Cyanolipids ofCardiospermum halicacabum L. and other sapindaceous seed oils
TL;DR: A number of seed oils have been investigated with respect to their cyanolipid constituents as mentioned in this paper, which consist of long-chain fatty acids esterified with an unsaturated isoprenoid hydroxy- or dihydroxynitrile.
Abstract: A number of sapindaceous seed oils have been investigated with respect to their cyanolipid constituents. All but one of the oils have this new class of lipids in amounts ranging from 13% to 55%. These cyanolipids are of four different types, but all consist of long-chain fatty acids esterified with an unsaturated isoprenoid hydroxy- or dihydroxynitrile. The large amounts of C20 acids usually found in these oils indicate an appreciable cyanolipid content because such acids are preferentially incorporated in nitrile-containing fractions.Cardiospermum halicacabum L. seed oil was shown to contain 49% of a diester having two fatty acid moieties esterified with 1-cyano-2-hydroxymethylprop-2-ene-1-ol and 6% of another diester derived from 1-cyano-2-hydroxymethylprop-1-ene-3-ol. Treatment of the latter diester with methanolic hydrogen chloride produces methyl 4,4-dimethoxy-3-(methoxymethyl) butyrate from the dihydroxynitrile moiety.
Citations
More filters
TL;DR: The literature dealing with the detection, isolation, purification and characterization of cyanogenic glycosides has been integrated with spectral and chemical data as well as other techniques from our laboratory as discussed by the authors.
131 citations
TL;DR: This study expands the limited knowledge of the frequency of cyanogenesis in natural plant communities, includes novel reports of cyanogenogenesis among a range of taxa and characterizes patterns in intra-plant and intra-population variation of cyanogensis.
52 citations
Cites background from "Cyanolipids ofCardiospermum halicac..."
...While cyanolipids have been identified from a few taxa (Mikolajczak et al., 1970), cyanogenesis in plants most commonly results from the hydrolysis of cyanogenic glycosides (Conn, 1981)....
[...]
...…the family is best known for cyanolipids in the seed oils of numerous species (e.g. Alectryon spp., Allophylus spp., Cardiospermum spp., Sapindus spp., Paullinia spp. and Ungnadia speciosa) (Mikolajczak et al., 1970; Seigler et al., 1971; Gowrikumar et al., 1976; Seigler and Kawahara, 1976)....
[...]
TL;DR: The distribution of plants in the northeastern United States that contain cyanogenic compounds is surveyed and investigation of the biology and chemistry of these plants should prove especially profitable.
Abstract: We have surveyed the distribution of plants in the northeastern United States that contain cyanogenic compounds. Approximately 200 species of plants from 45 families are known to contain compounds capable of liberating hydrogen cyanide upon hydrolysis. These are primarily found in the Gramineae, Ranunculaceae and the Rosaceae. The chemical structures compounds of the cyanogens have been studied in only a small number of the species included, and investigation of the biology and chemistry of these plants should prove especially profitable.
43 citations
TL;DR: The use of psychotropic drugs has been well documented in early post-contact times as mentioned in this paper, including the use of peyote, Lophophora williamsi, Sophora secundiflora, and mescal beans.
Abstract: In the context of this paper, northeastern Mexico refers primarily to the state of Coahuila and immediately adjacent portions of Chihuahua on the west and Nuevo Leon on the south and east. Trans-Pecos Texas herein refers to that portion of the state of Texas west of the Pecos River. The term psychotropic drug collectively designates those agents whose ingestion results in an altered state of consciousness including specifically hallucinations and euphoria. Within the arid area noted above, the use of psychotropic drugs is well documented in early post-contact times. The aboriginal Coahuiltecan speakers of this region were using both peyote, Lophophora williamsi, and the so-called "red" or "mescal bean," Sophora secundiflora at first European contact (La Barre 1938, 1969). Both plants were also used extensively by the Tamaulipecans and Tarahumari of the northern and northeastern deserts (La Barre 1938, 1969). The earliest reference to the use of the red bean from the area under discussion is Cabeza de Vaca's report of 1539 (Schultes 1963), while early references to peyote are many. Though the Pre-Columbian use of psychotropic agents has long been known and a considerable time depth postulated, until quite recently no exact dates were available on the antiquity of this practice. Recently, however, a series of well dated archaeological sites from northeastern Mexico and Trans-Pecos Texas have demonstrated that the use of psychotropic drugs extends back to the ninth millennium B. C. Moreover, as will be shown, the evidence further indicates an evolutionary development
38 citations
TL;DR: In this article, the seed oils of Paullina meliaefolia, Urvillea uniloba and Cardiospermum grandiflorum have been analyzed as their methyl esters and 4,4-dimethyloxazoline derivatives by GC and GC-mass spectrometry.
36 citations
References
More filters
Book•
01 Jan 1962
TL;DR: In this article, the authors present a survey of research work in physics, physical sciences, and physical chemistry, focusing on physics, chemistry, physics, and biology. But they do not discuss their work in this paper.
Abstract: This book should be of interest to senior undergraduates, postgraduates and research workers in physics, physical sciences, physical chemistry.
8,754 citations
445 citations
TL;DR: The white clover (Trifolium repens L) most commonly used in New Zealand contains the cyanogenetic glucosides lotaustralin and linamarin this paper.
Abstract: THE strains of white clover (Trifolium repens L.) most widely used in New Zealand contain the cyanogenetic glucosides lotaustralin and linamarin (1), which are the glucosides of methylethylketone cyanhydrin and acetone cyanhydrin respectively1. Melville and Doak2 isolated a mixture of the two glucosides from white clover in quantities as high as 1.5 gm. per kgm. fresh material. The pharmacology of these compounds for ruminants grazing on white clover has been studied from the points of view of potential cyanide toxicity3 and goitrogenic action4–6.
41 citations
TL;DR: Euphoria oil contains considerably larger amounts of cyclopropanoid fatty acids than previously reported in other seed oils, and is apparently a triglyceride constituent.
Abstract: The seed oil ofEuphoria longana, Sapindaceae, contains 17.4% of 9,10-methyleneoctadecanoic (dihydrosterculic) acid. This identification is based on information from thin layer chromatography, infrared analysis, gas liquid chromatography, nuclear magnetic resonance and mass spectroscopy. Since GLC of the oil showed components that emerged between the usual triglycerides, the cyclopropanoid acid is apparently a triglyceride constituent. The presence of smaller amounts, less than 1%, of cyclopropanoid fatty acids of different chain lengths is indicated by GLC and TLC analyses of the methyl esters. The other major fatty acids in this oil are: 16∶0 (19%), 18∶0 (7%), 18∶1 (36%), 18∶2 (6%), 18∶3 (5%) and 20∶0 (4%).Euphoria oil contains considerably larger amounts of cyclopropanoid fatty acids than previously reported in other seed oils.
35 citations