Four aliphatic esters of Chamaemelum fuscatum essential oil

Pascual-T., J. De; Caballero, Esther; Caballero, C.; Anaya, Josefa; González, Myriam

doi:10.1016/s0031-9422(00)80265-4

Cited by 16 publications

(10 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is also worth noting that several new aliphatic esters with relative abundances higher than 1% and showing very similar structures to compounds previously reported in [8][9][10] were also identified for the first time in this paper (see Figure 1). We have identified for the first time in this species new aliphatic esters with relative abundances higher than 1% and showing very similar structures to those of compounds previously reported in [8][9][10]. It is also worth noting that several new aliphatic esters with relative abundances higher than 1% and showing very similar structures to compounds previously reported in [8][9][10] were also identified for the first time in this paper (see Figure 1).…”

Section: Chemical Composition Of C Fuscatum Essential Oilssupporting

confidence: 85%

“…2-Methylene-3-oxobutyl methacrylate, a methacrylic ester previously isolated from the essential oil of C. fuscatum [10] was not found either in the essential oils here analyzed. However, we have identified in a relative high abundance (>1%) the esters isobutyl methacrylate and isoamyl butyrate, which had not been cited in previous literature of this species [8][9][10]. These differences could be attributed to the different extraction procedures with respect to [8][9][10], but also to the different environments since the population here analyzed was collected in Badajoz (Spain) and the samples analyzed in the cited studies were from Cáceres (Spain).…”

Section: Discussionmentioning

confidence: 65%

“…As mentioned, aliphatic esters had been previously reported in C. fuscatum [8][9][10] and also in related chamomile species as Chamaemelum nobile and in several species of the Anthemis genus [39]. (E)-2-methyl-2-butenyl methacrylate had been described in the hexane extract of the aerial parts by De Pascual et al [8], together with other methacrylates (2-hydroxy-2-methyl-3-butenyl methacrylate and 2-hydroxy-2-methyl-3-oxobutyl methacrylate) that have not been detected here. 2-Methylene-3-oxobutyl methacrylate, a methacrylic ester previously isolated from the essential oil of C. fuscatum [10] was not found either in the essential oils here analyzed.…”

Section: Discussionmentioning

confidence: 71%

“…Regarding the chemical composition of C. fuscatum, it started to be studied in the eighties at Salamanca University (Spain). De Pascual Teresa et al [8] analyzed the hexane extract of the aerial parts of the plant, and first identified the methacrylic esters of 2-methyl-2-(E)-butenol, 2-hydroxy-2-methyl-3-butenol and 2-hydroxy-2-methyl-3-oxobutanol by spectral measurements and analysis of the corresponding standards. After that, these authors used spectroscopic methods and chemical transformations to elucidate the structures of different eudesmanolides in the chloroform extract of the aerial parts of this plant [9], and two years later, they reported four new eudesmanolides in the same extract and a new aliphatic ester (2-methylene-3-oxobutyl methacrylate) in the essential oil isolated from flowers [10].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Analysis of the Essential Oils of Chamaemelum fuscatum (Brot.) Vasc. from Spain as a Contribution to Reinforce Its Ethnobotanical Use

Fernández-Cervantes

Pérez‐Alonso

Salas

et al. 2019

Forests

View full text Add to dashboard Cite

Chamaemelum fuscatum (Brot.) Vasc. is a south west Iberian chamomile that has been traditionally used as folk medicine in its natural distribution area but currently it is underestimated regarding its biological activities. For this reason, it is proposed in this paper to get insight into the scientific validation of the traditional knowledge of this plant with the aim of taking advantage of its anti-inflammatory, gastroprotective and antinociceptive activities, among others. To this aim, the chemical composition of the essential oil from the whole plant, the flowers and the green parts of this plant has been evaluated by gas chromatography–mass spectrometry (GC–MS). Plant materials were collected in Badajoz (Spain). A total of 61 components including monoterpenoids, sesquiterpenoids and aliphatic esters were identified. (E)-2-Methyl-2-butenyl methacrylate (27.57%–18.53%) and 2-methylallyl isobutyrate (9.79%–7.51%) were the most abundant compounds in the essential oils of flowers and of the whole plant, whereas α-curcumene, trans-pinocarveol, α-bergamotene and pinocarvone were the major terpenoids irrespective of the plant part considered. Certain compounds showing a relative high abundance as isobutyl methacrylate, isoamyl butyrate, α-bergamotene and pinocarvone were identified for the first time in this species. Finally, we have reviewed the bioactivity of several compounds to relate the ethnobotanical use of this plant in Spain with its volatile profile. This work is a preliminary contribution to reinforce the use to this Mediterranean endemic plant as a natural source of bioactives.

show abstract

Section: Chemical Composition Of C Fuscatum Essential Oilssupporting

confidence: 85%

Section: Discussionmentioning

confidence: 65%

Section: Discussionmentioning

confidence: 71%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Analysis of the Essential Oils of Chamaemelum fuscatum (Brot.) Vasc. from Spain as a Contribution to Reinforce Its Ethnobotanical Use

Fernández-Cervantes

Pérez‐Alonso

Salas

et al. 2019

Forests

View full text Add to dashboard Cite

show abstract

“…The compound with most promising activity was 1 (bisabolene-1,4-endoperoxide=1,4-epidioxy-bisabolan-2,12-diene) (Figure 1), for which in vitro an IC 50 0.05 was observed, in comparison with the value 0.005 for artemisinine as reference compound (Heinzmann, 1996;. Since the compound 1 was isolated from Heterothalamus psiadioides, H. alienus, Senecio selloi and Eupatorium rufescens (Heinzmann, 1996;Rücker et al, 1996;Rücker et al, 1996) it seems to have a wide occurrence, being first reported from Rudbeckia lasciniata (Bohlmann et al, 1978), and also from Ligularia speciosa (Bohlmann, Fritz, 1980), Chamaemelum fuscatum (Pascual et al 1983) and Senecio desfontnei (Metwally, Dawidar, 1986). Two others bisabolan-type sesquiterpenes, zingiberene-3,6-aand zingiberene-3,6-b-endoperoxides (3 and 4) were isolated from S. selloi and E. rufescens and also showed antimalarial activity in vitro, but this activity was weaker than the activity of bisabolene-1,4-endoperoxide.…”

Section: Resultsmentioning

confidence: 95%

Screening of brazilian plants for the presence of peroxides

Schenkel¹,

Rüċker²,

Manns³

et al. 2002

Rev. Bras. Cienc. Farm.

View full text Add to dashboard Cite

Uniterms:• Peroxides• Antimalarial activity• Asteraceae INTRODUCTIONThe occurrence of natural products which contain a peroxide group has been known since 1911, when ascaridole was isolated from the essential oil of Chenopodium ambrosioides (Chenopodiaceae). This oil was utilized as anthelmintic and ascaridole was identified as responsible for its activity (Gessner, 1953;Hope, 1958). In the following decades, compounds with a similar structure were not isolated; peroxides were considered to be too unstable and ascaridole was thought to be an exception.In the meantime, as much as 320 peroxides have been isolated from natural material (Casteel, 1992). They occur mainly as terpene derivatives, although cumarine, fatty acids and alkaloids peroxides derivatives have also been isolated. Beside plants, many species of fungi and marine organisms produce metabolites containing a peroxide group. The peroxide function has been detected in different classes of natural compounds that are mentioned in Table I, based on the review published by Casteel (1992). The occurrence in vascular plant families according the literature published until 1999 is summarized by Table II. Many biological activities were described for the peroxides. They show ichthyotoxic and antimicrobial activity, fungicide, anthelmintic and cytotoxic activity. At the moment, the most important activity exhibited by peroxides is the antimalarial activity (Vennerstrom, Easton, 1988;Rücker, 1994). The prevention and cure of malaria depends on a limited number of drugs. Resistance of the malaria parasites Plasmodium ssp. to drugs such as quinine (and more lately chloroquine) occurs with increasing frequency and emphasize the necessity to develop new agents for malaria chemotherapy (Kirby, 1996). Quinghaosu (artemisinin), a sesquiterpene isolated from Artemisia annua, is the best known plant derivative as an antimalarial drug after quinine (Klayman, 1985). Another sesquiterpene peroxide, named yingzhaosu, was isolated from Artabotrys uncinatus (Annonaceae) and also possesses a significant antimalarial activity. Both compounds contain an endoperoxid group, which is responsible for their activity (Klayman, 1985) and have opened a new chapter in the chemotherapy of malaria. The majority of drugs active against malaria are in fact derived from natural products or from structures suggested by natural products prototypes, but, as a source of novel drugs, plants remain largely understudied (Kirby, 1996). Falkenberg et al. 192 Herewith we report the screening for detection of peroxides in extracts from higher plants from the states of Rio Grande do Sul and Santa Catarina, Brazil, based on Huber & Fröhlke's chromatographic test. The screening was developed to select promising plants for detailed investigation, aiming the isolation and structure elucidation of new peroxides. Fresh plant material (10-20 g) was crushed and extracted with CH 2 Cl 2 or CHCl 3 (10-20 mL) previously tested for peroxides. The extraction procedures were performed at the same day of the plant c...

show abstract