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Cholesterol sulfate, or cholest-5-en-3beta-ol sulfate, is an endogenous steroid and the C3beta sulfate ester of cholesterol. It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase) and is converted back into cholesterol by steroid sulfatase (STS). Accumulation of cholesterol sulfate in the skin is implicated in the pathophysiology of X-linked ichthyosis, a congenital disorder in which STS is non-functional and the body cannot convert cholesterol sulfate back into cholesterol. Cholesterol sulfate is quantitatively the most important known sterol sulfate in human plasma, where it is present in a concentration that overlaps that of the other abundant circulating steroid sulfate, dehydroepiandrosterone (DHEA) sulfate (PMID 12730293). Cholesterol sulfate has a stabilizing function on the membrane, supports platelet adhesion and is involved in signal transduction (PMID 12730293). It plays a role in protecting erythrocytes from osmotic lysis and regulating sperm capacitation. Cholesterol sulfate can regulate the activity of serine proteases, e.g., those involved in blood clotting, fibrinolysis, and epidermal cell adhesion (PMID 12730293). As a result of its ability to regulate the activity of selective protein kinase C isoforms and modulate the specificity of phosphatidylinositol 3-kinase, cholesterol sulfate is involved in signal transduction (PMID 12730293). Cholesterol sulfate functions in keratinocyte differentiation, inducing genes that encode for key components involved in development of the barrier (PMID 12730293).

3,5,5-Trimethyl-2-cyclohexen-1-one is found in fruits. 3,5,5-Trimethyl-2-cyclohexen-1-one is a flavouring ingredient. 3,5,5-Trimethyl-2-cyclohexen-1-one is present in cranberries (Vaccinium microcarpa) and saffron (Crocus sativus

12-Hydroxyeicosatetraenoic acid (CAS: 71030-37-0), also known as 12-HETE, is an eicosanoid, a 5-lipoxygenase metabolite of arachidonic acid. 5-Lipoxygenase (LO)-derived leukotrienes are involved in inflammatory glomerular injury. LO product 12-HETE is associated with the pathogenesis of hypertension and may mediate angiotensin II and TGFbeta induced mesangial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contributes to high blood pressure in (renovascular) hypertension and pregnancy-induced hypertension. A significant percentage of patients suffering from a selective increase in plasma LDL cholesterol (type IIa hyperlipoproteinemia) exhibits increased platelet reactivity. This includes enhanced platelet responsiveness against a variety of platelet-stimulating agents ex vivo and enhanced arachidonic acid metabolism associated with increased generation of arachidonic acid metabolites such as 12-HETE, and secretion of platelet-storage products (PMID: 7562532, 12480795, 17361113, 8498970, 1333255, 2119633). 12-HETE is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumour cell metastatic potential through activation of protein kinase C. 12-HETE has a diversity of biological actions and is generated by a number of tissues including the renal glomerulus and the vasculature. 12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. 12-HETE is a neuromodulator that is synthesized during ischemia. Its neuronal effects include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation. 12-HETE is found to be associated with peroxisomal biogenesis defect and Zellweger syndrome, which are inborn errors of metabolism.

Prunin

Sphingomyelin (d18:1/14:0) or SM(d18:1/14:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(d18:1/14:0) consists of a sphingosine backbone and a myristic acid chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition, it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2, an enzyme that breaks down sphingomyelin into ceramide, has been found to localize exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme sphingomyelinase, which causes the accumulation of sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase.

8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593, 9113987).

LysoPC(18:1(11Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position. The vaccenic acid moiety is derived from butter fat and animal fat. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.

15-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12-, and 15-lipoxygenase (LO) pathways. The 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro, 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation, and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE also has some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells (PMID: 11104340). 15(S)-HETE is found to be associated with Zellweger syndrome, which is an inborn error of metabolism.

12R-HETE

15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is also known as 15R-HETE. 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is an eicosanoid lipid molecule

20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor of renal, cerebral, and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase, and the mitogen-activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal, and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries. A fall in levels of 20-HETE contributes to the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries (PMID: 16258232).

4-hydroxynon-2-enal is an enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position. It has a role as a human metabolite. It is a hydroxyaldehyde, an enal and a 4-hydroxynonenal. 4-Hydroxynonenal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. 4-Hydroxynonenal (HNE), one of the major end products of lipid peroxidation, has been shown to be involved in signal transduction and available evidence suggests that it can affect cell cycle events in a concentration-dependent manner. glutathione S-transferases (GSTs) can modulate the intracellular concentrations of HNE by affecting its generation during lipid peroxidation by reducing hydroperoxides and also by converting it into a glutathione conjugate. Overexpression of the Alpha class GSTs in cells leads to lower steady-state levels of HNE, and these cells acquire resistance to apoptosis induced by lipid peroxidation-causing agents such as H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics, suggesting that signaling for apoptosis by these agents is transduced through HNE. Cells with the capacity to exclude HNE from the intracellular environment at a faster rate are relatively more resistant to apoptosis caused by H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics as well as by HNE, suggesting that HNE may be a common denominator in mechanisms of apoptosis caused by oxidative stress. Transfection of adherent cells with HNE-metabolizing GSTs leads to transformation of these cells due to depletion of HNE. (A3295).

2-Deoxycastasterone, also known as typhasterol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols, and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, 2-deoxycastasterone is considered to be a sterol lipid molecule. 2-Deoxycastasterone is found in cereals and cereal products. 2-Deoxycastasterone is a constituent of green tea (Thea sinensis) and wheat grains (Triticum aestivum).

Floribundoside is found in fruits. Floribundoside occurs in Persica vulgaris (peach).

Ursodeoxycholic acid, also known as ursodeoxycholate or acid deoxyursocholic, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Ursodeoxycholic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

12-keto-eicosatetraenoic acid is a biologically active eicosanoid in the nervous system of Aplysia.It is a metabolite of 12-HPETE formed by Aplysia nervous tissue. 12-KETE was identified in incubations of the tissue with arachidonic acid using HPLC, UV spectrometry, and gas-chromatography/mass spectrometry. [3H]12-KETE is formed from endogenous lipid stores in nervous tissue, labeled with [3H]arachidonic acid upon stimulation by application of histamine. In L14 and L10 cells, identified neurons in the abdominal ganglion, applications of 12-KETE elicit changes in membrane potential similar to those evoked by histamine.[PMID:2774398].

(2E,6E)-2,6-Nonadienal is found in animal foods. (2E,6E)-2,6-Nonadienal occurs in beef and mutton tallows and is formed during deep frying of fat. Also present in lingonberry, cowberry, mango, cucumber, cornmint oil, raw lean fish, cooked trassi and cooked shrimp. (2E,6E)-2,6-Nonadienal is a flavouring agent

Violet-leaf aldehyde is found in cereals and cereal products. Violet-leaf aldehyde is a constituent of cherry, melon, peas, cooked potato, wheat bread, other breads, milk, lean and fatty fish, black tea, oyster, clam and other foods. Primary odourant in cucumbers. Violet-leaf aldehyde is present in cucumber juice. Violet-leaf aldehyde is a flavouring agent.

Tetradecanedioic acid, also known as 1,14-tetradecanedioate or NSC 9504, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Tetradecanedioic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

N1,N10-Dicoumaroylspermidine is found in fats and oils. N1,N10-Dicoumaroylspermidine is an alkaloid from Helianthus annuus (sunflower) Vicia faba and Pyrus communis (pear).

19(S)-HETE is an intermediate in Arachidonic acid metabolism. 19(S)-HETE is converted from Arachidonic acid via the enzyme CYP2U and Unspecific. Monooxygenase. (EC:1.14.14.1).

4-Hydroxynonenal (HNE), one of the major end products of lipid peroxidation, has been shown to be involved in signal transduction and available evidence suggests that it can affect cell cycle events in a concentration-dependent manner. glutathione S-transferases (GSTs) can modulate the intracellular concentrations of HNE by affecting its generation during lipid peroxidation by reducing hydroperoxides and also by converting it into a glutathione conjugate. Overexpression of the Alpha class GSTs in cells leads to lower steady-state levels of HNE, and these cells acquire resistance to apoptosis induced by lipid peroxidation-causing agents such as H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics, suggesting that signaling for apoptosis by these agents is transduced through HNE. Cells with the capacity to exclude HNE from the intracellular environment at a faster rate are relatively more resistant to apoptosis caused by H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics as well as by HNE, suggesting that HNE may be a common denominator in mechanisms of apoptosis caused by oxidative stress. Transfection of adherent cells with HNE-metabolizing GSTs leads to transformation of these cells due to depletion of HNE. (PMID 15288119). HNE has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821).

4-HDoHE is an endogenous oxidized unsaturated fatty acids. Human and mouse plasma samples also catalyzed 4-HDoHE lactonization and 5-HETE lactone hydrolysis. (PMID: 12963475) 4-HDoHE is a hydroxydocosahexaenoic acid that consists of 5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid bearing an additional 4-hydroxy substituent. (CHEBI:72624)

7-HDoHE is an autoxidation product of docosahexaenoic acid DHA. 7-HDoHE is a long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism. (CHEBI:72790)

Beta-pinone, also known as B-pinone, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Beta-pinone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-pinone can be found in pepper (spice), which makes beta-pinone a potential biomarker for the consumption of this food product.

A trihydroxyflavanone in which the three hydroxy substituents are located at positions 3, 5 and 7." []