Loganin | CAS#18524-94-2 | β-secretase inhibitor

MedKoo Cat#: 540272 | Name: Loganin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Loganin is an inhibitor of β-secretase found in Cornus officialis. It improves memory impairment, downregulates expression of MCP-1, NF-χB, and iNOS, and modulates ERK signaling.

Chemical Structure

Loganin

CAS#18524-94-2

Theoretical Analysis

MedKoo Cat#: 540272

Name: Loganin

CAS#: 18524-94-2

Chemical Formula: C17H26O10

Exact Mass: 390.1526

Molecular Weight: 390.39

Elemental Analysis: C, 52.30; H, 6.71; O, 40.98

Price and Availability

Size	Price	Availability
50mg	USD 250.00	2 weeks
100mg	USD 400.00	2 weeks
250mg	USD 750.00	2 weeks

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Related CAS #

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Synonym

Loganin

IUPAC/Chemical Name

methyl (1S,4aR,6R,7S,7aR)-6-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

InChi Key

AMBQHHVBBHTQBF-CBQOGAMZSA-N

InChi Code

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+/m1/s1

SMILES Code

O=C(C1=CO[C@@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@]3([H])[C@@]1([H])C[C@@H](O)[C@H]3C)OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Loganin, a major iridoid glycoside obtained from Corni fructus, has been shown to have anti-inflammatory and anti-shock effects.

In vitro activity:

For BACE1, loganin showed noncompetitive type inhibitory effects, while morroniside and 7-O-galloyl-D-sedoheptulose were found to be mixed inhibitors. Loganin was the most potent inhibitor against both ChEs and BACE1. Reference: Arch Pharm Res. 2016 Jun;39(6):794-805. https://pubmed.ncbi.nlm.nih.gov/27106028/

In vivo activity:

Pre-treatment of loganin reduced pancreatic damage and AP-associated lung injury in mice and attenuated the severity of AP, as evidenced by (1) a reduction in several biochemical parameters (pancreatic weight to body weight ratio, myeloperoxidase activity, and level of amylase) and (2) production of pro-inflammatory cytokines such as interleukin (IL)-1β and tumor necrosis factor (TNF)-α. Reference: Eur J Pharmacol. 2015 Oct 15;765:541-50. https://pubmed.ncbi.nlm.nih.gov/26407655/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	38.42
	DMSO	46.0	117.83
	PBS (pH 7.2)	10.0	25.62

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 390.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bhakta HK, Park CH, Yokozawa T, Min BS, Jung HA, Choi JS. Kinetics and molecular docking studies of loganin, morroniside and 7-O-galloyl-D-sedoheptulose derived from Corni fructus as cholinesterase and β-secretase 1 inhibitors. Arch Pharm Res. 2016 Jun;39(6):794-805. doi: 10.1007/s12272-016-0745-5. Epub 2016 Apr 22. PMID: 27106028. 2. Li M, Wang W, Wang P, Yang K, Sun H, Wang X. The pharmacological effects of morroniside and loganin isolated from Liuweidihuang Wan, on MC3T3-E1 cells. Molecules. 2010 Oct 21;15(10):7403-14. doi: 10.3390/molecules15107403. PMID: 20966881; PMCID: PMC6259177. 3. Tsai WH, Wu CH, Cheng CH, Chien CT. Ba-Wei-Di-Huang-Wan through its active ingredient loganin counteracts substance P-enhanced NF-κB/ICAM-1 signaling in rats with bladder hyperactivity. Neurourol Urodyn. 2016 Sep;35(7):771-9. doi: 10.1002/nau.22816. Epub 2015 Aug 19. PMID: 26287995. 4. Kim MJ, Bae GS, Jo IJ, Choi SB, Kim DG, Shin JY, Lee SK, Kim MJ, Shin S, Song HJ, Park SJ. Loganin protects against pancreatitis by inhibiting NF-κB activation. Eur J Pharmacol. 2015 Oct 15;765:541-50. doi: 10.1016/j.ejphar.2015.09.019. Epub 2015 Sep 25. PMID: 26407655.

In vitro protocol:

In vivo protocol:

1. Tsai WH, Wu CH, Cheng CH, Chien CT. Ba-Wei-Di-Huang-Wan through its active ingredient loganin counteracts substance P-enhanced NF-κB/ICAM-1 signaling in rats with bladder hyperactivity. Neurourol Urodyn. 2016 Sep;35(7):771-9. doi: 10.1002/nau.22816. Epub 2015 Aug 19. PMID: 26287995. 2. Kim MJ, Bae GS, Jo IJ, Choi SB, Kim DG, Shin JY, Lee SK, Kim MJ, Shin S, Song HJ, Park SJ. Loganin protects against pancreatitis by inhibiting NF-κB activation. Eur J Pharmacol. 2015 Oct 15;765:541-50. doi: 10.1016/j.ejphar.2015.09.019. Epub 2015 Sep 25. PMID: 26407655.

1: Kim MJ, Bae GS, Jo IJ, Choi SB, Kim DG, Shin JY, Lee SK, Kim MJ, Shin S, Song HJ, Park SJ. Loganin protects against pancreatitis by inhibiting NF-κB activation. Eur J Pharmacol. 2015 Oct 15;765:541-50. doi: 10.1016/j.ejphar.2015.09.019. Epub 2015 Sep 25. PubMed PMID: 26407655. 2: Kim H, Youn K, Ahn MR, Kim OY, Jeong WS, Ho CT, Jun M. Neuroprotective effect of loganin against Aβ25-35-induced injury via the NF-κB-dependent signaling pathway in PC12 cells. Food Funct. 2015 Apr;6(4):1108-16. doi: 10.1039/c5fo00055f. PubMed PMID: 25778782. 3: Liu K, Xu H, Lv G, Liu B, Lee MK, Lu C, Lv X, Wu Y. Loganin attenuates diabetic nephropathy in C57BL/6J mice with diabetes induced by streptozotocin and fed with diets containing high level of advanced glycation end products. Life Sci. 2015 Feb 15;123:78-85. doi: 10.1016/j.lfs.2014.12.028. Epub 2015 Jan 23. PubMed PMID: 25623853. 4: Liu XD, Huang P, Lu YH, Ma M, Zhou RB, Yuan LX, Peng XJ. [Pharmacokinetics of loganin, ferulic acid and stilbene glucoside in Bushen Tongluo formula in vivo]. Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(12):2428-34. Chinese. PubMed PMID: 26591537. 5: Babri S, Hasani Azami S, Mohaddes G. Effect of Acute Administration of loganin on Spatial Memory in Diabetic Male Rats. Adv Pharm Bull. 2013;3(1):91-5. doi: 10.5681/apb.2013.015. Epub 2013 Feb 7. PubMed PMID: 24312818; PubMed Central PMCID: PMC3846062. 6: Li Y, Li Z, Shi L, Zhao C, Shen B, Tian Y, Feng H. Loganin inhibits the inflammatory response in mouse 3T3L1 adipocytes and mouse model. Int Immunopharmacol. 2016 Jul;36:173-179. doi: 10.1016/j.intimp.2016.04.026. Epub 2016 May 4. PubMed PMID: 27155393. 7: Lee CM, Jung HA, Oh SH, Park CH, Tanaka T, Yokozawa T, Choi JS. Kinetic and molecular docking studies of loganin and 7-O-galloyl-D-sedoheptulose from Corni Fructus as therapeutic agents for diabetic complications through inhibition of aldose reductase. Arch Pharm Res. 2015 Jun;38(6):1090-8. doi: 10.1007/s12272-014-0493-3. Epub 2014 Oct 15. PubMed PMID: 25315636. 8: Jiang WL, Zhang SP, Hou J, Zhu HB. Effect of loganin on experimental diabetic nephropathy. Phytomedicine. 2012 Feb 15;19(3-4):217-22. doi: 10.1016/j.phymed.2011.08.064. Epub 2011 Oct 5. PubMed PMID: 21978885. 9: Berger A, Kostyan MK, Klose SI, Gastegger M, Lorbeer E, Brecker L, Schinnerl J. Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae). Phytochemistry. 2015 Aug;116:162-9. doi: 10.1016/j.phytochem.2015.05.013. Epub 2015 Jun 1. PubMed PMID: 26043882. 10: Youn K, Jeong WS, Jun M. β-Secretase (BACE1) inhibitory property of loganin isolated from Corni fructus. Nat Prod Res. 2013;27(16):1471-4. doi: 10.1080/14786419.2012.718774. Epub 2012 Aug 29. PubMed PMID: 22931211. 11: Kwon SH, Kim JA, Hong SI, Jung YH, Kim HC, Lee SY, Jang CG. Loganin protects against hydrogen peroxide-induced apoptosis by inhibiting phosphorylation of JNK, p38, and ERK 1/2 MAPKs in SH-SY5Y cells. Neurochem Int. 2011 Mar;58(4):533-41. doi: 10.1016/j.neuint.2011.01.012. Epub 2011 Jan 15. PubMed PMID: 21241762. 12: Park CH, Tanaka T, Kim JH, Cho EJ, Park JC, Shibahara N, Yokozawa T. Hepato-protective effects of loganin, iridoid glycoside from Corni Fructus, against hyperglycemia-activated signaling pathway in liver of type 2 diabetic db/db mice. Toxicology. 2011 Nov 28;290(1):14-21. doi: 10.1016/j.tox.2011.08.004. Epub 2011 Aug 12. PubMed PMID: 21864639. 13: Bhakta HK, Park CH, Yokozawa T, Min BS, Jung HA, Choi JS. Kinetics and molecular docking studies of loganin, morroniside and 7-O-galloyl-D-sedoheptulose derived from Corni fructus as cholinesterase and β-secretase 1 inhibitors. Arch Pharm Res. 2016 Jun;39(6):794-805. doi: 10.1007/s12272-016-0745-5. Epub 2016 Apr 22. PubMed PMID: 27106028. 14: He K, Song S, Zou Z, Feng M, Wang D, Wang Y, Li X, Ye X. The Hypoglycemic and Synergistic Effect of Loganin, Morroniside, and Ursolic Acid Isolated from the Fruits of Cornus officinalis. Phytother Res. 2016 Feb;30(2):283-91. doi: 10.1002/ptr.5529. Epub 2015 Dec 1. PubMed PMID: 26619955. 15: Tan D, Gu R, Zhang Y, Meng X, Lai X. [Determination of loganin in Pterocephalus hookeri by HPLC]. Zhongguo Zhong Yao Za Zhi. 2011 Dec;36(24):3472-4. Chinese. PubMed PMID: 22368859. 16: Tsai WH, Wu CH, Cheng CH, Chien CT. Ba-Wei-Di-Huang-Wan through its active ingredient loganin counteracts substance P-enhanced NF-κB/ICAM-1 signaling in rats with bladder hyperactivity. Neurourol Urodyn. 2016 Sep;35(7):771-9. doi: 10.1002/nau.22816. Epub 2015 Aug 19. PubMed PMID: 26287995. 17: Zhao M, Tao J, Qian D, Liu P, Shang EX, Jiang S, Guo J, Su SL, Duan JA, Du L. Simultaneous determination of loganin, morroniside, catalpol and acteoside in normal and chronic kidney disease rat plasma by UPLC-MS for investigating the pharmacokinetics of Rehmannia glutinosa and Cornus officinalis Sieb drug pair extract. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jan 15;1009-1010:122-9. doi: 10.1016/j.jchromb.2015.12.020. Epub 2015 Dec 14. PubMed PMID: 26720701. 18: Kwon SH, Kim HC, Lee SY, Jang CG. Loganin improves learning and memory impairments induced by scopolamine in mice. Eur J Pharmacol. 2009 Oct 1;619(1-3):44-9. doi: 10.1016/j.ejphar.2009.06.062. Epub 2009 Aug 7. PubMed PMID: 19666019. 19: Yamabe N, Noh JS, Park CH, Kang KS, Shibahara N, Tanaka T, Yokozawa T. Evaluation of loganin, iridoid glycoside from Corni Fructus, on hepatic and renal glucolipotoxicity and inflammation in type 2 diabetic db/db mice. Eur J Pharmacol. 2010 Dec 1;648(1-3):179-87. doi: 10.1016/j.ejphar.2010.08.044. Epub 2010 Sep 15. PubMed PMID: 20826139. 20: Hwang ES, Kim HB, Lee S, Kim MJ, Lee SO, Han SM, Maeng S, Park JH. Loganin enhances long-term potentiation and recovers scopolamine-induced learning and memory impairments. Physiol Behav. 2017 Mar 15;171:243-248. doi: 10.1016/j.physbeh.2016.12.043. Epub 2017 Jan 6. PubMed PMID: 28069458.