NCBI Taxonomy: 469774

Rhinanthus angustifolius (ncbi_taxid: 469774)

found 40 associated metabolites at species taxonomy rank level.

Child Taxonomies: none taxonomy data.

Aucubin

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C15H22O9 (346.1263762)

Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety. Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis. The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1 Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1. Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

Tyrosol

4-hydroxy-Benzeneethanol;4-Hydroxyphenylethanol;beta-(4-Hydroxyphenyl)ethanol

C8H10O2 (138.06807600000002)

Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285). 2-(4-hydroxyphenyl)ethanol is a phenol substituted at position 4 by a 2-hydroxyethyl group. It has a role as an anti-arrhythmia drug, an antioxidant, a cardiovascular drug, a protective agent, a fungal metabolite, a geroprotector and a plant metabolite. It is functionally related to a 2-phenylethanol. 2-(4-Hydroxyphenyl)ethanol is a natural product found in Thalictrum petaloideum, Casearia sylvestris, and other organisms with data available. Tyrosol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Sedum roseum root (part of); Rhodiola crenulata root (part of). D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents A phenol substituted at position 4 by a 2-hydroxyethyl group. D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

Aucubin

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C15H22O9 (346.1263762)

Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Origin: Plant; SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids; Origin: Plant Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

Tyrosol

InChI=1\C8H10O2\c9-6-5-7-1-3-8(10)4-2-7\h1-4,9-10H,5-6H

C8H10O2 (138.06807600000002)

Tyrosol, also known as 4-hydroxyphenylethanol or 4-(2-hydroxyethyl)phenol, is a member of the class of compounds known as tyrosols. Tyrosols are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. Tyrosol is soluble (in water) and a very weakly acidic compound (based on its pKa). Tyrosol can be synthesized from 2-phenylethanol. Tyrosol is also a parent compound for other transformation products, including but not limited to, hydroxytyrosol, crosatoside B, and oleocanthal. Tyrosol is a mild, sweet, and floral tasting compound and can be found in a number of food items such as breadnut tree seed, sparkleberry, loquat, and savoy cabbage, which makes tyrosol a potential biomarker for the consumption of these food products. Tyrosol can be found primarily in feces and urine, as well as in human prostate tissue. Tyrosol exists in all eukaryotes, ranging from yeast to humans. Tyrosol present in wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosols SIRT1, Akt and eNOS activating power adds another dimension to the wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart . D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].