Loganetin

CAS# 29748-10-5

Loganetin

Catalog No. BCN5202----Order now to get a substantial discount!

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Quality Control of Loganetin

Number of papers citing our products

Chemical structure

Loganetin

3D structure

Chemical Properties of Loganetin

Cas No. 29748-10-5 SDF Download SDF
PubChem ID 10466307 Appearance Powder
Formula C11H16O5 M.Wt 228.2
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl (1R,4aS,6S,7R,7aS)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES CC1C(CC2C1C(OC=C2C(=O)OC)O)O
Standard InChIKey XWOHZIIPBYAMJX-KHBMLBSESA-N
Standard InChI InChI=1S/C11H16O5/c1-5-8(12)3-6-7(10(13)15-2)4-16-11(14)9(5)6/h4-6,8-9,11-12,14H,3H2,1-2H3/t5-,6+,8-,9+,11+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Loganetin

The seeds of Strychnos nux-vomica

Biological Activity of Loganetin

DescriptionStandard reference
In vitro

Metabolism of ginsenoside Rb1 by human intestinal microflora and cloning of its metabolizing β-D-glucosidase from Bifidobacterium longum H-1.[Pubmed: 22466563]

Biol Pharm Bull. 2012;35(4):573-81.

To understand the role of intestinal microflora in expressing the pharmacological effect of ginsenoside Rb1, the metabolic activity of ginsenoside Rb1 by 148 fecal specimens was measured and its metabolizing β-glucosidase was cloned.
METHODS AND RESULTS:
The average activities for p-nitrophenyl-β-D-glucopyranoside and ginsenoside Rb1 were 0.097±0.059 μmol/min/mg and 0.311±0.118 pmol/min/mg, respectively. These enzyme activities were not different between male and female, or between ages. A gene encoding β-D-glucosidase (BglX) was cloned from Bifidobacterium longum H-1, which transformed ginsenoside Rb1 to compound K. The probe for cloning was synthesized from the genes encoding a β-D-glucosidase of previously reported B. longum DJO10A. The sequences of the cloned gene revealed 2364 bp open reading frame (ORF) encoding a protein containing 787 amino acids (molecular weight of 95 kDa). The gene exhibited 99% homology (identities) to that of B. longum. The cloned gene was expressed under T7 promoter of the expression vector, pET-39b(+), in Escherichia coli BL21(DE3), and the expressed enzyme was purified by using HiTrap immobilized metal affinity chromatography (IMAC) HP. The enzyme potently biotransformed ginsenoside Rb1, loganin, arctiin and arbutin to ginsenoside Rd, Loganetin, arctigenin and hydroquinone, respectively, but was not active in the case of hesperidin, and kakkalide.
CONCLUSIONS:
This is the first report on cloning and expression of β-D-glucosidase from B. longum. Based on these findings, ginsenoside Rb1 may be metabolized to bioactive compound(s) by exo-β-D-glucosidase(s) produced from the intestinal bacteria and its pharmacological effects may be dependent on intestinal bacterial exo-β-D-glucosidase(s) activity.

seco-iridoids from Calycophyllum spruceanum (Rubiaceae).[Pubmed: 12943773]

Phytochemistry. 2003 Sep;64(2):549-53.


METHODS AND RESULTS:
Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids Loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established.
CONCLUSIONS:
7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).

Protocol of Loganetin

Structure Identification
Nat Prod Commun. 2009 Nov;4(11):1581-4.

Composition of diethyl ether flower extracts of Lonicera fragrantissima Lindl. & Paxton (caprifoliaceae).[Pubmed: 19967996]


METHODS AND RESULTS:
GC and GC-MS analyses of two diethyl ether extracts of Lonicera fragrantissima flowers (extraction times 1 and 20 days) enabled the identification of 61 components that represented ca. 90% of the extract volatiles. 10-Nonacosanol (18.1-24.1%), nonacosane (14.4-15.0%) and the rather rare long-chained fatty acid hexyl esters (octadecanoate, eicosanoate, docosanoate, tetracosanoate, hexacosanoate, octacosanoate and triacontanoate, in total 19.1-19.5%) were among the main constituents of both extracts. However, a number of differences were observed in the chemical composition of the 1 and 20 day extracts, the relative percentage of the iridoid Loganetin being the most striking (19.1 and 2.1%, respectively). To the best of our knowledge, this is the first report on the GC behavior of Loganetin.
CONCLUSIONS:
It seems that this and the long-chain fatty acid hexyl esters could have chemotaxonomic significance at the generic level.

Loganetin Dilution Calculator

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Loganetin Molarity Calculator

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Preparing Stock Solutions of Loganetin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.3821 mL 21.9106 mL 43.8212 mL 87.6424 mL 109.553 mL
5 mM 0.8764 mL 4.3821 mL 8.7642 mL 17.5285 mL 21.9106 mL
10 mM 0.4382 mL 2.1911 mL 4.3821 mL 8.7642 mL 10.9553 mL
50 mM 0.0876 mL 0.4382 mL 0.8764 mL 1.7528 mL 2.1911 mL
100 mM 0.0438 mL 0.2191 mL 0.4382 mL 0.8764 mL 1.0955 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Loganetin

seco-iridoids from Calycophyllum spruceanum (Rubiaceae).[Pubmed:12943773]

Phytochemistry. 2003 Sep;64(2):549-53.

Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids Loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).

Metabolism of ginsenoside Rb1 by human intestinal microflora and cloning of its metabolizing beta-D-glucosidase from Bifidobacterium longum H-1.[Pubmed:22466563]

Biol Pharm Bull. 2012;35(4):573-81.

To understand the role of intestinal microflora in expressing the pharmacological effect of ginsenoside Rb1, the metabolic activity of ginsenoside Rb1 by 148 fecal specimens was measured and its metabolizing beta-glucosidase was cloned. The average activities for p-nitrophenyl-beta-D-glucopyranoside and ginsenoside Rb1 were 0.097+/-0.059 mumol/min/mg and 0.311+/-0.118 pmol/min/mg, respectively. These enzyme activities were not different between male and female, or between ages. A gene encoding beta-D-glucosidase (BglX) was cloned from Bifidobacterium longum H-1, which transformed ginsenoside Rb1 to compound K. The probe for cloning was synthesized from the genes encoding a beta-D-glucosidase of previously reported B. longum DJO10A. The sequences of the cloned gene revealed 2364 bp open reading frame (ORF) encoding a protein containing 787 amino acids (molecular weight of 95 kDa). The gene exhibited 99% homology (identities) to that of B. longum. The cloned gene was expressed under T7 promoter of the expression vector, pET-39b(+), in Escherichia coli BL21(DE3), and the expressed enzyme was purified by using HiTrap immobilized metal affinity chromatography (IMAC) HP. The enzyme potently biotransformed ginsenoside Rb1, loganin, arctiin and arbutin to ginsenoside Rd, Loganetin, arctigenin and hydroquinone, respectively, but was not active in the case of hesperidin, and kakkalide. This is the first report on cloning and expression of beta-D-glucosidase from B. longum. Based on these findings, ginsenoside Rb1 may be metabolized to bioactive compound(s) by exo-beta-D-glucosidase(s) produced from the intestinal bacteria and its pharmacological effects may be dependent on intestinal bacterial exo-beta-D-glucosidase(s) activity.

Composition of diethyl ether flower extracts of Lonicera fragrantissima Lindl. & Paxton (caprifoliaceae).[Pubmed:19967996]

Nat Prod Commun. 2009 Nov;4(11):1581-4.

GC and GC-MS analyses of two diethyl ether extracts of Lonicera fragrantissima flowers (extraction times 1 and 20 days) enabled the identification of 61 components that represented ca. 90% of the extract volatiles. 10-Nonacosanol (18.1-24.1%), nonacosane (14.4-15.0%) and the rather rare long-chained fatty acid hexyl esters (octadecanoate, eicosanoate, docosanoate, tetracosanoate, hexacosanoate, octacosanoate and triacontanoate, in total 19.1-19.5%) were among the main constituents of both extracts. However, a number of differences were observed in the chemical composition of the 1 and 20 day extracts, the relative percentage of the iridoid Loganetin being the most striking (19.1 and 2.1%, respectively). To the best of our knowledge, this is the first report on the GC behavior of Loganetin. It seems that this and the long-chain fatty acid hexyl esters could have chemotaxonomic significance at the generic level.

Description

Loganetin is a non-toxic natural product that may be applied in the antibacterial drug development for treating multidrug-resistant Gram negative infections.

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