Triphenylphosphonium Analogues of Betulin and Betulinic Acid with Biological Activity: A Comprehensive Review.

doi:10.1021/acs.jnatprod.8b00830

Paper

Triphenylphosphonium Analogues of Betulin and Betulinic Acid with Biological Activity: A Comprehensive Review.

Published May 29, 2019 · M. Grymel, Mateusz Zawojak, J. Adamek

Journal of natural products

Q1 SJR score

48

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1

Influential Citations

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Abstract

Naturally occurring pentacyclic lupane triterpenoids such as betulin (1) or betulinic acid (2) and their synthetic derivatives display a broad spectrum of biological activities and, therefore, have been the subject of great interest. However, the use of these compounds as potential therapeutic agents is limited by their low bioavailability, high hydrophobicity, and insufficient intracellular accumulation. In this context, research on modifications of the parent structures that will improve their pharmacokinetic properties is particularly important. In the past few years, methods of synthesis as well as cytotoxic and antiparasitic properties of a series of lupane triterpenoids modified by introducing one or two triphenylphosphonium moieties at the C-2, C-3, C-28, or C-30 positions by carbon-carbon or ester bonds have been described. The presence of triphenylphosphonium groups affects not only physical properties but also the mechanism of action of a potential drug. This review summarizes published findings on synthetic methods and biological properties of the triphenylphosphonium derivatives of betulin and betulinic acid.

Literature Review

Study Snapshot

Triphenylphosphonium derivatives of betulin and betulinic acid show potential as therapeutic agents due to their improved bioavailability, hydrophobicity, and intracellular accumulation.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Triphenylphosphonium Analogues of Betulin and Betulinic Acid with Biological Activity: A Comprehensive Review.

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References

Betulin and betulinic acid in cancer research

Betulin and betulinic acid show potential as potent anticancer agents by inducing cancer cell death while sparing normal cells, offering a promising new therapeutic strategy for human tumors.

Structure and Anti-HIV Activity of Betulinic Acid Analogues

Betulinic acid analogues show promising anti-HIV activity at nanomolar concentrations, and some compounds have entered phase II clinical trials.

Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin.

Triphenylphosphonium derivatives of betulin show promising antiproliferative activity against cancer cells, with a low IC50 value of 0.045 M for vinblastine-resistant MCF-7 cells.

Synthesis and cytotoxicity of Baylis-Hillman template derived betulinic acid-triazole conjugates

Two series of lead compounds were identified for further development based on their cytotoxicity against murine breast cancer and human pancreatic cancer cell lines.

Mitochondria-Targeted Lupane Triterpenoid Derivatives and Their Selective Apoptosis-Inducing Anticancer Mechanisms.

Mitochondria-targeted derivatives of betulin and betulinic acid show stronger cytotoxicity and more apoptotic effects in cancer cells, potentially due to reactive oxygen species production and reduced mitochondrial membrane potential.

Citations