The Search for Anticarcinogenic Organoselenium Compounds from Natural Sources

Abstract

Conswnption of Se-enriched plants or yeast-based nutritional supplements is reported to reduce the risk of cancer. S ep aration and identifi cation of natural organoselenium compounds in these plants is essential to understand the basis for their biological activity. Earlier work suggests that plants convert inorganic selenium in the soil or growth medium into organoselenium compounds, such as selenoamino acids, following a route similar to the sulfur assimilatory pathway. To separate and detect selenoamino acids in plant extracts, we employ ion pair LC with an inductively coupled plasma mass spectrometer (ICP-MS) detector and capill ary GC with an atomic emission detector (AED), for underivatized and derivatized compounds, respectively. Volatile selenium compounds, such as those found in human garlic breath, have been analyzed using GC AED. Results involving Se-enriched garlic and yeast-based nutritional supplements are presented.

Natural product-based synthesis of novel anti-infective isothiocyanate- and isoselenocyanate-functionalized amphilectane diterpenes

“…12a Remarkably, no studies assessing the potential antiplasmodial or antimycobacterial properties of isoselenocyanate-containing compounds (synthetic or natural) have been reported so far. 14 In the present work, the syntheses of analogs 2–6 were swiftly accomplished through the isothio- and isoselenocyanation of metabolite 1 , previously isolated by us from the marine sponge Svenzea flava . 9 All compounds were characterized by detailed inspection of 1 H NMR, 13 C NMR, DEPT-NMR, 2D NMR (COSY, HSQC, HMBC, and NOESY), mass spectrometry, and UV and IR spectra.…”

Iodine-catalyzed $$\hbox {sp}^{3}$$ sp 3 C–H bond activation by selenium dioxide: synthesis of diindolylmethanes and di(3-indolyl)selanides

“…Diarylselenides are recognized as an interesting class of compounds that exhibit diverse biological properties, such as anticancer and antioxidant activities [20,21]. They are also used as precursors in the synthesis of various selenonium salts, selenoxides, selenimines, and selenide dihalides of biological importance [22,23].…”

On the selenepin/benzene selenide valence tautomerizations: electronic and steric effects at theoretical levels

“…The structures of organo-selenium compounds are mentioned in the literature as being similar to those of organo-sulfur compounds, but their properties present significant differences, and perhaps, because of the toxicity and instability of many Se compounds, their synthesis is much less developed. Organo-selenium compounds, mainly benzisoselenazol-3(2H)-ones and other cyclic selenenamides, seleninate esters, spirodioxyselenuranes, selenium-containing nucleoside analogs, selenazines, and selenazoles, have been tested as antibacterial, antiviral, antifungal, antiparasitic, anti-inflammatory, antihistamine, and anticancer agents [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Moreover, the heterocyclic compounds with selenium atom in the ring such as selenirenes, selenophenes, selenadiazoles, selenatriazoles, benzisoselanazolones, and some others are presented as the reagents and intermediates employed in synthesis of alkenes, alkynes, and nonselenium heterocycles or as the catalysts for hydroperoxide oxidation of various groups of organic compounds [23].…”