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Sophoflavescenol

$605

  • Brand : BIOFRON

  • Catalogue Number : BD-P0131

  • Specification : 98.0%(HPLC)

  • CAS number : 216450-65-6

  • Formula : C21H20O6

  • Molecular Weight : 368.4

  • PUBCHEM ID : 9929189

  • Volume : 10mg

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Catalogue Number

BD-P0131

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

368.4

Appearance

Yellow powder

Botanical Source

Structure Type

Flavonoids

Category

SMILES

CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)OC)O)C

Synonyms

3,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chromen-4-one

IUPAC Name

3,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chromen-4-one

Applications

Anti-tumorigenic activity of sophoflavescenol against Lewis lung carcinoma in vitro and in vivo. PUMID/DOI:DOI: 10.1007/s12272-011-1212-y Arch Pharm Res. 2011 Dec;34(12):2087-99. This study examined the in vitro cytotoxic activity and in vivo antitumor activity as well as intracellular apoptotic capacities of a prenylated flavonol, sophoflavescenol from Sophora flavescens, to evaluate prospective anti-tumorigenic drugs, and antitumor potential. In addition, the in vitro antioxidant and anti-inflammatory capacities were evaluated. Despite the small effect on human breast adenocarcinoma (MCF-7), sophoflavescenol showed cytotoxicity against human leukaemia (HL-60), Lewis lung carcinoma (LLC), and human lung adenocarcinoma epithelial (A549) cells. Interestingly, it also exerted potent in vivo antitumor activity by tumor growth inhibition in the LLC tumor model as well as apoptotic activity by caspase-3 activation in HL-60 cells. In addition, it exhibited potent antioxidant activities in 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radicals and lipid peroxidation assays. Sophoflavescenol exerted notable anti-inflammatory activity by inhibiting nitric oxide generation and tert-butylhydroperoxide-induced ROS generation rather than inhibiting nuclear factor kappa B activation in RAW 264.7 cells. The findings show that the antioxidant, anti-inflammatory, and apoptotic activities of sophoflavescenol might contribute to the antitumor activity without severe side effects, highlighting its potential for chemoprevention and/or anticancer drugs due to multi-effective targets in almost all stages of tumorigenesis, including initiation, promotion, and progression. Antidiabetic complications and anti-Alzheimer activities of sophoflavescenol, a prenylated flavonol from Sophora flavescens, and its structure-activity relationship. PUMID/DOI:DOI: 10.1002/ptr.3326 Phytother Res. 2011 May;25(5):709-15. It was previously reported that prenylated flavonols from Sophora flavescens are inhibitors of rat lens aldose reductase (RLAR), human recombinant aldose reductase (HRAR), advanced glycation endproducts (AGE), β-secretase (BACE1) and cholinesterases (ChE). Based upon structure-activity relationships, 3,4'-dihydroxy flavonols with a prenyl or lavandulyl group substitution at the C-8 position, and a hydroxy group at the C-5, are important for such inhibition. In our ongoing study to isolate active principles from S. flavescens by an activity-guided isolation procedure, further detailed phytochemical investigations of the CH(2)Cl(2) fraction were conducted via repeated chromatography over silica gel and Sephadex LH-20 columns. This ultimately resulted in the isolation of a promising active sophoflavescenol with higher inhibitory activities among the current prenylated flavonols isolated from S. flavescens against RLAR, HRAR, AGE, BACE1 and ChEs. The results further support that 3,4'-dihydroxy flavonols with a prenyl or lavandulyl substitution at the C-8 position and a methoxy group at C-5 represent a new class of RLAR, HRAR and AGE inhibitors. Nevertheless, the C-5 hydroxyl group of prenylated flavonoids is important for inhibition of BACE1 and ChEs, indicating that the hydroxyl group at C-5 might be the main contributor to the augmentation and/or modification of prenylated flavonol activity. Prenylated flavonoids as tyrosinase inhibitors. PUMID/DOI:15595416 Arch Pharm Res. 2004 Nov;27(11):1132-5. In order to find new tyrosinase inhibitors and the effects of prenyl residue on flavonoid molecules, eight prenylated and three synthetic vinylated flavonoids were examined on their inhibitory effect against tyrosinase activity. From the results, kuwanon C, papyriflavonol A, sanggenon D and sophoflavescenol were found to possess the considerable inhibitory activity. Especially, sanggenon D is revealed as a potent inhibitor (IC50 = 7.3 microM), compared to the reference compound, kojic acid (IC50 = 24.8 microM). However, the prenylation with isoprenyl group or the vinylation to flavonoid molecules did not enhance

Density

1.359±0.06 g/cm3

Solubility

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

Flash Point

226.2±25.0°C

Boiling Point

631.8±55.0 °C at 760 mmHg

Melting Point

273-275°C

InChl

InChI=1S/C21H20O6/c1-11(2)4-9-14-15(23)10-16(26-3)17-18(24)19(25)20(27-21(14)17)12-5-7-13(22)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3

InChl Key

VMLJAWUWVVHRNG-UHFFFAOYSA-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#:216450-65-6) 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

216450

Abstract

1 4-Aminopyridine methiodide (4-APMI), a quaternary analogue of aminopyridine (4-AP), was tested for neuromuscular facilitatory actions on the chick biventer cervicis and frog sartorius nerve-muscle preparations. 2 In the chick, 4-APMI (10(-4) to 10(-2) M) augmented indirectly elicited twitches and reversed tubocurarine-induced neuromuscular block. Reversal of tubocurarine block was observed after treatment of the muscle with an anticholinesterase. 4-APMI did not itself produce contracture but augmented responses to added acetylcholine. 3 4-APMI (10(-4) M) prolonged the time courses of endplate potentials (e.p.ps) and miniature endplate potentials (m.e.p.ps) in the frog. 4 4-APMI (10(-4) M) increased e.p.p. quantal content. 4-AP was about 100 times more active than 4-APMI in increasing quantal content. Both compounds prolonged muscle action potentials at similar concentrations. 5 4-APMI (10(-3) to 3 X 10(-3) M) possessed anticholinesterase activity in homogenates of chick biventer cervicis muscle. 6 It is concluded that 4-APMI increases evoked acetylcholine release and also possesses a weak anticholinesterase action. The greater action of 4-AP on quantal content is probably due to an intracellular action, possibly involving the release of calcium ions.

Title

A comparison of the facilitatory actions of 4-aminopyridine methiodide and 4-aminopyridine on neuromuscular transmission.

Author

A S Horn, J J Lambert, and I G Marshall

Publish date

1979 Jan;

PMID

25092028

Abstract

Comamonas testosteroni TA441 degrades steroids via aromatization and meta-cleavage of the A ring, followed by hydrolysis, and produces 9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid as an intermediate compound. Herein, we identify a new intermediate compound, 9α-hydroxy-17-oxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid. Open reading frame 28 (ORF28)- and ORF30-encoded acyl coenzyme A (acyl-CoA) dehydrogenase was shown to convert the CoA ester of 9α-hydroxy-17-oxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid to the CoA ester of 9α-hydroxy-17-oxo-1,2,3,4,10,19-hexanorandrost-6-en-5-oic acid. A homology search of the deduced amino acid sequences suggested that the ORF30-encoded protein is a member of the acyl-CoA dehydrogenase_fadE6_17_26 family, whereas the deduced amino acid sequence of ORF28 showed no significant similarity to specific acyl-CoA dehydrogenase family proteins. Possible steroid degradation gene clusters similar to the cluster of TA441 appear in bacterial genome analysis data. In these clusters, ORFs similar to ORFs 28 and 30 are often found side by side and ordered in the same manner as ORFs 28 and 30.

Title

Identification of 9α-Hydroxy-17-Oxo-1,2,3,4,10,19-Hexanorandrostan-5-Oic Acid in Steroid Degradation by Comamonas testosteroni TA441 and Its Conversion to the Corresponding 6-En-5-Oyl Coenzyme A (CoA) Involving Open Reading Frame 28 (ORF28)- and ORF30-Encoded Acyl-CoA Dehydrogenases

Author

Masae Horinouchi,corresponding authora Toshiaki Hayashi,a Hiroyuki Koshino,b,* Michal Malon,b Hiroshi Hirota,c and Toshiaki Kudoa

Publish date

2014 Oct;

PMID

21581522

Abstract

The crystal structure of the title compound, [Ru(C12H12O6)(C18H15P)2(CO)], confirms its formulation as a ruthenabenzofuran, with a slightly distorted octa­hedral coordination environment at the RuII ion, and mutually trans triphenyl­phosphine ligands. The metallabicyclic ring system is essentially planar (maximum deviation 0.059 a).

Title

Dimethyl 7a-carbonyl-2-meth­oxy-7a,7a-bis­(triphenyl­phosphino)-7a-ruthena-1-benzofuran-4,7-dicarboxyl­ate

Author

George R. Clark,a,* Warren R. Roper,a Deborah M. Tonei,a and L. James Wrighta

Publish date

2009 Jan 1;