A thymol derivative from Calea nelsonii

Maldonado, Emma; Márquez, C.; Ortega, Alfredo

doi:10.1016/0031-9422(92)83316-q

Cited by 17 publications

(15 citation statements)

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“…Using this procedure, the known 6-acetyl-2,2-dimethylchroman-4-one (12) and 10-acetoxy-8,9-epoxy-thymolisobutyrate (13) were isolated and identified by comparison of their spectral properties ( 1 H, 1 H-1 H COSY, 13 C-NMR, and for compound 12 additionally by EI-MS, gHMQCR and gHSQCR) to those reported in literature (see Fig. 1) [27], [28]. 13 C-NMR data of compound 12 are reported for the first time (see Materials and Methods).…”

Section: Resultsmentioning

confidence: 99%

New Sesquiterpene Lactones from Arnica Tincture Prepared from Fresh Flowerheads ofArnica montana

et al. 2005

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Investigation of an ethanolic extract prepared from fresh Arnica montana flowers afforded three new 1,5- trans-guaianolides, of which 11alpha,13-dihydro-2-O-tigloylflorilenalin and the respective 2-O-isovaleryl derivative are reported for the first time. Additionally, three new and one known 2beta-ethoxy-2,3-dihydrohelenalin esters were isolated. GC/MS studies of the extract after a two year storage at 4 degrees C demonstrated that the latter were artefacts that had been formed by addition of ethanol to the cyclopentenone structure of helenalin. Formation of these adducts gave compounds possessing an inhibitory activity comparable to that of 11alpha,13-dihydrohelenalin derivatives in the NF-kappaB EMSA and the IL-8 ELISA in vitro assays as well as in the in vivo croton oil-induced mouse ear edema test for one adduct, namely 2beta-ethoxy-6-O-acetyl-2,3-dihydrohelenalin. As expected, 6-O-(2-methylbutyryl)- and 6-O-methacryloyl-helenalin exhibited a stronger activity in the NF-kappaB EMSA and IL-8 ELISA. Sesquiterpene lactones seem to be the most important NF-kappaB inhibiting compounds in the Arnica extract. Bioguided fractionation using the luciferase reporter gene assay resulted in the isolation of only moderately active compounds, such as 6-acetoxy-2,2-dimethylchroman-4-one and 10-acetoxy-8,9-epoxythymol isobutyrate.

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Section: Resultsmentioning

confidence: 99%

New Sesquiterpene Lactones from Arnica Tincture Prepared from Fresh Flowerheads ofArnica montana

et al. 2005

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“…As represented in Table , 26 thymol derivatives (230–255) have been isolated from Calea plants since 1979. Among these species, Calea nelsonii Robinson, C. villosa , and C. urticifolia present the highest proportion of thymol derivatives (Bohlmann et al, ; Bohlmann & Jakupovic, ; Maldonado, Marquez, & Ortega, ; Martinez, Sanchez, et al, ).…”

Section: Chemical Constituentsmentioning

confidence: 99%

“…Thymol derivatives comprise the second most widely distributed group of secondary metabolites, and they appear in 17 Calea species. As represented in Table 1 Maldonado, Marquez, & Ortega, 1992;.…”

Section: Thymol Derivativesmentioning

confidence: 99%

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

Lima

Souza

Silva

et al. 2018

Phytotherapy Research

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Calea L. is a genus of shrubs and perennial herbs belonging to Asteraceae family. It is a very well‐known genus, consisting of approximately 125 neotropical species. Calea genus is a rich source of phytochemicals, and some of its species have been used in folk medicine to treat several health problems such as diabetes, arterial hypertension, respiratory and gastrointestinal disorders, gastric ulcers, and inflammation. Many studies have demonstrated the pharmacological potential of this genus, including antinociceptive, antihypertensive, antidiarrheal, antimicrobial, anti‐inflammatory, antidiabetic, antiproliferative, and cytotoxic activities. Moreover, bioactive constituents related to these properties are mainly sesquiterpene lactones and phenolic derivatives. In this review, we compiled the literature data up to December 2016, furnishing a comprehensive survey about medicinal uses, chemistry, and biological activities from Calea species. Bibliographic search was performed in several search engines using “Calea” as search keyword. Further, a manual literature search of references found in the selected studies was also conducted. There was no initial time limit.

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“…Previous study on this plant led to the isolation of a new chiral 8,9-epoxythymol derivative, whose structure and absolute configuration was established as [(2S)-2-{4-formyl-5-hydroxy-2-[(2-methylpropanoyl)-oxy]phenyl}oxiran-2-yl]methyl benzoate (8). [1] Thymol derivative 8, which we wish to name cylindrinol A, showed a high antidiarrheal activity.…”

Section: Introductionmentioning

confidence: 98%

“…This kind of compounds has been described as artifacts formed during the isolation process [8] or after the purification. [9] Recently, the structure of a related compound isolated from Ageratina glabrata was established as the 10-(benzoyloxy)-6,8,9-trihydroxythymol 2-methylpropanoate.…”

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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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A thymol derivative from Calea nelsonii

Cited by 17 publications

References 4 publications

New Sesquiterpene Lactones from Arnica Tincture Prepared from Fresh Flowerheads ofArnica montana

New Sesquiterpene Lactones from Arnica Tincture Prepared from Fresh Flowerheads ofArnica montana

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

Further Thymol Derivatives from Ageratina cylindrica

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