(-)-Huperzine a

• CAS: 102518-79-6
• Catalog Number: ACM102518796
• Category: Main Products
• Molecular Weight: 242.32
• Molecular Formula: C₁₅H₁₈N₂O
• Synonyms: (5r-(5-alpha,9-beta,11e))-ydro-7-methyl;5,9-methanocycloocta(b)pyridin-2(1h)-one,5-amino-11-ethylidene-5,6,9,10-tetrah;HUPERIZINE;(-)-HUPERZINE A FROM HUPERZIA SERRATA;HuperziaSerrateP.E120786-18-7/;Huperzine-A1-5%;HUP, [5R-(5a,911E)]-5-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2-(1H)-one, Selagine,;5,9-Methanocyclooctabpyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-
• IUPAC Name: huperzine A
• Boiling Point: 505ºC at 760 mmHg
• Melting Point: 211-216oC
• Flash Point: 259.2ºC
• Density: 1.2 g/cm³
• Appearance: white to slight white crystaline powder
• Exact Mass: 242.14200
• Hazard Statements: T+
• Safety Description: 26-36/37/39-45
• Supplemental Hazard Statements: H300
• Symbol: GHS06
• WGK Germany: 3

Case Study

Neuroprotective Effect of Huperzine A on Alzheimer's Disease

Friedli M J, et al. Molecules, 2021, 26(21), 6531.

Huperzine A (HupA) is an alkaloid found in Huperzia vulgaris that has the ability to inhibit the cholinergic enzyme acetylcholinesterase (AChE), acting as an acetylcholinesterase inhibitor (AChEI). Based on in vitro and in vivo studies, HupA exhibits neuroprotective effects against Alzheimer's disease (AD) through interactions with different molecular signaling pathways.
Neuroprotective Effects
· The neuroprotective effects of HupA in AD are attributed to its interaction with various molecular signaling pathways, including Wnt signaling, synaptic mechanisms, APP processing, Aβ accumulation, and mitochondrial protection.
· Modulation of Wnt signaling by HupA treatment may be the most promising therapeutic target because Wnt is involved in neuronal survival and synaptic plasticity. HupA affects canonical and noncanonical Wnt signaling. It regulates the Wnt/β-catenin pathway by downregulating GSK-3β activity and stabilizing β-catenin.

Retrosynthetic Analysis of Lycopod Alkaloid Huperzine A/B/U

Ding R, et al. The Journal of Organic Chemistry, 2014, 79(1), 240-250.

Huperzine A, huperzine B, and huperzine U are trace homologues isolated from the traditional Chinese medicine Huperzia serrata. Among them, Huperzine A is the most potent natural product with acetylcholinesterase (AChE) inhibitory activity. The retrosynthetic analysis process of huperzine A, huperzine B and huperzine U is introduced here.
Retrosynthetic Analysis
· It was envisioned that both the exocyclic olefinic bond in 1 and the piperidine ring in 2 and 3 could be traced back to an α-amino ketone function, and all of the Δ15(8) double bonds in 1-3 could stem from olefin isomerization of a Δ14(15) double bond, thus reducing targets 1-3 to a common precursor 6.
· The subsequent bond disconnection would allow 6 to be produced from 7 via an intramolecular Heck reaction, which entails a trans relative stereochemistry in 7. This defined stereochemistry could be created via diastereoselective alkylation of the key intermediate 9 with bromide 8.
· An unprecedented Buchwald-Hartwig coupling reaction of the simple α-trifloxy enone 10 with Boc-NH2 would generate 9. The chiral compound 10 was envisaged to stem from (R)- pulegone in a chiral-pool synthetic strategy.