cretaceous Second White Specks, Niobrara, Mowry and Eagle Ford Fms in the Western Interior Seaway) are discussed and compared. These data provide new insights into resource plays using novel and relatively rapid analytical methods. Molecular isotopic data and carotenoid biomarker distributions of petroleum systems tend to be distinct so that, in combination with commonly used sterane and hopane biomarkers, oil-oil and oil-source correlations can be made with much greater fidelity. Statement of the background This paper addresses novel application of compound-specific isotope analysis and carotenoid hydrocarbon characterization to better understand, and perhaps predict the productivity of hydrocarbons from source-rock reservoirs. This work provides new and detailed insight into resource play petroleum systems. Aims and Objectives Stable isotope analysis is a powerful tool in understanding the generation, history and correlation of hydrocarbons. Compound-specific δ13C measurements of oils allow detailed comparison of individual compound groupings; however, most studies separate and isolate individual fractions based on the chemistries of particular compound groups, potentially losing or corrupting valuable data. -
Deep Sea Drilling Project Initial Reports Volume 63
33. GEOCHEMISTRY OF TETRAPYRROLE, CAROTENOID, AND PERYLENE PIGMENTS IN SEDIMENTS FROM THE SAN MIGUEL GAP (SITE 467) AND BAJA CALIFORNIA BORDERLAND (SITE 471), DEEP SEA DRILLING PROJECT LEG 631 J. William Louda and Earl W. Baker, Organic Geochemistry Group, College of Science, Florida Atlantic University, Boca Raton, Florida INTRODUCTION for perylene, and homologues, is proposed: the role of diagenetic-geothermal history indicator. That is, as Twenty-one core samples from DSDP/IPOD Leg 63 depth of burial and in situ sediment temperature in- were analyzed for products of chlorophyll diagenesis. In creased, the proportion of C-21, C-22, and C-23 alkyl- addition to the tetrapyrrole pigments, perylene and ated derivatives of perylene (C-20) increased. On the carotenoid pigments were isolated and identified. basis of sediment depth and thermal profiles, the alkyl- The 16 core samples from the San Miguel Gap site perylenes were found to be generated prior to the ap- (467) and the five from the Baja California borderland pearance of nickel porphyrin homologues above C-32 location (471) afforded the unique opportunity of exam- and the release or formation of the vanadyl pigments. ining tetrapyrrole diagenesis in clay-rich marine sedi- Alkylation of perylene within DSDP/IPOD sample ments that are very high in total organic matter. suites has previously been mentioned (Brassell et al., The chelation reaction, whereby free-base porphyrins 1980). give rise to metalloporphyrins (viz., nickel), is well ß-Carotene was found to be present in Site 467 upper documented within the downhole sequence of sediments Pliocene and Quaternary sections (viz., 467-18-5 and from the San Miguel Gap (Site 467). -
This Article Was Published in an Elsevier Journal. the Attached Copy
This article was published in an Elsevier journal. The attached copy is furnished to the author for non-commercial research and education use, including for instruction at the author’s institution, sharing with colleagues and providing to institution administration. Other uses, including reproduction and distribution, or selling or licensing copies, or posting to personal, institutional or third party websites are prohibited. In most cases authors are permitted to post their version of the article (e.g. in Word or Tex form) to their personal website or institutional repository. Authors requiring further information regarding Elsevier’s archiving and manuscript policies are encouraged to visit: http://www.elsevier.com/copyright Author's personal copy Available online at www.sciencedirect.com Geochimica et Cosmochimica Acta 72 (2008) 1396–1414 www.elsevier.com/locate/gca Okenane, a biomarker for purple sulfur bacteria (Chromatiaceae), and other new carotenoid derivatives from the 1640 Ma Barney Creek Formation Jochen J. Brocks a,*, Philippe Schaeffer b a Research School of Earth Sciences and Centre for Macroevolution and Macroecology, The Australian National University, Canberra, ACT 0200, Australia b Laboratoire de Ge´ochimie Bio-organique, CNRS UMR 7177, Ecole Europe´enne de Chimie, Polyme`res et Mate´riaux, 25 rue Becquerel, 67200 Strasbourg, France Received 20 June 2007; accepted in revised form 12 December 2007; available online 23 December 2007 Abstract Carbonates of the 1640 million years (Ma) old Barney Creek Formation (BCF), McArthur Basin, Australia, contain more than 22 different C40 carotenoid derivatives including lycopane, c-carotane, b-carotane, chlorobactane, isorenieratane, b-iso- renieratane, renieratane, b-renierapurpurane, renierapurpurane and the monoaromatic carotenoid okenane. -
Supporting Information for Low-Priority Substance Tetracosane, 2,6,10,15,19,23-Hexamethyl-(CASRN 111-01-3) (Squalane) Final Desi
Supporting Information for Low-Priority Substance Tetracosane, 2,6,10,15,19,23-Hexamethyl- (CASRN 111-01-3) (Squalane) Final Designation February 20, 2020 Office of Pollution Prevention and Toxics U.S. Environmental Protection Agency 1200 Pennsylvania Avenue Washington, DC 20460 Contents 1. Introduction ................................................................................................................................................................ 1 2. Background on Squalane .......................................................................................................................................... 3 3. Physical-Chemical Properties ................................................................................................................................... 4 3.1 References ...................................................................................................................................................... 6 4. Relevant Assessment History ................................................................................................................................... 7 5. Conditions of Use ....................................................................................................................................................... 8 6. Hazard Characterization .......................................................................................................................................... 10 6.1 Human Health Hazard ................................................................................................................................... -
Squalene Emulsions for Parenteral Vaccine and Drug Delivery
Molecules 2009, 14, 3286-3312; doi:10.3390/molecules14093286 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Review Squalene Emulsions for Parenteral Vaccine and Drug Delivery Christopher B. Fox Infectious Disease Research Institute, 1124 Columbia St, Ste 400, Seattle, WA 98104, USA; E-mail: [email protected] Received: 13 August 2009; in revised form: 25 August 2009 / Accepted: 31 August 2009 / Published: 1 September 2009 Abstract: Squalene is a linear triterpene that is extensively utilized as a principal component of parenteral emulsions for drug and vaccine delivery. In this review, the chemical structure and sources of squalene are presented. Moreover, the physicochemical and biological properties of squalene-containing emulsions are evaluated in the context of parenteral formulations. Historical and current parenteral emulsion products containing squalene or squalane are discussed. The safety of squalene-based products is also addressed. Finally, analytical techniques for characterization of squalene emulsions are examined. Keywords: squalene; squalane; adjuvant; emulsion; parenteral 1. Introduction to Squalene and Emulsions Squalene is widely used for numerous vaccine and drug delivery emulsions due to its stability- enhancing effects and biocompatibility. Emulsions containing squalene facilitate solubilization, modified release, and cell uptake of drugs, adjuvants, and vaccines. Squalene and its hydrogenated form, squalane, have unique properties that are ideally suited for making stable and non-toxic nanoemulsions. Because of these characteristics, numerous squalene-based emulsions have been effectively developed for drug and vaccine applications. The chemical structure of squalene is that of a linear triterpene (Figure 1). The hydrocarbon composition of the molecule results in a highly hydrophobic nature; the calculated values for octanol/water partitioning coefficient (log P) and solubility of squalene in water are 10.67 and 0.124 mg/L, respectively [1]. -
Squalene – Antioxidant of the Future?
This is a summary of an article which appeared in The South African Journal of Natural Medicine 2007, 33, p106-112. Squalene – antioxidant of the future? HEIDI DU PREEZ is a Sourced primarily from the liver of the deep-sea professional natural scientist, shark, squalene has been referred to as the with a Masters degree in 1 ‘antioxidant of the future’. Heidi du Preez food science. She is currently discusses this unique molecule. studying for a degree in nutritional medicine. Heidi qualene is an isoprenoid hydrocarbon with six isoprene units. It is consults for both the food produced in our bodies and also found in nature. Many and health industries. She S antioxidants are either isoprenoids or have an isoprenoid tail. Vitamin E, vitamin A, beta-carotene and flavonoids are all uses a holistic, naturopathic isoprenoids. Isoprenoids are found abundantly in nature, but biologists approach, incorporating are mainly interested in studying the few, including squalene and diet, supplementation, lycopene, that have extraordinary antioxidant properties. detoxification and spiritual wellbeing in her treatment Since squalene is a pure isoprenoid, containing only isoprene units, it has an effective and stable antioxidant configuration. Squalene is regimen. Her focus is on the considered by many to be the most powerful and stable of the prevention and cure of isoprenoids.2 chronic, metabolic and degenerative diseases. Heidi In its purified form squalene is a colourless, almost tasteless, serves on the council of the transparent liquid without a significant odour. It is the major hydrocarbon in fish oils. Since squalene is a polyunsaturated ‘lipid’, South African Association for derived from fish oil, it should not be confused with being an essential Nutritional Therapy, and is fatty acid. -
Deep Sea Drilling Project Initial Reports Volume 66
21. PRELIMINARY LIPID ANALYSES OF TWO QUATERNARY SEDIMENTS FROM THE MIDDLE AMERICA TRENCH, SOUTHERN MEXICO TRANSECT, DEEP SEA DRILLING PROJECT LEG 661 S. C. Brassell, G. Eglinton, and J. R. Maxwell, School of Chemistry, University of Bristol, Bristol, United Kingdom ABSTRACT We investigated the solvent-extractable hydrocarbons, ketones, alcohols, and carboxylic acids of two Quaternary sediments from the Middle America Trench (Sections 487-2-3 and 491-1-5). These lipids are derived from a mixed input of autochthonous and allochthonous materials, with minor contributions from thermally mature sources. Their com- positions are typical of those of immature Quaternary marine sediments, and their lipid distributions show many similarities to those of Japan Trench sediments. INTRODUCTION RESULTS The solvent-extractable lipids of two Quaternary sed- The distributions of aliphatic hydrocarbons, ketones, iments (Sections 487-2-3 and 491-1-5) from the oceanic alcohols, and carboxylic acids and of aromatic hydro- plate and central slope of the Middle America Trench carbons are reported herein. In addition, other suites of were investigated by gas chromatography and comput- components such as a, co-dicarboxylic acids and numer- erized gas chromatography-mass spectrometry. The sec- ous minor or unrecognized compounds were detected, tions were chosen to permit the comparison of environ- but are not included. ments on either side of the trench. This preliminary re- port describes the lipid compositions of these two sam- Aliphatic Hydrocarbons ples and interprets them in terms of their input sources, conditions of deposition, and extent of diagenesis. We Acyclic Components also make a brief comparison of their lipid distributions The n-alkanes of Sections 487-2-3 and 491-1-5 both with those of Quaternary sediments from the Japan ranged from C14 to C35 with «-C29 dominant. -
Cosmedix Active Ingredients Glossary
COSMEDIX ACTIVE INGREDIENTS GLOSSARY INCI Name Function Acetyl Hexapeptide-1 Is a biomimetic peptide antagonist specific of the alpha-melanocyte stimulating hormone by preventing any further activation of the tyrosinase, and thus blocking melanin synthesis. Adenine is a nucleobase with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and protein synthesis, as a chemical component of DNA and . Alcohol Carrier, Solubilizer and Antiseptic Alcohol Denat. Carrier, Solubilizer and Antiseptic Allantoin it is derived from the extracts of a comfrey plant. It softens the skin and enables it to absorb more moisture. It’s particularly effective at treating wounds, burns, skin ulcers, eczema, and any other abrasion in the skin. Aloe Barbadensis Leaf Juice Powder it is a species of succulent plant in the genus Aloe that grows in arid climates and is widely distributed in Africa, India, and other arid areas. As a soothing, moisturizing and conditioning agent, Aloe vera extracts may be useful in the treatment of wound and burn healing, minor skin infections, Sebaceous cyst, diabetes, and elevated blood lipids in humans.These positive effects are thought to be due to the presence of compounds such as polysaccharides, mannans, anthraquinones, and lectins. Amino Esters-1 Skin-Conditioning Agent - Aminoguanidine HCL It is an investigational drug for the treatment of diabetic nephropathy. It is a diamine oxidase and nitric oxide synthase inhibitor and acts as an anti-oxidant that helps reducing the formation of advanced glycation end-products (AGEs) which destroy collagen and contribute skin aging. Arabinogalactan Protein (AGP) is a polysaccharide extracted from larch trees. -
Squalene: a Multi-Task Link in the Crossroads of Cancer and Aging
Functional Foods in Health and Disease 2013; 3(12):462-476 Page 462 of 476 Review Open Access Squalene: a multi-task link in the crossroads of cancer and aging Alvaro L. Ronco1,2 and Eduardo De Stéfani3 1Department of Epidemiology and Scientific Methods, IUCLAEH School of Medicine, Prado and Salt Lake p.16, Maldonado 20100, Uruguay; 2Unit of Oncology and Radiotherapy, Pereira Rossell Women’s Hospital, Bvar. Artigas 1550, Montevideo 11300, Uruguay; 3Epidemiology Group, Department of Pathology, Clinicas Hospital, Av. Italia s/n, Montevideo 11300, Uruguay Correspondent author: Alvaro Ronco, MD, 1Department of Epidemiology and Scientific Methods, IUCLAEH School of Medicine, Prado and Salt Lake p.16, Maldonado 20100, Uruguay Submission date: September 5, 2013; Acceptance date: December 14, 2013; Publication date: December 20, 2013 ABSTRACT Since its discovery in the beginning of the XXth century, squalene has been recognized as an important link in metabolic pathways. More recently, it has been further recognized as an intermediate step in the biosynthesis of cholesterol. Its well known antioxidant capability, together with its ability to protect skin, improve the immune system, and modulate the lipid profile, confer a high potential to this natural substance, which is spread all across the body structure, though mainly in the epithelial tissues, and in particular the skin sebum. This review will focus mainly on its major properties, which are related to anticancer properties, the maintenance of the oxidation/antioxidation balance, and its antiaging capabilities. Although the substance was originally obtained from shark liver oil, it is currently possible to obtain useful amounts from vegetable sources like extra virgin olive oil, therefore avoiding the dependence on capturing the aforementioned animal species.