Steroids phenolic, activity

Waggot and Britcher [38] have discussed experimental considerations in the determination of organic carbon content of sewage effluent. Close attention is paid to the determination of particular classes of organic compounds in sewage including carbohydrates, amino acids, volatiles, steroids, phenols, surface active materials, fluorescent materials, organochlorine pesticides and ethylene diamine tetracetic acid. 

Estradiol A notable application of phenol activation by [Os] is the CIO alkylation of estradiol 89 (Figure 5). The metal fragment preferentially binds to the a face of the steroid (to form 90) and thus promotes the addition of MVK to the ji face. This forms a quaternary... 

Some alcohols, arylamines, and phenols are sulfated. The sulfate donor in these and other biologic sulfation reactions (eg, sulfation of steroids, glycosaminoglycans, glycolipids, and glycoproteins) is adenosine 3 -phos-phate-S -phosphosulfate (PAPS) (Chapter 24) this compound is called active sulfate. ... 

Some steroid molecules (estrone, estradiol, and estriol) have phenolic hydroxyl in the ring A (Figure 29.12) and therefore, are able to react as free radical scavengers. In 1987, Japanese authors [264,265] showed that all these compounds inhibited iron adriamycin- or iron ADP-ascorbate-dependent phospholipid and liposomal lipid peroxidation. Later on, most attention was drawn to the study of antioxidative properties of estradiol-17(3 (estrogen E2) it has been proposed that E2 antioxidant activity may contribute to cardioprotection observed after estrogen therapy in postmenopausal women. The necessity for the phenolic hydroxyl has been shown by studying the effects of several estrogens on LDL oxidation. It was found [266]... 

The sulfoxide method was introduced by Kahne and coworkers,1 and was heralded as a new method for rapid glycosylation of unreactive substrates in high yield under mild conditions. The reaction involves the sulfoxide donor [sulfoxide (I)], an activating agent (usually triflic anhydride), a hindered, nonnucleophilic base (2,6-di-tert-butyl-4-mcthylpyridine, DTBMP) and a nucleophilic acceptor (most often an alcohol) (Scheme 3.1). The glycosylation of sterically hindered steroidal alcohols, phenols and the /V-glycosylation of an acetamide was reported (Table 3.1). 

This enzyme [EC 2.8.2.15] catalyzes the reaction of 3 -phosphoadenylylsulfate with a phenolic steroid to produce adenosine 3, 5 -bisphosphate and a steroid O-sulfate. The enzyme is very similar in its activity to alcohol sulfotransferase. However, steroid sulfotransferase can utilize estrone as a substrate. 

Sulfotransferases (SULTs) are important for the metabolism of a number of drugs, neurotransmitters, and hormones, especially the steroid hormones. The cosubstrate for these reactions is 3 -phosphoadenosine 5 -phosphosulfate (PAPS) (Fig. 4.1). Like the aforementioned enzymes, sulfate conjugation typically renders the compound inactive and more water soluble. However, this process can also result in the activation of certain compounds, such as the antihypertensive minoxidil and several of the steroid hormones. Seven SULT isoforms identified in humans, including SULTs lAl to 1A3, possess activity toward phenolic substrates such as dopamine, estradiol, and acetaminophen. SULTIBI possesses activity toward such endogenous substrates as dopamine and triiodothyronine. SULTIEI has substantial activity toward steroid hormones, especially estradiol and dehydroepiandrosterone, and toward the anti-... 

In addition to steroids there are plant flavonoids (Box 21-E) that have estrogenic activity. These labile compounds are among the "environmental estrogens." In addition, there are many much more stable compounds, including the insecticides atrazine and DDT, PCBs, and phenolic softeners for plastics, that have weak estrogenic activity. Alarm has been sounded... 

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