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Secoxyloganin

$280

  • Brand : BIOFRON

  • Catalogue Number : BD-P0814

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 58822-47-2

  • Formula : C17H24O11

  • Molecular Weight : 404.4

  • PUBCHEM ID : 162868

  • Volume : 25mg

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Catalogue Number

BD-P0814

Analysis Method

Specification

98.0%(HPLC&TLC)

Storage

-20℃

Molecular Weight

404.4

Appearance

Solid

Botanical Source

This product is isolated and purified from the vines of Lonicera japonica

Structure Type

Category

SMILES

COC(=O)C1=COC(C(C1CC(=O)O)C=C)OC2C(C(C(C(O2)CO)O)O)O

Synonyms

2H-Pyran-4-acetic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2S,3R,4S)-/Secoxyloganin/[(2S,3R,4S)-2-(β-D-Glucopyranosyloxy)-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid/Secoquettamine

IUPAC Name

Applications

Isolation and identification of chemical constituents in effective fraction anti-PRRSV of the branches and leaves of the Lonicera japonica.[Reference: WebLink]Journal of Huazhong Normal University, 2013,52(2):213. The antiviral effect of the extracts of the Lonicera japonica leaves on PRRSV in vitro was evaluated by determining the minimum protection concentration on PRRSV infected Marc-145 cell and TCID50. METHODS AND RESULTS: The results showed that the 60% ethanol/water elution fraction possess the perfect protective effect on PRRSV infected cell and with the minimum protection concentration of 6. 25 Âμg/mL. The 6. 25 Âμg/mL 60% ethanol/water elution fractions decreased PRRSV titer from 105.8 TCID50 to 100.3 TCID50. That is to say, 60% ethanol/water elution fractions of Lonicera japonica is a potential antiviral drug owing to its perfect anti-PRRSV effect. To study the chemical constituents of the Lonicera japonica , the air-dried branches and leaves of this plant were extracted with 95% ethanol. The extracts were separated and purified by normal-phase, Sephadex LH-20 and RP-HPLC. CONCLUSIONS: Five compounds were obtained from the effective fractions anti-PRRSV of the branches and leaves of the Lonicera japonica and their structures were identified as Dihydrodehydrodiconiferyl alcohol 4'-O-Î2-D-glucoside (1), Apigenin 5-O-Î2-D-glucopyranoside (2) , Secoxyloganin (3) , Benzyl alcohol O-(6 -O-p-D-xylopyranosyl)-Î2-D-glucopyranoside (4) and Sweroside (5).

Density

1.5±0.1 g/cm3

Solubility

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

Flash Point

231.8±25.0 °C

Boiling Point

649.5±55.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

MQLSOVRLZHTATK-PEYNGXJCSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:58822-47-2) 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

29897205

Abstract

To study the chemical composition and their anti-inflammatory activities of honeysuckle (Lonicera japonica Thunb.) roots, seventeen compounds were isolated from the roots of L. japonica Thunb. by various chromatography, including silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by MS, IR, and nuclear magnetic resonance spectra, as 1-oxo-(1H)-cyclopenta[b]benzofuran-7-carbaldehyde (1), 4-hydroxycinnamic acid (2), chlorogenic acid (3), loganin aglycone (4), caffeic acid (5), secologanin dimethyl acetal (6), korolkoside (7), coniferin (8), sweroside (9), secoxyloganin (10), 5-O-caffeoylquinic acid (11), chlorogenic acid methyl ester (12), chlorogenic acid ethyl ester (13), 3,5-O-dicaffeoylquinic acid (14), 4,5-O-dicaffeoylquinic acid (15), grandifloroside (16), and 4,5-O-dicaffeoylquinic acid (17). Among those, compound 1 is a new compound, and compound 8 is found in L. japonica for the first time. Compounds 1, 3, 14-17 showed significant anti-inflammatory activities against macrophage in zebrafish.

Title

[Chemical constituents of Lonicera japonica roots and their anti-inflammatory effects].

Author

Yu JQ, Wang ZP, Zhu H, Li G, Wang X.

Publish date

2016 Jul;

PMID

26927220

Abstract

The phytochemical study of the leaves, roots, and flowers of Palicourea rigida led to the isolation of the triterpenes betulinic acid (1) and lupeol (2), the diterpene phytol (3), and the iridoid glycosides sweroside (4) and secoxyloganin (5). These compounds were identified using NMR 1H and 13C and comparing the spectra with published data. We studied the antiedematogenic activity of crude extracts from the organs, and of different fractions, in mice and found that the n-hexane fraction of the leaf extract significantly inhibited the ear edema resulting from croton oil administration. The crude extract from leaves was not acutely toxic to the mice.

Title

Acute toxicity, antiedematogenic activity, and chemical constituents of Palicourea rigida Kunth.

Author

Alves VG, da Rosa EA, de Arruda LL, Rocha BA, Bersani Amado CA, Santin SM, Pomini AM, da Silva CC.

Publish date

2016 Mar;

PMID

26285573

Abstract

BACKGROUND:
Transcriptome sequencing offers a great resource for the study of non-model plants such as Catharanthus roseus, which produces valuable monoterpenoid indole alkaloids (MIAs) via a complex biosynthetic pathway whose characterization is still undergoing. Transcriptome databases dedicated to this plant were recently developed by several consortia to uncover new biosynthetic genes. However, the identification of missing steps in MIA biosynthesis based on these large datasets may be limited by the erroneous assembly of close transcripts and isoforms, even with the multiple available transcriptomes.

RESULTS:
Secologanin synthases (SLS) are P450 enzymes that catalyze an unusual ring-opening reaction of loganin in the biosynthesis of the MIA precursor secologanin. We report here the identification and characterization in C. roseus of a new isoform of SLS, SLS2, sharing 97 % nucleotide sequence identity with the previously characterized SLS1. We also discovered that both isoforms further oxidize secologanin into secoxyloganin. SLS2 had however a different expression profile, being the major isoform in aerial organs that constitute the main site of MIA accumulation. Unfortunately, we were unable to find a current C. roseus transcriptome database containing simultaneously well reconstructed sequences of SLS isoforms and accurate expression levels. After a pair of close mRNA encoding tabersonine 16-hydroxylase (T16H1 and T16H2), this is the second example of improperly assembled transcripts from the MIA pathway in the public transcriptome databases. To construct a more complete transcriptome resource for C. roseus, we re-processed previously published transcriptome data by combining new single assemblies. Care was particularly taken during clustering and filtering steps to remove redundant contigs but not transcripts encoding potential isoforms by monitoring quality reconstruction of MIA genes and specific SLS and T16H isoforms. The new consensus transcriptome allowed a precise estimation of abundance of SLS and T16H isoforms, similar to qPCR measurements.

CONCLUSIONS:
The C. roseus consensus transcriptome can now be used for characterization of new genes of the MIA pathway. Furthermore, additional isoforms of genes encoding distinct MIA biosynthetic enzymes isoforms could be predicted suggesting the existence of a higher level of complexity in the synthesis of MIA, raising the question of the evolutionary events behind what seems like redundancy.

Title

Characterization of a second secologanin synthase isoform producing both secologanin and secoxyloganin allows enhanced de novo assembly of a Catharanthus roseus transcriptome

Author

Duge de Bernonville T1, Foureau E2, Parage C3, Lanoue A4, Clastre M5, Londono MA6,7, Oudin A8, Houille B9, Papon N10, Besseau S11, Glevarec G12, Atehortùa L13, Giglioli-Guivarc'h N14, St-Pierre B15, De Luca V16, O'Connor SE17, Courdavault V18.

Publish date

2015 Aug 19