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The Intrinsic Apoptotic Pathway

The Intrinsic Apoptotic Pathway

Internal cellular stress, such as cellular injury or hypoxia, triggers intrinsic apoptosis. The B-cell lymphoma 2 (Bcl-2) family of proteins are the primary regulators of the intrinsic apoptotic pathway. For example, during DNA damage, checkpoint proteins, such as Ataxia Telangiectasia Mutated (ATM protein) and Checkpoints Factor-2 (Chk2) proteins, are activated. These proteins phosphorylate p53 which further activates pro-apoptotic proteins, such as Bax, Bak, PUMA, and Noxa, and inhibits...

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Synthesis of demethylxanthohumol, a new potent apoptosis-inducing agent from hops.

Reinhard A Diller¹, Herbert M Riepl, Oliver Rose

¹Institute of Technology for Biogenic Resources, Technical University of Munich, Petersgasse 18, D-94315 Straubing.

Chemistry & Biodiversity

|December 29, 2006

Summary

Researchers synthesized demethylxanthohumol, a hops-derived prenylchalcone, which showed significant antiproliferative effects. This compound also induced apoptosis in cancer cell lines, including Burkitt lymphoma and acute lymphoblastic leukemia.

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Area of Science:

Natural Product Chemistry
Medicinal Chemistry
Cancer Biology

Background:

Xanthohumol, a prenylchalcone from hops (Humulus lupulus), possesses various biological activities.
Derivatives of xanthohumol are being explored for enhanced therapeutic potential.
The 6'-O-methyl group in xanthohumol can influence its properties.

Purpose of the Study:

To synthesize demethylxanthohumol (4), a novel xanthohumol derivative lacking the 6'-O-methyl group.
To evaluate the antiproliferative and apoptotic effects of demethylxanthohumol (4) in cancer cell lines.

Main Methods:

Synthesis of demethylxanthohumol (4) via aldol condensation of MOM-protected acetophenone (2) and MOM-protected benzaldehyde (3).
Starting material: Commercially available phloracetophenone (1-(2,4,6-trihydroxyphenyl)ethanone).
Assessment of antiproliferative activity and apoptosis induction in BJAB cells and primary lymphoblasts from childhood acute lymphoblastic leukemia (ALL).

Main Results:

Successful synthesis of demethylxanthohumol (4).
Demethylxanthohumol (4) demonstrated significant antiproliferative properties.
Demethylxanthohumol (4) induced apoptosis through the mitochondrial pathway in BJAB cells and ALL lymphoblasts.

Conclusions:

Demethylxanthohumol (4) is a potent antiproliferative agent.
The compound effectively induces apoptosis in B-cell lymphoma and leukemia cell lines.
This derivative represents a promising lead compound for cancer therapy development.