The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Parise-Filho, Roberto; Pastrello, Michelli; Camerlingo, Carla Emygdio Pereira; Silva, Gisele Juni; Agostinho, Leonardo Aguiar; Souza, Thaís de; Magri, Fátima Maria Motter; Ribeiro, Roberto Rodrigues; Brandt, Carlos A.; Polli, Michelle Carneiro

doi:10.3109/13880209.2011.575793

Cited by 58 publications

(42 citation statements)

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“…Stem essential oil composition was very close to the root essential oil composition determined in literature for dillapiol chemotype [7]. Dillapiol is a well-known phenylpropanoid, extracted from essential oils of several plants as matico (Piper aduncum), parsley (Petroselinum crispum), pepper elder (Peperomia pellucida) or dill (Anethum graveolens) [21][22][23][24]. This compound presents in vitro antieishmanial, gastropotective and anti-inflammatories activities [21][22][23].…”

Section: Essential Oil Analysissupporting

confidence: 55%

“…Dillapiol is a well-known phenylpropanoid, extracted from essential oils of several plants as matico (Piper aduncum), parsley (Petroselinum crispum), pepper elder (Peperomia pellucida) or dill (Anethum graveolens) [21][22][23][24]. This compound presents in vitro antieishmanial, gastropotective and anti-inflammatories activities [21][22][23]. Its structure, close to phenylisopropylamine structures could suggest a possible psychotropic activity as tonic or exciting [25].…”

Section: Essential Oil Analysismentioning

confidence: 99%

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First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

A¹,

A²

2015

Med Aromat Plants

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Plant material was collected in May 2011 in Mantet Col (Pyrénées-Orientales, France) during inflorescence emergence stage, as stems are traditionally consumed. All plants specimen were 3-4 years old and were identified by Cédric Bertrand based on morphological description. A voucher specimen was deposited at the Herbarium of the University Claude Bernard Lyon1, city of Villeurbanne, France, under the name ''Collection Piola'' and collector number 4. An aliquot was dried and conserved for phytochemical analysis. Dry mass stems was 15% w:w. Global characterization of pl™ant material Protein dosage was determined according to the AOAC Official Method 984.13 [8]. Lipid amount was determined using the ISO 1443 method [9] and lipid profile was analyzed according to the AOCS Ce 1h-05 method [10]. Soluble sugar content was determined after oximation and silylation then analyzed by gas chromatography with a 30 m SIL5CB column coupled with FID detection, using xylitol as internal standard. Mineral amount was evaluated according to the AOAC Official Method 923.03 [11]. Fiber dosage was determined according to the AOAC Official Method 985.29 [12]. Energetic values were calculated according European regulation 1169/2011 [13]. All essays were done on a mix of stems from six different plants. Essential oil distillation 100 g of fresh stem parts from six Molopospermum peloponnesiacum specimen from the same mountain area were directly subjected to hydrodistillation for 2 h. Volatile oil was collected by extraction using Abstract "Coscoll"(Molopospermum peloponnesiacum (L.) Koch) whose stems are traditionally consumed raw in salads in Catalonia is associated in oral tradition with many virtues as digestive, purifying, exciting, antioxidant and hematocathartic activities. However, stem composition and biological activity had never been studied. Nutritive values of plant material were determined by official methods and constituents from essential oil of Molopospermum peloponnesiacum stems were characterized for the first time in this study. The main constituents were dillapiol (60.1%) and 3-carene (15.2%). Moreover, total polyphenol content using Folin-Ciocalteu method, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity were determined. Molopospermum peloponnesiacum stem total polyphenol content was 101.0 ± 10.0 mg/100 g fresh weight (Gallic Acid Equivalent) and DPPH radical scavenging activity, relatively high, was close from spinach one. Thus, these first results reveal the potential beneficial properties of this plant, in relation with its traditional use in Catalonia.

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Section: Essential Oil Analysissupporting

confidence: 55%

Section: Essential Oil Analysismentioning

confidence: 99%

First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

A¹,

A²

2015

Med Aromat Plants

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“…Piper aduncum is one particularly specie from the Peperomia pellucid. Dillapiole, a phenylpropanoid, is the main component of Piper aduncum [6,7], with reported antileishmanial [8], anti-inflammatory [9], antifungal [6], and acaricidal [10] bioactivities. However, the cytotoxic effects of this organic compound are not well documented at present.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Effects of Dillapiole on Embryonic Development of Mouse Blastocysts in Vitro and in Vivo

Chan

2014

IJMS

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We examined the cytotoxic effects of dillapiole, a phenylpropanoid with antileishmanial, anti-inflammatory, antifungal, and acaricidal activities, on the blastocyst stage of mouse embryos, subsequent embryonic attachment and outgrowth in vitro, and in vivo implantation via embryo transfer. Blastocysts treated with 2.5–10 μM dillapiole exhibited a significant increase in apoptosis and corresponding decrease in total cell number. Notably, the implantation success rates of blastocysts pretreated with dillapiole were lower than those of their control counterparts. Moreover, in vitro treatment with 2.5–10 μM dillapiole was associated with increased resorption of post-implantation embryos and decreased fetal weight. Our results collectively indicate that dillapiole induces apoptosis and retards early post-implantation development, both in vitro and in vivo. However, the extent to which this organic compound exerts teratogenic effects on early human development is not known at present. Further studies are required to establish effective protection strategies against the cytotoxic effects of dillapiole.

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“…The dominant component in the essential oil of E. crassicaule was dillapiole (78.4%), a phenylpropanoid derivative. Dillapiole, isolated from the essential oil of Piper aduncum as the main constituent, has shown moderate antiphlogistic activity and can be used as a prototype for newer anti-inflammatory compounds [8,9].…”

mentioning

confidence: 99%

Composition of the Essential Oil of Erysimum crassicaule

Akhgar

Roknabadi

2015

Chem Nat Compd

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The Brassicaceae, which has about 350 genera and 3500 species, is one of the ten most economically important plant families [1]. The plants display enormous diversity and are used as sources of oil, vegetables, mustard condiments, and fodder [2].The genus Erysimum belongs to the Brassicaceae family. The Iranian Flora consists of 25 species of Erysimum, including 13 endemics, and the popular Persian name of the species is "Khakshir-e-Talkh" [3]. Erysimum crassicaule Boiss. is a biennial plant distributed in Iran and Pakistan [3,4].A literature search did not reveal any references to previous work on the essential oils of Erysimum species. The present work studies the chemical composition of the essential oil from the aerial parts of E. crassicaule for the first time.The plant material was collected during the flowering stage from Rayen (at an altitude of 2900-3000 m) Kerman Province, Iran in May 2013. A voucher specimen (No. 8522) has been deposited in the Herbarium of the Research Center of Agriculture and Natural Resources of Kerman, Iran. The air-dried aerial parts of the plant (200 g) were crushed and subjected to hydrodistillation for 3 h using a Clevenger-type apparatus. The yield of the essential oil was 0.2% (w/w) relative to the dried material.The constituents of the oil were analyzed by GC and GC/MS. GC analysis of the volatile components was carried out using a Hewlett-Packard 6890 instrument coupled to a flame ionization detector (FID). Compounds were separated on an HP-5 capillary column (30 m u 0.25 mm, film thickness 0.25 Pm). The column temperature was kept at 60qC for 3 min and programmed to 220qC at a rate of 5qC/min. Injector and detector temperatures were 270qC, and the flow rate of helium as carrier gas was 1 mL/min. The percentage composition of the individual components was computed from the GC-FID peak areas without the use of correction factors. GC/MS analysis was performed using an Agilent 5975C mass spectrometer coupled to an Agilent 7890A gas chromatograph equipped with an HP-5MS capillary column (30 m u 0.25 mm, film thickness 0.25 Pm). The carrier gas was helium, and the chromatographic conditions were as above. All mass spectra were acquired in electron-impact (EI) mode. The spectrometer was scanned over the 40-400 amu range with an ionization voltage of 70 eV and an ionization current of 150 PA. Retention indices were determined using the retention times of n-alkanes, injected after the essential oil under the same chromatographic conditions, according to the Van Den Dool method [5].The chemical compounds, which were identified on the basis of their mass spectral characteristics and retention indices [6,7], are listed in Table 1. As is shown, 13 components were identified in the essential oil, amounting to 100% of the total volatiles. The chemical class distributions of the volatile constituents are summarized at the end of Table 1. Based on the analysis of the oil, the components were classified in four groups as follows: phenylpropanoid derivatives, oxygenated monoterpenes, sesqui...

show abstract

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Cited by 58 publications

References 36 publications

First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

Cytotoxic Effects of Dillapiole on Embryonic Development of Mouse Blastocysts in Vitro and in Vivo

Composition of the Essential Oil of Erysimum crassicaule

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The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Cited by 58 publications

References 36 publications

First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

Cytotoxic Effects of Dillapiole on Embryonic Development of Mouse Blastocysts in Vitro and in Vivo

Composition of the Essential Oil of Erysimum crassicaule

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Product

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First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)

First Phytochemical Characterization and Essential Oil Analysis of the Traditional Catalan Wild Salad: Ã¢ÂÂCoscollÃ¢ÂÂ (Molopospermum peloponnesiacum (L.) Koch)