Saponins occur widely in plant species and exhibit a range of biological properties, both beneficial and deleterious. This review, which covers the literature to mid 1986, is concerned with their occurrence in plants and their effects when consumed by animals and man. After a short discussion on the nature, occurrence, and biosynthesis of saponins, during which the distinction between steroidal and triterpenoid saponins is made, the structures of saponins which have been identified in a variety of plants used as human foods, animal feedingstuffs, herbs, and flavorings are described. Many of these compounds have been characterized only during the last 2 decades, and modern techniques of isolation, purification, and structural elucidation are discussed. Particular consideration is given to mild chemical and enzymatic methods of hydrolysis and to recent developments in the application of NMR and soft ionization MS techniques to structural elucidation. Methods currently used for the quantitative analysis of saponins, sapogenols, and glycoalkaloids are critically considered; advances in the use of newer methods being emphasized. The levels of saponins in a variety of foods and food plants are discussed in the context of the methods used and factors affecting these levels, including genetic origin, agronomic, and processing variables, are indicated. Critical consideration is given to the biological effects of saponins in food which are very varied and dependent upon both the amount and chemical structure of the individual compounds. The properties considered include membranolytic effects, toxic and fungitoxic effects, adverse effects on animal growth and performance, and the important hypocholesterolemic effect. A final section deals briefly with the pharmacological effects of saponins from ginseng, since use of this plant is increasing in certain sections of western society as well as being traditional in the Orient.

The chemistry and biological significance of saponins in foods and feedingstuffs.

S-Adenosyl-l-methionine: Beyond the universal methyl group donor

Structure and occurrence of unusual fatty acids in minor seed oils

Bioorthogonal reactions have found widespread use in applications ranging from glycan engineering to in vivo imaging. Researchers have devised numerous reactions that can be predictably performed in a biological setting. Depending on the requirements of the intended application, one or more reactions from the available toolkit can be readily deployed. As an increasing number of investigators explore and apply chemical reactions in living systems, it is clear that there are a myriad of ways in which the field may advance. This article presents an outlook on the future of bioorthogonal chemistry. I discuss currently emerging opportunities and speculate on how bioorthogonal reactions might be applied in research and translational settings. I also outline hurdles that must be cleared if progress toward these goals is to be made. Given the incredible past successes of bioorthogonal chemistry and the rapid pace of innovations in the field, the future is undoubtedly very bright.

The Future of Bioorthogonal Chemistry.

This review discusses the occurrence and distribution (within a plant) of methyl eugenol in different plant species (> 450) from 80 families spanning many plant orders, as well as various roles this chemical plays in nature, especially in the interactions between tephritid fruit flies and plants.

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Methyl Eugenol: Its Occurrence, Distribution, and Role in Nature, Especially in Relation to Insect Behavior and Pollination

Fatty acid compositions of seed oils from three species of Bombacaceae, eleven from Malvaceae, and six from Sterculiaceae were determined. Each of the seed oils contains varying amounts of both malvalic and sterculic acids accompanied by one or both of the corresponding cyclopropane fatty acids. In addition, the seed oil of Pachira aquatic Aubl. (Bombacaceae) contains 12.8% alpha-hydroxysterculic acid.

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Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae.

A series of isomeric methyl octadecynoates was analyzed by mass spectrometry; each isomer gave a unique spectrum. The characteristic ions were those resulting from a McLafferty rearrangement of the allenic sites or of the already-rearranged allenic sites. The acetylenic esters were also subjected to oxymercuration whereupon a carbonyl group was formed at either of the original actylenic carbon atoms providing two oxostearates. Further reaction with NaBH4 formed hydroxy esters which, after silylation, gave diagnostic mass spectra indicative of the triple bond location. Applied to esters with both double and triple bonds, this procedure permitted differentiation between the two types of unsaturation. Methoxyl groups marked the original double bond locations and hydroxyls did so for triple bonds.

Mass spectra of acetylenic fatty acid methyl esters and derivatives.

Screening seed of Trigonella and three related genera for diosgenin

Portenschlagia ramosissima (Port.) vis. (Umbelliferae) seed contains 15% essential oils, 70% of which is the aromatic ether myristicin. These structural assignments were made from nuclear magnetic resonance, combined gas chromatography-mass spectrometry (GC-MS), and infrared and ultraviolet data. GC-MS data also indicate the presence of pinene, cymene, terpinene, elemicin, methyl eugenol, and a variety of sesquiterpene hydrocarbons.

Maerean B. Bohannon

Papers

Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae.

Mass spectra of acetylenic fatty acid methyl esters and derivatives.

Screening seed of Trigonella and three related genera for diosgenin

Myristicin. The major volatile component in mature seed ofPortenschlagia ramosissima