Carotenoid DB: CA00608

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Carotenoids DB: CA00608

Entry

CA00608

Classification

C40 carotenoids including C40 originated apocarotenoids and intermediates
2.2 beta,epsilon Carotene
C40 Hydroxycarotenoids

Carotenoid Name

Loroxanthin

IUPAC name

(3R,3'R,6'R)-beta,epsilon-Carotene-3,19,3'-triol

Formula

C40H56O3

Molecular Weight

584.848 g/mol

Structure

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Mol file

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(3R,3'R,6'R), 3-OH, 19-OH, 3'-OH, beta,epsilon
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Biological functions/Properties

Not an active antenna pigment but instead participates in the loroxanthin/lutein interconversion (Ref.626)

Number of
conjugated double bonds

Number of
conjugated multiple bonds

Isomers

Constitutional isomer: CA00227, CA00228, CA00394, CA00340, CA00377, CA00378, CA00339, CA00342, CA00338, CA00341, CA00410, CA00436, CA00437, CA00407, CA00408, CA00412, CA00438, CA00411, CA00409, CA00583, CA00607, CA00606, CA00609, CA00618, CA00627, CA00630, CA00624, CA00625, CA01047, CA00761, CA00762, CA00739

InChI

InChIKey

Canonical SMILES

XLogP

9.402

Hydrogen Bond donors
(Lipinski's definition)

Hydrogen Bond Acceptors
(Lipinski's definition)

LipinskiFailures

Complexity of molecule

0.303

Number of heavy atoms

TPSA
(Topological Polar Surface Area)

60.690 Å²

Reaction

Substrate: CR00246, CR00284

Product: CR00195

Pathway

Pathway: CB000065, CB000066, CB000132

Major carotenoid information

Minor carotenoid information

Minor carotenoid in some chlorophytes and prasinophytes (Ref.707).

Source organisms

Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga (Chlorophyta - Chlamydomonadaceae)
Basicladia sp. (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Chaetomorpha okamurae (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora horii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora kosterae (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Aegagrophila linnaei (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Chaetomorpha crassa (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora conchopheria (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora albida (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora japonica (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora pellucida (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora sericea (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora vagabunda (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora glomerata (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Rhizoclonium grande (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Pithophora sp. (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
Wittrockiella lyallii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
Wittrockiella paradoxa (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
Cladophoropsis fasciculatus (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
Tetraselmis suecica (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Tetraselmis tetrathele (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Tetraselmis chui (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Tetraselmis marina (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Tetraselmis rubens (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Tetraselmis subcordiformis (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Pyramimonas parkeae (Ref.48) - Green alga: Prasinophyte (Chlorophyta - Pyramimonadales)
Chlorella vulgaris (Ref.23) - Green alga: Trebouxiophyceae (Chlorophyta - Chlorellaceae)
Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
Botryococcus braunii Kawaguchi-1 (Ref.231) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
Euglena sanguinea (Ref.43) - Alga: Euglena (Euglenida - Euglenaceae)
Protousnea sp. (Ref.388) - Fungi: lichen (Ascomycota - Lecanorineae)
Corbicula clams (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
Corbicula sandai (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)

References

Ref.12: N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".

Ref.13: PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".

Ref.14: S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".

Ref.19: Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".

Ref.23: Märki-Fischer, E., Bütikofer, P.-A., Buchecker, R., and Eugster, C.H.　Helv. Chim. Acta, 66 PAGE: 1175 -1182 (1983) "Absolute configuration of loroxanthin (=(3R,3'R,6'R)-b,e-carotene-3,19,3'-triol)".

Ref.24: Y. Yoshii, I,. Wakana, K. Miriya, S. Arai, K. Ueda, and I. Inouye, J. Phycol. 40, 1170-1177 (2004) "Carotenoid comositions of Cladophora Balls (Aegagropila linnaei) and some members of the Cladophorales (Ulvophyceae, Chlorophyta): their taxonomic and evolutionary implication".

Ref.43: Merte grung et.al, S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 21, No. 8, pp. 757-763, 1993 "Algal Carotenoids52*; Secondary carotenoids of Algae 3; Carotenoids in natural bloom of Euglena sanguinea".

Ref.48: Jose L. Carrido, Francisco Rodriguez, and Mannuel Zapata J. Phycol. 15, 366-374 (2009) "Occurrence of Loroxanthin, Loroxanthin decenoate, and Loroxanthin dodecenoate in Tetraselmis species (Prasinophyceae, Chlorophyta)".

Ref.231: Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok, Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok., "Isolation and HPLC method development of azafrin from Alectra parasitica var. chitrakutensis".

Ref.221: Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".

Ref.388: B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".

Ref.626: Yukie Yoshii, Takeaki Hanyuda, Isamu Wakana, Kazuyuki Miyaji, Shogo Arai, Kunihiko Ueda, and Isao Inouye, J. Phycol. 40, 1170–1177 (2004), DOI: 10.1111/j.1529-8817.2004.03210.x, "CAROTENOID COMPOSITIONS OF CLADOPHORA BALLS (AEGAGROPILA LINNAEI) AND SOME MEMBERS OF THE CLADOPHORALES (ULVOPHYCEAE, CHLOROPHYTA): THEIR TAXONOMIC AND EVOLUTIONARY IMPLICATION1".

Ref.707: Suzanne Roy et al., Phytoplankton Pigments Characterization, Chemotaxonomy and Applications in Oceanography, October 2011, Cambridge University Press, pp 665-674, "Part VII - Data sheets aiding identification of phytoplankton carotenoids and chlorophylls", available at http://www.cambridge.org/gb/files/2013/6697/5826/Data_sheets_part_3_Xanthophylls.pdf, ISBN: 9781107000667.

CAS

27637-71-4

Links to other DB

KNApSAcK: C00022916
LipidBank: VCA1074

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