NCBI Taxonomy: 111782
Tolypothrix (ncbi_taxid: 111782)
found 95 associated metabolites at genus taxonomy rank level.
Ancestor: Tolypothrichaceae
Child Taxonomies: Tolypothrix curta, Tolypothrix tenuis, Tolypothrix brevis, Tolypothrix nodosa, Tolypothrix fragilis, Tolypothrix carrinoi, Tolypothrix distorta, environmental samples, Tolypothrix bouteillei, Tolypothrix rechingeri, Tolypothrix pseudorexia, Tolypothrix fasciculata, unclassified Tolypothrix, Tolypothrix scytonemoides, Tolypothrix campylonemoides, [Scytonema hofmanni] UTEX B 1581
Zeaxanthin
Zeaxanthin is a carotenoid xanthophyll and is one of the most common carotenoid found in nature. It is the pigment that gives corn, saffron, and many other plants their characteristic color. Zeaxanthin breaks down to form picrocrocin and safranal, which are responsible for the taste and aroma of saffron Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. Zeaxanthin is one of the two carotenoids (the other is lutein) that accumulate in the eye lens and macular region of the retina with concentrations in the macula greater than those found in plasma and other tissues. Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has been suggested. The xanthophylls may act to protect the eye from ultraviolet phototoxicity via quenching reactive oxygen species and/or other mechanisms. Some observational studies have shown that generous intakes of lutein and zeaxanthin, particularly from certain xanthophyll-rich foods like spinach, broccoli and eggs, are associated with a significant reduction in the risk for cataract (up to 20\\%) and for age-related macular degeneration (up to 40\\%). While the pathophysiology of cataract and age-related macular degeneration is complex and contains both environmental and genetic components, research studies suggest dietary factors including antioxidant vitamins and xanthophylls may contribute to a reduction in the risk of these degenerative eye diseases. Further research is necessary to confirm these observations. (PMID: 11023002). Zeaxanthin has been found to be a microbial metabolite, it can be produced by Algibacter, Aquibacter, Escherichia, Flavobacterium, Formosa, Gramella, Hyunsoonleella, Kordia, Mesoflavibacter, Muricauda, Nubsella, Paracoccus, Siansivirga, Sphingomonas, Zeaxanthinibacter and yeast (https://reader.elsevier.com/reader/sd/pii/S0924224417302571?token=DE6BC6CC7DCDEA6150497AA3E375097A00F8E0C12AE03A8E420D85D1AC8855E62103143B5AE0B57E9C5828671F226801). It is a marker for the activity of Bacillus subtilis and/or Pseudomonas aeruginosa in the intestine. Higher levels are associated with higher levels of Bacillus or Pseudomonas. (PMID: 17555270; PMID: 12147474) Zeaxanthin is a carotenol. It has a role as a bacterial metabolite, a cofactor and an antioxidant. It derives from a hydride of a beta-carotene. Zeaxanthin is a most common carotenoid alcohols found in nature that is involved in the xanthophyll cycle. As a coexistent isomer of lutein, zeaxanthin is synthesized in plants and some micro-organisms. It gives the distinct yellow color to many vegetables and other plants including paprika, corn, saffron and wolfberries. Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye and plays a predominant component in the central macula. It is available as a dietary supplement for eye health benefits and potential prevention of age-related macular degeneration. Zeaxanthin is also added as a food dye. Zeaxanthin is a natural product found in Bangia fuscopurpurea, Erythrobacter longus, and other organisms with data available. Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA. See also: Saffron (part of); Corn (part of); Lycium barbarum fruit (part of). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
Canthaxanthin
Canthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4 of the beta carotene molecule. Food colouring. Constituent of the edible mushroom (Cantharellus cinnabarinus), sea trout, salmon and brine shrimp. It is used in broiler chicken feed to enhance the yellow colour of chicken skin D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
echinenone
A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.
Zeaxanthin
Meso-zeaxanthin (3R,3´S-zeaxanthin) is a xanthophyll carotenoid, as it contains oxygen and hydrocarbons, and is one of the three stereoisomers of zeaxanthin. Of the three stereoisomers, meso-zeaxanthin is the second most abundant in nature after 3R,3´R-zeaxanthin, which is produced by plants and algae. To date, meso-zeaxanthin has been identified in specific tissues of marine organisms and in the macula lutea, also known as the "yellow spot", of the human retina . Meso-zeaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Meso-zeaxanthin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Meso-zeaxanthin can be found in channel catfish, crustaceans, and fishes, which makes meso-zeaxanthin a potential biomarker for the consumption of these food products. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.
Toyocamycin
C12H13N5O4 (291.09674980000005)
An N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents Toyocamycin (Vengicide) is an adenosine analog produced by Streptomyces diastatochromogenes, acts as an XBP1 inhibitor. Toyocamycin blocks RNA synthesis and ribosome function, and induces apoptosis. Toyocamycin affects IRE1α-XBP1 pathway, and inhibits XBP1 mRNA cleavage with an IC50 value of 80 nM with affecting IRE1α auto-phosphorylation. Toyocamycin specifically inhibits CDK9 with an IC50 value of 79 nM[1][2][3].
canthaxanthin
A carotenone that consists of beta,beta-carotene bearing two oxo substituents at positions 4 and 4. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
tubercidin
An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents Tubercidin (7-Deazaadenosine) is an antibiotic obtained from Streptomyces tubercidicus. Tubercidin inhibits the growth of Streptococcus faecalis (8043) with an IC50 of 0.02 μM[1]. Tubercidin inhibits polymerases by incorporating DNA or RNA, thereby inhibiting DNA replication, RNA and protein synthesis[2]. Tubercidin is a weak inhibitor of adenosine phosphorylase, and interferes with the phosphorylation of adenosine and AMP[1]. Tubercidin has antiviral activity[2]. Tubercidin (7-Deazaadenosine) is an antibiotic obtained from Streptomyces tubercidicus. Tubercidin inhibits the growth of Streptococcus faecalis (8043) with an IC50 of 0.02 μM[1]. Tubercidin inhibits polymerases by incorporating DNA or RNA, thereby inhibiting DNA replication, RNA and protein synthesis[2]. Tubercidin is a weak inhibitor of adenosine phosphorylase, and interferes with the phosphorylation of adenosine and AMP[1]. Tubercidin has antiviral activity[2].
Tolypodiol
A diterpenoid natural product obtained from the cyanobacterium Tolypothrix nodosa. It shows strong anti-inflammatory activity in the mouse ear edema assay.
14-hydroxy-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,6(24),7,9,11,13(22),16,18-nonaen-4-yl acetate
methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate
5,15-bis(3,5-dihydroxy-6-methyloxan-2-yl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaene-4,14-dione
n-{3-[(2s,5r,8s,11s,14r,17s,20s,23r,26s,29s,32r,35s,38z)-32-benzyl-38-ethylidene-3,6,9,12,15,18,21,24,27,30,33,36,39-tridecahydroxy-14-[(1r)-1-hydroxyethyl]-20-[(1s)-1-hydroxyethyl]-5-[(4-hydroxyphenyl)methyl]-11,23,26,29,35-pentaisopropyl-8-[2-(methylsulfanyl)ethyl]-17-(sec-butyl)-1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriaconta-1(39),3,6,9,12,15,18,21,24,27,30,33,36-tridecaen-2-yl]propyl}guanidine
C72H114N16O16S (1490.8319004000002)
(1r)-1-[(3s,6r,9s,12s,15s,18s,21z,24s,27s,30s,33s,36s,41as)-18-benzyl-12,15-bis[(2s)-butan-2-yl]-3-(3-carbamimidamidopropyl)-21-ethylidene-1,4,7,10,13,16,19,22,25,28,31,34-dodecahydroxy-9,30-bis[(1r)-1-hydroxyethyl]-24,33,36-triisopropyl-6-(2-methylpropyl)-37-oxo-3h,6h,9h,12h,15h,18h,24h,27h,30h,33h,36h,39h,40h,41h,41ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriacontan-27-yl]ethyl acetate
n-{3-[(2s,5s,8s,11s,14s,17s,23s,26s,29s,32s,35s,38z)-32-benzyl-17-[(2s)-butan-2-yl]-38-ethylidene-3,6,9,12,15,18,21,24,27,30,33,36,39-tridecahydroxy-14-[(1r)-1-hydroxyethyl]-20-[(1s)-1-hydroxyethyl]-5-[(3-hydroxyphenyl)methyl]-11,23,26,29,35-pentaisopropyl-8-[2-(methylsulfanyl)ethyl]-1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriaconta-1(39),3,6,9,12,15,18,21,24,27,30,33,36-tridecaen-2-yl]propyl}guanidine
C72H114N16O16S (1490.8319004000002)
(1r)-1-[(3s,6r,9r,12s,15r,18s,21z,24s,27s,30s,33s,36s,41as)-18-benzyl-12,15-bis[(2s)-butan-2-yl]-3-(3-carbamimidamidopropyl)-21-ethylidene-1,4,7,10,13,16,19,22,25,28,31,34-dodecahydroxy-9,30-bis[(1r)-1-hydroxyethyl]-24,33,36-triisopropyl-6-(2-methylpropyl)-37-oxo-3h,6h,9h,12h,15h,18h,24h,27h,30h,33h,36h,39h,40h,41h,41ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriacontan-27-yl]ethyl acetate
n-{3-[(2s,5s,8s,11s,14s,17s,20s,23s,26s,29s,32s,35s,38e)-32-benzyl-17-[(2s)-butan-2-yl]-38-ethylidene-3,6,9,12,15,18,21,24,27,30,33,36,39-tridecahydroxy-14,20-bis[(1r)-1-hydroxyethyl]-5-[(4-hydroxyphenyl)methyl]-11,23,26,29,35-pentaisopropyl-8-[2-(methylsulfanyl)ethyl]-1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriaconta-1(39),3,6,9,12,15,18,21,24,27,30,33,36-tridecaen-2-yl]propyl}guanidine
C72H114N16O16S (1490.8319004000002)
n-{3-[32-benzyl-38-ethylidene-3,6,9,12,15,18,21,24,27,30,33,36,39-tridecahydroxy-14,20-bis(1-hydroxyethyl)-5-[(4-hydroxyphenyl)methyl]-11,23,26,29,35-pentaisopropyl-8-[2-(methylsulfanyl)ethyl]-17-(sec-butyl)-1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriaconta-1(39),3,6,9,12,15,18,21,24,27,30,33,36-tridecaen-2-yl]propyl}guanidine
C72H114N16O16S (1490.8319004000002)
1-[18-benzyl-3-(3-carbamimidamidopropyl)-21-ethylidene-1,4,7,10,13,16,19,22,25,28,31,34-dodecahydroxy-9,30-bis(1-hydroxyethyl)-24,33,36-triisopropyl-6-(2-methylpropyl)-37-oxo-12,15-bis(sec-butyl)-3h,6h,9h,12h,15h,18h,24h,27h,30h,33h,36h,39h,40h,41h,41ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriacontan-27-yl]ethyl acetate
4-amino-7-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
C12H13N5O4 (291.09674980000005)
n-{3-[(2s,5s,8s,11s,14s,17s,20s,23s,26s,29s,32s,35s,38z)-32-benzyl-17-[(2s)-butan-2-yl]-38-ethylidene-3,6,9,12,15,18,21,24,27,30,33,36,39-tridecahydroxy-14-[(1r)-1-hydroxyethyl]-20-[(1s)-1-hydroxyethyl]-5-[(3-hydroxyphenyl)methyl]-11,23,26,29,35-pentaisopropyl-8-[2-(methylsulfanyl)ethyl]-1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriaconta-1(39),3,6,9,12,15,18,21,24,27,30,33,36-tridecaen-2-yl]propyl}guanidine
C72H114N16O16S (1490.8319004000002)
(3r,5r,6r)-2-[(4r,14r)-14-[(3r,5r,6r)-3-(acetyloxy)-5-hydroxy-6-methyloxan-2-yl]-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl]-5-hydroxy-6-methyloxan-3-yl acetate
5-hydroxy-2-{14-hydroxy-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl}-6-methyloxan-3-yl acetate
14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate
2-[14-(3,5-dihydroxy-6-methyloxan-2-yl)-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,6(24),7,9,11,13(22),16,18-nonaen-4-yl]-5-hydroxy-6-methyloxan-3-yl acetate
2-[14-(3,5-dihydroxy-6-methyloxan-2-yl)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl]-5-hydroxy-6-methyloxan-3-yl acetate
2-{5-hydroxy-4,10,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,5,7,9,11(23),12,14,16(22),17,19-undecaen-4-yl}-6-methyloxane-3,5-diol
C30H32N4O4 (512.2423431999999)
14-hydroxy-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate
14-[3-(acetyloxy)-5-hydroxy-6-methyloxan-2-yl]-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,6(24),7,9,11,13(22),16,18-nonaen-4-yl acetate
(1s)-1-[(3r,6r,9r,12s,15r,18s,21z,24r,27s,30s,33r,36s,41as)-18-benzyl-3-(3-carbamimidamidopropyl)-21-ethylidene-1,4,7,10,13,16,19,22,25,28,31,34-dodecahydroxy-9-[(1r)-1-hydroxyethyl]-30-[(1s)-1-hydroxyethyl]-24,33,36-triisopropyl-6-(2-methylpropyl)-37-oxo-12,15-bis(sec-butyl)-3h,6h,9h,12h,15h,18h,24h,27h,30h,33h,36h,39h,40h,41h,41ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22,25,28,31,34,37-tridecaazacyclononatriacontan-27-yl]ethyl acetate
5,15-dihydroxy-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaene-4,14-dione
(2s,3r,5r,6r)-2-{5-hydroxy-4,10,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,5,7,9,11(23),12,14,16(22),17,19-undecaen-4-yl}-6-methyloxane-3,5-diol
C30H32N4O4 (512.2423431999999)