Amygdalin is known as vitamain B17, and it was called laetrile. Amygdalin is composed of two molecules of glucose, one molecule of benzaldehyde which induces an analgesic action, and one molecule of hydrocyanic acid which is an anti-neoplastic compound. Amygdalin had been used to treat cancers and relieve pain. In order to evaluate whether the analgesic action of amygdalin is related with descending pain control system, we performed patch clamp study. In the present study, the modulatory effects of amygdalin on glycine- and glutamate-induced ion currents in periaqueductal gray (PAG) neurons were investigated using the nystatin-perforated patch clamp method. Continuous application of lipopolysaccharides (LPS) on PAG neurons resulted in increased glycine-induced ion current, and in decreased glutamate-induced ion current. In contrast, continuous application of amygdalin with LPS resulted in decreased glycine-induced ion current increased by LPS, and increased glutamate- induced ion current decreased by LPS in concentration- and time-dependent fashion. These results demonstrate that amygdalin modulates neuronal activity of PAG by modulation of glycine and glutamate. Based on the present results, it can be suggested that amygdalin participates in the regulation of the descending pain control system in the level of PAG neurons. The present study demonstrated that activation of the descending pain control system is one of the possible analgesic mechanisms of amygdalin.
Amygdalin ; Animals ; Benzaldehydes ; Cyclooxygenase 2 ; Glucose ; Glutamic Acid ; Glycine ; Hydrogen Cyanide ; Lipopolysaccharides ; Neurons ; Periaqueductal Gray ; Rats

The conversion of exogenous p-hydroxybenzaldehyde to p-hydroxy-methyl-phenol-beta-D-glucoside (gastrodin) was studied by using cell suspension culture of Datura tatula L. The chemical structure of this synthesized gastrodin was identified based on the spectral analysis and chemical evidence. The conversion procedure of p-hydroxybenzaldehyde into gastrodin by D. tatula L. cell suspension cultures was established. The synthesized gastrodin (II) was isolated from the ferment liquor and identified by spectral analysis. At the same time, the p-hydroxybenzyl alcohol (I) converted through biotransformation of p-hydroxybenzaldehyde by cell suspension cultures of D. tatula L. was also isolated and identified. The efficiency of glucosylation of p-hydroxybenzaldehyde was remarkably enhanced by adding salicylic acid (0.1 mg/L) and keeping the lower pressure (0.001MPa) in 25L airlift loop bioreactor. The biotransformation of exogenous p-hydroxybenzaldehyde to gastrodin by cell suspension culture of D. tatula L. is a promising approach.
Benzaldehydes ; metabolism ; Benzyl Alcohols ; chemistry ; Bioreactors ; Biotransformation ; Datura ; metabolism ; Glucosides ; biosynthesis ; chemistry ; Salicylic Acid ; pharmacology ; Suspensions

Sixteen compounds were isolated from Conioselinum vaginatum by silica column chromatography over silica gel and Sephadex LH-20, as well as recrystallization. On the basis of their physical and chemical properties and spectral data, their structures were identified as ligustilide (1), 1,3-dilinolein (2), coniferaldehyde (3), myristicin (4), stigmasterol (5), beta-sitosterol (6), vanillin (7), pregnenolone (8), bergapten (9), xanthotoxin (10), methyl indole-3-carboxylate (11), ferulic acid (12), (E)-3-methoxy-4,5-methylenedioxy-cinnamic alcohol (13), p-hydroxybenzaldehyde (14), 3-methoxy-4,5-methylenedioxy-acetophenone (15), and alpha-(ethoxymethyl)-4-hydroxy- benzenemethanol (16). Among them, compound 15 was a new natural product, and compounds 2, 3, 10, 11, 14, and 16 were obtained from this genus for the first time.
Apiaceae ; chemistry ; Benzaldehydes ; chemistry ; Dextrans ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Mass Spectrometry ; Molecular Structure ; Sitosterols ; chemistry

OBJECTIVETo develop a RP-HPLC method for determining the contents of atranol, lecanorin, ethyl orsellinate and methyl orsellinate in Usnea diffracta.

METHODA Kromasil-C18 column (4.6 mm x 250 mm, 5 microm) was used at 25 degrees C with the mobile phases of acetonitrile -1% acetic acid in a gradient manner. The flow rate was set at 1.0 mL x min(-1). The detection wavelength was 280 nm.

RESULTThe correlation coefficients of atranol, lecanorin, ethyl orsellinate, and methyl orsellinate were higher than 0.999. Recoveries were from 102.9% to 95.30%; with RSD from 2.3% to 1.9%.

CONCLUSIONThe method is quick, simple and repeatable for simultaneous determination of atranol, lecanorin, ethyl orsellinate and methyl orsellinate in U. diffracta.

Benzaldehydes ; analysis ; Chromatography, High Pressure Liquid ; methods ; Resorcinols ; analysis ; Usnea ; chemistry

OBJECTIVETo develop an HPLC method for gradient elution determination of danshensu and protocatechuic aldehyde in Shengkangling granula.

METHODThe analysis was carried on a column of Hypersil ODS2-C18 with a mobile phase consisted of methanol-1% glacial acetic acid 0-8 min (5:95), 8-11 min (6:94-5:95), 11-20 min (5:95) gradient elution at the flow rate of 1 mL x min(-1). The detection wavelength was 280 nm.

RESULTThe linearity was obtained in the range of 0.0504-0.504 microg (r = 0.9998) for tanshinol and 0.1090-1.090 microg (r = 0.9999) for protocatechuic aldehyde, respectively. The average recoveries of tanshinol and protocatechuic aldehyde in Shenkangling granula were 98.40% and 98.85%, and the RSDs were all less than 2.0%.

CONCLUSIONThe method is simple, accurate and rapid. It may be suitable for the usual quality control of tanshinol and protocatechuic aldehyde in Shengkangling granula.

Benzaldehydes ; analysis ; Catechols ; analysis ; Chromatography, High Pressure Liquid ; methods ; Dosage Forms ; Drugs, Chinese Herbal ; analysis

OBJECTIVETo report the pharmacokinetic parameters of helicid HD in rats after intravenous administration at different doses.

METHODFifteen Wistar rats were randomly assigned as three groups (n=5, male) to be given helicid solution via tail vein injection at a single dose of 2.23, 4.46, 6.70 mg x kg(-1), respectively. Blood samples were collected via tail vein at time intervals after HD injection. 6% perchloric acid was to precipitate plasma protein. Separation was achieved on a reversed-phase C18 column with UV detection at 270 nm.

RESULTThe calibration curves were linear ranging from 43.8 to 43,800 microg x L(-1). The intra-and inter-day precisions were no more than 6%. The average recovery of helicid was more than 87% from plasma. With minimum akaike information criterion (AIC) values, a two-compartment open pharmacokinetic model was proposed and validated through the DAS 2.0 to explain the apparent diphasic phenomenon of (HD) in rat blood after intravenous administration. Helicid appeared to be distributed rapidly into a highly perfused central compartment (first compartment), with a less rapidly elimination. The diphasic phenomenon could be observed from the compartment model parameters t(1/2alpha) and t(1/2beta). The least squares regression analysis indicated that the plasma concentrations and AUC of helicid in rat plasma were proportional to the administrated doses. At the administrated doses of 2.23, 4.46, 6.70 mg x kg(-1), the values of distribution half-life (t(1/2alpha)) were 4.582, 5.097, 4.727 min, respectively. And the values of elimination half-life (t(1/2beta)) were 23.945, 26.508 and 25.396 min, respectively. The volume of distribution from these three different doses were 0.036, 0.035, 0.035 L, respectively. The AUCo(0-->t) (area under the concentration-time curve) increase was proportional to the administrated dose.

CONCLUSIONIn the range of the doses examined, the pharmacokinetics of helicid in rats is based on linear dynamics.

Animals ; Benzaldehydes ; administration & dosage ; blood ; pharmacokinetics ; Chromatography, High Pressure Liquid ; Male ; Random Allocation ; Rats ; Rats, Wistar

OBJECTIVETo study the chemical constituents from leaves of Phyllostachys pubescens.

METHODColumn chromatography on sephadex LH-20 as well as preparative HPLC and spectral analysis were used to isolate and elucidate the constituents.

RESULTSix compounds were isolated from leaves of Phyllostachys pubescens, and identified as vanillin (I), syringic aldehyde (II), p-hydroxybenzaldehyde (III), vanillic acid (IV), syringic acid (V), 4-hydroxy-3-methoxy cinnamic acid, ethyl ester (VI).

CONCLUSIONAll above the compounds were isolated from the plant for the first time.

Benzaldehydes ; chemistry ; isolation & purification ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Poaceae ; chemistry ; Vanillic Acid ; chemistry ; isolation & purification

Enzymatic preparations obtained from young plants and cell cultures of capulin were screened for hydroxynitrile lyase activity. The three week old plants, grown under sterile conditions, were used to establish a solid cell culture. Crude preparations obtained from this plant material were evaluated for the transformation of benzaldehyde to the corresponding cyanohydrin (mandelonitrile). The results show that the crude material from roots, stalks, and leaves of young plants and calli of roots, stalks, internodes and petioles biocatalyzed the addition of hydrogen cyanide (HCN) to benzaldehyde with a modest to excellent enantioselectivity.
Acetonitriles ; metabolism ; Aldehyde-Lyases ; metabolism ; Benzaldehydes ; metabolism ; Biocatalysis ; Cells, Cultured ; Hydrogen Cyanide ; metabolism ; Nitriles ; metabolism ; Prunus ; cytology ; enzymology

Eighteen compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as adinoside A (1), stryspinoside (2), benzyl alcohol beta-glucopyranoside (3), benzyl 2-o-beta-D-glucopyranosyl-2,6-dihydroxybenzoate (4) , gentisic acid 2-O-beta-D-glucopyranoside (5), eugenyl beta-D-glucopyranoside (6) , eugenyl-P-xylopyranosyl-(1-->6)-beta-glucopyranoside (7), (-)-lyoniresinol 9-O-fP-D-glucopyranoside (8) , (+)-lyoniresinol 9-O-beta-D-glucopyranoside (9) , apigenin-7-O-L-rhamnopyranoside (10), luteolin-3 '-O-L-rhamnoside (11) , ursolic acid (12) , beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (13), abscisic acid (14), guanosine (15), 5-methyluracil (16), trans-cinnamic acid (17), and 4-hydroxybenzaldehyde(18). These compounds were obtained from this plant for the first time.
Benzaldehydes ; analysis ; Flowers ; chemistry ; Gentisates ; analysis ; Glucosides ; analysis ; Hydroxybenzoates ; analysis ; Lonicera ; chemistry ; Luteolin ; analysis ; Thymine ; analysis ; Triterpenes ; analysis

Marine fungi are important members of the marine microbiome, which have been paid growing attention by scientists in recent years. The secondary metabolites of marine fungi have been reported to contain rich and diverse compounds with novel structures (Chen et al., 2019). Aspergillus terreus, the higher level marine fungus of the Aspergillus genus (family of Trichocomaceae, order of Eurotiales, class of Eurotiomycetes, phylum of Ascomycota), is widely distributed in both sea and land. In our previous study, the coral-derived A. terreus strain C23-3 exhibited potential in producing other biologically active (with antioxidant, acetylcholinesterase inhibition, and anti-inflammatory activity) compounds like arylbutyrolactones, territrems, and isoflavones, and high sensitivity to the chemical regulation of secondary metabolism (Yang et al., 2019, 2020; Nie et al., 2020; Ma et al., 2021). Moreover, we have isolated two different benzaldehydes, including a benzaldehyde with a novel structure, from A. terreus C23-3 which was derived from Pectinia paeonia of Xuwen, Zhanjiang City, Guangdong Province, China.
Acetylcholinesterase/metabolism* ; Animals ; Anthozoa/microbiology* ; Anti-Inflammatory Agents/pharmacology* ; Aspergillus/chemistry* ; Benzaldehydes/pharmacology* ; Mice ; RAW 264.7 Cells ; Signal Transduction