Volatile terpenoids as potential drug leads in Alzheimer’s disease

Wojtunik-Kulesza, Karolina; Targowska-Duda, Katarzyna M.; Klimek, Katarzyna; Ginalska, Grażyna; Jóźwiak, Krzysztof; Waksmundzka‐Hajnos, Monika; Cieśla, Łukasz

doi:10.1515/chem-2017-0040

Cited by 37 publications

(25 citation statements)

References 35 publications

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“…[ 14 ]. The main component of essential oils are terpenoids, which are low-molecular and lipophilic compounds that can easily cross the blood-brain barrier [ 15 ]. The compounds separated from lavender essential oil could lay the foundation for subsequent drug research.…”

Section: Introductionmentioning

confidence: 99%

Study on Lavender Essential Oil Chemical Compositions by GC-MS and Improved pGC

Dong

Aimila

et al. 2020

Molecules

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Lavender essential oil from the aerial parts of Lavandula angustifolia Mill. was analyzed by GC-MS equipped with three capillary columns of different polarities, which were HP-1, HP-5 ms and HP-INNOWax. A total of 40 compounds were identified by GC-MS, accounting for 92.03% of the total essential oil compositions. Nineteen monomers were separated by column chromatography and improved preparative gas chromatography (pGC), six of which could not be retrieved from the NIST 14 (National Institute of Standards and Technology, USA; 14th edition) library database. Fifteen compounds were identified for the first time in lavender essential oil. The improved pGC not only doubled the efficiency but also greatly reduced the cost.

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Section: Introductionmentioning

confidence: 99%

Study on Lavender Essential Oil Chemical Compositions by GC-MS and Improved pGC

Dong

Aimila

et al. 2020

Molecules

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“…In contrast to the biotransformation of (4R)-(-)-carvone (1), the reduction of the double bond in (4S)-(+)-carvone (6) ensued predominantly during the first day of transformation. The principal product formed was (1R, 4S)-dihydrocarvone (7). The process had high diastereoselectivity because almost no formation of a second dihydrocarvone stereoisomer was observed.…”

Section: Verifying the Biotransformation Of (4s)-(+)-carvone (6) Overmentioning

confidence: 98%

“…Chromatograms of the standards and products obtained by biotransformation using a ground potato are shown in Figure 5. Products (7) and (8) were identified as (1R, 4S)-dihydrocarvone (7) and (1S, 4S)-dihydrocarvone (8) by means of gas chromatography by comparing the Rf values with the standards. Chromatograms of the standards and products obtained by biotransformation using a ground potato are shown in Figure 5.…”

Section: Biotransformation Of (4s)-(+)-carvone (6)mentioning

confidence: 99%

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Plant-Mediated Biotransformations of S(+)- and R(–)-Carvones

et al. 2018

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The enzymatic system of vegetables is well known as an efficient biocatalyst in the stereoselective reduction of ketones. Therefore, we decided to use the comminuted material of several plants including five vegetables (Apium graveolens L., Beta vulgaris L., Daucus carota L., Petroselinum crispum L., and Solanum tuberosum L.) and three fruits (Malus pumila L. “Golden” and “Kortland” as well as Pyrus communis L. “Konferencja”) to obtain enantiomerically pure carveol, which is commercially unavailable. Unexpectedly, all of the used biocatalysts not only reduced the carbonyl group of (4R)-(–)-carvone and (4S)-(+)-carvone, but also reduced the double bond in the cyclohexene ring. The results revealed that (4R)-(–)-carvone was transformed into (1R, 4R)- and (1S, 4R)-dihydrocarvones, and (1R,2R,4R)-dihydrocarveol. Although the enzymatic system of the potato transformed the substrate almost completely, the %de was not the highest. Potato yielded 92%; however, when carrot was used as the biocatalyst, it was possible to obtain 17% of (1R, 4R)-(+)-dihydrocarvone with 100% diastereomeric excess. In turn, the (4S)-(+)-carvone was transformed, using the biocatalysts, into (1R, 4S)- and (1S, 4S)-dihydrocarvones and dihydrocarveols. Complete substrate conversion was observed in biotransformation when potato was used. In the experiments using apple, (1R, 4S)-dihydrocarvone with 100% diastereomeric excess was obtained. Using NMR spectroscopy, we confirmed both diastereoisomers of 4(R)-1,2-dihydrocarveols, which were unseparated in the GC condition. Finally, we proved the high usefulness of vegetables for the biotransformation of both enantiomers of carvone as well as dihydrocarvone.

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“…Terpenoids are found in vegetables and spices like salvia, peppermint, ginger, Curcuma longa, cinnamon, cloves, and mustard. Used in traditional medicine [ 72 , 73 ] for improving cognitive functions, several authors cite terpenoids as promising therapeutic substances against AD [ 74 , 75 ].…”

Section: Introductionmentioning

confidence: 99%

Alzheimer’s Disease as a Result of Stimulus Reduction in a GABA-A-Deficient Brain: A Neurocomputational Model

Aguiar-Furucho

Peláez

2020

Neural Plasticity

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Several research studies point to the fact that sensory and cognitive reductions like cataracts, deafness, macular degeneration, or even lack of activity after job retirement, precede the onset of Alzheimer’s disease. To simulate Alzheimer’s disease earlier stages, which manifest in sensory cortices, we used a computational model of the koniocortex that is the first cortical stage processing sensory information. The architecture and physiology of the modeled koniocortex resemble those of its cerebral counterpart being capable of continuous learning. This model allows one to analyze the initial phases of Alzheimer’s disease by “aging” the artificial koniocortex through synaptic pruning, by the modification of acetylcholine and GABA-A signaling, and by reducing sensory stimuli, among other processes. The computational model shows that during aging, a GABA-A deficit followed by a reduction in sensory stimuli leads to a dysregulation of neural excitability, which in the biological brain is associated with hypermetabolism, one of the earliest symptoms of Alzheimer’s disease.

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Volatile terpenoids as potential drug leads in Alzheimer’s disease

Cited by 37 publications

References 35 publications

Study on Lavender Essential Oil Chemical Compositions by GC-MS and Improved pGC

Study on Lavender Essential Oil Chemical Compositions by GC-MS and Improved pGC

Plant-Mediated Biotransformations of S(+)- and R(–)-Carvones

Alzheimer’s Disease as a Result of Stimulus Reduction in a GABA-A-Deficient Brain: A Neurocomputational Model

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