L-Stepholidine

• CAS: 16562-13-3
• Catalog Number: ACM16562133
• Category: Main Products
• Molecular Weight: 327.4
• Molecular Formula: C19H21NO4
• Synonyms: 3,9-Dimethoxy-13a-alpha-berbine-2,10-diol
• InChI: InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
• InChI Key: JKPISQIIWUONPB-HNNXBMFYSA-N
• Melting Point: 120-122 °C
• Appearance: White to off-white crystalline powder
• Complexity: 447
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 2
• Isomeric SMILES: COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• Monoisotopic Mass: 327.14705815
• Physical State: Powder
• Rotatable Bond Count: 2
• Topological Polar Surface Area: 62.2 Ų

Case Study

Effects of L-Stepholidine on Memory Deficits and Synaptic Plasticity in Alzheimer's Disease Models

Hao, J. R., et al. Cell death & disease, 2015, 6(11), e1965-e1965.

Amyloid β-derived diffusible ligands (ADDLs) serve as key contributors to the onset of initial cognitive impairments in Alzheimer's disease (AD). The study focused on understanding how L-stepholamine (L-SPD) affects cognitive abilities and synaptic plasticity in APP and PS1 double transgenic (APP/PS1) mice and hippocampal cultures or slices that received ADDL treatment. L-Stepholidine demonstrated dopamine D1-type receptor agonist effects while simultaneously serving as a D2-type receptor antagonist.
Potential Mechanisms of L-Stepholidine in Treating AD
· L-SPD has the potential to enhance hippocampus-dependent memory, increase the surface expression of AMPA receptors containing glutamate receptor A (GluA1), and improve spine density in the hippocampus of APP/PS1 transgenic mice. It not only counteracted reductions in GluA1 phosphorylation and surface expression in hippocampal cultures but also preserved long-term potentiation in hippocampal slices triggered by ADDLs.
· Similarly, the PKA agonist Sp-cAMPS and the D1-type receptor agonist SKF81297 produced comparable effects, while the PKA antagonist Rp-cAMPS and the D1-type receptor antagonist SCH23390 negated the influence of L-SPD on GluA1 trafficking. This effect is primarily mediated by PKA, which phosphorylates the serine residue at position 845 of GluA1.
· Thus, The D1/PKA signaling pathway activation by L-SPD improves AMPA receptor trafficking and synaptic plasticity which makes it a candidate therapeutic drug for AD.

L-Stepholidine as a Potential Cognitive Enhancer

Hu, Zhengwei, et al. Biomedicines, 2024, 12(12), 2680.

L-Stepholidine (L-SPD) is a compound extracted from traditional Chinese medicine with potential for treating psychosis. The effects of L-SPD on executive function, working memory, and response inhibition, two core indicators of learning and memory, were studied here. This work confirmed that L-SPD can improve executive function, enhance memory, and upregulate the expression of glutamate receptors in PFC, providing clues for the treatment of psychotic cognitive dysfunction.
· Evaluation Methods
This work examined the effects of l-SPD on working memory through a delayed alternation T-maze task (DAT), assessed its influence on response inhibition via the stop-signal task (SST), and evaluated its impact on learning and memory through trace fear conditioning in Sprague-Dawley rats. Additionally, researchers assessed its effects on the expression of prefrontal glutamate receptors using western blot analysis.
· Evaluation Results
The rats treated with l-SPD showed a reduction in errors on the T-maze, increased speed in stopping their actions in response to the stop signal, and improved memory retention. Investigations into the underlying molecular mechanisms indicated that l-SPD enhances the expression of prefrontal glutamate receptors. Overall, these findings suggest that l-SPD enhances executive function and memory.

Custom Q&A

What is the molecular formula of l-Stepholidine?

The molecular formula of l-Stepholidine is C19H21NO4.

What are some synonyms for l-Stepholidine?

Some synonyms for l-Stepholidine include stepholidine, (-)-Stepholidine, and (S)-3,9-Dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,10-diol.

Where is l-Stepholidine found?

l-Stepholidine is a natural product found in Desmos cochinchinensis, Meiogyne monosperma, and other organisms.

What is the molecular weight of l-Stepholidine?

The molecular weight of l-Stepholidine is 327.4 g/mol.

What is the IUPAC name of l-Stepholidine?

The IUPAC name of l-Stepholidine is (13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol.

What is the InChI key of l-Stepholidine?

The InChI key of l-Stepholidine is JKPISQIIWUONPB-HNNXBMFYSA-N.

What is the canonical SMILES of l-Stepholidine?

The canonical SMILES of l-Stepholidine is COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O.

What is the CAS number of l-Stepholidine?

The CAS number of l-Stepholidine is 16562-13-3.

What is the XLogP3-AA value of l-Stepholidine?

The XLogP3-AA value of l-Stepholidine is 2.6.

Is l-Stepholidine a canonicalized compound?

Yes, l-Stepholidine is a canonicalized compound.