13 epi 12 oxo phytodienoic acid

13-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenic acid in the leaves of green plants such as corn. ω-3 and ω-6 polyunsaturated fatty acids in plants are substrates for plant lipoxygenases. 12-oxo PDA is one of the best studied end metabolites of this enzymatic pathway. While the initial enzymatic product and major isomer of 12-oxo PDA contains side chains in the cis position, both being β to the ring, the upper side chain attached at C-13, can and frequently does, isomerize when 12-oxo PDA is extracted, isolated, or stored. 13-epi-12-oxo PDA is the product of this isomerization.

Phorbol 12-myristate 13-acetate (PMA) belongs to the phorbol ester group of natural products and is an activator of PKC, SphK, and NF-κB. Phorbol 12-myristate 13-acetate induces THP1 cell differentiation.

6-chloro-1-ethyl-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid is a compound used as a molecular structural unit for pefloxacin impurities.

1-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID targets GRK2.

2-Oxo-6-phenyl-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid belonging to the pyrimidine family, which has been shown to have anti-inflammatory, anticonvulsant and antitumor properties.

(±)12(13)-DiHOME is the diol form of (±)12(13)-EpOME , a cytochrome P450-derived epoxide of linoleic acid also known as isoleukotoxin. [1] It is formed from 12(13)-EpOME by soluble epoxide hydrolase (sEH) in neutrophils. [2] 12(13)-DiHOME is toxic to Sf21 cells expressing sEH and to lacZ-expressing control cells, unlike isoleukotoxin, which is only toxic to cells containing sEH.[1] [2] Levels of 12(13)-DiHOME are increased in rat spinal cord following burn injury, and it enhances cold tolerance, increases fatty acid uptake into brown adipocytes, and decreases serum triglyceride levels in mice. Levels are also elevated in bronchoalveolar lavage fluid (BALF) in humans following exposure to biodiesel exhaust and in exhaled breath condensate in patients with allergic asthma following allergen exposure.[5] [6] Plasma levels of 12(13)-DiHOME are increased immediately following moderate-intensity exercise in mice and humans, an effect that can be prevented by brown adipose tissue removal in the mouse.[7]

3α-Acetoxyurs-5:12-dien-24-oic acid, a natural compound, is isolatable from Boswellia sacra Fluckiger [1].

(3ξ,4ξ,5ξ,6ξ,7ξ,11ξ)-3,6-Dihydroxy-8-oxo-9-eremophilene-12-oic acid, a phytotoxin recently identified in Alternaria alternata ssp. tenuissima isolates, is associated with fruit spots on apples.

3,19-Dihydroxy-6,23-dioxo-12-ursen-28-oic acid is a natural product for research related to life sciences. The catalog number is TN2853 and the CAS number is 261768-88-1.

2α,3α,24-Trihydroxyurs-12-en-28-oic acid, a triterpenoid phytoalexin, shows antifungal activity against the fungus mentioned. It also shows in vitro cytotoxic activity against tumor cell lines including PLC,Hep3B,HepG2,HeLa,SW480,MCF-7 and Bel7402.

4-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid exhibits hypoglycemic activity and operates through a mechanism dependent on the response to oral glucose overload.

Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway. It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. 12-oxo LTB4 is an initial metabolite of LTB4 formed via the LTB4 12-hydroxydehydrogenase pathway. It is rapidly converted to 10,11-dihydro-12-oxo-LTB4, followed by reduction of the 12-oxo group to give 10,11-dihydro-LTB4. 12-oxo-LTB4 (EC50 = 33 nM) is about 70-fold less potent than LTB4 (EC50 = 0.46 nM) at stimulating Ca2+ mobilization in human neutrophils. It is also significantly less potent than LTB4 at stimulating neutrophil migration with EC50 values of 170 and 2.7 nM for 12-oxo-LTB4 and LTB4, respectively.

5,6-epoxy-13-cis Retinoic Acid is a metabolite of 13-cis retinoic acid.

6,19-Dihydroxyurs-12-en-3-oxo-28-oic acid is a natural product for research related to life sciences. The catalog number is TN3143 and the CAS number is 194027-11-7.

2α,3β,24-Trihydroxyurs-12-en-28-oic acid, a natural product, is isolated from Salvia palaestina [1].

Stevia impurity (13-[(2-O-6-deoxy-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester) is a natural product for research related to life sciences. The catalog number is TN6498 and the CAS number is 1309929-72-3.

7-Epi-10-oxo-docetaxel (Docetaxel Impurity 2) is an impurity of docetaxel detected by HPLC.

3-Hydroxy-12-oleanene-23,28-dioic acid is a natural product for research related to life sciences. The catalog number is TN2937 and the CAS number is 226562-47-6.

Docosapentaenoic acid (DPA) is a ω-3 fatty acid found in fish oils. 17-oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DPA that is produced endogenously by aspirin-enhanced COX-2 activity. It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 μM).

9(S),12(S),13(S)-TriHOME is a linoleic acid-derived oxylipin that has diverse biological activities.1,2,3,4It has been found in various plants and is produced in human eosinophils in a 15-lipoxygenase-dependent, soluble epoxide hydrolase-independent manner.1,59(S),12(S)13(S)-TriHOME inhibits antigen-induced β-hexosaminidase release from RBL-2H3 mast cells (IC50= 28.7 μg/ml).2It inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50= 40.95 μM).3In vivo, 9(S),12(S),13(S)-TriHOME (1 g/animal) enhances the antiviral IgA and IgG antibody responses induced by a nasal influenza hemagglutinin (HA) vaccine by 5.2- and 2-fold, respectively, in mice.4 1.Hamberg, M., and Hamberg, G.Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acidPlant Physiol.110(3)807-815(1996) 2.Hong, S.S., and Oh, J.S.Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat branJ. Korean Soc. Appl. Biol. Chem.5569-74(2012) 3.Kim, C.S., Kwon, O.W., Kim, S.Y., et al.Five new oxylipins from Chaenomeles sinensisLipids49(11)1151-1159(2014) 4.Shirahata, T., Sunazuka, T., Yoshida, K., et al.Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acidsTetrahedron62(40)9483-9496(2006) 5.Fuchs, D., Tang, X., Johnsson, A.-K., et al.Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent processBiochim. Biophys. Acta Mol. Cell Biol. Lipids1865(4)158611(2020)

12-Hydroxyganoderic acid D is a natural product

22-Hydroxy-3-oxo-12-ursen-30-oic acid is a natural product for research related to life sciences. The catalog number is TN2812 and the CAS number is 173991-81-6.

17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DHA that is produced endogenously by aspirin-enhanced COX-2 activity. It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 μM).

Lanosta-7,9(11),23,25(27)-tetraen-26-oic acid, 23,27-epoxy-3-oxo-, a lanosterane-type compound, can be isolated from Tu-Jin-Pi, the root bark of Pseudolarix kaempferi [1].

1-Decarboxy-3-oxo-ceanothic acid shows in vitro cytotoxic activity in a human ovarian adenocarcinoma cell line, the cytotoxic effect is mediated, at least in part, by the induction of apoptosis. It shows cytotoxic against OVCAR-3 and HeLa cancer cell line

Leukotriene B4 (LTB4) compounds are produced by both enzymatic and non-enzymatic processes. The products of enzymatic origin, via Leukotriene A4 (LTA4) hydrolase, are stereospecifically 12(R). Non-enzymatic hydrolysis products are 50:50 mixtures at C-12, but are almost exclusively trans at C-6. Thus, the non-enzymatic hydrolysis product of LTA4 is 6-trans-12-epi LTB4. 12-epi LTB4 is an isomer which would not be expected to occur in either non-enzymatic hydrolysis products, or in the enzymatic products of LTA4 hydrolase. Compared to LTB4, 12-epi LTB4 has significantly reduced activity for the LTB4 receptor on human neutrophils (IC50 of 7.5 mM), and on guinea pig lung membranes with a (Ki of 4.7 mM). 12-epi LTB4 is an weak agonist at both the recombinant human BLT1 and BLT2 receptors, requiring approximately 10 mM for full activation of the receptor.

2,3-Dihydroxy-olean-12-en-28-oic acids show a low cytotoxicity towards several human tumor cell lines.

9(Z),12(Z),15(Z),18(Z),21(Z)-Tetracosapentaenoic acid is an ω-3 very long-chain polyunsaturated fatty acid. It has been used to study the desaturation and elongation of ω-3 polyunsaturated fatty acids. It is elongated to form C26:5 or acted on by δ6 desaturase to form C24:6. 9(Z),12(Z),15(Z),18(Z),21(Z)-Tetracosapentaenoic acid is found at low levels in mouse brain and spleen and levels decrease in the brain and spleen of old and exceptionally old mice.

The compound is extracted from Croton tiglium dried fruit.

11β,13-Dihydrotaraxinic acid β-D-glucopyranosyl ester is a natural product for research related to life sciences. The catalog number is TN6271 and the CAS number is 75911-16-9.

13-Hydroxy-8,11,13-podocarpatrien-18-oic acid is a natural product for research related to life sciences. The catalog number is TN2612 and the CAS number is 61597-83-9.

9(E),11(E),13(E)-Octadecatrienoic acid (β-ESA) is a conjugated polyunsaturated fatty acid that is found in plant seed oils and in mixtures of conjugated linolenic acids synthesized by the alkaline isomerization of linolenic acid. It reduces growth of Caco-2 colon cancer cells in a dose-dependent and time-dependent manner. In vitro, β-ESA induces DNA fragmentation and upregulation of pro-apoptotic Bax mRNA. β-ESA decreases protein expression of the apoptosis suppression factor Bcl-2 and induces apoptosis in T24 bladder cancer cells via production of reactive oxygen species. It also inhibits bacterial fatty acid dioxygenase with a Ki value of 49 nM in vitro.

2β,3β,23α-Trihydroxy-12-oleanen-28-oic acid shows cytotoxic activities to human lung adenocarcinoma(A-549)cell lines. 2α,3β,23-Trihydroxyolean-12-en-28-oic acid and 2α,3β,23-trihydroxyurs-12-en-28-oic acid exhibit cytotoxicity in vitro against the growth of human cancer cells lines HepG-2,with IC50 values of 16.13 ± 3.83, 15.97 ± 2.47 uM, respectively.

12-Oxograndiflorenic acid is a natural product that can be extracted from Anemone and Porphyra and is cytotoxic to some cells.

2alpha,19alpha-Dihydroxy-3-oxo-urs-12-en-28-oic acid has anti-HIV activity. It shows an inhibitory effect on the activation of Epstein-Barr virus early antigen (EBV-EA) induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and causes a significant delay o

3-Oxo-7-hydroxychol-4-enoic acid, an endogenous metabolite, is potentially a significant prognostic marker for adverse outcomes in hepatobiliary disease [1].

9(Z),11(E),13(E)-Octadecatrienoic Acid (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ. In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 μM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 μM for different isoforms of the enzymes.

13-methyl Myristic acid methyl ester is a methylated bacterial fatty acid methyl ester. It has been used as a marker of bacteria in sewage sludges and of bacterial contaminants in pharmaceutical manufacturing by GC-MS.

3,5-Dicaffeoyl-epi-quinic acid shows anti-inflammatory activity, it may improve mast cell-mediated inflammatory diseases.

2α,3α,24-Trihydroxyolean-12-en-28-oic acid, a triterpenoid phytoalexin, isolated from peel of unripe fruits of nectarine (Prunus persica cv Fantasia), shows antifungal activity against the fungus mentioned.

13-Oxo-ODE is an octadecadienoic acid isolated from moxa and Artemisia argyi leaves [1].

12-Chlorodehydroabietic acid is a chlorinated resin acid.

9(E),11(E)-12-nitro Conjugated linoleic acid (9(E),11(E)-12-nitro CLA) is a nitrated fatty acid. It is formed from 9(Z),11(E)-CLA upon exposure to acidified nitrite, peroxynitrite, gaseous nitrogen dioxide, or a combination of myeloperoxidase, hydrogen peroxide, and nitrite.1It is also formed in LPS-stimulated RAW 264.7 macrophages, an effect that can be reduced by the nitric oxide synthase (NOS) inhibitor L-NAME .29(E),11(E)-12-nitro CLA has been found in human plasma. 1.Woodcock, S.R., Salvatore, S.R., Bonacci, G., et al.Biomimetic nitration of conjugated linoleic acid: Formation and characterization of naturally occurring conjugated nitrodienesJ. Org. Chem.79(1)25-33(2014) 2.Bonacci, G., Baker, P.R.S., Salvatore, S.R., et al.Conjugated linoleic acid is a preferential substrate for fatty acid nitrationJ. Biol. Chem.287(53)44071-44082(2012)

ent-6,11-Dihydroxy-15-oxo-16-kauren-19-oic acid beta-D-glucopyranosyl ester is a natural product for research related to life sciences. The catalog number is TN3951 and the CAS number is 81263-97-0.

12-oxo-13-HOME is an oxylipin derived from linoleic acid .1It is formedviaa 13-HpODE intermediate that is produced by lipoxygenase-mediated metabolism of linoleic acid.2,3,112-oxo-13-HOME has been found in corn and sunflower seedlings.4 1.Ogorodnikova, A.V., Gorina, S.S., Mukhtarova, L.S., et al.Stereospecific biosynthesis of (9S,13S)-10-oxo-phytoenoic acid in young maize rootsBiochim. Biophys. Acta1851(9)1262-1270(2015) 2.Veldink, G.A., and Vliegenthart, J.F.G.The enzymic conversions of 13-hydroperoxy-cis-9-trans-11-octadecadienoic acid into 13-hydroxy-12-oxo-cis-9-octadecenoic acidBiochem. J.110(4)58P(1968) 3.Gardner, H.W.Sequential enzymes of linoleic acid oxidation in corn germ: Lipoxygenase and linoleate hydroperoxide isomeraseJ. Lipid Res.11(4)311-321(1970) 4.Vick, B.A., and Zimmerman, D.C.Levels of oxygenated fatty acids in young corn and sunflower plantsPlant Physiol.69(5)1103-1108(1982)

3,22-Dihydroxyolean-12-en-29-oic acid is a natural product for research related to life sciences. The catalog number is TN2860 and the CAS number is 808769-54-2.

13-Oxopodocarp-8(14)-en-18-oic acid is a natural product for research related to life sciences. The catalog number is TN2619 and the CAS number is 63976-69-2.

12-Doxyl stearic acid, a derivative of stearic acid featuring a 4,4-dimethyl-3-oxazolinyloxy (DOXYL) group, functions as a hydrophobic spin label. This compound is prevalently utilized in research to investigate the molecular characteristics of membranes and hydrophobic proteins.

12-Bromododecanoic acid, a halogenated derivative of lauric acid, serves in the synthesis of clickable myristic acid derivatives and functions as a model fatty acid ligand for elucidating the X-ray crystal structure of bovine β-lactoglobulin-ligand complexes. This compound, at a concentration of 10 µg/ml, has been shown to diminish virion DNA in the culture supernatant of primary hepatocytes from a duckling model of hepatitis B virus (HBV) infection and exhibits inhibitory activity against HIV replication in CEM-SS T cells with an EC50 value of 38 µM.