Studies on the Biological Activites of Rare Phenylpropanoids of the Genus Pimpinella

Reichling, Jürgen; Merkel, Bernhard; Hofmeister, P.

doi:10.1021/np50077a032

Cited by 14 publications

(5 citation statements)

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“…Even minor compounds can have a critical function due to coupled effects, additive action between chemical classes and synergy or antagonism 29. Plants in the Apiaceae such as Pimpinella were found to have a rare class of simple but biologically active phenylpropanoids 33. Individually, the three major phenylpropanoids PPA, PPT, MPPA of P. isaurica oil, were benign to L. pseudobrassicae .…”

Section: Discussionmentioning

confidence: 99%

“…A monoterpenoid, 1,8‐cineole, also makes up a large portion of Eucalyptus and Laurus oils, and can be an effective component of a contact insecticide, miticide, feeding deterrent or repellent 19. Among the more noxious herbs in the Apiaceae ( = Umbelliferae), those in the genus Pimpinella have insecticidal compounds derived mainly from pseudoisoeugenol‐type phenylpropanoids: 2‐hydroxy‐5‐methoxy‐1‐( E )‐propenylbenzene 20–23…”

Section: Introductionmentioning

confidence: 99%

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Insecticidal activity of 23 essential oils and their major compounds against adult Lipaphis pseudobrassicae (Davis) (Aphididae: Homoptera)

Sampson¹,

Tabanca

Kırımer

et al. 2005

Pest Management Science

114

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Essential oils from 23 species of plants comprising 14 genera and 4 plant families were obtained by Clevenger-type water distillation. The major compounds in these essential oils were identified with GC-MS and their insecticidal activity against adult turnip aphids, Lipaphis pseudobrassicae (Davis), tested with dosage-mortality bioassays. We examined mortality only for viviparous adults because sizeable aphid populations on crucifer (Brassicaceae) hosts are largely produced by these wingless, parthenogenic females. Twenty-two of the oils were directly applied to aphid females in randomized blocks at concentrations of 0.0, 1.0, 2.5, 5.0 and 10.0 mg ml(-1). Essential oils mixed with a non-toxic emulsifying agent, dimethyl sulfoxide (DMSO), more easily penetrated the waxy insect cuticle. Probit analysis and LC(50) at three different exposures showed aphids were quickly incapacitated and killed by aliphatic aldehydes, phenols and monocyclic terpenes contained in Bifora and Satureja oils and at applied concentrations as low as 0.3 to 1.0 mg ml(-1). Only enough Pimpinella isaurica oil and its three phenylpropanoid fractions were available for testing at a single concentration of 10 mg ml(-1). We could not spare any additional P. isaurica oil for testing at other concentrations. Phenylpropanoids isolated from P. isaurica oil when recombined or left naturally blended in the oil were highly bioactive against L. pseudobrassicae at 10 mg ml(-1).

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Insecticidal activity of 23 essential oils and their major compounds against adult Lipaphis pseudobrassicae (Davis) (Aphididae: Homoptera)

Sampson¹,

Tabanca

Kırımer

et al. 2005

Pest Management Science

114

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“…These secondary metabolites carry epoxide groups which are powerful electrophiles. They can react with nucleophilic groups (e.g., NH 2 , NH, and SH groups of amino acid) in proteins and thus affect the biological system in microorganisms [2,31,32]. In the EO of P. pruatjan epoxypseudoisoeugenols are present in low amounts which would explain the absence of antibacterial activity as compared to some other Pimpinella species [2,16].…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Chemical Composition of the Essential Oil from Aerial Parts of Javanian Pimpinella pruatjan Molk. and Its Molecular Phylogeny

et al. 2016

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The species-rich and diverse genus Pimpinella is mainly distributed in Europe and Asia; a few species occur in Africa. Yet, the Javanian Pimpinella, P. pruatjan, which has been used as an aphrodisiac in Indonesian traditional medicine, was studied for the first time in the context of chemical composition, as well as phylogeny analysis and antimicrobial activity. We examined the chemical composition of the essential oil (EO) from aerial parts of P. pruatjan by gas liquid chromatography-mass spectrometry (GLC-MS). The main component of EO was (Z)-γ-bisabolene. Several oxygenated monoterpenes, oxygenated sesquiterpenes, and sesquiterpenes were also detected. The genetic relationship of Pimpinella pruatjan Molk. to other Pimpinella species was reconstructed using nucleotide sequences of the nuclear DNA marker ITS (Internal Transcribed Spacer). P. pruatjan clusters as a sister group to the African Pimpinella species. The EO did not exhibit an apparent antimicrobial activity.

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“…The 2-hydroxy-5-methoxy-1-(E)-propenylbenzene skeleton of these compounds, known as pseudoisoeugenol, is unique to Pimpinella (Kubeczka, 1997). Antigermination, insecticidal, acaricidal, weak antitumour, antimalarial, antifungal, antimicrobial and oestrogen activities of phenylpropanoids from Pimpinella have been reported (Marcus and Lichtenstein, 1979;Kleiman et al, 1988;Reichling and Merkel, 1991;Tabanca et al, 2003Tabanca et al, , 2004Tabanca et al, , 2005. The distributions of the compounds, although intriguing, have not been investigated within a phylogenetic framework.…”

Section: Introductionmentioning

confidence: 99%

Patterns of essential oil relationships in Pimpinella (Umbelliferae) based on phylogenetic relationships using nuclear and chloroplast sequences

Tabanca

Douglas

Bedir

et al. 2005

Plant Genet. Resour.

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Hydro-distilled essential oils from fruits, aerial parts (without fruits) and roots of Pimpinella species native to Turkey and their phylogenetic relationships to one another were examined. Phytochemical investigation of the essential oils of 19 species resulted in isolation of 16 phenylpropanoids, four sesquiterpenes and two azulene-type norsesquiterpenes. The structures of the isolated compounds were determined primarily from 1D-and 2D-NMR experiments as well as liquid chromatography -mass spectrometry and gas chromatography -mass spectrometry. Phylogenetic relationships among 26 species were evaluated using ITS 1, ITS 4 nuclear rDNA and psbA-trnH cpDNA sequences. In this study, significance and occurrence of phenylpropanoids, azulenes and geijerenes are discussed from a phylogenetic, chemical and biosynthetic perspective. The distribution of different classes of compounds and their putative associations with one another as per current knowledge of their biosynthetic pathways indicates that this information, in conjunction with the phylogeny, could provide valuable information regarding the presence and perhaps evolution of the different classes of compounds. Analysis of the phenylpropanoid components indicates that (E)-anethole is an obligatory intermediate of this pathway. The various Pimpinella species differ primarily in their ability to acylate anethole, suggesting that while the pathway leading to anethole is common to this genus, species differ in their enzymatic machinery leading to acylate. The relationship between azulenes and geijerenes is not as intuitive, but all Pimpinella species analysed in this study have the biochemical machinery required to synthesize these chemical classes.

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Studies on the Biological Activites of Rare Phenylpropanoids of the Genus Pimpinella

Abstract: Several rare phenylpropanoids of the genus Pimpinella were tested for biological activity. Compounds with epoxy groups have a negative effect on the growth of plants, and they also show insecticidal and acaricidal activities.

Cited by 14 publications

References 5 publications

Insecticidal activity of 23 essential oils and their major compounds against adult Lipaphis pseudobrassicae (Davis) (Aphididae: Homoptera)

Insecticidal activity of 23 essential oils and their major compounds against adult Lipaphis pseudobrassicae (Davis) (Aphididae: Homoptera)

Chemical Composition of the Essential Oil from Aerial Parts of Javanian Pimpinella pruatjan Molk. and Its Molecular Phylogeny

Patterns of essential oil relationships in Pimpinella (Umbelliferae) based on phylogenetic relationships using nuclear and chloroplast sequences

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