Steroid sulfates

Several sulfated polyhydroxysterols have been recently isolated from sponges. Most of these natural products are characterized by the 2p,3a,6a-tri-0-sulfate functions together with additional alkylation in the side chain. These steroids are of interest not only because of their structures but 

Steroids isolated from sponges frequently contain substantially modified side chains, such as those with high degrees of alkylation or other unusual functionalization. Biosynthetic studies have been performed on the mechanism and scope of sterol side-chain dealkylation in sponges  

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Within the OAT family, OAT4 is the only transporter expressed at appreciable levels in both the placenta and in the kidney [54]. The membrane localization of OAT4 within these tissues has not been examined. Steroid sulfates, and ochratoxinA are efficient transport substrates of OAT4, whereas PAH is weakly transported [54]. The functional importance of OAT4 in regulating placental permeability and renal drug elimination is currently unknown. 

Bortfeld, M., Rius, M., Konig, J., Herold-Mende, C., Nies, A.T. and Keppler, D. (2006) Human multidrug resistance protein 8 (MRP8/ABCC11), an apical efflux pump for steroid sulfates, is an axonal protein of the CNS and peripheral nervous system. Neuroscience, 137, 1247-1257. 

The recent development of mixed-mode stationary phases may provide new approaches for the separation of neuroactive steroids from biological matrices. These stationary phases typically embed a charged functional group within the nonpolar carbon chains typically employed in RP separations, and as such separations based on both RP and ion-exchange characteristics can be designed. Examples of this column type are the Primesep line of columns from SIELC Technologies. This separation approach maybe quite useful for the separation of steroid sulfates from complex mixtures. 

Bowers LD, SanauUah. 1996. Direct measurement of steroid sulfate and glucuronide conjugates with high-performance liquid chromatography-mass spectrometry. J Chromatogr B 687 61-68. 

Iversen SD 5-HT and anxiety. Neuropharmacology 23 156-164, 1984 Iwamori M, Moser HW, Kishimoto Y Steroid sulfatase in brain comparison of sulfohydrolase activities for various steroid sulfates in normal and pathological brains, including various forms of metachromatic leukodystrophy. J Neurochem 27 1389-1395, 1976... 

Table 5,3.1 Unconjugated steroids and steroid sulfates of diagnostic importance Reference ranges (ng/ml, classical techniques or mass... 

In the neonatal period, additionally unsaturated forms of the conventional 3/ -hy-droxy-5-ene steroid sulfates can be the principal urinary components (e.g., 3/1,16a-dihydroxy-5,7-pregnadien-20-one and related steroids) [88]. It is during early pregnancy that profile analysis is most used for SLOS diagnosis, and this will be discussed in the final section of the chapter. 

An Acanthodendrilla sp. from Japan contained ten steroidal sulfates, acanthosterol sulfates A-J (561-570). Acanthosterol sulfates I (569) and J (570) showed antifungal activity against Saccharomyces cervisiae and its mutants [463]. Clathsterol (571), was isolated from the Red Sea sponge Clathria sp. The structure was established mainly by interpretation of spectral data and a chemical transformation. Clathsterol (571) was active against HIV-1 reverse transcriptase (RT) at a concentration of 10 iM [464]. Toxadocia zumi contains three sterol sulfates (572-574) that are antimicrobial, cytotoxic, ichthyotoxic and larvicidal [465]. 

Crellastatin A (592) is the first of a series of cytotoxic bis-steroidal sulfates isolated from a Crella sp. from Vanuatu [476]. 

A female-specific 15(3 hydroxylase acts on steroid sulfates such as corticosterone sulfate and forms the major urinary excretion product of that hormone in female rats.292 These sex-specific differences in enzymes are thought to be related to secretions of growth hormone that are in turn controlled by the "programming" of the hypothalamus by androgen during the neonatal period in rats272 or during human fetal development. 

Additionally, sulfated sterols have been described from a wide variety of marine organisms, particularly sponges and echinoderms, and several of these steroidal sulfates have exhibited a broad range of activities. Halistanol sulfates are a group of sulfated polyhydroxysteroids from... 

Although it has been stated that only phenols are conjugated with sulfuric acid,1 three urinary steroid sulfate esters (androsterone sulfate, dehydro-epi-androsterone sulfate, and A 6-aZZo-pregnene-3(/3)-ol-20-one sulfate) have been isolated in which the sulfuric acid is esterified by an alcoholic hydroxyl group.111 It is true that no alcohol administered to... 

Fusetani, N., Matsunaga, S., and Konosu, S., Halistanol sulfate an antimicrobial steroid sulfate from Halichondria cf. moorei Bergquist, Tetrahedron Lett., 22, 1985, 1981. 

Alumina, which is discussed in greater detail in Chapter 5, and cellulose are the two most often used nonsilica-based sorbents. Alumina has been used to separate compounds such as fat-soluble vitamins, alkaloids, and antibiotics. Cellulose-based ion-exchange layers have wide application for sulfonamides, nucleic acids, and steroid sulfates. 

Grube M, Reuther S, Meyer Zu, et al. Organic anion transporting polypeptide 2B1 and breast cancer resistance protein interact in the transepithelial transport of steroid sulfates in human placenta. Drug Metah Dispos 2007 35 30-35. 

In early studies, LC-ESI-MS was applied in the analysis of steroid sulfates in eqnine mine [12], and in the identification of methandrostenolone and stanozolol metabolites in eqnine and human urine [13-15]. 

L.O.G. Weidolf, E.D. Lee, J.D. Henion, Determination of boldenone sulfoconjugate and related steroid sulfates in equine urine by LC-AdS-AdS, Biomed. Environ. Mass Spectrom., 15 (1988)283. 

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