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

Abstract

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.

Local Anesthetic Activity from Extracts, Fractions and Pure Compounds from the Roots of Ottonia anisum Spreng. (Piperaceae)

“…Again, exception for piperovatine that has a methoxy as substituent. This chemical pattern is in agreement with those from literature records for N-akylamides from Piper species (Parmar et al 1997, Boonen et al 2012, Greger 2016. Besides, some other amides isolated from the genus Ottonia, such as piperlonguminine, corcovadine and isocorcovadine fit in this profile (Costa and Mors 1981).…”

“…Those N-alkylamides without an aromatic group in the end of the chain have an uneven number of carbon atoms such as filfiline (n = 22) from P. officinarum. The most common N-moiety groups are isobutyl, n-pentyl, isopentyl, piperidine, pyrrole and pyrrolidine (Parmar et al 1997, Boonen et al 2012, Greger 2016. Considering the amides isolated from O. anisum, here presented, six of them have an acid chain with uneven number of carbon atoms (n = 5, 7 and 9), being five with isobutyl N-moiety (exception for piperine).…”

An ethnopharmacological survey conducted in the Bolivian Amazon, and identification of N-alkylamides and lignans from Lepidium meyenii and Heliopsis helianthoides var. scabra with effects on the central nervous system

“…35 The unsaturated fatty acid amides, the alkylamide macamides are typical markers of the Maca plant. To date, 19…”

“…Numerous studies have dealt with the antibacterial and antifungal, and also the antiparasitic, molluscicidal and insecticidal activities of NAAs. 35 The antibacterial effects of several NAAs against Escherichia coli, Pseudomonas solanacearum, Erwinia carotovora, and Bacillus subtilis were studied by Molina-Torres et al…”

“…The amide moiety impacts the inhibitory effect, phenylethylamides generally exhibiting higher activities, than those of isobutylamides. 35 Affinin isolated from H. longipes inhibited the growth of E. coli and S.…”