Bioactive Compounds and 1,3-Di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol from Apium Graveolens L. Seeds

Abstract

Bioassay-directed isolation and purification of the hexane extract of Apium graveolens L. seeds led to the characterization of three compounds: beta-selinene (1), 3-n-butyl-4,5-dihydrophthalide (2) and 5-allyl-2-methoxyphenol (3). The structures of these compounds were established by using (1)H and (13)C NMR spectral methods. Compounds, 1-3 demonstrated 100% mortality on fourth-instar Aedes aegyptii larvae at 50, 25, and 200 microg mL(-)(1), respectively, in 24 h. Also, 2 inhibited the growth of Candida albicans and Candida kruseii at 100 microg mL(-)(1). It inhibited both topoisomerase-I and -II enzyme activities at 100 microg mL(-)(1). Compound 2 displayed 100% mortality at 12.5 and 50 microg mL(-)(1), respectively, when tested on nematodes, Panagrellus redivivus and Caenorhabditis elegans. The triglyceride, 1,3-di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9, 12-octadecadienoyl]glycerol (4) and 3 were isolated for the first time from A. graveolens seeds, although 4 was not biologically active.

Chemical Identification and Ethological Function of Soldier-Specific Secretion in Japanese Subterranean TermiteReticulitermes speratus(Rhinotermitidae)

“…10,16,21) To the best of our knowledge, although such a termite sesquiterpene has been previously reported, almost the authors have not shown full data identifying its chemical structure due to its low or trace amount. 10,16) The report of Momin et al 44) has presented its 1 H and 13 C spectral data, but they did not show a precise 1 H assignment nor any stereochemical evidence for some reasons. This is therefore the first report confirming the presence of -selinene as a major component in R. speratus soldier and presenting a full and detailed description of its chemical structure.…”

Isolation and Characterization of 1,3-Dicapryloyl-2-linoleoylglycerol: A Novel Triglyceride from Berries of Hippophae rhamnoides

“…The presence of only two carbon signals for three ester carbonyls at d C 173.1 (C-1Љ), 172.9 (C-1Ј, C-1ٞ) suggested 1 as a symmetrical triglyceride, [14][15][16][17] hence, confirming position of linoleic acid moiety at C-2. Saponification of 1 followed by methylation of the obtained acid upon GC-MS analysis also confirmed the presence of one linoleic and two caprylic acid moieties in 1, confirming it as 1,3-dicapryloyl-2-linoleoylglycerol.…”

Natural products as leads to potential mosquitocides

“…The 3-n-butyl-4,5-dihydrophthalide (33) isolated from seeds of Apium graveolens shows 100% mortality on fourth-instar Ae. aegypti larvae at 25 μg/mL concentration (Momin et al 2000). The sedanolide (34) isolated from seeds An.…”