A novel cyclization product from the polyphosphoric acid catalyzed addition of propanal to limonene

The polyphosphoric acid catalyzed addition of propanal to limonene yielded a novel bicyclic ether 2,2,6-trimethyl-4-ethyl-3-oxabicyclo[3.3.1]non-6-ene (I). The yield of (I) was significantly increased by carrying out the reaction under nitrogen rather than in air.

Polyquinanes from (R)-(+)-limonene. Enantioselective total synthesis of the novel tricyclic sesquiterpene (-)-ceratopicanol

The first total synthesis of the biogenetically important and structurally novel triquinane sesquiterpene (-)-ceratopicanol has been accomplished.

Synthesis and in vitro activity of limonene derivatives against Leishmania and Trypanosoma

The synthesis and in vitro activity of R(+)-Limonene derivatives against Leishmania and Trypanosoma cruzi strains are reported. Seven compounds have shown better in vitro activity against Leishmania (V.)braziliensis than the standard drug pentamidine. Additionally, we have identified two promising new anti-T. cruzi limonene derivatives. (C) 2010 Elsevier Masson SAS. All rights reserved.

Inhibitory activity of limonene against Leishmania parasites in vitro and in vivo

Limonene is a monoterpene that has antitumoral, antibiotic and antiprotozoal activity. In this study we demonstrate the activity of limonene against Leishmania species in vitro and in vivo. Limonene killed Leishmania amazonensis promastigotes and amastigotes with 50% inhibitory concentrations of 252.0 +/- 49.0 and 147.0 +/- 46.0 mu M, respectively. Limonene was also effective against Leishmania major, Leishmania braziliensis and Leishmania chagasi promastigotes. The treatment of L. amazonensis-infected macrophages with 300 mu M limonene resulted in 78% reduction in infection rates. L. amazonensis-infected mice treated topically or intrarectally with limonene had significant reduction of lesion sizes. A significant decrease in the parasite load was shown in the lesions treated topically with limonene by histopathological examination. The intrarectal treatment was highly effective in decreasing the parasite burden, healing established lesions and suppressing the dissemination of ulcers. Limonene presents low toxicity in humans and has been shown to be effective as an agent for enhancing the percutaneous permeation of drugs. Our results suggest that limonene should be tested in different experimental models of infection by Leishmania. (C) 2009 Elsevier Masson SAS. All rights reserved.

Preliminary studies on the effects of d-limonene to workers of the leaf-cutting ant Atta sexdens rubropilosa and its implications for control

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Gastroprotective mechanisms of Citrus lemon (Rutaceae) essential oil and its majority compounds limonene and beta-pinene: Involvement of heat-shock protein-70, vasoactive intestinal peptide, glutathione, sulfhydryl compounds, nitric oxide and prostaglandin E-2

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Effects of limonene and essential oil from Citrus aurantium on gastric mucosa: Role of prostaglandins and gastric mucus secretion

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Effect of substrata on the development of stem cuttings of Lippia alba (Mill.) NEBR. - Limonene-carvone chemotype

Studies were conducted to show the effect of different substrata on the development of stem cuttings of Lippia alba made of limonene-carvone chemotype. The experiment was done in the College of Agronomical Sciences, UNESP, Botucatu, SP, Brazil in 2000. The cuttings were planted in polystyrene trays consisting of 72 cells. The cuttings had about 0.20 m of length and were put in the following substrata:Fine sand (T1), commercial substratum (T2), carbonised rice peel and local soil (T3), local soil, cow manure and carbonised rice peel (T4), vermiculite (T5), and carbonised rice peel (T6). After 40 days the development of stem cuttings were evaluated. High rate of rooting of stem cuttings was verified, with average of 95 10 and no significant difference between the treatments. In relation to dry mass of aerial parts and dry mass of roots, significant differences were found. For dry mass production of aerial parts the commercial substratum (T2) and the local soil, cow manure, carbonised rice peel (T4) were optimal. For mass of roots the local soil, cow manure, carbonised rice peel (T4) proved to be the best.

Effect of substrata on the development of stem cuttings of Lippia alba (Mill.) N. E. BR. - Limonene-carvone chemotype

Studies were conducted to show the effect of different substrata on the development of stem cuttings of Lippia alba made of limonene-carvone chemotype. The experiment was done in the College of Agronomical Sciences, UNESP, Botucatu, SP, Brazil in 2000. The cuttings were planted in polystyrene trays consisting of 72 cells. The cuttings had about 0.20 m of length and were put in the following substrata: Fine sand (T1), commercial substratum (T2), carbonised rice peel and local soil (T3), local soil, cow manure and carbonised rice peel (T4), vermiculite (T5), and carbonised rice peel (T6). After 40 days the development of stem cuttings were evaluated. High rate of rooting of stem cuttings was verified, with average of 95% and no significant difference between the treatments. In relation to dry mass of aerial parts and dry mass of roots, significant differences were found. For dry mass production of aerial parts the commercial substratum (T2) and the local soil, cow manure, carbonised rice peel (T4) were optimal. For mass of roots the local soil, cow manure, carbonised rice peel (T4) proved to be the best.

Healing Actions of Essential Oils from Citrus aurantium and d-Limonene in the Gastric Mucosa: The Roles of VEGF, PCNA, and COX-2 in Cell Proliferation

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1 : I. Demonstration of Enzyme Activities and Their Changes with Development

The biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway (Carum carvi L.) proceeds from geranyl diphosphate via a three-step pathway. First, geranyl diphosphate is cyclized to (+)-limonene by a monoterpene synthase. Second, this intermediate is stored in the essential oil ducts without further metabolism or is converted by limonene-6-hydroxylase to (+)-trans-carveol. Third, (+)-trans-carveol is oxidized by a dehydrogenase to (+)-carvone. To investigate the regulation of monoterpene formation in caraway, we measured the time course of limonene and carvone accumulation during fruit development and compared it with monoterpene biosynthesis from [U-14C]Suc and the changes in the activities of the three enzymes. The activities of the enzymes explain the profiles of monoterpene accumulation quite well, with limonene-6-hydroxylase playing a pivotal role in controlling the nature of the end product. In the youngest stages, when limonene-6-hydroxylase is undetectable, only limonene was accumulating in appreciable levels. The appearance of limonene-6-hydroxylase correlates closely with the onset of carvone accumulation. At later stages of fruit development, the activities of all three enzymes declined to low levels. Although this correlates closely with a decrease in monoterpene accumulation, the latter may also be the result of competition with other pathways for substrate.

Extrusion of mixtures of starch and D-limonene encapsulated with beta-cyclodextrin: Flavour retention and physical properties

d-Limonene was encapsulated with beta-cyclodextrin to improve its retention during pre-added flavour starch extrusion. The objective of this work was to determine the effect of processing condition on the flavour retention and extrudate properties. Corn starch containing five levels of beta-cyclodextrin-d-limonene capsules (0-5%) were extruded at five different maximum barrel temperatures (133-167 degrees C) and screw speeds (158-242 rpm) using a twin screw extruder. The effect of these parameters on the flavour retention, expansion, texture, colour difference (Delta E), Water Absorption Index, Water Solubility Index, and residence time distribution (RTD) were investigated. Barrel temperature and capsule level predominantly influenced flavour retention and extrudate properties, while screw speed primarily affected extruder performances such as torque, die pressure, specific mechanical energy and RTD. (c) 2005 Elsevier Ltd. All rights reserved.