Halenaquinone CAS No. 86690-14-4

Product Description

Halenaquinone is a bioactive marine-derived polycyclic quinone isolated primarily from sponges of the Xestospongia and Petrosia genera, exhibiting a range of pharmacological properties. Structurally characterized by a pentacyclic polyketide core with a quinone moiety, it demonstrates notable biological activities, including inhibition of phosphatidylinositol 3-kinase (PI3K; IC₅₀ 3 μM) and Ca²⁺ ATPase, induction of apoptosis (e.g., in PC12 cells, EC₅₀ 10 μM), and suppression of RANKL-induced osteoclastogenesis. Additionally, halenaquinone exhibits antibacterial effects against pathogens like Staphylococcus aureus and Escherichia coli at concentrations of 500–1000 μg/mL, as well as potential anti-infective properties by inhibiting sortase A (SrtA), thereby disrupting S. aureus virulence. Its broader therapeutic potential extends to hematological malignancies, where it acts as a histone deacetylase (HDAC) inhibitor, and to cancer research due to its antiproliferative and signal transduction-modulating effects.

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Product Use & Characteristics

Chemical Properties

• Molecular Formula: C₂₀H₁₂O₅

• Molecular Weight: 332.3 g/mol

• IUPAC Name: (1S)-1-methyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-2(11),3,6,9,13(20),15-hexaene-5,8,12,17-tetrone

• Structure: Polycyclic aromatic compound with fused rings and quinone moieties.

• Melting Point: >250°C

• Optical Rotation: [α]²².²° (c₀.₁₂₄, CH₂Cl₂)

• UV Spectrum (MeCN): λmax at 216 (ε 18100), 232 (sh, 16500), 253 (21600), 260 (sh, 20400), 278 (15900), and 325 (sh, 6000) nm.

Biological Activities

• Enzyme Inhibition:

  • Phosphatidylinositol 3-kinase (PI3K) inhibitor (IC₅₀: 3 μM).

  • Ca²⁺ ATPase inhibitor.

  • Protein tyrosine kinase inhibitor.

  • Sortase A (SrtA) inhibitor (blocks S. aureus virulence).

• Apoptosis Induction:

  • Induces apoptosis in PC12 cells (EC₅₀: 10 μM).

  • Inhibits RANKL-induced osteoclastogenesis.

• Antibacterial Activity:

  • Inhibits Staphylococcus aureus and Escherichia coli (1000–500 μg/mL).

• Anticancer Potential:

  • Antiproliferative effects on L1210 cells.

  • Inhibits RAD51-mediated homologous recombination, potentially suppressing tumor growth.

Source and Isolation

• Marine Sponges:

  • Xestospongia exigua (Okinawan sea sponge).

  • Petrosia alfiani, Haliclona spp.

• Extraction Methods:

  • Methanol maceration, followed by purification via vacuum liquid chromatography (VLC), radial chromatography (RC), and thin-layer chromatography (TLC).

Synthesis Methods

• Asymmetric Total Synthesis:

  • Developed by the Trauner group using an inverse-electron-demand Diels-Alder reaction of vinyl quinones.

  • Key steps: Diastereoselective intramolecular Heck cyclization and Diels-Alder cycloaddition.

Uses and Applications

• Cancer Research:

  • Potential therapeutic agent for hematological malignancies (e.g., leukemia, lymphoma).

  • RAD51 inhibitor, disrupting DNA repair in cancer cells.

• Antibacterial Agent:

  • Targets S. aureus by inhibiting SrtA, preventing bacterial adhesion.

• Neuropharmacology:

  • Apoptosis inducer in PC12 cells, useful for studying neuronal cell death pathways.

• Cardiotonic Activity:

  • Exhibits protein tyrosine kinase inhibitory effects, potentially beneficial for cardiovascular research.

Mechanism of Action

• PI3K Inhibition: Blocks Akt signaling, leading to apoptosis.

• RAD51 Inhibition: Specifically disrupts dsDNA binding, impairing homologous recombination repair.

• Antibacterial Action: Forms irreversible complexes with bacterial membrane proteins, causing cell lysis.

Derivatives and Structure-Activity Relationship

• Xestoquinone: Lacks the C-3 carbonyl group, showing reduced activity compared to halenaquinone.

• Key Functional Groups:

  • C-3 carbonyl and C-16 hydroxyl critical for SrtA inhibition.

Research Significance

• A promising lead compound for drug development due to its multifunctional bioactivity.

• Serves as a pharmacological tool for studying apoptosis, DNA repair, and bacterial virulence.

Why us!

Qingdao Sigma Chemical Co., Ltd., established in January 2017 and headquartered in Qingdao, China, is a reliable chemical supplier. Specializing in pharmaceuticals, biochemical intermediates, and research chemicals, the company offers a diverse product portfolio, including peptides (e.g., Tirzepatide, Semaglutide), nootropics, veterinary products, and APIs, often marketed with ≥99% purity and COA certification. We provides R&D, custom synthesis, and contract manufacturing services at various scales, while claiming a global export presence across 100+ countries. With international warehouses in the USA, Europe, Australia, and Canada, Qingdao Sigma Chemical also facilitates drop-shipping and reshipments, positioning itself as a key supplier for laboratory and research applications.