Studies on crude drugs effective on visceral larva migrans. IV. Isolation and identification of larvicidal principles in pepper.

Kiuchi, Fumiyuki; Nakamura, Norio; Tsuda, Yoshisuke; Kondo, Kaoru; Yoshimura, Hidetoshi

doi:10.1248/cpb.36.2452

Cited by 87 publications

(57 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[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 ...…”

mentioning

confidence: 99%

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

Siddiqui

Gulzar

Mahmood

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

mentioning

confidence: 99%

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

Siddiqui

Gulzar

Mahmood

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

“…The results of the study showed that piperine and piperiline may have a synergistic effect when combined as an insecticide. However, piperiline has been reported to have no toxic effect against Toxocara canis (de Paula et al, 2000;Kiuchi, Nakamura, Tsuda, Kondo, & Yoshimura, 1988). Piperine has also been found to be toxic to Callosobruchus chinensis L. (Dev & Koul, 1997).…”

Section: Pesticidal Activitymentioning

confidence: 99%

Piperine-Type Amides: Review of the Chemical and Biological Characteristics

Okwute¹,

Egharevba²

2013

IJC

View full text Add to dashboard Cite

A new group of alkaloids emerged in 1819 following the isolation of piperine from the fruits of Piper nigrum. Since then, a large number of these compounds now referred to as piperine-type alkaloids or alkamides or piperamides have been isolated commonly from species belonging to the genus piper (piperaceae) which have worldwide geographical distribution. As a result of the traditional uses of piper species as spices in foods and in phytomedicines globally a number of their extractives and indeed the constituent amides have been screened for pharmacological properties. The biogenesis of the amides has been investigated and a number of synthetic pathways have been developed to make them readily available for biological studies. It has now been established that piperine and its analogues are potential pesticides and possess a number of medicinal properties. They are regarded as universal enhancers in pesticide and drug formulations. This review enhances our knowledge of these amides and paves way for further work.

show abstract

“…In lieu of four-carbon (crotonate) Wadsworth -Emmons homologation of the elusive IV (x = 2, R' = H), followed by amidation, the 9:3(2E,4E,8E) amides (3,9,10) could be prepared via a suitable three-carbon homologation of I11 (x = 3), readily available from cyclopentanone and piperonal as described above. Methodology recently developed by Ma and Lu (14) and Trost and Kazmaier (15), involving transition metal or triphenylphosphine-catalyzed isomerization of an activated alkyne, proved to be ideally suited to effect the desired 3C homologation at the appropriate oxidation level.…”

Section: C Homologation Amidationmentioning

confidence: 99%

“…An aldol condensation -fragmentation sequence involving cyclobutanone and piperonal (if feasible) could, for instance, with subsequent 4C homologation, lead to facile syntheses of compounds like retrofractamide A, 4 (piperamide-B9:3(2E,4E,8E) from Piper refracturn (9), piperamide-A9:3(2E,4E,8E) from P. longurn (10) and piperamide-C9:3(2E,4E,8E) from P. nigrutn (3) (Scheme 1). On the other hand, synthesis of guineensine 5 (piperamide-B13:3(2E,4E,12E)) from P. guineense (1 1) or piperolein B (piperamide-A9: l(8E)) from P. nigr~lrn (12) dictates an aldol condensation -fragmentation involving cyclooctanone and piperonal.…”

Section: Introductionmentioning

confidence: 99%

Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

Strunz¹,

Finlay²

1996

Can. J. Chem.

View full text Add to dashboard Cite

The Sakai aryl aldehyde -cyclic ketone aldol -Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonalxyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonalxyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other nonaromatic 2E,4E-dienoic Piper amide alkaloids.Key words: Piper; amides, alkaloids, insecticides, aldol, fragmentation, cinnamaldehydes, alkyne, redox, isomerization.RCsumk : La stquence de Sakai, qui peut consister en une reaction d'aldol entre un aldehyde et une cetone cyclique suivie d'une fragmentation de Grob, fut utiliske pour preparer des analogues de l'alcalo'ide piperstachine B partir du cinnamaldehyde et de la cyclohexanone. L'influence des substituants sur la reaction du cinnamaldthyde furent tgalement ttudiees. La sequence aldol fragmentation entre le benzaldthyde et la cyclooctanone ou la cyclobutanone ne fonctionne pas malgrt que la cyclopentanone et la cyclohexanone produisent le resultat anticipk. Ce resultat fut CtudiC en detail. Le produit obtenu B paritr de la cyclobutanone, suite i i une homologation de Wittig de quatre carbones, aurait ainsi donne accbs aux alcalo'ides tels la rtfractamide A. Cependant, une homologation de trois carbones sur le produit de la skquence de Sakai entre le pipkronal et la cyclopentanone fournit ces alcalo'ides en d'excellents rendements en utilisant la chimie acttylenique dkveloppt rtcemment par Lu et Trost. L'isomerisation acttylenique fut aussi employte pour la synthbse de la ptllitorine et plusieurs autres alcalo'ids amidiques non-aromatiques 2E,4E-dienoiques des espbces Piper.

show abstract

Studies on crude drugs effective on visceral larva migrans. IV. Isolation and identification of larvicidal principles in pepper.

Cited by 87 publications

References 1 publication

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

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

Piperine-Type Amides: Review of the Chemical and Biological Characteristics

Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

Contact Info

Product

Resources

About