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PubMed2003

Cyanide toxicosis in goats after ingestion of California Holly (Heteromeles arbutifolia).

Cyanogenic glycosides are found in many native and naturalized plants throughout North America. The glycosides themselves are not toxic, but they yield hydrogen cyanide (hydrocyanic or prussic acid) when they are hydrolyzed by beta-glycosidases, either as a result of injury to the plant cells or by microbial action in the rumen. Hydrogen cyanide is readily absorbed from the gastrointestinal tract. Cyanide ion binds with iron in cytochrome oxidase, interfering with cellular respiration. The clinical effects are peracute, often resulting in death less than 1 hour after ingestion. This study describes a case that resulted in significant morbidity and mortality in a herd of goats after exposure to California holly (Heteromeles arbutifolia).

Animals↗
PubMed2002

One-pot asymmetric synthesis of beta-cyanohydroxymethyl alpha-amino acid derivatives: formation of three contiguous stereogenic centers.

[reaction: see text] One-pot asymmetric Mannich-hydrocyanation reactions are described. Reaction of unmodified aldehydes with N-PMP-protected alpha-imino ethyl glyoxylate in the presence of catalytic amounts of L-proline followed by the addition of Et(2)AlCN provided highly enantiomerically pure beta-cyanohydroxymethyl alpha-amino acid derivatives possessing three contiguous stereogenic centers as single diastereomers (93-99% ee). Control of reaction temperature during the cyanation step directed whether cyclization of the products to lactones occurred.

Aldehydes↗
PubMed1999

Proximate composition and mineral content of two edible species of Cnidoscolus (tree spinach).

Proximate composition and mineral content of raw and cooked leaves of two edible tree spinach species (Cnidoscolus chayamansa and C. aconitifolius), known locally as 'chaya', were determined and compared with that of a traditional green vegetable, spinach (Spinicia oleraceae). Results of the study indicated that the edible leafy parts of the two chaya species contained significantly (p<0.05) greater amounts of crude protein, crude fiber, Ca, K, Fe, ascorbic acid and beta-carotene than the spinach leaf. However, no significant (p>0.05) differences were found in nutritional composition and mineral content between the chaya species, except minor differences in the relative composition of fatty acids, protein and amino acids. Cooking of chaya leaves slightly reduced nutritional composition of both chaya species. Cooking is essential prior to consumption to inactivate the toxic hydrocyanic glycosides present in chaya leaves. Based on the results of this study, the edible chaya leaves may be good dietary sources of minerals (Ca, K and Fe) and vitamins (ascorbic acid and beta-carotene).

Ascorbic Acid↗
PubMed2003

Cyanobenzoylation and hydrocyanation of aldehydes with benzoyl cyanide using no catalyst.

[reaction: see text] In the presence of MS 4A in DMSO, cyanobenzoylation of various aldehydes with benzoyl cyanide proceeded very smoothly to give the corresponding cyanohydrin benzoates in high to excellent yields without an acid or a base. On the other hand, reaction of aldehydes with BzCN in DMSO-H(2)O also occurred readily to afford the corresponding free cyanohydrins exclusively.

Journal Article↗
PubMed2003

Synthesis of the 7alpha-cyano-(17alpha,20E/Z)-[125I]iodovinyl-19-nortestosterones: potential radioligands for androgen and progesterone receptors.

We report the preparation of the 7alpha-cyano derivative of the isomeric (17alpha,20E/Z)-[125I]iodovinyl-19-nortestosterones (IVNT) together with their binding affinity for the androgen receptor (AR) and their biodistribution in two different animal models. The cyano group was introduced at the 7alpha-position by hydrocyanation of 4,6-estradien-17beta-ol-3-one with diethylaluminum cyanide. Selective protection of the A-ring enone system as the dienol ether followed by ethynylation and deprotection under base and acid hydrolysis condition gave 7alpha-cyano-17alpha-ethynyl-19-nortestosterone. The stannyl derivatives were prepared by addition of tri-n-butylstannyl hydride and converted stereospecifically to the corresponding [125I]iodovinyl analog using [125I]NaI and H2O2. The [125I]iodovinylsteroids were intravenously administered to male rats and estrogen-primed immature female rats and tissue uptake was measured up to 6h post-injection. Co-administration of NLP-004 or ORG-2058, highly selective ligands for the progesterone receptor, to the female rats did not affect uterus uptake of the 125I-ligands. However co-injection of testosterone to DES-primed male rats induced a marked increase in prostate uptake of the 20Z-isomer of 7alpha-cyano-[125I]-IVNT. The relative binding affinity (RBA) of either 7alpha-cyano-(17alpha,20E/Z)-IVNT isomer for the AR is low (RBA=4 and 3, respectively, versus 100 for 5alpha-dihydrotestosterone (DHT)), suggesting the absence of a possible role of the AR in the localization process. These findings contrast previously reported data for the analogous 7alpha-methyl-[125I]-IVNT where co-administration of testosterone was shown to result in a 50% drop in prostate uptake. These data indicate that the addition of an electron withdrawing 7alpha-cyano group to 123I-labeled nortestosterone derivatives does not improve their potential to serve as SPECT agents for the imaging of AR densities in the prostate.

Androgens↗
PubMed2001

The development of new monometallic bifunctional catalysts with Lewis acid and Lewis base properties, and their application in asymmetric cyanation reactions.

Bifunctional catalysts can drastically improve the efficiency of asymmetric processes with respect to enantioselectivity and/or conversion rate. A new type of chiral bifunctional catalyst has been developed recently in the Shibasaki group that contains both Lewis acid and Lewis base moieties. These monometallic and bifunctional phosphinoyl-containing catalysts are able to coordinate both nucleophilic and electrophilic substrates in the transition state. Several successful applications of this new catalytic concept in the field of asymmetric cyanation reactions have already been reported, for example, the asymmetric hydrocyanation of aldehydes and imines as well as the asymmetric Reissert reaction. The development and principle of this catalytic concept as well as main applications thereof are reviewed in this article.

Journal Article↗
PubMedDate not supplied

Synthesis and characterization by 1H and 13C nuclear magnetic resonance spectroscopy of 17 alpha-cyano, 17 alpha-aminomethyl, and 17 alpha-alkylamidomethyl derivatives of 5 alpha-dihydrotestosterone and testosterone.

17 alpha-Aminomethyl, 17 alpha-acetamidomethyl, and 17 alpha-hemiglutaramidomethyl derivatives of dihydrotestosterone and testosterone have been prepared by hydrocyanation of 3,3'-(ethylenedioxy)-5 alpha-androstan-17-one and 3,3'-ethylenedioxyandrost-5-en-17-one, reduction of the corresponding acetylated 17 alpha-cyanohydrins with lithium aluminium hydride, and acylation of the resulting 17 alpha-aminomethyl derivatives with either acetic anhydride or the mono acid chloride of glutaric acid mono methyl ester. Saponification of the 17 alpha-hemiglutaramidomethyl methyl esters gave the corresponding hemiglutaramido derivatives, while acid hydrolysis of the 3-ethylene ketal group of 17 alpha-acetamidomethyl and 17 alpha-hemiglutaramidomethyl derivatives regenerated the 3-oxo and 3-oxo-4-ene functions. The 17 alpha-configuration of 17-substituted steroids was determined by 1H and 13C NMR and confirmed by comparing with NMR data for 17 alpha- and 17 beta-cyano-17-hydroxyandrost-4-en-3-one, 17 beta-cyano-3,3'-(ethylenedioxy)androst-5-en-17-ol, 17 alpha-alkynyl, and 17 alpha-hexanoic derivatives of dihydrotestosterone and testosterone, of known 17-configurations. Several ambiguous assignments of 13C NMR signals of 17 alpha-substituted steroids and unsubstituted 17 beta-hydroxy or 17-oxo precursors have been resolved using steroid analogs deuterated at positions C5-7, or C16 for androstane derivatives, and at positions C6-7, or C7 for androstene derivatives. 17 alpha-Aminomethyl and 17 alpha-alkylamidomethyl derivatives of dihydrotestosterone and testosterone are useful intermediates for the access to potential ligands of androgen-binding proteins necessary for affinity chromatography purification or affinity-labeling experiments.

Acetamides↗
PubMed1992

Hydrocyanate, oxalate, phytate, calcium and zinc in selected brands of Nigerian cocoa beverage.

Hydrocyanate, oxalate, phytate, calcium and zinc were determined in five brands of cocoa beverage which were coded NC, BT, PN, CT and CA. Hydrocyanate ranged from 5.40 to 9.64 mg/100 g dry matter (DM), oxalate 68 to 146 mg/100 g DM, phytate 590 to 750 mg/100 g DM, calcium 28.7 to 116.4 mg/100 g DM and zinc 0.516 to 0.675 mg/100 g DM. The computed phytate:zinc, calcium:phytate and [calcium] [phytate]/[zinc] molar ratios ranged from 89 to 132, 0.80 to 3.01 and 0.64 to 3.03 respectively. The discussion is focused on toxic levels of hydrocyanate and oxalate, and the significance of the molar ratios in predicting the bioavailability of dietary zinc.

Beverages↗