99-18-3

Usage

Uses

Used in the Synthesis of Cyanogen Glycosides:
PRUNASIN is used as a precursor in the synthesis of cyanogen glycosides, which are compounds containing a cyano group attached to a glycosidic moiety. These glycosides are of interest in various chemical and biological applications.
Used in Personal Care Products:
PRUNASIN is used as an ingredient in antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair conditioners. Its inclusion in these products is due to its potential antimicrobial and astringent properties, which can contribute to the effectiveness of personal care formulations.
Used in Pharmaceutical Applications:
Due to its inhibitory effects on plant growth and its ability to inhibit rat DNA polymerase β, PRUNASIN may have potential applications in the development of pharmaceuticals, particularly in areas related to DNA repair mechanisms and plant growth regulation.
Used in Chemical Research:
As a cyanogenic glucoside, PRUNASIN is also used in chemical research to study the properties and reactions of cyanogenic compounds, which can provide insights into the development of new chemical processes and applications.

Enzyme inhibitor

This cyanogenic glucoside (FW = 295.29 g/mol; CAS 99-18-3), also known as D(R)-mandelonitrile-b-D-glucoside, is readily obtained from amygdalin and is found in the pits of Prunus serotina. Prunasin is soluble in water and will give rise to prulaurasin (i.e., the diastereoisomeric mixture of DL(RS)- mandelonitrile-b-D-glucoside [i.e., prunasin and sambunigrin]). Target(s): DNA-directed DNA polymerase; DNA polymerase b; and a,a trehalase.

InChI:InChI=1/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/m0/s1

Upstream product

• 60981-47-7 (2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile 
• 4358-86-5 (2R)-mandelamide 
• 207512-68-3 (R)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy(phenyl)acetamide 
• 1169800-49-0 (2R)-β-D-(6-O-acetyl)-glucosyl-2-phenylacetonitrile 
• 151649-54-6 (R)-α-(β-D-glucopyranosyloxy)phenylacetamide 
• 100-52-7 benzaldehyde 
• 29883-15-6 amygdalin 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 100-63-0 phenylhydrazine 

Downstream Products

• 60981-47-7 (2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile 
• 100-52-7 benzaldehyde 
• 611-71-2 MANDELIC ACID 
• 151649-54-6 (R)-α-(β-D-glucopyranosyloxy)phenylacetamide 
• 99-19-4 (2S)-2-(β-D-glucopyranosyloxy)phenylacetonitrile 

Relevant academic research and scientific papers

New flavonoid glycosides and cyanogenic glycosides from dracocephalum peregrinum

Separation of ethyl acetate fractionation of Dracocephalum peregrinum afforded three new flavonoid glucosides (1-3), and a new cyanogenic glucoside (4). Their structures were elucidated based on HR-electron spray ionization (ESI)-MS, EI-MS, UV, IR, 1D-, a

Pharmacokinetics and anti-liver fibrosis characteristics of amygdalin: Key role of the deglycosylated metabolite prunasin

Background: Amygdalin (Amy) is a cyanoside and is one of the chief active ingredients in Persicae Semen, Armeniacae Semen Amarum, and Pruni Semen. Amy has extensive and remarkable pharmacological activities, including against anti-hepatic fibrosis. However, the pharmacokinetic and anti-liver fibrosis effects of Amy and its enzyme metabolite prunasin (Pru) in vivo have not been studied and compared, and studies on Pru are limited. Purpose: To investigate the pharmacokinetic characteristics and anti-liver fibrosis effect of Amy and its metabolite Pru in vivo and in vitro, and elucidate whether the metabolism of Amy in vivo for Pru is activated. Methods: Pru was prepared from Amy via the enzymatic hydrolysis of β-glucosidase, and isolated by silica gel column chromatography. An efficient and sensitive ultrahigh-performance liquid chromatography-Q exactive hybrid quadrupole orbitrap high-resolution accurate mass spectrometry was developed and validated to determine simultaneously Amy and Pru in rat plasma after dosing intravenously and orally for pharmacokinetic studies. The affinities of Amy and Pru for β-glucosidase were compared by enzyme kinetic experiments to explain the possible reasons for the differences in pharmacokinetic behavior. In vitro, the inhibitory effects of Amy and Pru on hepatic stellate cell activation and macrophage inflammation on JS1 and RAW 264.7 cells were determined. In vivo, the ameliorative effects of Amy and Pru on liver fibrosis effects were comprehensively evaluated by CCl4-induced liver fibrosis model in mice. Results: The standard curves of Amy and Pru in rat plasma showed good linearity within the concentration range of 1.31–5000.00 ng/ml, with acceptable selectivity, carry-over, detection limit and quantification limits, intra- and inter-day precision, accuracy, matrix effect, and stability. The Cmax and AUC (0?∞) of Pru (Cmax = 1835.12 ± 268.09 ng/ml, AUC (0?∞) = 103,913.17 ± 14,202.48 ng?min/ml) were nearly 79.51- and 66.22-fold higher than those of Amy (Cmax = 23.08 ± 5.08 ng/ml, AUC (0?∞) = 1569.22 ± 650.62 ng?min/ml) after the oral administration of Amy. The oral bioavailability of Pru (64.91%) was higher than that of Amy (0.19%). The results of enzyme hydrolysis kinetics assay showed that the Vmax and Km of Pru were lower than those of Amy in commercial β-glucosidase and intestinal bacteria. In vitro cellular assays showed that Amy and Pru were comparable in inhibiting the NO production in the RAW264.7 cell supernatant and the mRNA expression of α-SMA and Col1A1 in JS1 cells. Amy and Pru were also showed comparable activity in ameliorating CCl4-induced liver fibrosis in mice. Conclusion: The pharmacokinetic characteristics of Amy and Pru in rat plasma were significantly different. After the separate gavage of Amy and Pru, Amy was absorbed predominantly as it's metabolite Pru, whereas Pru was absorbed predominantly as a prototype. The anti-liver fibrosis effects of Amy and its deglycosylated metabolite Pru were comparable in vivo and in vitro. The deglycosylated activated metabolite Pru of Amy plays an important role in anti-liver fibrosis. These findings will facilitate the further exploitation of Amy and Pru.

Toxicity and Toxicokinetics of Amygdalin in Maesil (Prunus mume) Syrup: Protective Effect of Maesil against Amygdalin Toxicity

Maesil (Prunus mume, green plum)-based products have been widely used in Asian cooking, which may contain amygdalin enzymatically converted to hydrogen cyanide after oral ingestion. In this study, the toxicity of Maesil syrups matured with and without Mae

General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides

An effective method for the chemical synthesis of cyanogenic glucosides has been developed as demonstrated by the synthesis of dhurrin, taxiphyllin, prunasin, sambunigrin, heterodendrin, and epiheterodendrin. O-Trimethylsilylated cyanohydrins were prepared and subjected directly to glucosylation using a fully acetylated glucopyranosyl fluoride donor with boron trifluoride-diethyl etherate as promoter to afford a chromatographically separable epimeric mixture of the corresponding acetylated cyanogenic glucosides. The isolated epimers were deprotected using a triflic acid/MeOH/ion-exchange resin system without any epimerization of the cyanohydrin function. The method is stereocontrolled and provides an efficient approach to chemical synthesis of other naturally occurring cyanogenic glucosides including those with a more complex aglycone structure.

Synthesis and Biological Evaluation of Cyanogenic Glycosides

An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum

Four acylated glycosides along with six known glycosides were isolated from the leaves of Monochaetum multiflorum. The new compounds were characterized as 4.0-(6′-O-galloyl- β- glucopyranosyl)-cis-p-coumaric acid, 6′-O- galloylprunasin, benzyl 6′-O-galloyl-β-glucopyranoside, and a novel diester of tetrahydroxy-μ-truxinic acid with 2 mol of hyperin (monochaetin), based on NMR and MS spectral data and chemical evidence.

Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin

A facile synthetic route is described to cyanogenic glycosides (R)-prunasin, linamarin and (S)-heterodendrin from O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate and the corresponding α-hydroxyamides by a 3-step reaction of glycosylation, cyanohydrin formation by dehydration of carboxamides, and deprotection.

PRUNASIN-6'-MALONATE, A CYANOGENIC GLUCOSIDE FROM MERREMIA DISSECTA

The cyanogenic glucosides prunasin and 6'-O-malonylprunasin have been isolated from the leaves of Merremia dissecta.Malonylprunasin is the first example of a malonyl conjugate of the cyanogenic glycosides. - Keywords: Merremia dissecta; Convolvulaceae; prunasin, malonylprunasin; cyanogenesis.

CYANOGENIC GLYCOSIDES IN LEAVES OF PERILLA FRUTESCENS VAR. ACUTA

Besides 7-(2-O-β-D-glucuronyl-β-D-glucuronyloxy)-5,3',4'-trihydroxyflavone, scutellarin, rosmarinic acid and caffeic acid, two cyanogenic glycosides have been isolated from the dried leaves of Perilla frutescens var. acuta.One of them is prunasin and the other is (R)-2-(2-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)-phenylacetonitrile, a new isomer of amygdalin.Key Word Index - Perilla frutescens var. acuta; Labiatae; cyanogenic glycoside; (R)-2-(2-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)-phenylacetonitrile; prunasin; 7-(2-O-β-D-glucuronyl-β-D-glucuronyloxy)-5,3',4'-trihydroxy-flavone; scutellarin; rosmarinic acid; caffeic acid.