657. The local anæsthetic in Fagara xanthoxyloides

Bowden, K.; Ross, William T.

doi:10.1039/jr9630003503

Cited by 19 publications

(17 citation statements)

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“…Z. zanthoxyloides (Lam.) Zepern and Timler 101a, 110a (Bowden and Ross 1963;Chaaib et al 2003) a With unknown configuration of the double bonds (Achenbach et al 1986) b With unsolved structure of a pentylamine moiety (Sun et al 2007) Phytochem Rev…”

Section: Phytochem Revmentioning

confidence: 99%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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Alkamides are natural products formed by connecting straight-chain, mostly unsaturated, aliphatic acids with various amines by an amide linkage. More than 300 derivatives are known from eight plant families consisting of various combinations of 200 acids with 23 amines. Apart from a few saturated derivatives alkamides with unsaturated acid parts are grouped into compounds with purely olefinic patterns and those with olefinic and acetylenic linkages. Derived from C 18 oleic acid the acid parts are modified either by chain elongations to C 28 or by oxidative shortenings to C 4 acid residues. Substrate and regiospecific desaturases and acetylenases are responsible for their characteristic patterns of unsaturation. Amine parts are derived from various amino acids by decarboxylation. Beside the widespread isobutylamines alkamides with six-and five-membered ring amines and those with phenylalanine derived amines are characteristic for the Asteraceae and Piperaceae while benzylamines are restricted to the Brassicaceae. Within the Asteraceae 2-methylbutylamine distinguishes the tribe Heliantheae from Anthemideae characterized by ring amines. Alkamides with elongated olefinic acid parts are mainly found in Piperaceae and Brassicaceae while acetylenic acid parts are typical for Asteraceae. A wide variety of biological activities ranges from the characteristic pungent/ tingling property and high insecticidal toxicity to significant antifungal, antibacterial, antiprotozoal, molluscicidal, cercaricidal, and acaricidal activity. They also act as plant growth-promoting substances. Position and stereochemistry of the double bonds are essential for the different qualities of the pungent taste. Medically alkamides possess anti-inflammatory and analgesic properties and are responsible for immunomodulatory and cannabinomimetic effects.

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Section: Phytochem Revmentioning

confidence: 99%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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“…The medicinal and insecticidal properties of other species of the Rutaceae family including Citrus , Xanthoxylum and Clausena have been reported (Bowden & Ross 1963; Su et al. 1972; Kubo et al.…”

Section: Introductionmentioning

confidence: 99%

Extracts from the bark of Fagara heitzii (Aubr. et Pel.) (Rutaceae) tree are toxic to two weevils and the American cockroach

Mikolo¹,

Matos

Massamba

et al. 2009

Entomological Research

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The bark of the Fagara heitzii tree in the west‐central African Republic of Congo (Congo–Brazzaville) is known anecdotally to provide protection for human residents against fleas and to be of use as a narcotic in fishing (similar to rotenone). We found that powder and hexane extracts from the bark of the Fagara heitzii tree contain insecticidal compounds. Dried powder (14.5 mg) on the bottom of a Petri dish is the residue at 14.494 mg per dish (LD50) for 20 adult maize weevils Sitophilus zeamays after four days. The LD50 of the same material to 20 adult cowpea weevils Callosobruchus maculatus was slightly higher at 16.144 mg/dish (after 48 h). These weevils cause significant economic damage to cowpea and maize in Congo–Brazzaville. Hexane extracts of the bark of Fagara heitzii were also toxic to these weevils. Symptoms of toxicity suggested the extracts were slow‐acting nerve poisons or respiratory inhibitors or both. The time needed to develop full toxicity suggested a respiratory poison. The hexane extract was also toxic to the American cockroach Periplaneta americana. The symptoms in the cockroach were similar, but cockroaches also exhibited apparent escape attempts suggesting they could detect the compounds. Signs of apparent irritation or exaggerated locomotion in all three insects also suggested irritation or nerve effects.

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“…This alkamide component, also known as pellitorine, has been previously identified in solvent extracts of Z . zanthoxyloides …”

Section: Resultsmentioning

confidence: 99%

“…Previous phytochemical studies on the secondary metabolites of Z . zanthoxyloides showed the presence of terpenes, alkaloids (benzophenanthridines, furoquinolines, aporphines), flavonoids, amides and coumarins in solvent extracts from various organs (roots, stem, bark, leaves and fruits). Moreover, some papers have reported the chemical composition and biological activities of fruit essential oils from various geographical origins such as Benin and Cameroun.…”

Section: Introductionmentioning

confidence: 99%

Chemical Diversity and Antimicrobial Activity of Volatile Compounds from Zanthoxylum zanthoxyloides Lam. according to Compound Classes, Plant Organs and Senegalese Sample Locations

Tine

Diop

Diatta

et al. 2016

Chemistry & Biodiversity

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The chemical diversity of Zanthoxylum zanthoxyloides growing wild in Senegal was studied according to volatile compound classes, plant organs and sample locations. The composition of fruit essential oil was investigated using an original targeted approach based on the combination of gas chromatography (GC) and liquid chromatography (LC) both coupled with mass spectrometry (MS). The volatile composition of Z. zanthoxyloides fruits exhibited relative high amounts of hydrocarbon monoterpenes (24.3 - 55.8%) and non-terpenic oxygenated compounds (34.5 - 63.1%). The main components were (E)-β-ocimene (12.1 - 39%), octyl acetate (11.6 - 21.8%) and decanol (9.7 - 15.4%). The GC and GC/MS profiling of fruit essential oils showed a chemical variability according to geographical locations of plant material. The LC/MS/MS analysis of fruit oils allowed the detection of seven coumarins in trace content. The chemical composition of fruit essential oils was compared with volatile fractions of leaves and barks (root and trunk) from the same plant station. Hexadecanoic acid, germacrene D and decanal were identified as the major constituents of leaves whereas the barks (root and trunk) were dominated by pellitorine (85.8% and 57%, respectively), an atypic linear compound with amide group. The fruit essential oil exhibited interesting antimicrobial activities against Staphylococcus aureus and Candida albicans, particularly the alcohol fraction of the oil.

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657. The local anæsthetic in Fagara xanthoxyloides

Cited by 19 publications

References 0 publications

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Extracts from the bark of Fagara heitzii (Aubr. et Pel.) (Rutaceae) tree are toxic to two weevils and the American cockroach

Chemical Diversity and Antimicrobial Activity of Volatile Compounds from Zanthoxylum zanthoxyloides Lam. according to Compound Classes, Plant Organs and Senegalese Sample Locations

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