The 95% ethanol extract of Baphicacanthis Cusiae Rhizoma et Radix was purified by multi-chromatographic methods including microporous resin, silica gel, Sephadex LH-20, and C_(18) reversed-phase column chromatography. Fourteen compounds were isolated and structurally identified, including five phenylethanoid glycosides, five phenylpropanoids, one lupinane triterpene, two alkaloids, and one flavonoid, listed as follows: 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol B(1), threo-2,3-bis-(4-hydroxy-3-methoxybenzene)-3-methoxypropanol(2), 2-(3-hydroxy-4-methoxyphenyl)-ethanol-1-O-[3,4-O-di-acetyl-(1→3)-O-α-L-rhamnopyranosyl]-β-D-glucopyranoside(3), verbascoside(4), 2″,3″-di-O-acetyl martynoside(5),(+)-pinore-sinol(6), diospyrosin(7), daidzein(8), wiedemannioside B(9), buddlenol A(10), 2″-O-acetyl martyonside(11), lupeol(12), indirubin(13), and tryptanthrin(14). Compound 3 was a new phenylethanoid glycoside, and the other 10 compounds were isolated for the first time from Baphicacanthis Cusiae Rhizoma et Radix except compounds 12, 13, and 14.
Cardiac Glycosides ; Flavonoids ; Glycosides ; Molecular Structure ; Phenylethyl Alcohol ; Rhizome

OBJECTIVETo study the chemical constituents of the corm of the planted Cremastra appendiculata.

METHODThe compounds were isolated by column chromatography with silica gel and Sephadex LH-20, and their structures were elucidated by means of spectroscopic methods including 2D NMR techniques.

RESULTSix compounds were isolated, and identified as isohircinol (I), flavanthrinin (II), p-hydroxyphenylethyl alcohol (III), 3,4-dihydroxyphenylethyl alcohol (IV), daucosterol (V), beta-sitosterol (VI).

CONCLUSIONThese compounds were not previously isolated from this plant, and isohircinol (I) was obtained from natural source for the first time.

Orchidaceae ; chemistry ; Phenylethyl Alcohol ; analogs & derivatives ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Sitosterols ; chemistry ; isolation & purification

2-Phenylethanol (2-PE) is an aromatic alcohol with a pleasant rose-like fragrance. It has been widely used in food, cosmetic, and pharmaceutical industry. Most of 2-PE is produced by chemical synthesis, but the use of chemically synthesized product is restricted in some fields. 2-PE from plant extraction is natural but its production is very low. Microbial biotransformation is a promising process to produce natural 2-PE. In this paper, we review recent research progress in the synthetic metabolic pathways and regulatory processes of 2-PE in yeast, and strategies for improving 2-PE production. Moreover, we discuss the limitation of current progress and future research directions.
Biotransformation ; Industrial Microbiology ; Metabolic Networks and Pathways ; Phenylethyl Alcohol ; metabolism ; Saccharomyces cerevisiae ; metabolism

To investigate the role of distribution and phylogeny of phenylethanoid glycoside in medicinal plants of Gesneriaceae, five phenylpropanoid glycosides, acteoside, paraboside B, isonuomioside A, paraboside II, and paraboside III were quantitatively determined in 12 species of Gesneriaceae by HPLC. The existence and content of these compounds were analyzed. The results showed that phenylethanoid glycosides were found in the most of those plants, but the kind of phenylethanoid glycosides varied in different species. Acteoside distribute in most of this plant group, paraboside B, isonuomioside A, paraboside II, and paraboside III were rare in those plants. The results of this study support morphological viewpoint that Trib. Trichosporeae is more developmental than Trib. Didymocarpeae.
Glucosides ; chemistry ; metabolism ; Magnoliopsida ; metabolism ; Phenylethyl Alcohol ; chemistry ; Plants, Medicinal ; metabolism

BACKGROUND: We investigated whether culture using an automated blood culture system enhances the recovery of bacteria and fungi from body fluids other than blood when compared to conventional solid media culture methods. METHODS: A total of 734 specimens [ascites (n=457), bile (n=5), CAPD (n=28), CSF (n=32), joint fluids (n=165), pericardial fluid (n=17), and pleural fluid (n=30)] were included in the study. Half of the volume of each specimen was inoculated directly into automated blood culture bottles (bioMeriux, Marcy-I'Etoile, France). The remaining volume was inoculated onto conventional solid media (sheep blood agar, chocolate agar, and phenylethyl alcohol agar) after centrifuging at 3,000 rpm for 10 min. RESULTS: Clinically significant microorganisms were isolated from 62 specimens (8.5%) by automated blood culture and 61 specimens (8.3%) by the conventional solid media culture (kappa index: 0.81, 95% confidence interval: 0.75~0.89). Contamination was observed in 11 (1.8%) of the automated blood culture specimens and 3 (0.4%) of the solid media culture specimens. The mean turnaround times of the automated blood cultures and the conventional solid media cultures were 3.7 and 2.8 days, respectively (P<0.0001). CONCLUSION: Compared with conventional culture methods, no improvement in the recovery of clinically significant microorganisms was noted with the use of the automated blood culture system for the culture of body fluids other than blood.
Agar ; Bacteria ; Bile ; Body Fluids ; Cacao ; Fungi ; Joints ; Peritoneal Dialysis, Continuous Ambulatory ; Phenylethyl Alcohol

Hydroxytyrosol is an important fine chemical and is widely used in food and medicine as a natural antioxidant. Production of hydroxytyrosol through synthetic biology is of important significance. Here we cloned and functionally characterized a hydroxylase encoding gene HpaBC from Escherichia coli BL21, and both subunits of this enzyme can be successfully expressed to convert the tyrosol into hydroxytyrosol. A HpaBC gene integration expression cassette under the tac promoter was constructed, and integrated into the genome of a tyrosol hyper-producing E. coli YMG5A*R using CRISPR-Cas9 technology. Meanwhile, the pathway for production of acetic acid was deleted, resulting in a recombinant strain YMGRD1H1. Shake flask fermentation showed that strain YMGRD1H1 can directly use glucose to produce hydroxytyrosol, reaching a titer of 1.81 g/L, and nearly no by-products were detected. A titer of 2.95 g/L was achieved in a fed-batch fermentation conducted in a 5 L fermenter, which is the highest titer for the de novo synthesis of hydroxytyrosol from glucose reported to date. Production of hydroxytyrosol by engineered E. coli lays a foundation for further construction of hydroxytyrosol cell factories with industrial application potential, adding another example for microbial manufacturing of aromatic compounds.
Escherichia coli/genetics* ; Fermentation ; Glucose ; Metabolic Engineering ; Phenylethyl Alcohol/analogs & derivatives*

Salidroside, the 8-O-beta-D-glucoside of tyrosol, is a novel adaptogenic drug extracted from the medicinal plant Rhodiola sachalinensis A. Bor. Due to the scarcity of R. sachalinensis and its low yield of salidroside, there is great interest in enhancing the production of salidroside by biotechnological process. Glucosylation of tyrosol is thought to be the final step in salidroside biosynthesis. In our related works, three UGT clones were isolated from the roots and the cultured cells. Our intention was to combine the catalytic specificity of these UGTs in vitro in order to change the level of salidroside in vivo by over-expression of the above UGTs. However, as the aglycone substrate of salidroside, the biosynthetic pathway of tyrosol and its regulation are less well understood. The results of related studies revealed that there are two different possibilities for the tyrosol biosynthetic pathway. One possibility is that tyrosol is produced from a p-coumaric acid precursor, which is derived mainly from phenylalanine. The second possibility is that the precursor of tyrosol might be tyramine, which is synthesized from tyrosine. Our previous work demonstrated that over-expression of the endogenous phenylalanine ammonia-lyase gene (PALrs1) and accumulation of p-coumaric acid did not facilitate tyrosol biosynthesis. In contrast, the data presented in our recent work provide in vitro and in vivo evidence that the tyrosine decarboxylase (RsTyrDC) is most likely to have an important function in the initial reaction of the salidroside biosynthesis pathway in R. Sachalinensis.
Genetic Engineering ; Glucosides ; biosynthesis ; Glycosylation ; Phenols ; Phenylethyl Alcohol ; analogs & derivatives ; chemistry ; metabolism ; Rhodiola ; metabolism ; Tyrosine ; metabolism ; Tyrosine Decarboxylase ; metabolism

(R)-chlorprenaline, a selective activator of beta2 receptor and an effective drug for bronchitis and asthma, is industrially prepared from (R)-2'-chloro-1-phenyl-ethanol. In this communication, we describe (1) the identification of Saccharomyces cerevisiae B5 as an effective host for stereoselective reduction of 2'-chloroacetophenone to (R)-2'-chloro-1-phenyl-ethanol; (2) the presence of ethanol enhances the conversion; and (3) the biochemical factors that effect the yield of the product. Among the four yeast strains capable of reduction 2'-chloroacetophenone to (R)-2'-chloro-1-phenyl-ethanol we screened, Saccharomyces cerevisiae B5 showed the highest activity and stereoselectivity, and was used for the subsequent study. The effect of the presence of methanol, ethanol, 2-propanol, 1-butanol, glucose, glycerol and lactic acid was first investigated, as it was previously reported that they increased the yield and stereoselectivity of the reaction. The addition of the co-substrate methanol, ethanol, 2-propanol, 1-butanol, glucose and glycerol favored the formation of the 2'-chloroacetophenone to (R)-2'-chloro-1-phenyl-ethanol. Lactic acid inhibited the enzyme activity. Ethanol is the best co-substrate among the seven co-substrates and under the optimum concentration of 5% , the yield of (R)-2'-chloro-1-phenyl-ethanol was increased from 17% to 74%. The oxidation of ethanol regenerates NADH required for the reduction. The effects of the reaction time, pH, cell concentration, substrate concentration and temperature on the reduction were investigated next. The enantiometric excess of (R)-2'-chloro-1-phenyl-ethanol reached 100% under the optimal condition: pH8.0, 25 degrees C and 5% ethanol. The product yield went up with the increasing Saccharomyces cerevisiae B5 concentration and reached 100% when the cell dry weight was 10.75 mg/mL and 2'-chloroacetophenone was 6.47 mmol/L. The yield of (R)-2'-chloro-1-phenyl-ethanol decreased sharply with the increase of substrate concentration, as the high concentration of substrates is toxic to the cell and inhibits the activity of reductases. The aerobic cultivation of the yeast and shaking during the reaction increased the yield of (R)-2'-chloro-1-phenyl-ethanol. The yeast can be reused up to 15 times. This research paves the way for economical preparation of chiral 2'-chloroacetophenone to R-2'-chloro-1-phenylethanol.
Ethanol ; metabolism ; Hydrogen-Ion Concentration ; Oxidation-Reduction ; Phenylethyl Alcohol ; chemistry ; metabolism ; Saccharomyces cerevisiae ; metabolism ; Stereoisomerism ; omega-Chloroacetophenone ; chemistry ; metabolism

Tyrosol, a phenylethanoid and a derivative of phenethyl alcohol, possesses various biological properties, such as anti-oxidative and cardioprotective activity. Olive oil is the principal source of tyrosol in the human diet. However, so far the anti-cancer activity of tyrosol has not yet been well defined. This study therefore undertakes to examine the cytotoxic activity and the mechanism of cell death exhibited by tyrosol in KB human oral cancer cells. Treatment of KB cells with tyrosol induced the cell growth inhibition in a concentration- and a time-dependent manner. Furthermore, the treatment of tyrosol induced nuclear condensation and fragmentation of KB cells. Tyrosol also promoted proteolytic cleavage of procaspase-3, -7, -8 and -9, increasing the amounts of cleaved caspase-3, -7, -8 and -9. In addition, tyrosol increased the levels of cleaved PARP in KB cells. These results suggest that tyrosol induces the suppression of cell growth and cell apoptosis in KB human oral cancer cells, and is therefore a potential candidate for anti-cancer drug discovery.
Apoptosis ; Caspase 3 ; Cell Death ; Diet ; Drug Discovery ; Humans* ; KB Cells ; Mouth Neoplasms* ; Olive Oil ; Phenylethyl Alcohol

The present study investigated the influence of the methyl jasmonate and salicylic acid elicitors on the formation of phenylethanoid glycosides (PeG) in the suspension cultures of Cistanche deserticola. The results showed that methyl jasmonate and salicylic acid enhanced greatly the accumulation of PeG and echinacoside (Echin), but their optimum elicitation dosage and addition time were different. The yields of PeG and Echin were significantly increased in the presence of 5 micromol/L methyl jasmonate on day 14 (up to 2.59-fold and 3.82-fold, respectively), whereas treated with 50 micromol/L salicylic acid on day 28, the maximum content of them were, respectively, 2.71 and 3.16-fold higher than the untreated cell cultures.
Acetates ; pharmacology ; Cell Culture Techniques ; Cistanche ; drug effects ; metabolism ; Culture Media ; Cyclopentanes ; pharmacology ; Glycosides ; biosynthesis ; Oxylipins ; pharmacology ; Phenylethyl Alcohol ; metabolism ; Salicylic Acid ; pharmacology