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Chemical Structure| 18524-94-2 Chemical Structure| 18524-94-2

Structure of Loganin
CAS No.: 18524-94-2

Chemical Structure| 18524-94-2

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Loganin is a naturally occuring iridoid glycoside with antioxidant, hepatoprotective and neuroprotective effects, as well as a COX-1 inhbitor with IC50 value of 3.55 µM, suppressing the formation of TNF-α, and diminishing the production of nitric oxide.

Synonyms: Loganoside; NSC 606403; 7-hydroxy-6-desoxy Verbenalin

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Product Citations

Product Citations

Krueger, Nadine ; Kronenberger, Thales ; Xie, Hang ; Rocha, Cheila ; Poehlmann, Stefan ; Su, Haixia , et al.

Abstract: The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has forced the development of direct-acting antiviral drugs due to the coronavirus disease 2019 (COVID-19) pandemic. The main protease of SARS-CoV-2 is a crucial enzyme that breaks down polyproteins synthesized from the viral RNA, making it a validated target for the development of SARS-CoV-2 therapeutics. New chem. phenotypes are frequently discovered in natural goods. In the current study, we used a fluorogenic assay to test a variety of natural products for their ability to inhibit SARS-CoV-2 Mpro. Several compounds were discovered to inhibit Mpro at low micromolar concentrations It was possible to crystallize robinetin together with SARS-CoV-2 Mpro, and the X-ray structure revealed covalent interaction with the protease's catalytic Cys145 site. Selected potent mols. also exhibited antiviral properties without cytotoxicity. Some of these powerful inhibitors might be utilized as lead compounds for future COVID-19 research.

Keywords: COVID-19 ; antivirals ; coronavirus ; covalent drugs ; dynamic light scattering ; inhibitors ; main protease ; natural products

Alternative Products

Product Details of Loganin

CAS No. :18524-94-2
Formula : C17H26O10
M.W : 390.38
SMILES Code : O=C(C1=CO[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)[C@@]3([H])[C@]1([H])C[C@H](O)[C@@H]3C)OC
Synonyms :
Loganoside; NSC 606403; 7-hydroxy-6-desoxy Verbenalin
MDL No. :MFCD00075645
InChI Key :AMBQHHVBBHTQBF-UOUCRYGSSA-N
Pubchem ID :87691

Safety of Loganin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Isoform Comparison

Biological Activity

Target
  • AChE

    AChE, IC50:3.95 μM

In Vitro:

Cell Line
Concentration Treated Time Description References
Transgenic cell line S10 200 μM 14 days To investigate the effect of continuous loganin supply on TIA accumulation, results showed that continuous loganin supply significantly increased TIA content but had no significant effect on TDC activity. Plant Physiol. 1998 Feb 1;116(2):853-7
Transgenic cell line S10 500 μM 3 days or 3 days To study the effect of loganin on TIA content, results showed that exogenous loganin significantly increased TIA content while depleting tryptamine content. Plant Physiol. 1998 Feb 1;116(2):853-7
BEnd.3 cells 6.25 µM 24 hours Evaluate the cytotoxicity of LA-1 and loganin on BEnd.3 cells, results showed LA-1 did not exhibit significant cytotoxicity under the given conditions Antioxidants (Basel). 2024 Nov 1;13(11):1339
Rat Schwann cell line RSC96 0.1, 1, 10, 25, 50 μM 48 hours Loganin pretreatment attenuated high glucose-induced RSC96 cell viability loss, ROS generation, NF-κB nuclear translocation, P2X7 purinergic receptor and TXNIP expression, NLRP3 inflammasome activation, IL-1β and IL-18 maturation, and gasdermin D cleavage. Cells. 2020 Aug 23;9(9):1948
SH-SY5Y cells 10 μM 24 hours Loganin attenuates high glucose-induced SH-SY5Y cell pyroptosis by inhibiting ROS generation and NLRP3 inflammasome activation, improving cell viability. Cells. 2021 Oct 8;10(10):2688
Mouse bone marrow monocytes 1, 5, 10 μM 5 days To investigate the effect of Loganin on the differentiation of mouse bone marrow monocytes. Results showed that Loganin treatment significantly decreased TRAP activity and the number of TRAP-positive multinucleated cells, indicating that Loganin inhibited osteoclast differentiation. Int J Mol Sci. 2022 Nov 16;23(22):14128
Mouse preosteoblast MC3T3-E1 cells 1, 5, 10 μM 3 days To investigate the effect of Loganin on the differentiation of mouse preosteoblasts. Results showed that Loganin treatment increased ALP activity and the number of ALP-positive cells, indicating that Loganin promoted osteoblast differentiation. Int J Mol Sci. 2022 Nov 16;23(22):14128
Adipose-derived stem cells (ADSCs) 2, 5, 10 μM 8 days Loganin reduced mRNA expression levels of Pparγ, Cebpa, Plin2, Fasn, and Srebp1 and decreased the number of oil Red O-positive cells. Int J Mol Sci. 2023 Mar 1;24(5):4752
3T3-L1 mouse preadipocytes 2, 5, 10 μM 8 days Loganin significantly decreased the mRNA expression levels of Pparg, Cebpa, Plin2, Fasn, and Srebp1 in a dose-dependent manner and reduced the number of oil Red O-positive cells. Int J Mol Sci. 2023 Mar 1;24(5):4752

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Sprague Dawley (SD) rats STZ-NA-induced diabetic neuropathy model Intraperitoneal injection 5 mg/kg Once daily for 4 weeks Loganin improved pain behaviors (allodynia and hyperalgesia), insulin resistance index (HOMA-IR), and serum levels of superoxide dismutase (SOD), catalase, and glutathione in diabetic neuropathic pain rats. Loganin also reduced the expression of pain-associated channel protein CaV3.2 and calcitonin gene-related peptide (CGRP) in the superficial spinal dorsal horn of PDN rats. Cells. 2021 Oct 8;10(10):2688
DdY mice Ovariectomy-induced osteoporosis model Oral 2, 10, 50 mg/kg/day Once daily for 12 weeks To investigate the effect of Loganin on ovariectomy-induced osteoporosis. Results showed that Loganin treatment prevented BMD loss, improved trabecular microstructure, and increased the serum OPG/RANKL ratio, indicating that Loganin has anti-osteoporotic effects. Int J Mol Sci. 2022 Nov 16;23(22):14128
Sprague-Dawley rats Chronic constriction injury (CCI) model Intraperitoneal injection 5 mg/kg/day Once daily for 7 days Loganin alleviates CCI-induced neuropathic pain by modulating autophagic flux and reducing neuroinflammation and apoptosis Int J Mol Sci. 2022 Dec 14;23(24):15873
C57BL/6 mice Cisplatin-induced acute kidney injury model Oral 1, 10, and 20 mg/kg Administered 1 h before cisplatin injection and lasted for 72 hours Loganin attenuates the severity of cisplatin-induced acute kidney injury by inhibiting ERK1/2 activation Int J Mol Sci. 2021 Jan 31;22(3):1421
Mice OVX- and high-fat diet (HFD)-induced obesity models Oral 2 and 10 mg/kg/day 12 weeks Loganin prevented weight gain induced by OVX and HFD, reduced hepatic steatosis and adipocyte enlargement, and decreased plasma leptin and insulin levels. Int J Mol Sci. 2023 Mar 1;24(5):4752

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.56mL

0.51mL

0.26mL

12.81mL

2.56mL

1.28mL

25.62mL

5.12mL

2.56mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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