Review Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides Jente Boonen a , Antoon Bronselaer b , Joachim Nielandt b , Lieselotte Veryser a , Guy De Tre ´ b , Bart De Spiegeleer a,n a Drug Quality and Registration (DruQuaR) Group, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, B-9000 Ghent, Belgium b Department of Telecommunications and Information Processing, Faculty of Engineering and Architecture, Ghent University, Sint-Pietersnieuwstraat 41, B-9000 Ghent, Belgium article info Article history: Received 9 February 2012 Received in revised form 21 May 2012 Accepted 22 May 2012 Available online 30 May 2012 Keywords: N-alkylamides (NAAs) Plant taxonomy Bioactivity Alkamid database Chemical structure classification abstract Ethnopharmacological 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 biological– pharmacological 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 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. & 2012 Elsevier Ireland Ltd. All rights reserved. Contents 1. Introduction ...................................................................................................... 564 2. Material and methods .............................................................................................. 564 3. Results and discussion .............................................................................................. 565 3.1. Alkamid database ............................................................................................ 565 3.2. Plant space ................................................................................................. 566 3.2.1. Plant families ........................................................................................ 566 3.2.2. Biosynthesis ......................................................................................... 570 3.2.3. Intrinsic role in the plant ............................................................................... 570 3.3. Chemical space .............................................................................................. 570 3.4. Functional space............................................................................................. 572 3.4.1. Antimicrobial and related activities....................................................................... 572 3.4.2. Tingling and related organoleptic effects .................................................................. 576 3.4.3. Anti-inflammatory and immunomodulatory effects .......................................................... 581 Contents lists available at SciVerse ScienceDirect journal homepage: www.elsevier.com/locate/jep Journal of Ethnopharmacology 0378-8741/$ - see front matter & 2012 Elsevier Ireland Ltd. All rights reserved. http://dx.doi.org/10.1016/j.jep.2012.05.038 n Corresponding author. Tel.: þ32 9264 8100; fax: þ32 9264 8193. E-mail address: Bart.DeSpiegeleer@UGent.be (B. De Spiegeleer). Journal of Ethnopharmacology 142 (2012) 563–590