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Strictosamide

$287

  • Brand : BIOFRON

  • Catalogue Number : BD-P0553

  • Specification : 98.0%(HPLC)

  • CAS number : 23141-25-5

  • Formula : C26H30N2O8

  • Molecular Weight : 498.52

  • PUBCHEM ID : 10345799

  • Volume : 25mg

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Catalogue Number

BD-P0553

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

498.52

Appearance

Powder

Botanical Source

Rhynchophylla

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

(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/Strictosamide/strictosamine/vincoside lactam/Oxayohimban-21-one, 19,20-didehydro-16-ethenyl-17-(β-D-glucopyranosyloxy)-, (15β,16α,17β)-

IUPAC Name

(1S,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-IUNANRIWSA-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#:23141-25-5) 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

25026342

Abstract

CONTEXT:
Strictosamide is the main representative constituent of Nauclea officinalis Pierre ex Pitard (Rubiaceae), which has been used for a long time in China to treat diseases related to infection and inflammation, but its pharmacological activities are not well studied.

OBJECTIVE:
This work evaluates the anti-inflammatory and analgesic activities of strictosamide by in vivo experiments.

MATERIALS AND METHODS:
The anti-inflammatory activity was assessed in mice by models of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema, acetic acid-elevated vascular permeability, and carboxymethylcellulose sodium (CMC-Na)-induced leukocyte migration. The analgesic activity was estimated in mice using acetic acid-induced writhing and hot-plate tests. Compound was injected to mice twice a day for 3 d at doses of 10, 20, and 40 mg/kg.

RESULTS:
At 20 and 40 mg/kg, strictosamide obviously decreased the TPA-induced mice ear edema (24.7 and 28.1% inhibition, respectively), and significantly inhibited acetic acid-stimulated peritoneal vascular permeability in mice (23.3 and 33.4% inhibition, respectively). It also significantly decreased the leukocytes in the mice peritoneal cavity induced by CMC-Na at all the tested doses (46.0, 49.1, and 58.7% inhibition, respectively). To acetic acid-induced writhing test in mice, strictosamide markedly prolonged the pain latency at 20 and 40 mg/kg and decreased the writhing counts at 40 mg/kg (49.7% inhibition). However, it did not obviously improve the pain threshold of mice in hot-plate test.

DISCUSSION AND CONCLUSION:
Strictosamide may have important effects on inflammation and inflammatory pain. The results provide scientific support for the role of strictosamide in the use of N. officinalis to treat inflammatory diseases.

KEYWORDS

Animal experiments; Rubiaceae; antinociceptive activity; inflammation

Title

In vivo anti-inflammatory and analgesic activities of strictosamide from Nauclea officinalis.

Author

Li N1, Cao L, Cheng Y, Meng ZQ, Tang ZH, Liu WJ, Wang ZZ, Ding G, Xiao W.

Publish date

2014 Nov

PMID

27989509

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE:
Nauclea officinalis Pierrc ex Pitard. is a Chinese medicinal herb that contains high level of alkaloids which is the most abundant and active constituent. Strictosamide isolated from Nauclea officinalis Pierrc ex Pitard. showed significant effects on inflammatory response, compared with pumiloside, 3-epi-pumiloside, vincosamide, 3α,5α-tetrahydrodeoxycordifoline lactam and naucleamide A-10-O-β-D-glucopyranoside of this plant.

AIM OF STUDY:
we investigated the biological activities of the six compounds mentioned-above, and the underlying molecular mechanism exerted by the most potent one, strictosamide.

MATERIALS AND METHODS:
The effects of strictosamide and other five compounds on the inhibitory activity of nitric oxide (NO) were screened by Griess test. The contents of tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) in media were detected by using Enzyme-linked immunosorbent (ELISA) kits. The effects on the mRNA expression of nitric oxide synthase (iNOS), TNF-α and IL-1β of strictosamide were further investigated by RT-qPCR. Western blot assay was conducted to illustrate the effects of strictosamide on iNOS and phosphorylation of p65, inhibitor of NF-κB (IκB)-α, IκB-kinase (IKK)-α as well as p-extracellular signal-regulated kinase (ERK), p-c-jun N-terminal kinase (JNK) and p-p38 in the protein levels.

RESULTS:
Strictosamide potently suppressed the productions of NO, TNF-α and IL-1β in LPS-induced RAW 264.7 macrophages, and it dose-dependently alleviated the LPS-simulated protein level of iNOS as well as the mRNA expressions of iNOS, TNF-α and IL-1β. In addition, molecular data revealed that strictosamide markedly decreased the expressions of p-p65, p-IκBα and p-IKKα. Furthermore, strictosamide significantly attenuated LPS-induced the phosphorylation of p38, ERK and JNK.

CONCLUSIONS:
At present study, the results indicated that the anti-inflammatory activity of strictosamide was associated with the restraint of NO, TNF-α and IL-1β via negative regulation of both NF-κB and mitogen-activated protein kinases (MAPKs) in LPS-induced RAW 264.7 cells.

Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

KEYWORDS

Anti-inflammation; DMSO (PubChem CID: 679); MAPK; NF-κB; NaNO(2) (PubChem CID: 23668193); Pro-inflammatory cytokines; Pumiloside (ChemSpider ID: 8521772); Strictosamide; Strictosamide (PubChem CID: 10345799); Vincosamide (PubChem CID: 10163855)

Title

Anti-inflammatory effect of the six compounds isolated from Nauclea officinalis Pierrc ex Pitard, and molecular mechanism of strictosamide via suppressing the NF-κB and MAPK signaling pathway in LPS-induced RAW 264.7 macrophages.

Author

Li D1, Chen J2, Ye J3, Zhai X1, Song J4, Jiang C5, Wang J4, Zhang H4, Jia X4, Zhu F6.

Publish date

2017 Jan 20