Amides of the fruit of Zanthoxylum spp.

Kashiwada, Yoshiki; Ito, Chikashi; Katagiri, Hitoshi; Mase, Izumi; Komatsu, Kenshi; Namba, Tsuneo; Ikeshiro, Yasumasa

doi:10.1016/s0031-9422(96)00683-8

Cited by 61 publications

(36 citation statements)

References 3 publications

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“…Dependent on their double bond configuration, the dodeca-2,6,8,10-tetraenoic acid IBAs are known as a-, b-, and e-sanshools (e.g. 158-160, 162, 163, 175, 176) (Chen et al, 1999;Jang et al, 2008;Kashiwada et al, 1997;Yang, 2008;Yasuda et al, 1982), while the g-sanshools are tetradeca-2,4,8,10,12-pentaenoic acid derivatives (e.g. 161, 164, 172, 174, 315) (Chen et al, 1999;Iseli et al, 2007;Kashiwada et al, 1997;Xiong et al, 1997;Yang, 2008).…”

Section: Q10mentioning

confidence: 99%

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

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

126

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

126

109

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“…Species containing high levels of alkamides are found in the Asteraceae, Piperaceae, and Rutaceae (Christensen and Lam, 1991;Kashiwada et al, 1997;Parmar et al, 1997). Two reports indicated that alkamides, a class of plant-produced amino compound-containing lipids, structurally related to NAEs, are also able to play a signaling role in plants.…”

mentioning

confidence: 99%

Cytokinin Receptors Are Involved in Alkamide Regulation of Root and Shoot Development in Arabidopsis

et al. 2007

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Alkamides and N-acilethanolamides are a class of lipid compounds related to animal endocannabinoids of wide distribution in plants. We investigated the structural features required for alkamides to regulate plant development by comparing the root responses of Arabidopsis (Arabidopsis thaliana) seedlings to a range of natural and synthetic compounds. The length of the acyl chain and the amide moiety were found to play a crucial role in their biological activity. From the different compounds tested, N-isobutyl decanamide, a small saturated alkamide, was found to be the most active in regulating primary root growth and lateral root formation. Proliferative-promoting activity of alkamide treatment was evidenced by formation of callus-like structures in primary roots, ectopic blades along petioles of rosette leaves, and disorganized tumorous tissue originating from the leaf lamina. Ectopic organ formation by N-isobutyl decanamide treatment was related to altered expression of the cell division marker CycB1:uidA and an enhanced expression of the cytokinin-inducible marker ARR5:uidA both in roots and in shoots. The involvement of cytokinins in mediating the observed activity of alkamides was tested using Arabidopsis mutants lacking one, two, or three of the putative cytokinin receptors CRE1, AHK2, and AHK3. The triple cytokinin receptor mutant was insensitive to N-isobutyl decanamide treatment, showing absence of callus-like structures in roots, the lack of lateral root proliferation, and absence of ectopic outgrowths in leaves under elevated levels of this alkamide. Taken together our results suggest that alkamides and N-acylethanolamides may belong to a class of endogenous signaling compounds that interact with a cytokinin-signaling pathway to control meristematic activity and differentiation processes during plant development.

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“…4) It can also be assumed that the pungency and distribution of the pungent components vary with the part of the Japanese pepper and the maturation stage of the fruits. Although -, -, and -sanshools, the all-trans isomer of -sanshool referred to here as -sanshool, and hydroxy -and -sanshools have been identified as the pungent substances in many varieties of Japanese pepper, [5][6][7][8][9][10][11] not much is known about their distribution in various parts of the plant, at different stages of development of the fruits, or in Japanese pepper grown in various locations.…”

mentioning

confidence: 99%

Quantitative Analysis of Sanshool Compounds in Japanese Pepper (Xanthoxylum piperitumDC.) and Their Pungent Characteristics

Sugai

Morimitsu

Kubota

2005

Bioscience, Biotechnology, and Biochemistry

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Amides of the fruit of Zanthoxylum spp.

Cited by 61 publications

References 3 publications

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

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

Cytokinin Receptors Are Involved in Alkamide Regulation of Root and Shoot Development in Arabidopsis

Quantitative Analysis of Sanshool Compounds in Japanese Pepper (Xanthoxylum piperitumDC.) and Their Pungent Characteristics

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