LC-MS Analysis and Structural Determination of New Amides from Javanese Long Pepper (Piper retrofractum)

New Insecticidal Amides from Petroleum Ether Extract of Dried Piper nigrum L. Whole Fruits

“…The cis nature of isolated double bond was evident from the same chemical shift of H-12/H-13 and by the upfield 13 C-NMR shifts of C-11 and C-14 between d 26.5-27.1, due to cis shielding. 29) The position of the isolated double bond at C-12/C-13 was determined by EI-MS and HR-EI-MS and confirmed by the reaction of 1 with OsO 4 and product analysis which yielded hexanal as identified in the reaction mixture by GC and GC/MS analysis 7,23) The mass 7,30) yielded (4-methylpentyl)amine, as found by GC (co-injection of authentic samples of similarly branched amines). In the light of above discussion, the structure of 1 was elucidated as (2E,4E,12Z)-N-(4-methylpentyl)octadeca-2,4,12-trienamide.…”

“…[1][2][3][4][5] In search of plant-based potent insecticides, [6][7][8][9][10] current investigations on the petroleum ether extract of the dried whole fruits of P. nigrum have resulted in the isolation of two new, seven hitherto unreported from this plant and eleven known compounds. Compounds isolated from petroleum ether extract included stigmastanol (3), 11) bsitosterol (4) 12) stigmasterol (5), 12) stigmastanol 3-O-b-D-glucopyranoside (6), 11,13) b-sitosterol 3-O-b-D-glucopyranoside (7), [13][14][15][16] [(2E,4E)-octadienoyl]-N-isobutylamide (8), 17) sarmentine (9), 18) [(2E,4E)-dodecadienoyl]-N-isobutylamide (10), 19) [(2E,4E)-dodecadienoyl]pyrrolidine (11) [4], hexadecanoic ethyl ester (12), 20) octadecanoic acid (13), 21) pellitorine (14) [18], hexadecanoylpyrrolidine (15), 22) [(2E)-octadecanoyl]pyrrolidine (16), 22) 1-[(2E,4E,12Z)-octadecatrienoyl]-N-isobutylamide (17), 23) piptaline (18), 24) 1-[7-(3,4-methylenedioxyphenyl)-(2E,4E)-heptadienoyl]-N-isobutylamide (19), 25) 1-(3,4-methylenedioxyphenyl)-(1E)-tetradecene (20), 18) using different chromatographic techniques. The toxicities of 8-11, 14-17 and 19 were determined against fourth instar larvae of Aedes aegypti by WHO method 26) and were found ...…”

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

“…Similar patterns of unsaturation suggest close biosynthetic connections with the elongated amides mentioned above, but also with those of the C 16 series. Octadeca-2E,4E,12Z-trienoic acid derived amides were isolated from P. retrofractum (37a) (Kikuzaki et al 1993), P. nigrum (37a,k,p) (Siddiqui et al 2004), and P. longum (37?) (Sun et al 2007), but were also detected in M. lianus of the Euphorbiaceae (37a,b) (Jiang et al 2009).…”

Preparative isolation and purification of two amides from Mallotus lianus Croiz by high‐speed counter‐current chromatography

“…5), indicating a D 18 double bond [29,32]. And based on the GS-MS data and two-dimension NMR, another double bond existed at C-10.…”

“…Compared with the data given in ref. [29], it was identified as N-isobutyl-2E,4E,12Z-octadecatrienamide (Fig. 1). i 2 -130.5), five allylic methylenes, and eleven methylenes.…”