(-)-Loganin
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(-)-Loganin
structure -
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CAS No:
18524-94-2
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Formula:
C17H26O10
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Chemical Name:
(-)-Loganin
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Synonyms:
Cyclopenta[c]pyran-4-carboxylic acid,1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-,methyl ester,(1S,4aS,6S,7R,7aS)-;Loganin;Cyclopenta[c]pyran-4-carboxylic acid,1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-,methyl ester,[1S-(1α,4aα,6α,7α,7aα)]-;Cyclopenta[c]pyran-4-carboxylic acid,1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-,methyl ester;(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,6,7,7aα-hexahydro-6α-hydroxy-7α-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester;7-Hydroxy-6-desoxyverbenalin;Loganoside;(-)-Loganin;NSC 606403;1416-12-2;28629-68-7
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CAS No:
Description
Loganin, a major iridoid glycoside obtained from Corni fructus, has been shown to have anti-inflammatory and anti-shock effects. Loganin exhibits an anti-inflammatory effect in cases of AP and its pulmonary complications through inhibition of NF-κB activation.
Loganin is an iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflammatory properties. It has a role as a plant metabolite, a neuroprotective agent, an EC 3.4.23.46 (memapsin 2) inhibitor, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, an anti-inflammatory agent and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is a cyclopentapyran, a beta-D-glucoside, an enoate ester, a monosaccharide derivative, an iridoid monoterpenoid, a methyl ester and a secondary alcohol.
Characteristics
155
-1.4
White Powder
1.5±0.1 g/cm3
223 °C
608.8°C at 760 mmHg
217.9±25.0 °C
1.600
Keep container tightly closed.
2.31E-17mmHg at 25°C
D20 -82.1° (water)
195.65 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|194.4 Ų [M+Na]+
(-)-Loganin Use and Manufacturing
468 mg of compound 1 and 10 mL of CH3OH, were added to 20 mL of a CH2N2/Et2O solutiongiving a yellow cloudy mixture, and the mixture was left at room temperature for 20 minuntil slow complete decolouration. The reaction mixture was bubbled with CO2 for 10 minuntil complete removal of excess diazomethane . The crude product was purified by columnchromatography on silica gel (BuOHsat) to give 428 mg of an amorphous brown powder(87.9percent yield). 1H NMR- 13C NMR and ESI-MS data and spectra are shown in S1, S2 and S3.
An iridoid glycoside that exhibits protective effects against hepatic injury and other diabetic complications associated with abnormal metabolic states and inflammation caused by oxidative stress and advanced glycation endproduct formation. A potential an
Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Computed Properties
Molecular Weight:390.4
XLogP3:-1.4
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:5
Exact Mass:390.15259702
Monoisotopic Mass:390.15259702
Topological Polar Surface Area:155
Heavy Atom Count:27
Complexity:580
Defined Atom Stereocenter Count:10
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Contributes to dual regulation of energy metabolism enhancement and neuroprotection
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