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Journal ArticleDOI

A new alkamide from Piper sylvaticum

01 Jan 1982-Phytochemistry (Pergamon)-Vol. 21, Iss: 6, pp 1321-1323

AbstractSylvamide, a new amide derivative, has been isolated from the petrol extract of the seeds of Piper sylvaticum (Roxb.). From spectral and chemical s

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Citations
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Journal ArticleDOI
Abstract: The secondary metabolites isolated from Piper species for the period 1907 to June 1996 have been reviewed. Nearly six hundred chemical constituents belonging to different classes of bioactive compounds are listed together with their source(s) and references. © 1997 Elsevier Science Ltd

802 citations

Journal ArticleDOI
Abstract: Two new unsaturated amides, retrofractamides A and C, were isolated from the total above-ground parts of Piper retrofractum . Retrofractamide A was shown to be N -isobutyl-9(3′,4′-methylenedioxyphenyl)2 E ,4 E ,8 E -nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and 3,4,5-trimethoxydihydrocinnamic acid as well as two higher homologues of retrofractamide A, viz. pipericide (retrofractamide B) and retrofractamide D was demonstrated. The synthesis of pipericide was also achieved.

41 citations

Journal ArticleDOI
Abstract: 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 C18 oleic acid the acid parts are modified either by chain elongations to C28 or by oxidative shortenings to C4 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 immuno-modulatory and cannabinomimetic effects.

40 citations


Additional excerpts

  • ...99a, 101a (Banerji and Pal 1982) P. trichostachyon (Miq.)...

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Journal ArticleDOI
TL;DR: Two new unsaturated amides were isolated from the total above-ground parts of Piper brachystachyum and were shown to be N-isobutyl-15 (3′,4′-methylenedioxyphenyl) 2E,4E-pentadecadienamide from spectroscopic and chemical investigations.
Abstract: Two new unsaturated amides, brachystamides-A and B, were isolated from the total above-ground parts of Piper brachystachyum. Brachystamide-A was shown to be N-isobutyl-15 (3′,4′-methylenedioxyphenyl) 2E,4E-pentadecadienamide from spectroscopic and chemical investigations. Brachystamide-B was N-isobutyl-15 (3′,4′-methylenedioxyphenyl) 2E,4E,14E-pentadecatrienamide.

24 citations

Journal ArticleDOI
Abstract: The structure of a novel 2,3,4- trisubstituted furanoid lignan, designated sylvone, was established as 1 from detailed spectroscopical and chemical studies.

18 citations