Short and stereoselective synthesis of α-methylene-β-hydroxy-γ-butyrolactone diastereomers : Structures revised by theoretical investigations

A short synthetic approach allowed the preparation, in two steps, of (3S,4R)- and (3R,4R)-2- methylene-3-hydroxy-4-(hydroxymethyl)-γ-butyrolactones from 2,3-O-(3-pentylidene)-D-glyceraldehyde, with overall yields of 32 % and 9 %, respectively. The structure of these γ-butyrolactones was revised by experimental and theoretical investigations.Colegio de Farmacéuticos de la Provincia de Buenos Aire

Triterpenos pentacíclicos e esteróides da casca do uchi (Sacoglottis uchi, Humiriaceae)

The ethanol extract from stem bark of Sacoglottis uchi Huber (popularly known as \x93uchi\x94 in the Amazon Region) was submitted to chromatographic fractionation. The dichloromethane fractions provided the pentacyclic triterpene 3-oxo-friedelin (1). The dichloromethane:methanol fractions provided the pentacyclic triterpenes pseudotaraxasterol (2), lupeol (3), a-amyrin (4), betulin (5), and methyl 2ß,3ß-dihydroxy-urs-12-en-28-oate (6) and a mixture of the steroids sitosterol (7) and stigmasterol (8). Their chemical structures were determined by NMR spectroscopy and comparison with spectroscopic data from the literature. All compounds are described for the first time in this species.O extrato etanólico da casca do caule de Sacoglottis uchi Huber (conhecida popularmente como \x93uchi\x94 na Amazônia) foi submetido a fracionamento cromatográfico. As frações eluídas com diclorometano forneceram o triterpeno pentacíclico 3-oxo-friedelina (1). As frações em diclorometano:metanol forneceram os triterpenos pentacíclicos pseudotaraxasterol (2), lupeol (3), a-amirina (4), betulina (5) e 2ß,3ß-di-hidroxi-urs-12-en-28-oato de metila (6), além de uma mistura dos esteróides sitosterol (7) e estigmasterol (8). Suas estruturas químicas foram determinadas por espectroscopia de RMN e comparação com os dados espectroscópicos descritos na literatura. Todas as substâncias isoladas são descritas pela primeira vez nesta espécie

Changes in the essential oil composition of leaves of Echinodorus macrophyllus exposed to

Leaves of Echinodorus macrophyllus (Kunth) Micheli, Alismataceae, were exposed to different doses of γ-radiation (0.00, 1.00, 3.00, 5.00, 10.00, and 20.00 kGy) and the chemical composition of their essential oils was investigated. The extractive process of the essential oil was more favored when the leaves were irradiated. The essential oil components were identified by correlation between GC-FID data and retention parameters obtained from the Kováts method. Moreover, GC-MS analyses of the essential oils were correlated with fragmentation profiles in the NIST standard mass fragmentation data bank. The essential oil of E. macrophyllus contains biologically active constituents of different chemical classes. Acyclic monoterpenes and sesquiterpenes showed increase in concentration when the leaves were exposed to γ-radiation. On the other hand, the component concentrations of some chemical classes were lightly decreased, i.e., for bicyclic monoterpenes, diterpenes, triterpenes, carboxylic esters, and carotenoid derivatives