ABSTRACT
The last decades have shown a spectacular and partially unexplained rise in the prevalence of autism spectrum disorders (ASD). This rise in ASD seems to parallel changes in the dietary composition of fatty acids. This change is marked by the replacement of cholesterol by omega-6 (n-6) fatty acids in many of our food products, resulting in a drastically increased ratio of omega-6/omega-3 (n-6/n-3). In this context, we review the available knowledge on the putative role of fatty acids in neurodevelopment and describe how disturbances in n-6/n-3 ratios may contribute to the emergence of ASDs. Both clinical and experimental research is discussed. We argue that a change in the ratio of n-6/n-3, especially during early life, may induce developmental changes in brain connectivity, synaptogenesis, cognition and behavior that are directly related to ASD.
Subject(s)
Child Development Disorders, Pervasive/metabolism , Diet , Fatty Acids, Essential/metabolism , Animals , Brain/growth & development , Brain/metabolism , Child Development Disorders, Pervasive/epidemiology , Child Development Disorders, Pervasive/etiology , HumansABSTRACT
(2R)-alpha-(beta-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile (taxiphyllin) dihydrate, C(14)H(17)NO(7) x 2H(2)O, is a naturally occurring cyanogenetic glycoside which has been isolated from Henriettella fascicularis (Sw.) C. Wright (Melastomataceae). Its structure is stabilized by a wealth of intermolecular O-H...O and O-H...N hydrogen bonds spun into a three-dimensional network. Further stabilization arises from an intramolecular O-H...O bond and weak intermolecular C-H...O interactions. The very anisotropic growth speeds of the basal pinacoids from methanol mirror a certain structural inhomogeneity.
Subject(s)
Nitriles/chemistry , Plants, Toxic/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Models, Molecular , Panama , Plant Extracts/chemistryABSTRACT
Activity-guided isolation of radical-scavenging compounds from the dichloromethane extract of the root bark of Lannea edulis led to isolation of two known bioactive alkylphenols [cardonol 7 (1) and cardonol 13 (2)], and three new dihydroalkylhexenones were also isolated (3-5). Their structures were elucidated by spectroscopic and chemical methods. The absolute configuration of 4 was determined by the Mosher ester method.
Subject(s)
Anacardiaceae/chemistry , Free Radical Scavengers/isolation & purification , Hexanones/isolation & purification , Phenols/isolation & purification , Plants, Medicinal/chemistry , Biphenyl Compounds , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Hexanones/chemistry , Hexanones/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Phenols/pharmacology , Picrates , Plant Bark/chemistry , Plant Roots/chemistry , Stereoisomerism , ZimbabweABSTRACT
A new isoflavone, 4',5,7-trihydroxy-6,8-dimethylisoflavone (1), and a new sesterterpenoic acid (2), together with five known compounds, lichexanthone (3), (-)-pinoresinol (4), betulinic acid, palmitic acid, and beta-sitosterol, were isolated from a dichloromethane extract of the branches of Henriettella fascicularis. Their structures were established by extensive spectroscopic methods. An attempt to determine the absolute stereochemistry of (2E,6S)-6-[(1R,5Z,3aS,9R,10Z,12aR)-1,2,3,3a,4,7,8,9,12,12a-decahydro-9-hydroxy-3a,6,10-trimethylcyclopentanocycloundecen-1-yl]-2-methylhept-2-enoic acid (2) was performed by single-crystal X-ray analysis, using Cu Kalpha radiation. Compound 1 showed significant competitive binding to estrogen receptor beta and moderate antiestrogenic activity with cultured Ishikawa cells.
Subject(s)
Estrogen Antagonists/isolation & purification , Estrogen Receptor Modulators/isolation & purification , Furans , Isoflavones/isolation & purification , Melastomataceae/chemistry , Phytosterols/isolation & purification , Plants, Medicinal/chemistry , Terpenes/isolation & purification , Alkaline Phosphatase/metabolism , Binding Sites , Cell Line/drug effects , Crystallography, X-Ray , Endometrium/drug effects , Estrogen Antagonists/chemistry , Estrogen Antagonists/pharmacology , Estrogen Receptor Modulators/chemistry , Estrogen Receptor Modulators/pharmacology , Female , Humans , Isoflavones/chemistry , Isoflavones/pharmacology , Lignans/chemistry , Lignans/isolation & purification , Methylation , Molecular Conformation , Molecular Structure , Palmitic Acid/chemistry , Palmitic Acid/isolation & purification , Panama , Phytosterols/chemistry , Phytosterols/pharmacology , Plant Shoots/chemistry , Sitosterols/chemistry , Sitosterols/isolation & purification , Stereoisomerism , Terpenes/chemistry , Terpenes/pharmacologyABSTRACT
The hydroalcoholic extract of Tinnevelli senna is widely used as a laxative phytomedicine. In order to improve the knowledge of the chemical composition of this extract, LC/MS and LC/MS(n) studies were performed, allowing the on-line identification of most of the known constituents, i. e., flavonoids, anthraquinones and the typical dianthronic sennosides. However, the identity of four compounds could not be ascertained on-line under the given LC/MS conditions. These substances were isolated and their structures elucidated as kaempferol, the naphthalene derivative tinnevellin 8-glucoside and two new carboxylated benzophenone glucosides.
Subject(s)
Benzophenones/isolation & purification , Flavonoids , Glucosides/isolation & purification , Kaempferols , Naphthalenes/isolation & purification , Quercetin/analogs & derivatives , Senna Extract/isolation & purification , Senna Plant , Benzophenones/chemistry , Chromatography, Liquid/methods , Glucosides/chemistry , Glucosides/pharmacology , Mass Spectrometry/methods , Naphthalenes/chemistry , Naphthalenes/pharmacology , Plant Structures/chemistry , Quercetin/chemistry , Quercetin/isolation & purification , Senna Extract/chemistryABSTRACT
Four new prenylated isoflavonoids, vogelins D-G (1-4), were isolated from the CH2Cl2 extract of Erythrina vogelii root bark in addition to the known compounds isolupalbigenin (5), ficuisoflavone (6), ulexone (7), isochandalon (8), and isoderrone (9). The structures 1-4 were elucidated by spectroscopic and chemical methods. The absolute configuration of compound 1 was determined on the basis of its CD spectrum. Possible biogenetic relationships among the E. vogelii isoflavonoids are briefly discussed.
