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Vincosamide

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0911

  • Specification : 98.0%(HPLC)

  • CAS number : 23141-27-7

  • Formula : C26H30N2O8

  • Molecular Weight : 498.52

  • PUBCHEM ID : 10163855

  • Volume : 25mg

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Catalogue Number

BD-P0911

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

498.52

Appearance

Powder

Botanical Source

White Crystal

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C=CC1C2CC3C4=C(CCN3C(=O)C2=COC1OC5C(C(C(C(O5)CO)O)O)O)C6=CC=CC=C6N4

Synonyms

(3β,15β,16α,17β)-21-Oxo-16-vinyl-19,20-didehydro-18-oxayohimban-17-yl β-D-glucopyranoside/(15β,16α,17β)-16-ethenyl-21-oxo-19,20-didehydro-18-oxayohimban-17-yl β-D-glucopyranoside/(15β,16α,17β)-21-Oxo-16-vinyl-19,20-didehydro-18-oxayohimban-17-yl β-D-glucopyranoside/Vincosamide/Oxayohimban-21-one, 19,20-didehydro-16-ethenyl-17-(β-D-glucopyranosyloxy)-, (3β,15β,16α,17β)-/Strictosamide/strictosamine/vincoside lactam/Oxayohimban-21-one, 19,20-didehydro-16-ethenyl-17-(β-D-glucopyranosyloxy)-, (15β,16α,17β)-

IUPAC Name

(1R,18S,19R,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaen-14-one

Applications

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

447.4±34.3 °C

Boiling Point

816.2±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12-,15+,18-,19-,21-,22+,23-,25+,26+/m1/s1

InChl Key

LBRPLJCNRZUXLS-AZVRXDBZSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:23141-27-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31102122

Abstract

Species from Psychotria are used in folk medicine against inflammatory diseases, respiratory disturbances, and anti-hallucinogenic. In the present study, the compound vincosamide (PL-1) was identified for the first time in methanolic extract of the Psychotria leiocarpa (ME-PL) leaves, as well as the anti-inflammatory and anticholinesteric effects in rodents and molecular docking simulations. The fractionation of the chloroform fraction (CF-PL) through chromatographic methods afforded the known compound PL-1. The anti-inflammatory activity of the ME-PL (30, 100, and 300 mg/kg) and PL-1 (3, 30, and 100 mg/kg) was analyzed using experimental models: paw edema, pleurisy, and mechanical and thermal hyperalgesia induced by carrageenan. The anticholinesterase activity of the ME-PL (30 and 100 mg/kg) and PL-1 (30 mg/kg) was showed by acetylcholinesterase (AChE) inhibitory in brain structures. The molecular docking simulations were performed using Molegro Virtual Docker v6.0. Overall, the results indicated that ME-PL and PL-1 demonstrated an anti-edematogenic effect in Cg-induced paw edema, leukocyte migration in the pleurisy model, and significantly reduced mechanical hyperalgesia, cold response to acetone in mice. The samples exhibited maximal inhibition of enzyme acetylcholinesterase (AChE) in the frontal cortex. The molecular coupling of PL-1 with the AChE showed significant interactions with the catalytic and peripheral site, corroborating the activity presented in the inhibition assay. The acute administration of ME-PL did not cause signs of toxicity in the treated animals. The results showed that P. leiocarpa inhibited AChE and anti-inflammatory activity, and alkaloid vincosamide could be responsible, at least in part, for the observed effects, supporting the popular use of this genus.

KEYWORDS

Grandiúva-de-anta; acetylcholinesterase; alkaloid; carrageenan; inflammation; molecular docking

Title

Psychotria leiocarpa Extract and Vincosamide Reduce Chemically-Induced Inflammation in Mice and Inhibit the Acetylcholinesterase Activity.

Author

Formagio ASN1,2, Volobuff CRF3, Kassuya CAL3, Cardoso CAL4, do Carmo Vieira M5, Pereira ZV6, Bagatin MC7, de Freitas Gauze G7.

Publish date

2019 Oct