68820-32-6Relevant articles and documents
Synthesis and biological testing of ester pheromone analogues for two fruitworm moths (Carposinidae)
Barker, David,Chhagan, Asha,Park, Kye Chung,Pilkington, Lisa I.,Suckling, David M.,Twidle, Andrew M.
, p. 9557 - 9567 (2020/10/13)
A range of ester pheromone analogues for carposinid moths were synthesized and evaluated for biological activity. The analogues aimed to take advantage of the structural commonality of (7Z)-alken-11-ones found in this family. Analogues were tested on two pest species: Heterocrossa rubophaga and Coscinoptycha improbana. Two of the analogues, (2Z)-nonenyl nonanoate and (4Z)-heptyl undecenoate, elicited significant electroantennogram responses. Only (4Z)-heptyl undecenoate gave consistent responses with both moth species in single sensillum recording. Field trapping trials were conducted with these two analogues both individually and in combination with the pheromone of each of the two moth species. No attraction was observed to either of the analogues alone, by either moth species. However, when (4Z)-heptyl undecenoate was coupled with the pheromone, it produced a strong inhibitory effect in H. rubophaga, reducing male moth trap catch by over 95%. No inhibitory effect on male moth trap catch was observed in C. improbana.
Isolation, Synthesis, and Biological Activity of Chlorinated Alkylresorcinols from Dictyostelium Cellular Slime Molds
Kikuchi, Haruhisa,Ito, Ikuko,Takahashi, Katsunori,Ishigaki, Hirotaka,Iizumi, Kyoichi,Kubohara, Yuzuru,Oshima, Yoshiteru
supporting information, p. 2716 - 2722 (2017/11/06)
Eight chlorinated alkylresorcinols, monochasiol A-H (1-8), were isolated from the fruiting bodies of Dictyostelium monochasioides. Compounds 1-8 were synthesized to confirm their structures and to obtain sufficient material for performing biological tests. Monochasiol A (1) selectively inhibited the concanavalin A-induced interleukin-2 production in Jurkat cells, a human T lymphocyte cell line. Monochasiols were biogenetically synthesized by the combination of biosynthetic enzymes relating to the principal polyketides, MPBD and DIF-1, produced by Dictyostelium discoideum.
Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route
Carballeira, Nestor M.,Emiliano, Anastacio,Guzman, Aikomari
, p. 33 - 40 (2007/10/03)
The Δ5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxolane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-α-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-1 position and Δ5,9 fatty acids at the sn-2 position. Copyright (C) 1999 Elsevier Science Ireland Ltd.
