Myrtle has been considered to be a medicinal plant since ancient times. In addition to a number of essential oils, myrtle contains myrtucommulone A, a pharmacologically interesting compound that has antibacterial, analgesic, and strong anti-inflammatory effects, among others. Recent tests also indicate a highly selective cytostatic effect on tumors. A team led by Johann Jauch has now successfully synthesized myrtucommulone A in the laboratory.
As the scientists report in the journal Angewandte Chemie, the synthetic compound has the same anti-inflammatory and cytostatic activity as the natural version.
The myrtle (Myrtus communis) is an evergreen shrub native to the Mediterranean region that has small, aromatically scented, leathery leaves, small white flowers, and blue-black berries. The leaves and berries are occasionally used in Mediterranean cooking. Since ancient times, the myrtle, rich in essential oils, has been known as a medicinal plant. Pharmacological researchers are particularly interested in a group of substances, called the myrtucommulones, from the myrtle plant. However, their extraction from the leaves of the myrtle is very difficult and delivers small yields.
“The synthetic preparation of myrtucommulones would make these substances available in quantities sufficient to better examine their pharmacological properties,” says Jauch. “Also, we could develop analogues that may be more effective than the original substances. The strength of the natural substance could thus be augmented.”
The researchers have now succeeded in such a total synthesis. Starting with commercially available starting materials or substances known from the literature, the team from Saarland University in Saarbrücken and the University of Tübingen has now synthesized myrtucommulone A, its natural variants C and F, and an analogue in a one-step reaction. Their structures could be confirmed by means of spectroscopic techniques and a crystal structure analysis.
“Laboratory tests demonstrated that the synthetic myrtucommulone A has just as strong an anti-inflammatory effect as the natural compound,” says Jauch. “Just like the agent derived from the plant extract, it triggers programmed cell death (apoptosis) in tumor cells.” The scientists next plan to determine the absolute spatial configuration of the compound and to produce and test more analogues.
Author: Johann Jauch, Universität des Saarlandes, Saarbrücken (Germany), http://www.uni-saarland.de/campus/fakultaeten/professuren/naturwissenschaftlich-technische-fakultaet-iii/chemie/professuren-fr-81-chemie/prof-dr-johann-jauch/mitarbeiter/prof-dr-j-jauch.html
Title: Total Synthesis of Myrtucommulone A
Angewandte Chemie International Edition, Permalink: http://dx.doi.org/10.1002/anie.200903906
A Map of the Cell’s Power Station
18.08.2017 | Albert-Ludwigs-Universität Freiburg im Breisgau
On the way to developing a new active ingredient against chronic infections
18.08.2017 | Deutsches Zentrum für Infektionsforschung
Whether you call it effervescent, fizzy, or sparkling, carbonated water is making a comeback as a beverage. Aside from quenching thirst, researchers at the University of Illinois at Urbana-Champaign have discovered a new use for these "bubbly" concoctions that will have major impact on the manufacturer of the world's thinnest, flattest, and one most useful materials -- graphene.
As graphene's popularity grows as an advanced "wonder" material, the speed and quality at which it can be manufactured will be paramount. With that in mind,...
Physicists at the University of Bonn have managed to create optical hollows and more complex patterns into which the light of a Bose-Einstein condensate flows. The creation of such highly low-loss structures for light is a prerequisite for complex light circuits, such as for quantum information processing for a new generation of computers. The researchers are now presenting their results in the journal Nature Photonics.
Light particles (photons) occur as tiny, indivisible portions. Many thousands of these light portions can be merged to form a single super-photon if they are...
For the first time, scientists have shown that circular RNA is linked to brain function. When a RNA molecule called Cdr1as was deleted from the genome of mice, the animals had problems filtering out unnecessary information – like patients suffering from neuropsychiatric disorders.
While hundreds of circular RNAs (circRNAs) are abundant in mammalian brains, one big question has remained unanswered: What are they actually good for? In the...
An experimental small satellite has successfully collected and delivered data on a key measurement for predicting changes in Earth's climate.
The Radiometer Assessment using Vertically Aligned Nanotubes (RAVAN) CubeSat was launched into low-Earth orbit on Nov. 11, 2016, in order to test new...
A study led by scientists of the Max Planck Institute for the Structure and Dynamics of Matter (MPSD) at the Center for Free-Electron Laser Science in Hamburg presents evidence of the coexistence of superconductivity and “charge-density-waves” in compounds of the poorly-studied family of bismuthates. This observation opens up new perspectives for a deeper understanding of the phenomenon of high-temperature superconductivity, a topic which is at the core of condensed matter research since more than 30 years. The paper by Nicoletti et al has been published in the PNAS.
Since the beginning of the 20th century, superconductivity had been observed in some metals at temperatures only a few degrees above the absolute zero (minus...
16.08.2017 | Event News
04.08.2017 | Event News
26.07.2017 | Event News
18.08.2017 | Life Sciences
18.08.2017 | Physics and Astronomy
18.08.2017 | Materials Sciences