Acmella Ciliata (H.B.K.) Cassini

Keipert, Ronald; Melzig, Matthias F.

doi:10.1055/s-0029-1214252

Cited by 2 publications

(3 citation statements)

References 17 publications

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“…With respect to the co-existence of 92a with the C 12 amide 66a in Acmella species, showing a similar pattern of unsaturation (Martin and Becker 1985;Keipert and Melzig 2009;Bae et al 2010;Sharma et al 2011), the formation of spilanthol (92a) may be explained by an elimination of C 2 from 66a by boxidation. Derivatives with oxygen functions in A. ciliata (88a, 97a, 98a) (Martin and Becker 1985;Keipert 2009), H. longipes , and A. oleracea ) (95a, 96a) can be regarded as oxidation products of spilanthol (92a). The detection of a bornylester of 92 in H. longipes and H. novogaliciana is of biogenetic interest ).…”

Section: Olefinic C 10 Alkamidesmentioning

confidence: 99%

“…The oxidation of the terminal carbon atom in 115c of Salmea scandens , 116a of A. ciliata (Keipert 2009), 116d (timuramide D) of Zanthoxylum armatum , and the shortest alkamide 117a of Piper hancei (Narui et al 1995) suggests chain shortening from the methyl end. However, it should be Table 2) Amine parts indicated by small letters are listed in Fig.…”

Section: Olefinic C 8 -C 4 Alkamidesmentioning

confidence: 99%

“…However, it should be Table 2) Amine parts indicated by small letters are listed in Fig. 2 Phytochem Rev pointed out that a large amount of fumaric acid was found together with the fumarylisobutylamide 117a in A. ciliata (Keipert 2009), possibly indicating a different biogenetic origin of this acid moiety.…”

Section: Olefinic C 8 -C 4 Alkamidesmentioning

confidence: 99%

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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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Section: Olefinic C 10 Alkamidesmentioning

confidence: 99%

Section: Olefinic C 8 -C 4 Alkamidesmentioning

confidence: 99%

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

Greger

2015

Phytochem Rev

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Heliopsis suffruticosa (Compositae, Heliantheae), a new species from western Zacatecas

2011

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Se describe Heliopsis suffruticosa de la Sierra de Sombrerete al occidente de Zacatecas, de bosque bajo abierto de piñonero sobre caliza. La especie difiere de otras del género por tener hábito sufruticoso, hojas angostamente lanceoladas a lineares, enteras a espaciadamente serruladas y pedúnculo gradualmente ensanchado hacia el ápice, características que comparte con algunas especies de Zinnia. Se presenta una clave para distinguir entre las especies mexicanas de hábito perenne de Heliopsis. Al igual que en otros representantes de este género, las raíces de H. suffruticosa presentan alcamidas, detectándose en este caso cinco isobutil alcamidas diacetilénicas conjugadas, unidas a un metilo terminal en posición omega.

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Acmella Ciliata (H.B.K.) Cassini

Cited by 2 publications

References 17 publications

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

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

Heliopsis suffruticosa (Compositae, Heliantheae), a new species from western Zacatecas

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