New anthranilic and methylsulfonylpropenoic acid amides from thai <i>Glycosmis</i> species

Hofer, Otmar; Zechner, Gabriela; Vajrodaya, Srunya; Lutz, G.; Greger, Harald

doi:10.1002/jlac.1995199510250

Cited by 21 publications

(23 citation statements)

References 7 publications

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“…226) (Riemer et al, 1997). Finally, sulfurcontaining NAAs are described in the leaves of Rutaceae Glycosmis genera, which represent a typical chemical character of this genus (Chansriniyom et al, 2009;Cuong et al, 1999;Greger et al, 1992Greger et al, , 1993aGreger et al, ,b, 1996Hinterberger et al, 1994Hinterberger et al, , 1998Hofer et al, 1995Hofer et al, , 2000Rahmani et al, 2004Rahmani et al, , 2010. Both, in the fatty acid residue, as well as in the amine moiety, a sulfur atom can occur, mostly two carbon atoms away from the amide function (e.g.…”

Section: Q10mentioning

confidence: 99%

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

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

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: Q10mentioning

confidence: 99%

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

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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“…From the various amides of the Rutaceae fatty acid derived alkamides were mostly found in the genus Zanthoxylum, but were also reported for Tetradium daniellii (Reisch et al 1985) and Pilocarpus trachylophus (Andrade-Neto et al 1996). The other amides of this family are characterized by different acid parts derived from cinnamic acid (Mester 1983;Kubo et al 1984;Riemer et al 1997), cysteine, anthranilic or isovalerianic acid (Hofer et al 1995;Greger et al 1996). The biogenetic origin of the different amine parts of the alkamides was not clarified fully to date, but they are most likely derived from amino acids by decarboxylation and, sometimes, by additional transformation processes Minto and Blacklock 2008;Cortez-Espinosa et al 2011).…”

Section: Introductionmentioning

confidence: 97%

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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“…In recent papers we have also reported on a series of novel anthranilic as well as isovaleric and senecioic acid derived amides from leaf extracts of different Glycosmis species ÐÐÐÐ [3,5]. In order to get more information about the general biogenetic capacity of the genus we have now investigated the lipophilic leaf extracts of two different provenances of Glycosmis parva Craib.…”

Section: Introductionmentioning

confidence: 99%

Phenethylamides With an Unusual 4-Oxo-2-oxolenyl Terpenoid Side Chain from Glycosmis Species

Hofer

Vajrodaya

Greger

1998

Monatshefte fuer Chemie

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Four new amides, glyparvin-A (1), dihydroglyparvin (2), khaochamide (3), and puhinamide (4) were isolated from the lipophilic leaf extracts of Glycosmis species collected in Thailand. Their structures were elucidated by spectroscopic methods. All amides have in common a phenethylamine moiety linked with a geranyloxy rest in para-position which is further transformed to an unusual terminal 4-oxo-2-oxolene ®ve-membered ring, a non-lactonic dihydrofuranone. The different acid parts are derived either from 3-methylsulfonylpropenoic (1, 2) or from isovaleric (3) and senecioic acid (4).

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New anthranilic and methylsulfonylpropenoic acid amides from thai Glycosmis species

Cited by 21 publications

References 7 publications

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

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

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

Phenethylamides With an Unusual 4-Oxo-2-oxolenyl Terpenoid Side Chain from Glycosmis Species

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