DOCSLIB.ORG

Carotenoids As Natural Functional Pigments

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Carotenoids As Natural Functional Pigments Journal of Natural Medicines (2020) 74:1–16 https://doi.org/10.1007/s11418-019-01364-x REVIEW Carotenoids as natural functional pigments Takashi Maoka1 Received: 5 June 2019 / Accepted: 22 September 2019 / Published online: 1 October 2019 © The Author(s) 2019 Abstract Carotenoids are tetraterpene pigments that are distributed in photosynthetic bacteria, some species of archaea and fungi, algae, plants, and animals. About 850 naturally occurring carotenoids had been reported up until 2018. Photosynthetic bacteria, fungi, algae, and plants can synthesize carotenoids de novo. Carotenoids are essential pigments in photosynthetic organs along with chlorophylls. Carotenoids also act as photo-protectors, antioxidants, color attractants, and precursors of plant hormones in non-photosynthetic organs of plants. Animals cannot synthesize carotenoids de novo, and so those found in animals are either directly accumulated from food or partly modifed through metabolic reactions. So, animal carotenoids show structural diversity. Carotenoids in animals play important roles such precursors of vitamin A, photo-protectors, anti- oxidants, enhancers of immunity, and contributors to reproduction. In the present review, I describe the structural diversity, function, biosyntheses, and metabolism of natural carotenoids. Keywords Carotenoids · Natural pigments · Biosyntheses · Metabolism · Function Introduction carotenoids containing oxygen atoms as hydroxy, carbonyl, aldehyde, carboxylic, epoxide, and furanoxide groups in Structure of carotenoids these molecules. Some xanthophylls are present as fatty acid esters, glycosides, sulfates, and protein complexes. Struc- Carotenoids are tetraterpene pigments, which exhibit yel- tures of xanthophylls show marked diversity. About 800 low, orange, red and purple colors. Carotenoids are the kinds of xanthophylls have been reported in nature up until most widely distributed pigments in nature and are present 2018 [1, 2]. Figure 1b shows structures of typical carotenes in photosynthetic bacteria, some species of archaea and and xanthophylls. Most carotenoids have 40-carbon skeleton fungi, algae, plants, and animals. Most carotenoids consist (C40 carotenoid). Some carotenoids have a 45- or 50-car- of eight isoprene units with a 40-carbon skeleton. Their gen- bon skeleton, which are called higher carotenoids. About 40 eral structures commonly consist of a polyene chain with kinds of higher carotenoids are present in some species of nine conjugated double bonds and an end group at both archaea. On the other hand, carotenoids composed of carbon ends of the polyene chain. The structures of the polyene skeletons with fewer than 40 carbons are called apocarot- chain and end groups of carotenoids are shown in Fig. 1a enoids. About 120 kinds of apocarotenoids are present in [1]. Carotenoids are divided into two groups: carotenes and some species of plants and animals as degradation products xanthophylls. Carotenes, such as α-carotene, β-carotene, of C40 carotenoids [1, 2]. β,ψ-carotene (γ-carotene), and lycopene, are hydrocarbons. About 50 kinds of carotenes are present in nature [1]. On the History of carotenoid research in natural product other hand, xanthophylls, such as β-cryptoxanthin, lutein, chemistry zeaxanthin, astaxanthin, fucoxanthin, and peridinin, are In the early part of the nineteenth century, carotenoids were found in paprika (1817), safron (1818), annatto (1825), * Takashi Maoka carrots (1831), and autumn leaves (1837). In 1906, Zwet [email protected] succeeded in the separation of carotene, xanthophyll and 1 Research Institute for Production Development, 15 chlorophyll from green leaves using column chromatogra- Shimogamo, Morimoto Cho, Sakyoku, Kyoto 606-0805, phy. In the 1930s, Karrer and Khun elucidated the structures Japan Vol.:(0123456789)1 3 2 Journal of Natural Medicines (2020) 74:1–16 Fig. 1 a Basic structures of A end group polyene chain end group carotenoids and end groups. b Structures of typical carotenes 18' 19 20 5' and xanthophylls 17 16 15 13' 6 9' 1' 1 6' 9 13 15' 19' 16' 17' 5 18 20' -Carotene end group -end group -end group -end group -end group -end group -end group -end group B Carotenes -Carotene Lycopene Xanthophyll OH HO HO -Cryptoxanthin Lutein O OH OH HO HO O Zeaxanthin Astaxanthin OH OH O O O . O O O O . O O Fucoxanthin HO HO Peridinin of β-carotene and lycopene. Furthermore, they found that by Kuhn and Karrer in 1928–1930, about 750 naturally β-carotene was a precursor of vitamin A. They won the occurring carotenoids had been reported up until 2004 Nobel Prize in chemistry for this work. Subsequently, struc- [1]. Improvements of analytical instruments such as NMR, tures of lutein, zeaxanthin, and astaxanthin were revealed by MS, and HPLC have made it possible to perform the struc- their groups. These structural studies were based on the oxi- tural elucidation of very minor carotenoids in nature [2]. dative degradation of carotenoids with KMnO4, and struc- Annually, several new structures of carotenoids are being tures were analyzed using elemental analysis. In the 1950s, reported. Our research group has performed the structural the Zechmeister group studied E/Z (cis–trans) isomeriza- elucidation and analysis of naturally occurring carotenoids tion of carotenoids. In the 1960s, the Weedon group and using NMR, MS, MS/MS, and LC/MS [2] over the last dec- Liaaen-Jensen group elucidated the structure of fucoxanthin ade. About 100 kinds of natural carotenoids were reported and peridinin, respectively, using NMR and MS spectrom- from 2004 to 2018 [2]. Synthetic studies of carotenoids etry [3]. Since the frst structural elucidation of β-carotene revealed the stereochemistry of several complex structures 1 3 Journal of Natural Medicines (2020) 74:1–16 3 of natural carotenoids such as peridinin, fucoxanthin, cras- by non-photochemical quenching, a mechanism to reduce sostreaxanthin B, and cucurbitaxanthin A [4]. the amount of energy that reaches the photosynthetic reac- tion centers. Non-photochemical quenching is one of the main ways to protect against photoinhibition. In higher Carotenoids in photosynthetic bacteria, plants, xanthophyll cycles consist of violaxanthin–anthe- some species of fungi, algae, and plants raxanthin–zeaxanthin. During light stress, violaxanthin is converted to zeaxanthin via the intermediate antheraxanthin, Carotenoid biosynthesis which plays a direct photo-protective role acting as a lipid- protective antioxidant and by stimulating non-photochemical Basic carotenoid biosynthetic pathways are indicated in quenching within light-harvesting proteins. This conversion Fig. 2a and b. The frst step, dimethylallyl pyrophosphate of violaxanthin to zeaxanthin is medicated by the enzyme is formed from acetyl CoA or pyruvic acid through meva- violaxanthin de-epoxidase, while the reverse reaction is per- lonate pathway or non-mevanolate pathway, respectively. formed by zeaxanthin epoxidase (Fig. 3) [6]. Lutein epox- Then, phytoene, with a C40 carotenoid skeleton, is formed ide and lutein are members of xanthophylls cycles in higher from dimethylallyl pyrophosphate through geranyl pyroph- plants. In diatoms, the xanthophyll cycle consists of diadi- osphate and geranylgeranyl pyrophosphate (Fig. 2a). Phy- noxanthin and diatoxanthin (Fig. 3) [6]. toene is a colorless carotenoid with three conjugated double bonds. Phytoene is stepwisely desaturated to form lycopene Carotenoids in non‑photosynthetic organs of plants via phytofluene, ζ-carotene, and neurosporene by phy- toene desaturase. Lycopene cyclases produce carotenoids Carotenoids are also present in non-photosynthetic organs with cyclic terminal end groups such as α-carotene and of plants such as fruits, pericarps, seeds, roots, and fow- β-carotene, as shown in Fig. 2b. Several xanthophylls are ers. Carotenoids in these none-photosynthetic organs show produced by carotene hydroxylases, ketolases, and epoxi- structural diversity and are formed by secondary metabolic dase. These carotenoid biosynthetic pathways have been reactions, such as oxidation, the cleavage of polyene chains, comprehensively revealed by enzymatic and genetic studies and (Z/E) (cis–trans) isomerization [5, 6]. Carotenoids in [5]. non-photosynthetic organs act as photo-protectors, antioxi- dants, color attractants, and precursors of plant hormones. Carotenoids in photosynthetic organs of plants Many fruits and seeds turn red or purple during the rip- ening stage. This color change is due to the formation of Carotenoids are essential compounds along with chloro- carotenoids and/or anthocyanins. For example, the color of phylls in photosynthetic bacteria, algae, and plants and are the pericarp of tomato turns from greenish-yellow to deep involved in photosynthesis and photo-protection. Carot- red during the ripening stage. This color change is due to enoids harvest light energy and transfer this energy to chlo- the conversion of phytoene to lycopene in the pericap of the rophylls through singlet–singlet excitation transfer. This tomato. Phytoene (colorless), which is the major carotenoid singlet–singlet transfer is a lower energy state transfer used in greenish-yellow tomato, is converted to phytofuene (pale during photosynthesis. Carotenoids absorb excessive energy yellow), ζ-carotene (yellow), neurosporene (orange), and from chlorophylls through triplet–triplet transfer and release lycopene (red) by phytoene desaturase, as shown in Fig. 2B excessive energy by polyene vibration. The triplet–triplet [5, 6]. Lycopene is a carotenoid with
Load more

Recommended publications
  • (12) United States Patent (10) Patent No.: US 8,834.855 B2 Johnsen Et Al
    USOO8834.855B2 (12) United States Patent (10) Patent No.: US 8,834.855 B2 Johnsen et al. (45) Date of Patent: Sep. 16, 2014 (54) SUNSCREEN COMPOSITIONS COMPRISING (56) References Cited CAROTENOIDS U.S. PATENT DOCUMENTS (75) Inventors: Geir Johnsen, Trondheim (NO); Per Age Lysaa, Oslo (NO); KristinO O Aamodt, 4,699,7815,210,186 A 10/19875/1993 MikalsenGoupil et al. Oslo (NO) 5,308,759 A 5/1994 Gierhart 5,352,793 A 10, 1994 Bird et al. (73) Assignee: Promar AS (NO) 5,382,714 A 1/1995 Khachik 5,648,564 A 7/1997 AuSich et al. (*) Notice: Subject to any disclaimer, the term of this 5,654,488 A 8/1997 Krause et al. patent is extended or adjusted under 35 5,705,146 A 1, 1998 Lindquist U.S.C. 154(b) by 1255 days. (Continued) (21) Appl. No.: 11/795,668 FOREIGN PATENT DOCUMENTS (22) PCT Filed:1-1. Jan. 23, 2006 CA 21777521310969 12/199612/1992 (86). PCT No.: PCT/GB2OO6/OOO220 (Continued) S371 (c)(1), OTHER PUBLICATIONS (2), (4) Date: Apr. 15, 2008 “A UV absorbing compound in HPLC pigment chromatograms (87) PCT Pub. No.: WO2006/077433 obtained from Iceland Basin Phytoplankton'. Liewellyn et al., PCT Pub. Date: Jul.e 27,af f 9 2006 Marine Ecology Progress Series, vol. 158.:283-287, 1997.* (65) Prior Publication Data (Continued)Continued US 2008/O260662 A1 Oct. 23, 2008 Primary Examiner — Ernst V Arnold (30) Foreign Application Priority Data Assistant Examiner — Hong Yu (74) Attorney, Agent, or Firm — Schwegman Lundberg & Jan. 21, 2005 (GB) ..................................
    [Show full text]
  • An Overview of the Fossil Record of Pteropoda (Mollusca, Gastropoda, Heterobranchia)
    Cainozoic Research, 17(1), pp. 3-10 June 2017 3 An overview of the fossil record of Pteropoda (Mollusca, Gastropoda, Heterobranchia) Arie W. Janssen1 & Katja T.C.A. Peijnenburg2, 3 1 Naturalis Biodiversity Center, Marine Biodiversity, Fossil Mollusca, P.O. Box 9517, 2300 RA Leiden, The Nether­ lands; [email protected] 2 Naturalis Biodiversity Center, Marine Biodiversity, P.O. Box 9517, 2300 RA Leiden, The Netherlands; Katja.Peijnen­ [email protected] 3 Institute for Biodiversity and Ecosystem Dynamics (IBED), University of Amsterdam, P.O. Box 94248, 1090 GE Am­ sterdam, The Netherlands. Manuscript received 23 January 2017, revised version accepted 14 March 2017 Based on the literature and on a massive collection of material, the fossil record of the Pteropoda, an important group of heterobranch marine, holoplanktic gastropods occurring from the late Cretaceous onwards, is broadly outlined. The vertical distribution of genera is illustrated in a range chart. KEY WORDS: Pteropoda, Euthecosomata, Pseudothecosomata, Gymnosomata, fossil record Introduction Thecosomata Mesozoic Much current research focusses on holoplanktic gastro- pods, in particular on the shelled pteropods since they The sister group of pteropods is now considered to belong are proposed as potential bioindicators of the effects of to Anaspidea, a group of heterobranch gastropods, based ocean acidification e.g.( Bednaršek et al., 2016). This on molecular evidence (Klussmann-Kolb & Dinapoli, has also led to increased interest in delimiting spe- 2006; Zapata et al., 2014). The first known species of cies boundaries and distribution patterns of pteropods pteropods in the fossil record belong to the Limacinidae, (e.g. Maas et al., 2013; Burridge et al., 2015; 2016a) and are characterised by sinistrally coiled, aragonitic and resolving their evolutionary history using molecu- shells.
    [Show full text]
  • Photosynthetic Pigments in Diatoms
    Mar. Drugs 2015, 13, 5847-5881; doi:10.3390/md13095847 OPEN ACCESS marine drugs ISSN 1660-3397 www.mdpi.com/journal/marinedrugs Review Photosynthetic Pigments in Diatoms Paulina Kuczynska 1, Malgorzata Jemiola-Rzeminska 1,2 and Kazimierz Strzalka 1,2,* 1 Faculty of Biochemistry, Biophysics and Biotechnology, Department of Plant Physiology and Biochemistry, Jagiellonian University, Gronostajowa 7, Krakow 30-387, Poland; E-Mails: [email protected] (P.K.); [email protected] (M.J.-R.) 2 Małopolska Centre of Biotechnology, Gronostajowa 7A, Krakow 30-387, Poland * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +48-126-646-509; Fax: +48-126-646-902. Academic Editor: Véronique Martin-Jézéquel Received: 10 July 2015 / Accepted: 7 September 2015 / Published: 16 September 2015 Abstract: Photosynthetic pigments are bioactive compounds of great importance for the food, cosmetic, and pharmaceutical industries. They are not only responsible for capturing solar energy to carry out photosynthesis, but also play a role in photoprotective processes and display antioxidant activity, all of which contribute to effective biomass and oxygen production. Diatoms are organisms of a distinct pigment composition, substantially different from that present in plants. Apart from light-harvesting pigments such as chlorophyll a, chlorophyll c, and fucoxanthin, there is a group of photoprotective carotenoids which includes β-carotene and the xanthophylls, diatoxanthin, diadinoxanthin, violaxanthin, antheraxanthin, and zeaxanthin, which are engaged in the xanthophyll cycle. Additionally, some intermediate products of biosynthetic pathways have been identified in diatoms as well as unusual pigments, e.g., marennine. Marine algae have become widely recognized as a source of unique bioactive compounds for potential industrial, pharmaceutical, and medical applications.
    [Show full text]
  • The Biochromes ) 1.2
    FORSCHUNG 45 CHIMIA 49 (1995) Nr. 3 (Miirz) Chim;a 49 (1995) 45-68 quire specific molecules, pigments or dyes © Neue Schweizerische Chemische Gesellschaft (biochromes) or systems containing them, /SSN 0009-4293 to absorb the light energy. Photoprocesses and colors are essential for life on earth, and without these biochromes and the photophysical and photochemical interac- tions, life as we know it would not have The Function of Natural been possible [1][2]. a Colorants: The Biochromes ) 1.2. Notation The terms colorants, dyes, and pig- ments ought to be used in the following way [3]: Colorants are either dyes or pig- Hans-Dieter Martin* ments, the latter being practically insolu- ble in the media in which they are applied. Indiscriminate use of these terms is fre- Abstract. The colors of nature belong undoubtedly to the beautiful part of our quently to be found in literature, but in environment. Colors always fascinated humans and left them wonderstruck. But the many biological systems it is not possible trivial question as to the practical application of natural colorants led soon and at all to make this differentiation. The consequently to coloring and dyeing of objects and humans. Aesthetical, ritual and coloring compounds of organisms have similar aspects prevailed. This function of dyes and pigments is widespread in natl)re. been referred to as biochromes, and this The importance of such visual-effective dyes is obvious: they support communication seems to be a suitable expression for a between organisms with the aid of conspicuous optical signals and they conceal biological colorant, since it circumvents revealing ones, wl,1eninconspicuosness can mean survival.
    [Show full text]
  • Algal Pigments As Biomarkers Linking Fish and Benthic Organisms with Type E Botulism
    Algal pigments in benthic organisms and fish: development of biomarkers to trace food-web relationships Katherine T. Alben, Maxime Bridoux, Monika Sobiechowska Wadsworth Center, New York State Department of Health Dept. Environmental Health Sciences, SUNY-Albany National Water Quality Monitoring Conference May 9, 2006 San Jose, CA U at ALBANY From R. Ruffin, with permission Type E botulism: what are the food-web pathways? loon grebe gull Hypothesis: algal scud pigments goby yellow orange red can be used to trace food-web connections http://www.combat-fishing.com/lakepondbalance.htm#coldwaterlglake http://www.dnr.state.mn.us/exotics/aquaticanimals/roundgoby/index.html http://www.vancouverisland.com/021wildl&cons/wildlife/birds/cw/cw_herringgull.html http://www.admiraltyaudubon.org/ [email protected] U at ALBANY Algal carotenoids found in the food web diatoms & fucoxanthin C42H60O6 55 chrysophytes diatoxanthin C40H54O2 55 cryptophytes alloxanthin C40H52O2 55 chlorophytes lutein C40H56O2 (5) 55 5 cyanobacteria zeaxanthin C40H56O2 55 5 5 cantha- C40H52O2 55 β-crypto- C40H56O 55 echinenone C40H54O 555 euglenophytes neoxanthin C40H56O4 5 dinoflagellates peridinin C39H52O7 NF NF NF NF crustacean astaxanthin C40H52O4 55 5 5 metabolism U at ALBANY Method Development Standards – high resolution separations Quantitation – NIST, reference materials, MDLs Sample prep – microanalytical procedures, SPE, enzymatic hydrolysis Applications – Phytoplankton Gastropods Dreissenids Fish – round gobies, drum, perch, bass Standards - chlorophyll & carotenoids
    [Show full text]
  • A Review on Biosynthesis, Health Benefits and Extraction Methods of Fucoxanthin, Particular Marine Carotenoids in Algae
    Journal of Medicinal Plants A Review on Biosynthesis, Health Benefits and Extraction Methods of Fucoxanthin, Particular Marine Carotenoids in Algae Irvani N (M.Sc.)1, Hajiaghaee R (Ph.D.)2, Zarekarizi A.R (M.Sc.)2* 1- Faculty of Biological Science and Technology, Shahid Beheshti University, Tehran, Iran 2- Medicinal Plants Research Center, Institute of Medicinal Plants, ACECR, Karaj, Iran * Corresponding author: Institute of Medicinal Plants, ACECR, Karaj, Iran P.O.BOX (Mehr Vila): 31375-369 Tel: +98 - 26 – 34764010-18, Fax: +98 – 26- 34764021 E-mail: [email protected] Received: 28 June 2017 Accepted: 18 July 2018 Abstract Fucoxanthin, an allenic carotenoid, is abundant in macro and microalgae as a component of the light-harvesting complex for photosynthesis and photo protection. This carotenoid has shown important pharmaceutical bioactivity, exerting antioxidant, anti-cancer, anti-diabetic, anti- obesity, anti-photoaging, anti-angiogenic, and anti-metastatic effects on a variety of biological models. This carotenoid has been proven to be safe for animal consumption, opening up the opportunity of using this bioactive compound in the treatment of different pathologies. In this paper, an updated account of the research progress in biosynthetic pathway and health benefits of fucoxanthin is presented. Meanwhile, a review on the various methods of extraction of fucoxanthin in macro and microalgae is also revisited. According to these studies providing important background knowledge, fucoxanthin can be utilized into drugs and nutritional products. Keywords: Fucoxanthin, Carotenoids, Biosynthesis pathway, Extraction methods 6 Volume 17, No. 67, Summer 2018 … A Review on Biosynthesis Introduction million species [5]. Microalgae are important Consumer awareness of the importance of a primary producers in marine environments and healthy diet, protection of the environment, play a significant role in supporting aquatic resource sustainability and using all natural animals [6].
    [Show full text]
  • OXIDATIVE STRESS in ALGAE: METHOD DEVELOPMENT and EFFECTS of TEMPERATURE on ANTIOXIDANT NUCLEAR SIGNALING COMPOUNDS Md Noman Siddiqui Purdue University
    Purdue University Purdue e-Pubs Open Access Theses Theses and Dissertations Spring 2014 OXIDATIVE STRESS IN ALGAE: METHOD DEVELOPMENT AND EFFECTS OF TEMPERATURE ON ANTIOXIDANT NUCLEAR SIGNALING COMPOUNDS Md Noman Siddiqui Purdue University Follow this and additional works at: https://docs.lib.purdue.edu/open_access_theses Part of the Fresh Water Studies Commons Recommended Citation Siddiqui, Md Noman, "OXIDATIVE STRESS IN ALGAE: METHOD DEVELOPMENT AND EFFECTS OF TEMPERATURE ON ANTIOXIDANT NUCLEAR SIGNALING COMPOUNDS" (2014). Open Access Theses. 256. https://docs.lib.purdue.edu/open_access_theses/256 This document has been made available through Purdue e-Pubs, a service of the Purdue University Libraries. Please contact [email protected] for additional information. Graduate School ETD Form 9 (Revised/) PURDUE UNIVERSITY GRADUATE SCHOOL Thesis/Dissertation Acceptance This is to certify that the thesis/dissertation prepared By MD NOMAN SIDDIQUI Entitled OXIDATIVE STRESS IN ALGAE: METHOD DEVELOPMENT AND EFFECTS OF TEMPERATURE ON ANTIOXIADANT NUCLEAR SIGNALING COMPOUNDS Master of Science For the degree of Is approved by the final examining committee: PAUL BROWN REUBEN GOFORTH THOMAS HOOK To the best of my knowledge and as understood by the student in the 7KHVLV'LVVHUWDWLRQ$JUHHPHQW 3XEOLFDWLRQ'HOD\DQGCHUWLILFDWLRQDisclaimer (Graduate School Form ), this thesis/dissertation DGKHUHVWRWKHSURYLVLRQVRIPurdue University’s “Policy on Integrity in Research” and the use of copyrighted material. PAUL BROWN Approved by Major Professor(s): ____________________________________
    [Show full text]
  • Carotenoids in Algae: Distributions, Biosyntheses and Functions
    Mar. Drugs 2011, 9, 1101-1118; doi:10.3390/md9061101 OPEN ACCESS Marine Drugs ISSN 1660-3397 www.mdpi.com/journal/marinedrugs Review Carotenoids in Algae: Distributions, Biosyntheses and Functions Shinichi Takaichi Department of Biology, Nippon Medical School, Kosugi-cho, Nakahara, Kawasaki 211-0063, Japan; E-Mail: [email protected]; Tel.: +81-44-733-3584; Fax: +81-44-733-3584 Received: 2 May 2011; in revised form: 31 May 2011 / Accepted: 8 June 2011 / Published: 15 June 2011 Abstract: For photosynthesis, phototrophic organisms necessarily synthesize not only chlorophylls but also carotenoids. Many kinds of carotenoids are found in algae and, recently, taxonomic studies of algae have been developed. In this review, the relationship between the distribution of carotenoids and the phylogeny of oxygenic phototrophs in sea and fresh water, including cyanobacteria, red algae, brown algae and green algae, is summarized. These phototrophs contain division- or class-specific carotenoids, such as fucoxanthin, peridinin and siphonaxanthin. The distribution of α-carotene and its derivatives, such as lutein, loroxanthin and siphonaxanthin, are limited to divisions of Rhodophyta (macrophytic type), Cryptophyta, Euglenophyta, Chlorarachniophyta and Chlorophyta. In addition, carotenogenesis pathways are discussed based on the chemical structures of carotenoids and known characteristics of carotenogenesis enzymes in other organisms; genes and enzymes for carotenogenesis in algae are not yet known. Most carotenoids bind to membrane-bound pigment-protein complexes, such as reaction center, light-harvesting and cytochrome b6f complexes. Water-soluble peridinin-chlorophyll a-protein (PCP) and orange carotenoid protein (OCP) are also established. Some functions of carotenoids in photosynthesis are also briefly summarized. Keywords: algal phylogeny; biosynthesis of carotenoids; distribution of carotenoids; function of carotenoids; pigment-protein complex 1.
    [Show full text]
  • Pigment-Based Chloroplast Types in Dinoflagellates
    Vol. 465: 33–52, 2012 MARINE ECOLOGY PROGRESS SERIES Published September 28 doi: 10.3354/meps09879 Mar Ecol Prog Ser Pigment-based chloroplast types in dinoflagellates Manuel Zapata1,†, Santiago Fraga2, Francisco Rodríguez2,*, José L. Garrido1 1Instituto de Investigaciones Marinas, CSIC, c/ Eduardo Cabello 6, 36208 Vigo, Spain 2Instituto Español de Oceanografía, Subida a Radio Faro 50, 36390 Vigo, Spain ABSTRACT: Most photosynthetic dinoflagellates contain a chloroplast with peridinin as the major carotenoid. Chloroplasts from other algal lineages have been reported, suggesting multiple plas- tid losses and replacements through endosymbiotic events. The pigment composition of 64 dino- flagellate species (122 strains) was analysed by using high-performance liquid chromatography. In addition to chlorophyll (chl) a, both chl c2 and divinyl protochlorophyllide occurred in chl c-con- taining species. Chl c1 co-occurred with chl c2 in some peridinin-containing (e.g. Gambierdiscus spp.) and fucoxanthin-containing dinoflagellates (e.g. Kryptoperidinium foliaceum). Chl c3 occurred in dinoflagellates whose plastids contained 19’-acyloxyfucoxanthins (e.g. Karenia miki- motoi). Chl b was present in green dinoflagellates (Lepidodinium chlorophorum). Based on unique combinations of chlorophylls and carotenoids, 6 pigment-based chloroplast types were defined: Type 1: peridinin/dinoxanthin/chl c2 (Alexandrium minutum); Type 2: fucoxanthin/ 19’-acyloxy fucoxanthins/4-keto-19’-acyloxy-fucoxanthins/gyroxanthin diesters/chl c2, c3, mono - galac to syl-diacylglycerol-chl c2 (Karenia mikimotoi); Type 3: fucoxanthin/19’-acyloxyfucoxan- thins/gyroxanthin diesters/chl c2, c3 (Karlodinium veneficum); Type 4: fucoxanthin/chl c1, c2 (K. foliaceum); Type 5: alloxanthin/chl c2/phycobiliproteins (Dinophysis tripos); Type 6: neoxanthin/ violaxanthin/a major unknown carotenoid/chl b (Lepidodinium chlorophorum).
    [Show full text]
  • Mechanisms of Protective Effects of Astaxanthin in Nonalcoholic Fatty Liver Disease
    Gao et al. Hepatoma Res 2021;7:30 Hepatoma Research DOI: 10.20517/2394-5079.2020.150 Opinion Open Access Mechanisms of protective effects of astaxanthin in nonalcoholic fatty liver disease Ling-Jia Gao, Yu-Qin Zhu, Liang Xu School of Laboratory Medicine and Life Sciences, Wenzhou Medical University, Wenzhou 325035, Zhejiang, China. Correspondence to: Liang Xu, School of Laboratory Medicine and Life Sciences, Wenzhou Medical University, Chashan University Town, Wenzhou 325035, Zhejiang, China. E-mail: [email protected] How to cite this article: Gao LJ, Zhu YQ, Xu L. Mechanisms of protective effects of astaxanthin in nonalcoholic fatty liver disease. Hepatoma Res 2021;7:30. https://dx.doi.org/10.20517/2394-5079.2020.150 Received: 20 Nov 2020 First Decision: 24 Dec 2020 Revised: 29 Dec 2020 Accepted: 6 Jan 2021 Available online: 9 Apr 2021 Academic Editor: Stefano Bellentani Copy Editor: Miao Zhang Production Editor: Jing Yu Abstract Nonalcoholic fatty liver disease is a major contributor to chronic liver disease worldwide, and 10%-20% of nonalcoholic fatty liver progresses to nonalcoholic steatohepatitis (NASH). Astaxanthin is a kind of natural carotenoid, mainly derived from microorganisms and marine organisms. Due to its special chemical structure, astaxanthin has strong antioxidant activity and has become one of the hotspots of marine natural product research. Considering the unique chemical properties of astaxanthin and the complex pathogenic mechanism of NASH, astaxanthin is regarded as a significant drug for the prevention and treatment of NASH. Thus, this review comprehensively describes the mechanisms and the utility of astaxanthin in the prevention and treatment of NASH from seven aspects: antioxidative stress, inhibition of inflammation and promotion of M2 macrophage polarization, improvement in mitochondrial oxidative respiration, regulation of lipid metabolism, amelioration of insulin resistance, suppression of fibrosis, and liver tumor formation.
    [Show full text]
  • Genes Functioned in Kleptoplastids of Dinophysis Are Derived From
    www.nature.com/scientificreports OPEN Genes functioned in kleptoplastids of Dinophysis are derived from haptophytes rather than from Received: 30 October 2018 Accepted: 5 June 2019 cryptophytes Published: xx xx xxxx Yuki Hongo1, Akinori Yabuki2, Katsunori Fujikura 2 & Satoshi Nagai1 Toxic dinofagellates belonging to the genus Dinophysis acquire plastids indirectly from cryptophytes through the consumption of the ciliate Mesodinium rubrum. Dinophysis acuminata harbours three genes encoding plastid-related proteins, which are thought to have originated from fucoxanthin dinofagellates, haptophytes and cryptophytes via lateral gene transfer (LGT). Here, we investigate the origin of these plastid proteins via RNA sequencing of species related to D. fortii. We identifed 58 gene products involved in porphyrin, chlorophyll, isoprenoid and carotenoid biosyntheses as well as in photosynthesis. Phylogenetic analysis revealed that the genes associated with chlorophyll and carotenoid biosyntheses and photosynthesis originated from fucoxanthin dinofagellates, haptophytes, chlorarachniophytes, cyanobacteria and cryptophytes. Furthermore, nine genes were laterally transferred from fucoxanthin dinofagellates, whose plastids were derived from haptophytes. Notably, transcription levels of diferent plastid protein isoforms varied signifcantly. Based on these fndings, we put forth a novel hypothesis regarding the evolution of Dinophysis plastids that ancestral Dinophysis species acquired plastids from haptophytes or fucoxanthin dinofagellates, whereas LGT from cryptophytes occurred more recently. Therefore, the evolutionary convergence of genes following LGT may be unlikely in most cases. Plastids in photosynthetic dinofagellates are classifed into fve types according to their origin1. Plastids in most photosynthetic dinofagellates are bound by three membranes and contain peridinin as the major carotenoid. Although peridinin is considered to have originated from an endosymbiotic red alga1, this hypothesis remains controversial2.
    [Show full text]
  • Carotenoids of Sea Angels Clione Limacina and Paedoclione Doliiformis from the Perspective of the Food Chain
    Mar. Drugs 2014, 12, 1460-1470; doi:10.3390/md12031460 OPEN ACCESS marine drugs ISSN 1660-3397 www.mdpi.com/journal/marinedrugs Article Carotenoids of Sea Angels Clione limacina and Paedoclione doliiformis from the Perspective of the Food Chain Takashi Maoka 1,*, Takashi Kuwahara 2 and Masanao Narita 3 1 Research Institute for Production Development, Shimogamo-Morimoto-cho 15, Sakyo-ku, Kyoto 606-0805, Japan 2 Okhotsk Sea Ice Museum of Hokkaido, Motomombetsu, Monbetsu, Hokkaido 094-0023, Japan; E-Mail: [email protected] 3 Hokkaido Research Organization, Abashiri Fisheries Research Institute, Minatomachi, Monbetsu, Hokkaido 094-0011, Japan; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +81-75-781-1107; Fax: +81-75-791-7659. Received: 16 January 2014; in revised form: 19 February 2014 / Accepted: 3 March 2014 / Published: 13 March 2014 Abstract: Sea angels, Clione limacina and Paedoclione doliiformis, are small, floating sea slugs belonging to Gastropoda, and their gonads are a bright orange-red color. Sea angels feed exclusively on a small herbivorous sea snail, Limacina helicina. Carotenoids in C. limacina, P. doliiformis, and L. helicina were investigated for comparative biochemical points of view. β-Carotene, zeaxanthin, and diatoxanthin were found to be major carotenoids in L. helicina. L. helicina accumulated dietary algal carotenoids without modification. On the other hand, keto-carotenoids, such as pectenolone, 7,8-didehydroastaxanthin, and adonixanthin were identified as major carotenoids in the sea angels C. limacina and P. doliiformis. Sea angels oxidatively metabolize dietary carotenoids and accumulate them in their gonads.
    [Show full text]