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Loganic acid

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-L2016

  • Specification : 98%

  • CAS number : 22255-40-9

  • Formula : C16H24O10

  • Molecular Weight : 376.36

  • PUBCHEM ID : 89640

  • Volume : 20mg

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Catalogue Number

BF-L2016

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

376.36

Appearance

Off-white crystalline powder

Botanical Source

Gentiana scabra,Gentiana macrophylla,Cyperus rotundus,Hydrangea macrophylla,Swertia macrosperma

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O

Synonyms

1-(Hexopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid/6-Hydroxy-7-methyl-1-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid/Loganic acid/Norloganin/Cyclopenta[c]pyran-4-carboxylic acid, 1-(hexopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-

IUPAC Name

(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Density

1.6±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

235.6±25.0 °C

Boiling Point

646.3±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1

InChl Key

JNNGEAWILNVFFD-CDJYTOATSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:22255-40-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29987205

Abstract

Obesity is caused by an excess storage of body fat, resulting from a chronic imbalance between energy intake and expenditure. Gentiana lutea L. (GL) root has been reported to reduce lipid accumulation in the aortic wall of diabetic rats. Here, we performed fractionation and isolation of the bioactive constituent(s) that may be responsible for the antiadipogenic effects of the GL root extract. A single compound, loganic acid, was identified as a candidate component in the 30% ethanol extract of GL. Loganic acid treatment significantly decreased the adipocyte differentiation of 3T3-L1 preadipocytes in a dose-dependent manner. The expression of key adipogenesis-related genes such as adiponectin (Adipoq), peroxisome proliferator-activated receptor gamma (Pparg), lipoprotein lipase (Lpl), perilipin1 (Plin1), fatty acid binding protein 4 (Fabp4), glucose transporter type 4 (Slc2a4), CCAAT/enhancer-binding protein alpha (Cebpa), and tumor necrosis factor-alpha (Tnf) were significantly reduced following treatment with loganic acid. In vivo experiments in an ovariectomy-induced obesity mouse model showed that loganic acid (oral administration with 10 and 50 mg/kg/day) significantly inhibited body weight gain, total fat increase, fatty hepatocyte deposition in the liver, and adipocyte enlargement in the abdominal visceral fat tissues. These results suggest that loganic acid in the GL root extract has antiadipogenic effects in vitro and in vivo. Loganic acid may be beneficial for the prevention and treatment of obesity, particularly in menopausal obese women.

KEYWORDS

3T3-L1 cell; Gentiana lutea L.; adipogenesis; loganic acid; obesity; ovariectomized mouse.

Title

Antiadipogenic Effects of Loganic Acid in 3T3-L1 Preadipocytes and Ovariectomized Mice

Author

Eunkuk Park 1 2 3 , Jeonghyun Kim 4 5 6 , Subin Yeo 7 8 , Gijeong Kim 9 10 , Eun-Hee Ko 11 12 , Sang Woo Lee 13 , Wan Yi Li 14 , Chun Whan Choi 15 , Seon-Yong Jeong 16 17 18

Publish date

2018 Jul

PMID

29790688

Abstract

Background: Cornelian cherry (Cornus mas L.) is a plant growing in southeast Europe, in the past used in folk medicine. There are many previous publications showing the preventive effects of (poly)phenolic compounds, especially anthocyanins, on cardiovascular diseases, but there is a lack of studies comparing the effects of (poly)phenolics and other constituents of fruits.
Objectives: We have attempted to determine if iridoids and anthocyanins from cornelian cherry fruits may affect the formation of atherosclerotic plaques in the aorta as well as lipid peroxidation and oxidative stress in the livers of cholesterol-fed rabbits.
Material and methods: Fractions of iridoids and anthocyanins were analyzed using the high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS) methods. Loganic acid (20 mg/kg b.w.) and a mixture of anthocyanins (10 mg/kg b.w.) were administered orally for 60 days to rabbits fed with 1% cholesterol. Histopathological samples of the aortas and the livers were stained with hematoxylin and eosin. Lipid peroxidation (malondialdehyde – MDA) and redox status (glutathione – GSH, glutathione peroxidase – Gpx and superoxide dismutase – SOD) were analyzed using spectrophotometrical methods.
Results: Both loganic acid (an iridoid) and a mixture of anthocyanins diminished the formation of atherosclerotic plaques in the aorta. Both substances also diminished lipid peroxidation, measured as a decrease of MDA, and attenuated oxidative stress, measured as an increase of GSH in the livers depleted by cholesterol feeding. Unexpectedly, cholesterol feeding decreased the Gpx activity in the liver, which was reversed by both investigated substances.
Conclusions: We have shown that both iridoids and anthocyanins help prevent fed-induced atherosclerosis, and the consumption of fruits rich in these substances may elicit beneficial effects on the cardiovascular system.

KEYWORDS

3T3-L1 cell; Gentiana lutea L.; adipogenesis; loganic acid; obesity; ovariectomized mouse.

Title

Loganic Acid and Anthocyanins From Cornelian Cherry (Cornus Mas L.) Fruits Modulate Diet-Induced Atherosclerosis and Redox Status in Rabbits

Author

Tomasz Sozański 1 , Alicja Z Kucharska 2 , Stanisław Dzimira 3 , Jan Magdalan 1 , Dorota Szumny 1 , Agnieszka Matuszewska 1 , Beata Nowak 1 , Narcyz Piorecki 4 5 , Adam Szelag 1 , Małgorzata Trocha 1

Publish date

2018 Nov

PMID

26124854

Abstract

One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important. The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated. Loganic acid (50%) and pelargonidin-3-galactoside (7%) were found as the main components. Among the other constituents, iridoid compound cornuside and the anthocyans cyanidin 3-O-galactoside, cyanidin 3-O-robinobioside, and pelargonidin 3-O-robinobioside were quantified in the fraction. In an animal model (New Zealand rabbits), the influence of loganic acid and the polyphenolic fraction isolated from Cornelian cherry fruit was investigated. We found a strong IOP-hypotensive effect for a 0.7% solution of loganic acid, which could be compared with the widely ophthalmologically used timolol. About a 25% decrease in IOP was observed within the first 3 hours of use.

Title

Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure

Author

Dorota Szumny 1 , Tomasz Sozański 2 , Alicja Z Kucharska 3 , Wojciech Dziewiszek 2 , Narcyz Piorecki 4 , Jan Magdalan 2 , Ewa Chlebda-Sieragowska 2 , Robert Kupczynski 5 , Adam Szelag 2 , Antoni Szumny 6

Publish date

2015


Description :

The protective effect of the Cornus mas fruits (cornelian cherry) on hypertriglyceridemia and atherosclerosis through PPARα activation in hypercholesterolemic rabbits. PUMID/DOI:25444446 Phytomedicine. 2014 Nov 15;21(13):1774-84. Cornelian cherry (Cornus mas L.) fruits have been used in traditional cuisine and in folk medicine in various countries. This study was conducted to evaluate the constituents and impact of cornelian cherry (C. mas L.) fruits lyophilisate on lipid levels, PPARα protein expression, atheromatous changes in the aorta, oxido-redox state, and proinflammatory cytokines in hypercholesterolemic rabbits. The HPLC-MS method was used for determining active constituents in cornelian cherry. In a subsequent in vivo study the protective effect of the cornelian cherry on diet-induced hyperlipidemia was studied using a rabbit model fed 1% cholesterol. Cornelian cherry (100mg/kg b.w.) or simvastatin (5mg/kg b.w.) were administered orally for 60 days. Two iridoids - Loganic acid and cornuside - and five anthocyanins were identified as the main constituents of the cornelian cherry. The administering of the cornelian cherry led to a 44% significant decrease in serum triglyceride levels, as well as prevented development of atheromatous changes in the thoracic aorta. Cornelian cherry significantly increased PPARα protein expression in the liver, indicating that its hypolipidemic effect may stem from enhanced fatty acid catabolism. Simvastatin treatment did not affect PPAR-α expression. Moreover, the cornelian cherry had a significant protective effect on diet-induced oxidative stress in the liver, as well as restored upregulated proinflammatory cytokines serum levels. In conclusion, we have shown Loganic acid to be the main iridoid constituent in the European cultivar of the cornelian cherry, and proven that the cornelian cherry could have protective effects on diet-induced hypertriglicerydemia and atherosclerosis through enhanced PPARα protein expression and via regulating oxidative stress and inflammation.