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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H26O10
Molecular Weight 390.383
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOGANIN

SMILES

C[C@@]1([H])[C@]([H])(C[C@]2([H])C(=CO[C@]([H])([C@]12[H])O[C@@]3([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O3)O)O)O)C(=O)OC)O

InChI

InChIKey=AMBQHHVBBHTQBF-UOUCRYGSSA-N
InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H26O10
Molecular Weight 390.383
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/13498714 | https://www.ncbi.nlm.nih.gov/pubmed/11945749 | https://www.ncbi.nlm.nih.gov/pubmed/26407655 | https://www.ncbi.nlm.nih.gov/pubmed/27241020

Loganin was found in parts of some trees and shrubs including bark of Mastixia arborea (Cornaceae family), Corni fructus and A. boonei (Apocynaceae), a West African herbal medicinal plant traditionally used for its antimalarial, aphrodisiac, antidiabetic, antimicrobial properties. A key intermediate in the biosynthesis of indole alkaloids loganin was synthesized in 1971 by carboxyl group methylation of loganic acid. It has been shown, that loganin possesses anti-shock effects, anti-oxidant, glucose-lowering and neuroprotective properties. Loganin exhibits an anti-inflammatory effect in cases of acute pancreatitis and its pulmonary complications through inhibition of NF-κB activation. It is an active ingredient of a new herbal formula KBMSI-2 which has been through Phase 4 clinical trial for the efficacy and safety in the treatment of Erectile Dysfunction. Loganin inhibits β-secretase in vitro and increases performance in Morris water maze and Y-maze tests in vivo, suggesting potential benefit in memory impairment and Alzheimer’s disease. In addition, it also modulates ERK signaling to decrease connective tissue growth factor (CTGF) and downregulates expression of MCP-1, NF-κB, and iNOS in animal models. Inhibition of CTGF may be a potential target in diabetic nephropathy (DN) therapy, which highlights the possibility of using loganin to treat DN.

CNS Activity

Curator's Comment:: Known to be CNS non-penetrant in rats. Human data not available. It was indicated that kidney was the major distribution tissue of loganin in rats, and that loganin had difficulty in crossing the blood-brain barrier.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Determination of glycosides in traditional Chinese medicine liu-wei di-huang by RP-HPLC].
2003 Aug
[Studies on pharmacokinetics of loganin and morroniside in Cornus officinalis injection in mice].
2003 Jun
Metabolomic analysis of Strychnos nux-vomica, Strychnos icaja and Strychnos ignatii extracts by 1H nuclear magnetic resonance spectrometry and multivariate analysis techniques.
2004 Jul
[Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].
2005 Jan
A comparative chemotaxonomic study on Vinca sardoa steam and Vinca difformis pourret.
2005 Sep
Morroniside and loganin extracted from Cornus officinalis have protective effects on rat mesangial cell proliferation exposed to advanced glycation end products by preventing oxidative stress.
2006 Dec
Effects of terpenoid precursor feeding on Catharanthus roseus hairy roots over-expressing the alpha or the alpha and beta subunits of anthranilate synthase.
2006 Feb 20
[Function of getting rid of cores of Cornus officinalis Sieb. et Zucc. and studies on method of processing in producing area].
2006 Jan
Precursor limitations in methyl jasmonate-induced Catharanthus roseus cell cultures.
2006 Jun
[A new indole alkaloid glycoside from stems of Nauclea officinalis].
2006 Nov
HPLC study of tissue distribution of loganin in rats.
2006 Oct
[Terpenoid glycosides from stem of Luculia pinceana].
2007 Dec
Simultaneous quantification of seven bioactive components in Caulis Lonicerae Japonicae by high performance liquid chromatography.
2007 Jun
UV-B-induced signaling events leading to enhanced-production of catharanthine in Catharanthus roseus cell suspension cultures.
2007 Nov 7
Quantitative and qualitative determination of Liuwei Dihuang tablets by HPLC-UV-MS-MS.
2007 Sep
Simultaneous determination of four bioactive constituents in Liuwei Dihuang Pills by micellar electrokinetic chromatography.
2007 Sep 3
The inhibitory effect of the components of Cornus officinalis on melanogenesis.
2007 Sep-Oct
Microbial metabolism of loganin by intestinal bacteria and identification of new metabolites in rat.
2008 Apr
[Investigation of JinKui ShenQi pills by ultraviolet spectra and tandem mass spectrometry].
2008 Aug
An approach based on HPLC-fingerprint and chemometrics to quality consistency evaluation of Liuwei Dihuang Pills produced by different manufacturers.
2008 Dec 1
[Studies on absorption mechanism of loganin in intestines of rats].
2008 May
Iridoidic pattern in endemic Sardinian plants: the case of Galium species.
2008 May 10
Fructus Corni suppresses hepatic gluconeogenesis related gene transcription, enhances glucose responsiveness of pancreatic beta-cells, and prevents toxin induced beta-cell death.
2008 May 22
[Determination of loganin and paeonol in Liuwei Dihuang pills by HPLC amalgamated of double UV waves].
2008 Oct
[Promoting effect of constituents in plasma after oral administration of liuwei dihuangwan on proliferation of rat osteoblast].
2008 Sep
Phenolic and bis-iridoid glycosides from Strychnos cocculoides.
2009
Iridoids from Gentiana loureirii.
2009 Apr
Chemical fingerprinting of Liuwei Dihuang Pill and simultaneous determination of its major bioactive constituents by HPLC coupled with multiple detections of DAD, ELSD and ESI-MS.
2009 Apr 5
Cornel iridoid glycoside promotes neurogenesis and angiogenesis and improves neurological function after focal cerebral ischemia in rats.
2009 Apr 6
Comparative 454 pyrosequencing of transcripts from two olive genotypes during fruit development.
2009 Aug 26
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
2009 Dec
Determination of sweroside in rat plasma and bile for oral bioavailability and hepatobiliary excretion.
2009 Jan
Isolation and identification of hemostatic ingredients from Lamiophlomis rotata (Benth.) Kudo.
2009 Jun
Cognitive-enhancing activity of loganin isolated from Cornus officinalis in scopolamine-induced amnesic mice.
2009 May
Preparative purification of morroniside and loganin from Fructus corni by combination of macroporous absorption resin and HSCCC.
2009 May-Jun
Loganin improves learning and memory impairments induced by scopolamine in mice.
2009 Oct 1
Assessing the limitations to terpenoid indole alkaloid biosynthesis in Catharanthus roseus hairy root cultures through gene expression profiling and precursor feeding.
2009 Sep-Oct
Anti-inflammatory and analgesic activities of SKLJI, a highly purified and injectable herbal extract of Lonicera japonica.
2010
Simultaneous determination of four marker components in Yukmijihwang Tang by high performance liquid chromatography/diode array detector.
2010 Apr
Cell-specific expression of tryptophan decarboxylase and 10-hydroxygeraniol oxidoreductase, key genes involved in camptothecin biosynthesis in Camptotheca acuminata Decne (Nyssaceae).
2010 Apr 19
Oleuropein in olive and its pharmacological effects.
2010 Apr-Jun
Bioactive constituents of Corni Fructus: The therapeutic use of morroniside, loganin, and 7-O-galloyl-D-sedoheptulose as renoprotective agents in type 2 diabetes.
2010 Aug
[Study on the best concentration of combination of the effects of the four original constituents of liu-wei di-huang pill on the proliferation and differentiation of rat preadipocyte].
2010 Dec
Evaluation of loganin, iridoid glycoside from Corni Fructus, on hepatic and renal glucolipotoxicity and inflammation in type 2 diabetic db/db mice.
2010 Dec 1
Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii.
2010 Mar
Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro.
2010 Mar
The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of α,β-unsaturated enol esters.
2010 Nov 5
The pharmacological effects of morroniside and loganin isolated from Liuweidihuang Wan, on MC3T3-E1 cells.
2010 Oct 21
Comparison of 454-ESTs from Huperzia serrata and Phlegmariurus carinatus reveals putative genes involved in lycopodium alkaloid biosynthesis and developmental regulation.
2010 Sep 21
Hepato-protective effects of loganin, iridoid glycoside from Corni Fructus, against hyperglycemia-activated signaling pathway in liver of type 2 diabetic db/db mice.
2011 Nov 28
Patents

Sample Use Guides

Two KBMSI-2 capsules (6 gm/capsule) daily at least 1 hour after food intake for 8 weeks for the treatment of Erectile Dysfunction. Capsule contain loganin 744.13ug/g in combination with ginsenoside-Rb1 260.53ug/g, -Rb2 543.91ug/g, -Rc 424.92ug/g, -Re 377.32ug/g, -Rf 1160.55ug/g, -Rg1 703.97ug/g, Curcumin 60.73ug/g, Allantoin 98.66ug.g
Route of Administration: Oral
Potential protective effects of loganin on spinal muscular atrophy (SMA) was studied using two cellular models, SMN-deficient NSC34 cells and SMA patient fibroblasts. In SMN-deficient NSC34 cells, loganin increased cell viability, neurite length, and expressions of SMN, Gemin2, SMN-Gemin2 complex, p-Akt, p-GSK-3β, p-CREB, BDNF and Bcl-2. In SMA patient fibroblasts, loganin up-regulated levels of SMN, FL-SMN2, and Gemins, increased numbers of SMN-containing nuclear gems, modulated splicing factors, and up-regulated p-Akt.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:22:05 UTC 2021
Edited
by admin
on Sat Jun 26 16:22:05 UTC 2021
Record UNII
H7WJ16Q93C
Record Status Validated (UNII)
Record Version
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Name Type Language
LOGANIN
MI  
Common Name English
METHYL (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLATE
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-
Common Name English
(-)-LOGANIN
Common Name English
LOGANIN, (-)-
Common Name English
7-HYDROXY-6-DESOXYVERBENALIN
Common Name English
NSC-606403
Code English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S,4AS,6S,7R,7AS)-
Common Name English
LOGANOSIDE
Common Name English
LOGANIN [MI]
Common Name English
(1S)-1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER
Common Name English
Code System Code Type Description
FDA UNII
H7WJ16Q93C
Created by admin on Sat Jun 26 16:22:05 UTC 2021 , Edited by admin on Sat Jun 26 16:22:05 UTC 2021
PRIMARY
MERCK INDEX
M6887
Created by admin on Sat Jun 26 16:22:05 UTC 2021 , Edited by admin on Sat Jun 26 16:22:05 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
Loganin
Created by admin on Sat Jun 26 16:22:05 UTC 2021 , Edited by admin on Sat Jun 26 16:22:05 UTC 2021
PRIMARY
ECHA (EC/EINECS)
242-398-0
Created by admin on Sat Jun 26 16:22:05 UTC 2021 , Edited by admin on Sat Jun 26 16:22:05 UTC 2021
PRIMARY
PUBCHEM
87691
Created by admin on Sat Jun 26 16:22:05 UTC 2021 , Edited by admin on Sat Jun 26 16:22:05 UTC 2021
PRIMARY
CAS
18524-94-2
Created by admin on Sat Jun 26 16:22:05 UTC 2021 , Edited by admin on Sat Jun 26 16:22:05 UTC 2021
PRIMARY
Related Record Type Details
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