Amides and other constituents from acmella ciliata

Martin, R.; Becker, Hans

doi:10.1016/s0031-9422(00)83030-7

Cited by 38 publications

(24 citation statements)

References 14 publications

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“…25) and can possess an epoxy-derivative in its acid chain (27) (Bohlmann et al, 1980). In addition, this epoxy group was identified with a PEA residue in Spilanthes acmella, radicans and ciliata and in Salmea scandens (12) (Bohlmann et al, 1985;Boonen et al, 2010;Martin and Becker, 1985;Rios-Chavez et al, 2003). Globally, C 8 -C 14 IBAs, 2-MBAs and PEAs are documented in the Spilanthes genus.…”

Section: Plant Familiesmentioning

confidence: 98%

“…Most straight chain fatty acids derive from nonaromatic acyl precursor, like oleic (18:1), linoleic (18:2) and linolenic (18:3) fatty acids (Greger and Hofer, 1987;Greger et al, 1983;Martin and Becker, 1985). Successive dehydrogenations and dehydrations, frequently accompanied by isomerization, lead to characteristic alkenyc and alkynic structures (Greger, 1984), while different oxidative processes contribute to chain shortening or epoxide structures (Christensen and Lam, 1991a;Greger, 1984;Greger et al, 1983Martin and Becker, 1985).…”

Section: Biosynthesismentioning

confidence: 99%

“…Next, NAEs are formed from N-acylphosphatidylethanolamine by phospholipase D, with a release of phosphatidic acid (Chapman, 2004). For most other NAAs, including the HCAAs and macrocyclic polyamides, specific transferases condense the CoA thioesters activated fatty acid with the amine part (Kang and Back, 2006;Martin and Becker, 1985;Nezbedová et al, 2001). For example, in the synthesis of HCAAs, the family of the BAHD-like acyltransferases is responsible for the transfer of het hydroxyl-cinnamoyl residues from CoA to the amine (Handrick et al, 2010).…”

Section: Biosynthesismentioning

confidence: 99%

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Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

132

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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Section: Plant Familiesmentioning

confidence: 98%

Section: Biosynthesismentioning

confidence: 99%

Section: Biosynthesismentioning

confidence: 99%

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Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

132

109

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“…Bei Verbindung A8 handelt es sich um 2,3(c)-Epoxy-nona-6,8-diinsäure-phenylethylamid, das bereits in Acmella ciliata [110,112] Diese Substanz wurde bereits in den Gattungsverwandten Acmella oleracea (L.) Jansen (als "Spilanthes acmella" L. var. oleracea Clarke) [132] und Acmella alba (L`Her.)…”

Section: A8unclassified

“…Verbindung A10, die in der vorliegenden Arbeit aus Sammelfraktion 2 hervorging, wurde bereits durch MARTIN [110,112] in Acmella ciliata nachgewiesen. Darüber hinaus wurde sie in "Spilanthes acmella" [144] gefunden sowie in zwei Echinacea-Arten [11,35], also in Pflanzen desselben Subtribus.…”

Section: Undeca-2e-en-810-diinsäure-isobutylamid (Verbindung A10)unclassified

Acmella Ciliata (H.B.K.) Cassini

Keipert¹,

Melzig²

2009

Z Phytother

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Formation of N- and O-methyl derivatives of lipids containing amino, amide or hydroxy groups by the pyrolytic reaction with trimethylsulfonium hydroxide

Vosmann¹,

Schulte²,

Klein

et al. 1998

Fett/Lipid

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Base‐catalyzed transesterification of acyl lipids with methanol in the presence of trimethylsulfonium hydroxide (TMSH) is an easy and convenient method for the preparation of fatty acid methyl esters for GC analyses. However, lipids containing functional groups such as amino, amide and hydroxy groups are converted in varying degrees to the corresponding N‐ and O‐methyl derivatives by the pyrolytic reaction of TMSH occurring in the injector of the gas chromatograph. For example, lipids containing amino or amide groups are converted into the corresponding N‐methyl and N,N‐dimethyl derivatives, fatty acid ethanolamides to the corresponding N‐methyl, O‐methyl and N,O‐dimethyl derivatives, whereas alkyl methyl ethers are formed from long‐chain alcohols. Furthermore, 2‐O‐ and 3‐O‐monomethyl ethers as well as 2,3‐di‐O‐methyl ethers are formed from 1‐O‐alkylglycerols, methoxy fatty acid methyl esters from hydroxy fatty acids as well as steryl 3β‐O‐methyl ethers from cholesterol and other sterols. Since some of the mentioned artefacts may interfere with fatty acid methyl esters in GC separations the TMSH derivatization method is recommended only with caution for lipids containing amino, amide and hydroxy groups. The methylation reactions, which finally lead to the corresponding N‐methyl, O‐methyl, N,N‐dimethyl or N,O‐dimethyl derivatives of fatty acids and lipids may, however, be of some diagnostic value for the structural analysis of such lipids by GC/MS.

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Amides and other constituents from acmella ciliata

Cited by 38 publications

References 14 publications

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Acmella Ciliata (H.B.K.) Cassini

Formation of N- and O-methyl derivatives of lipids containing amino, amide or hydroxy groups by the pyrolytic reaction with trimethylsulfonium hydroxide

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