Systematic evaluation of thymol derivatives possessing stereogenic or prostereogenic centers

Talavera-Alemán, Armando; Rodríguez-García, Gabriela; López, Yliana; García-Gutiérrez, Hugo A.; Torres-Valencia, J. Martı́n; Río, Rosa E. del; Cerda-Garcı́a-Rojas, Carlos M.; Joseph‐Nathan, Pedro

doi:10.1007/s11101-015-9412-6

Cited by 23 publications

(37 citation statements)

References 101 publications

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“…In some Inula, Doronicum and Pulicaria species, thymyl derivatives rather than sesquiterpenoids are the major root constituents. [20][21][22][23] A review by Talavera-Aleman and collaborators 24 estimated that only 10% of known functionalized thymyl derivatives have been employed in biological testing, showing vast array of diverse activities, such as antimicrobial 4,5,22,[25][26][27] (several papers reporting inhibitory activity against plants' pathogenic fungi 22,26 ), antioxidant, 28 antinociceptive, 29 anti-parasitic (antileishmanial), 30,31 antiprotozoal, 32 insecticidal 33 and piscicidal 34 activity. The usefulness of thymyl derivatives as transdermal drug delivery enhancers has also been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Lazarević

Kolarević

Stojanović

et al. 2017

ACSi

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Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Lazarević

Kolarević

Stojanović

et al. 2017

ACSi

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“…Since an additional signal for an aromatic H-atom was observed at d(H) 7.75 (dt, J = 8.0, 0.4 Hz), we concluded that compound 2 is closely related to 8 and is devoid of the OH group at the C(6) position present in compound 8. Thus, cylindrinol C must be named as (2-{4-formyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (2). A careful analysis of the fine structure of the thymol aromatic H-atom signals indicated that H-C(5) at d(H) 7.75, has long range couplings with the benzylic H-C (7), and the para H-C(2) ( 5 J = 0.4 Hz), while the H-C(2) showed only meta and para couplings ( Table 2) was similar to that of 1 except for the chemical shift of the CH 2 (7) CH 2 H-atoms which were observed at lower shift respect to 1 at d(H) 5.10 (br.…”

Section: Resultsmentioning

confidence: 99%

“…Besides the genus Ageratina, this type of compounds are distributed in 42 genera of the Asteraceae family, although only around 10% of the known thymol derivatives have been evaluated biologically as antibacterial, anti-inflammatory, antiprotozoal, antioxidant, cytotoxic, and allelopathic agents. [2] In this paper, we describe the isolation, structural characterization, and antiprotozoal evaluation of the compounds 1 -5 against Entamoeba histolytica and Giardia lamblia trophozoites, two of the most common causes of diarrheal disease in developing countries responsible for about three million deaths of children under 5 years of age per year. [3] Thymol derivatives 2 -5 were also tested for antipropulsive effect activity using the charcoal-gum acacia-induced hyperperistalsis model in rats.…”

Section: Introductionmentioning

confidence: 99%

Further Thymol Derivatives from Ageratina cylindrica

Bustos-Brito

Esquivel

Calzada

et al. 2016

Chemistry & Biodiversity

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From the leaves of Ageratina cylindrica, in addition to the described [(2S)-2-{4-formyl-5-hydroxy-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl]methyl benzoate (cylindrinol A, 8), seven new thymol derivatives were isolated and named cylindrinols B - H (1 - 7). The structures of these compounds were established as (2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (1), (2-{4-formyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (2), (2-{4-[(acetyloxy)methyl]-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (3), [2-(2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (4), [2-(5-hydroxy-2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (5), 2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}prop-2-en-1-yl benzoate (6), and 2-hydroxy-2-[2-hydroxy-4-(hydroxymethyl)-phenyl]-3-[(2-methylpropanoyl)oxy]propyl benzoate (7), by spectroscopic means. Compounds 1 showed moderate antiprotozoal activity on both protozoa. Compounds 4 and 5 showed selectivity on Giardia lamblia trophozoites. All isolated compounds were less active than two antiprotozoal drugs, metronidazole and emetine, used as positive controls. Compound 5 exhibited a high inhibitory effect on hyperpropulsive movement of the small intestine in rats; its effect was best than loperamide, antidiarrheal drug used as a positive control.

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“…The active fraction F1 was further chromatographed, using column chromatography on silica gel eluted with hexanes-ethyl acetate of increasing polarity to obtain three fractions: F1A (25.0 mg), F1B (131.0 mg), and F1C (13.0 mg). thymol derivatives have been evaluated as antibacterial, anti-inflammatory, antioxidant, antiprotozoal, cytotoxic, piscicidal, or allelophatic agents [25]. Regarding epoxythymol derivatives, evaluation on Entamoeba histolytica and Giardia lamblia of thymol isobutyrate derivatives revealed a moderate antiprotozoal activity on both protozoa [26].…”

Section: Bioassay-guided Fractionationmentioning

confidence: 99%

“…Only about 10% of the known functionalized Compound 1 has been isolated from 40 different plants that represent 60% of the total reported vegetal species containing epoxythymol derivatives. Only about 10% of the known functionalized thymol derivatives have been evaluated as antibacterial, anti-inflammatory, antioxidant, antiprotozoal, cytotoxic, piscicidal, or allelophatic agents [25]. Regarding epoxythymol derivatives, evaluation on Entamoeba histolytica and Giardia lamblia of thymol isobutyrate derivatives revealed a moderate antiprotozoal activity on both protozoa [26].…”

Section: General Experimental Proceduresmentioning

confidence: 99%

Antioxidant and Leishmanicidal Evaluation of Pulicaria Inuloides Root Extracts: A Bioguided Fractionation

et al. 2019

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Leishmaniasis remains a major world health problem, and in particular, Algeria ranks second for the incidence of cutaneous leishmaniasis. Pulicaria inuloides is a well-known Arabian Peninsula medicinal plant. In the present study, the chloroform, ethyl acetate and n-butanol extracts from the roots of Pulicaria inuloides were analyzed for antioxidant activity and its correlation with the total phenolic and flavonoid contents. The highest antioxidant activity using a DPPH assay was showed by the ethyl acetate extract (IC 50 4.08 µg/mL), which also had the highest total phenolic content (307.12 µgAGE). Furthermore, P. inuloides root extracts were evaluated against Leishmania amazonensis and Leishmania donovani. The results highlighted the chloroform extract as the most active one against both tested Leishmania strains. A bioguided fractionation of the chloroform extract led to the isolation of (8R:8S)-(75:25 er)-10-isobutyryloxy-8,9-epoxy-thymol isobutyrate as the main bioactive component, showing a potent leishmanicidal activity on L. amazonensis promatigote and amastigote stages (IC 50 5.03 and 2.87 µM, respectively) and a good selectivity index on murine macrophages (CC 50 19.37 µM). This study provides the first report of the antioxidant and leishmanicidal activities of P. inuloides root extracts and the results point to this species as a source of potential bioactive agents.

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Systematic evaluation of thymol derivatives possessing stereogenic or prostereogenic centers

Cited by 23 publications

References 101 publications

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Further Thymol Derivatives from Ageratina cylindrica

Antioxidant and Leishmanicidal Evaluation of Pulicaria Inuloides Root Extracts: A Bioguided Fractionation

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