This product is isolated and purified from the herbs of Myrica rubra
α-Hydroxy-o-cresol/2-Hydroxymethylphenol/salicyl alcohol/a,2-Dihydroxytoluene/Benzenemethanol, 2-hydroxy-/2-Hydroxybenzenemethanol/2-(Hydroxymethyl)phenol/2-Hydroxybenzyl alcohol/α,2-Dihydroxytoluene/O-HYDROXYBENZYL ALCOHOL/2-Hydroxybenzylalcohol/a-Hydroxy-o-cresol/salicylic alcohol/1-(o-Hydroxyphenyl)methanol
Comparative evaluation of gastroulcerogenic potential of nitrogen isoforms of salicyl alcohol and aspirin in rats: biochemical and histological study.[Pubmed: 24085627]Arch Pharm Res. 2014 Jul;37(7):916-26. The aim of the current study was to explore in vivo any relative gastroulcerogenic prospective propensity of newly synthesized nitrogen containing derivatives of Salicyl alcohol; compound (I) [1-(2-hydroxybenzyl)piperidinium chloride], compound (II) [4-carbamoyl-1-(2-hydroxybenzyl)piperidinium chloride] and aspirin in albino rats. METHODS AND RESULTS: The experimental groups received the following oral treatments daily for 6 days: group I saline control; group II, standard (aspirin) treatment group [150 mg/kg of body weight]; group III, test (compound I) treatment group [100, 150 mg/kg]; group IV, test (compound II) treatment group [100, 150 mg/kg]. The results showed that in the case of the aspirin treated group and compound (I) [150 mg/kg], there was a significant increase in gastric volume, free acidity, total acidity, ulcer score and a decrease in gastric pH. Furthermore, histopathological examination of gastric mucosa of these treated groups revealed detectable morphological changes. Utilizing the same protocol, synthetic compound (I) [100 mg/kg] and (II) [100, 150 mg/kg] exhibited no statistically significant ulcerogenic or cytotoxic properties. A cyclooxygenase (COX) selectivity test indicated the preferential inhibition of COX-I and COX-II enzymes by compounds (I) and (II). CONCLUSIONS:This study therefore indicates that these synthetic compounds may possess reduced ulcerogenic potential and could be a functional substitute to aspirin.
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Willow bark (Salicis cortex) is a herbal medicinal drug used to treat fever and pain, such as headaches and lower back pain. Until now, it has not been fully understood which compounds are responsible for the efficacy of the drug.
Although salicylic acid is known as a metabolite of salicylic alcohol derivatives of willow bark in vivo, it has been shown in previous studies that its concentration is too low to account for the overall efficacy of Salicis cortex. The aim this study was to broaden the knowledge regarding phenolic phase-II metabolites after oral intake of a willow bark extract.
Serum samples of a human pharmacokinetic study (Salicis cortex extract intake corresponding to 240 mg of total salicin, 10 volunteers, 12 h fasting time, controlled diet low in phenolics, and 12 blood withdrawals over a period of 24 h) were analyzed by LC-ESI-MS. A library of 142 possible metabolites associated with salicylic alcohol derivatives, flavonoids, and proanthocyanidins was used to characterize possible metabolization products. Their structures were confirmed by LC-ESI-MS experiments with reference compounds after a cleavage reaction using glucuronidase and sulfatase as well as by LC-MS/MS experiments.
In the serum samples, phase-II metabolites of naringenin (2x glucuronides, 2x sulfates, 2x mixed glucuronide-sulfates), eriodictyol (3x glucuronides, 1x sulfate), taxifolin (1x sulfate), catechin (1x sulfate, 1x mixed glucuronide sulfate), ferulic acid (1x sulfate), hydroxyphenyl-propionic acid (1x sulfate), dihydroxyphenyl-valerolactone (1x sulfate), saligenin (1x glucuronide, 1x sulfate), salicylic acid (1x sulfate, 1x unconjugated, 1x salicyluric acid), and catechol (1x glucuronide, 1x sulfate) were characterized. Because taxifolin, dihydroxyphenyl-valerolactone, ferulic acid, and hydroxyphenyl-propionic acid could not be detected in the willow bark preparation, they could be metabolization products of genuine flavanones and flavan-3-ols as well as coumaric acid or C-ring cleavage products of flavonoids, which were present in the extract. No phase-II metabolites of procyanidins and no genuine flavonoid glycosides were detected in all serum samples.
This is the first study to identify human metabolites of flavonoids, proanthocyanidins and salicylic alcohol derivatives of Salicis cortex beside salicylic acid or catechol. For the most characterized metabolites, anti-inflammatory activity has been described in the literature, and the present results are an important step in understanding the anti-inflammatory efficacy of willow bark in vivo.
Copyright © 2018 Elsevier GmbH. All rights reserved.
Flavonoids; Metabolization; Phase-II metabolites; Salicis cortex; Serum samples; Willow bark
Identification of phase-II metabolites from human serum samples after oral intake of a willow bark extract.
Untergehrer M1, Kiermaier J2, Reintjes S1, Heilmann J1, Jurgenliemk G3.
Inulavosin, a natural melanogenesis inhibitor, has been synthesized smoothly from readily available and inexpensive starting materials by using a Ga(OTf)3-catalyzed room temperature hetero Diels-Alder dimerization of salicyl alcohol derivative and a regioselective phenol monobromination as the key steps.
Diels-Alder reaction; Ga(OTf)3; Natural product; inulavosin; synthesis
Synthesis of natural product inulavosin via Ga(OTf)3-Catalyzed Hetero Diels-Alder Dimerization of salicyl alcohol derivative.
Gong PX1, Li HJ1, Wang M2, Cheng YF1, Wu YC1,3.
Salicyl alcohol and gentisyl alcohol are two important phenolic alcohols that possess significant biological activities and pharmaceutical properties. Here, we report establishment of novel biosynthetic pathways for microbial production of salicyl alcohol and gentisyl alcohol from renewable feedstocks. We first examined the promiscuity of the carboxylic acid reductase CAR toward salicylic acid and 2,5-DHBA, which enabled efficient synthesis of salicyl alcohol and gentisyl alcohol. Then, we employed a novel salicylic acid 5-hydroxylase to achieve 2,5-DHBA production from salicylic acid. After that, the de novo biosynthetic pathways were assembled and optimized by programming the carbon flux into the shikimate pathway. The final titers of salicyl alcohol and gentisyl alcohol reached to 594.4 mg/L and 30.1 mg/L, respectively. To our knowledge, this work achieved microbial production of salicyl alcohol and gentisyl alcohol for the first time. Our present study also demonstrated application of enzyme promiscuity to establish non-natural biosynthetic pathways for the production of high-value compounds.
gentisyl alcohol; metabolic engineering; salicyl alcohol; shikimate pathway
Establishment of Novel Biosynthetic Pathways for the Production of Salicyl Alcohol and Gentisyl Alcohol in Engineered Escherichia coli.
Shen X1,2, Wang J1,2, Gall BK3, Ferreira EM3, Yuan Q1,2, Yan Y4.
2018 Apr 20