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Journal articles on the topic 'Steroid biosynthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Batth, Rituraj, Clément Nicolle, Ilenuta Simina Cuciurean, and Henrik Toft Simonsen. "Biosynthesis and Industrial Production of Androsteroids." Plants 9, no. 9 (September 3, 2020): 1144. http://dx.doi.org/10.3390/plants9091144.

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Steroids are a group of organic compounds that include sex hormones, adrenal cortical hormones, sterols, and phytosterols. In mammals, steroid biosynthesis starts from cholesterol via multiple steps to the final steroid and occurs in the gonads, adrenal glands, and placenta. This highly regulated pathway involves several cytochrome P450, as well as different dehydrogenases and reductases. Steroids in mammals have also been associated with drug production. Steroid pharmaceuticals such as testosterone and progesterone represent the second largest category of marketed medical products. There heterologous production through microbial transformation of phytosterols has gained interest in the last couple of decades. Phytosterols being the plants sterols serve as inexpensive substrates for the production of steroid derivatives. Various genes and biochemical pathways involved in phytosterol degradation have been identified in many Rhodococcus and Mycobacterium species. Apart from an early investigation in mammals, presence of steroids such as androsteroids and progesterone has also been demonstrated in plants. Their main role is linked with growth, development, and reproduction. Even though plants share some chemical features with mammals, the biosynthesis is different, with the first C22 hydroxylation as an example. This is performed by CYP11A1 in mammals and CYP90B1 in plants. Moreover, the entire plant steroid biosynthesis is not fully elucidated. Knowing this pathway could provide new processes for the industrial biotechnological production of steroid hormones in plants.

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Hoshino, Yosuke, and Eric A. Gaucher. "Evolution of bacterial steroid biosynthesis and its impact on eukaryogenesis." Proceedings of the National Academy of Sciences 118, no. 25 (June 15, 2021): e2101276118. http://dx.doi.org/10.1073/pnas.2101276118.

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Steroids are components of the eukaryotic cellular membrane and have indispensable roles in the process of eukaryotic endocytosis by regulating membrane fluidity and permeability. In particular, steroids may have been a structural prerequisite for the acquisition of mitochondria via endocytosis during eukaryogenesis. While eukaryotes are inferred to have evolved from an archaeal lineage, there is little similarity between the eukaryotic and archaeal cellular membranes. As such, the evolution of eukaryotic cellular membranes has limited our understanding of eukaryogenesis. Despite evolving from archaea, the eukaryotic cellular membrane is essentially a fatty acid bacterial-type membrane, which implies a substantial bacterial contribution to the evolution of the eukaryotic cellular membrane. Here, we address the evolution of steroid biosynthesis in eukaryotes by combining ancestral sequence reconstruction and comprehensive phylogenetic analyses of steroid biosynthesis genes. Contrary to the traditional assumption that eukaryotic steroid biosynthesis evolved within eukaryotes, most steroid biosynthesis genes are inferred to be derived from bacteria. In particular, aerobic deltaproteobacteria (myxobacteria) seem to have mediated the transfer of key genes for steroid biosynthesis to eukaryotes. Analyses of resurrected steroid biosynthesis enzymes suggest that the steroid biosynthesis pathway in early eukaryotes may have been similar to the pathway seen in modern plants and algae. These resurrected proteins also experimentally demonstrate that molecular oxygen was required to establish the modern eukaryotic cellular membrane during eukaryogenesis. Our study provides unique insight into relationships between early eukaryotes and other bacteria in addition to the well-known endosymbiosis with alphaproteobacteria.

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3

Curnow, Kathleen M., Perrin C. White, and Leigh Pascoe. "Adrenal steroid biosynthesis." Current Opinion in Endocrinology and Diabetes 1, no. 1 (January 1994): 10–15. http://dx.doi.org/10.1097/00060793-199400010-00004.

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4

BLAIS, Catherine, Chantal DAUPHIN-VILLEMANT, Nikolay KOVGANKO, Jean-Pierre GIRAULT, Charles DESCOINS, and René LAFONT. "Evidence for the involvement of 3-oxo-Δ4 intermediates in ecdysteroid biosynthesis." Biochemical Journal 320, no. 2 (December 1, 1996): 413–19. http://dx.doi.org/10.1042/bj3200413.

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Although the involvement of 3-oxo-Δ4 compounds as intermediates in arthropod ecdysteroid biosynthesis has been postulated for a long time, it has not yet been directly demonstrated. In the present study, 3-oxo-Δ4-steroids have been synthesized and incubated in vitro with dissociated moulting gland cells from the crab Carcinus maenas. The tritiated compounds were converted into 3-dehydroecdysone, ecdysone and/or 25-deoxyecdysone, i.e. final ecdysteroids. This means that the 3-oxo-Δ4 compounds had undergone a 5β-reduction, to give the 5β-conformation of ecdysteroids. Our results suggest that the 3-oxo-Δ4-steroid 4,7-cholestadien-14α-ol-3,6-dione may be an intermediate in the biosynthetic pathway. The 5β-reduction reaction involves a cytosolic enzyme which requires NADPH as electron donor and seems specific for 3-oxo-Δ4 substrates. This reaction was the most active in crab Y-organs, as compared with other tissues. The characteristics of the 5β-reductase (subcellular localization, substrate and cofactor requirements) appear similar to those of the vertebrate 3-oxo-Δ4-steroid 5β-reductase involved in steroid hormone catabolism and bile acid biosynthesis.

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5

Henriques, Rachael G., Theodore S. Widlanski, Tingsen Xu, and J. David Lambeth. "Inhibition of steroid biosynthesis by steroid sulfonates." Journal of the American Chemical Society 114, no. 18 (August 1992): 7311–13. http://dx.doi.org/10.1021/ja00044a062.

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6

Stocco, Douglas M. "106 Randel Lecture: The history of the discovery of the Steroidogenic Acute Regulatory (StAR) Protein." Journal of Animal Science 97, Supplement_1 (July 2019): 39. http://dx.doi.org/10.1093/jas/skz053.088.

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Abstract This two-part presentation regarding acute regulation of steroid biosynthesis documents discovery of the StAR protein and resolves controversy regarding mitochondrial cholesterol transport. The acute regulation of steroid biosynthesis was known to require de novo synthesis of a regulator protein to mediate the transfer of cholesterol, the substrate for steroids, from the outer to the inner mitochondrial membrane where it was converted to pregnenolone by the cytochrome P450 side chain cleavage enzyme. We discovered a novel protein that was tightly correlated with steroid biosynthesis and had the requisite characteristics for the putative acute regulator of cholesterol transfer for steroid synthesis. Further studies confirmed that StAR protein is an indispensable component in the process of mitochondrial uptake of the cholesterol substrate for steroidogenesis. The translocator protein (TSPO) is a mitochondrial outer membrane protein suggested to import cholesterol to the inner mitochondrial membrane. However, it was demonstrated in vivo in Leydig cell specific TSPO conditional knockout mice that TSPO was not required for testosterone production or fertility. Similarly, global TSPO knockout (TSPO/-) mice were viable and fertile with fecundity equivalent to TSPO floxed (TSPOfl/fl) controls. Adrenal and gonadal steroidogenesis did not differ between TSPOfl/ fl and TSPO-/- mice. In vitro use of different steroidogenic cell line models (MA-10, MLTC, Y-1, H295R and R2C) demonstrated that siRNA-knockdown of TSPO did not affect steroidogenesis. Also, CRISPR/ Cas9-mediated TSPO deletion did not affect MA-10 cell steroidogenesis. These results directly 1) refute the suggestion that TSPO is indispensable for viability and steroid hormone biosynthesis; and, 2) substantiate the primal role of the StAR protein as the rate limiting factor in steroid hormone biosynthesis.

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7

Sharifi, Nima, and Richard J. Auchus. "Steroid biosynthesis and prostate cancer." Steroids 77, no. 7 (June 2012): 719–26. http://dx.doi.org/10.1016/j.steroids.2012.03.015.

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8

Li, Jiehan, Vassilios Papadopoulos, and Veera Vihma. "Steroid biosynthesis in adipose tissue." Steroids 103 (November 2015): 89–104. http://dx.doi.org/10.1016/j.steroids.2015.03.016.

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9

Bourne, Anthony R., and Paul Licht. "Steroid biosynthesis in turtle testes." Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 81, no. 3 (1985): 793–96. http://dx.doi.org/10.1016/0305-0491(85)90407-9.

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10

Ivanchina, Natalia V., Vladimir I. Gorbach, Anatoly I. Kalinovsky, Alla A. Kicha, Timofey V. Malyarenko, Pavel S. Dmitrenok, and Valentin A. Stonik. "Synthesis of Deuterium-Labeled Steroid 3,6-Diols." Natural Product Communications 12, no. 9 (September 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200908.

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A facile synthesis of a set of deuterium-labeled steroid 3,6-diols with different steroid A/B ring fusion, unsaturations, and configurations of hydroxyl groups at C-3 and C-6 is described. Reduction and deuteration, based on deuterium-exchange of the obtained the cholest-4-ene-3,6-dione from cholesterol using sodium borodeuteride and deuterium water, were used. The obtained steroid diols are intended to be used as precursors in the studies on biosynthesis of some marine polar steroids.

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11

Penning, Trevor M., Phumvadee Wangtrakuldee, and Richard J. Auchus. "Structural and Functional Biology of Aldo-Keto Reductase Steroid-Transforming Enzymes." Endocrine Reviews 40, no. 2 (August 20, 2018): 447–75. http://dx.doi.org/10.1210/er.2018-00089.

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Abstract Aldo-keto reductases (AKRs) are monomeric NAD(P)(H)-dependent oxidoreductases that play pivotal roles in the biosynthesis and metabolism of steroids in humans. AKR1C enzymes acting as 3-ketosteroid, 17-ketosteroid, and 20-ketosteroid reductases are involved in the prereceptor regulation of ligands for the androgen, estrogen, and progesterone receptors and are considered drug targets to treat steroid hormone–dependent malignancies and endocrine disorders. In contrast, AKR1D1 is the only known steroid 5β-reductase and is essential for bile-acid biosynthesis, the generation of ligands for the farnesoid X receptor, and the 5β-dihydrosteroids that have their own biological activity. In this review we discuss the crystal structures of these AKRs, their kinetic and catalytic mechanisms, AKR genomics (gene expression, splice variants, polymorphic variants, and inherited genetic deficiencies), distribution in steroid target tissues, roles in steroid hormone action and disease, and inhibitor design.

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12

HENRIQUES, R. G., T. S. WIDLANSKI, T. XU, and J. D. LAMBETH. "ChemInform Abstract: Inhibition of Steroid Biosynthesis by Steroid Sulfonates." ChemInform 23, no. 51 (December 22, 1992): no. http://dx.doi.org/10.1002/chin.199251272.

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13

Sushko, T. A., A. A. Gilep, A. V. Yantsevich, and S. A. Usanov. "Role of microsomal steroid hydroxylases in Δ7-steroid biosynthesis." Biochemistry (Moscow) 78, no. 3 (March 2013): 282–89. http://dx.doi.org/10.1134/s0006297913030103.

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14

Knuuttila, Matias, Esa Hämäläinen, and Matti Poutanen. "Applying mass spectrometric methods to study androgen biosynthesis and metabolism in prostate cancer." Journal of Molecular Endocrinology 62, no. 4 (May 2019): R255—R267. http://dx.doi.org/10.1530/jme-18-0150.

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Recent development of gas chromatography and liquid chromatography-tandem mass spectrometry (GC-MS/MS, LC-MS/MS) has provided novel tools to define sex steroid concentrations. These new methods overcome several of the problems associated with immunoassays for sex steroids. With the novel MS-based applications we are now able to measure small concentrations of the steroid hormones reliably and with high accuracy in both body fluids and tissue homogenates. The sensitivity of the tandem mass spectrometry assays allows us also for the first time to reliably measure picomolar or even femtomolar concentrations of estrogens and androgens. Furthermore, due to a high sensitivity and specificity of MS technology, we are also able to measure low concentrations of steroid hormones of interest in the presence of pharmacological concentration of other steroids and structurally closely related compounds. Both of these features are essential for multiple preclinical models for prostate cancer. The MS assays are also valuable for the simultaneous measurement of multiple steroids and their metabolites in small sample volumes in serum and tissue biopsies of prostate cancer patients before and after drug interventions. As a result, novel information about steroid hormone synthesis and metabolic pathways in prostate cancer has been obtained. In our recent studies, we have extensively applied a GC-MS/MS method to study androgen biosynthesis and metabolism in VCaP prostate cancer xenografts in mice. In the present review, we shortly summarize some of the benefits of the GC-MS/MS and novel LC-MS/MS assays, and provide examples of their use in defining novel mechanisms of androgen action in prostate cancer.

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15

WATERMAN, MICHAEL R., JOHAN LUND, RAGNHILD AHLGREN, DONGAHI WU, and EVAN R. SIMPSON. "Regulation of steroid hydroxylase gene expression and steroid hormone biosynthesis." Biochemical Society Transactions 18, no. 1 (February 1, 1990): 26–28. http://dx.doi.org/10.1042/bst0180026.

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16

Auchus, Mary Louise, and Richard J. Auchus. "Human Steroid Biosynthesis for the Oncologist." Journal of Investigative Medicine 60, no. 2 (February 1, 2012): 495–503. http://dx.doi.org/10.2310/jim.0b013e3182408567.

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17

Edwards, A., S. M. Jones, and N. Davies. "Steroid biosynthesis in a viviparous reptile." Comparative Biochemistry and Physiology Part A: Molecular & Integrative Physiology 124 (August 1999): S112. http://dx.doi.org/10.1016/s1095-6433(99)90444-0.

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18

Praseetha, S., and Raghava V. Thampan. "Regulatory Factors in Steroid Hormone Biosynthesis." Critical Reviews™ in Eukaryotic Gene Expression 19, no. 4 (2009): 253–65. http://dx.doi.org/10.1615/critreveukargeneexpr.v19.i4.10.

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19

Biason-Lauber, Anna. "Molecular medicine of steroid hormone biosynthesis." Molecular Aspects of Medicine 19, no. 3 (June 1998): 155–220. http://dx.doi.org/10.1016/s0098-2997(98)00004-1.

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20

D'Agata, R., S. Malozowski, A. Barkan, F. Cassorla, and D. Loriaux. "Steroid Biosynthesis in Human Adrenal Tumors." Hormone and Metabolic Research 19, no. 08 (August 1987): 386–88. http://dx.doi.org/10.1055/s-2007-1011831.

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21

Rego, Jean-Luc Do, Jae Young Seong, Delphine Burel, Van Luu-The, Dan Larhammar, Kazuyoshi Tsutsui, Georges Pelletier, Marie-Christine Tonon, and Hubert Vaudry. "Steroid Biosynthesis within the Frog Brain." Annals of the New York Academy of Sciences 1163, no. 1 (April 2009): 83–92. http://dx.doi.org/10.1111/j.1749-6632.2008.03664.x.

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22

Mukhin, A. G., V. Papadopoulos, E. Costa, and K. E. Krueger. "Mitochondrial benzodiazepine receptors regulate steroid biosynthesis." Proceedings of the National Academy of Sciences 86, no. 24 (December 1, 1989): 9813–16. http://dx.doi.org/10.1073/pnas.86.24.9813.

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23

Herman, Bianka Edina, János Gardi, János Julesz, Csaba Tömböly, Eszter Szánti-Pintér, Klaudia Fehér, Rita Skoda-Földes, and Mihály Szécsi. "Steroidal ferrocenes as potential enzyme inhibitors of the estrogen biosynthesis." Biologia Futura 71, no. 3 (June 25, 2020): 249–64. http://dx.doi.org/10.1007/s42977-020-00023-7.

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Abstract The potential inhibitory effect of diverse triazolyl-ferrocene steroids on key enzymes of the estrogen biosynthesis was investigated. Test compounds were synthesized via copper-catalyzed cycloaddition of steroidal azides and ferrocenyl-alkynes using our efficient methodology published previously. Inhibition of human aromatase, steroid sulfatase (STS) and 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) activities was investigated with in vitro radiosubstrate incubations. Some of the test compounds were found to be potent inhibitors of the STS. A compound bearing ferrocenyl side chain on the C-2 displayed a reversible inhibition, whereas C-16 and C-17 derivatives displayed competitive irreversible binding mechanism toward the enzyme. 17α-Triazolyl-ferrocene derivatives of 17β-estradiol exerted outstanding inhibitory effect and experiments demonstrated a key role of the ferrocenyl moiety in the enhanced binding affinity. Submicromolar IC50 and Ki parameters enroll these compounds to the group of the most effective STS inhibitors published so far. STS inhibitory potential of the steroidal ferrocenes may lead to the development of novel compounds able to suppress in situ biosynthesis of 17β-estradiol in target tissues.

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24

Storbeck, Karl-Heinz, Lina Schiffer, Elizabeth S. Baranowski, Vasileios Chortis, Alessandro Prete, Lise Barnard, Lorna C. Gilligan, et al. "Steroid Metabolome Analysis in Disorders of Adrenal Steroid Biosynthesis and Metabolism." Endocrine Reviews 40, no. 6 (July 11, 2019): 1605–25. http://dx.doi.org/10.1210/er.2018-00262.

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Abstract Steroid biosynthesis and metabolism are reflected by the serum steroid metabolome and, in even more detail, by the 24-hour urine steroid metabolome, which can provide unique insights into alterations of steroid flow and output indicative of underlying conditions. Mass spectrometry–based steroid metabolome profiling has allowed for the identification of unique multisteroid signatures associated with disorders of steroid biosynthesis and metabolism that can be used for personalized approaches to diagnosis, differential diagnosis, and prognostic prediction. Additionally, steroid metabolome analysis has been used successfully as a discovery tool, for the identification of novel steroidogenic disorders and pathways as well as revealing insights into the pathophysiology of adrenal disease. Increased availability and technological advances in mass spectrometry–based methodologies have refocused attention on steroid metabolome profiling and facilitated the development of high-throughput steroid profiling methods soon to reach clinical practice. Furthermore, steroid metabolomics, the combination of mass spectrometry–based steroid analysis with machine learning–based approaches, has facilitated the development of powerful customized diagnostic approaches. In this review, we provide a comprehensive up-to-date overview of the utility of steroid metabolome analysis for the diagnosis and management of inborn disorders of steroidogenesis and autonomous adrenal steroid excess in the context of adrenal tumors.

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Salchert, Klaus, Rishikesh Bhalerao, Zsuzsanna Koncz–Kálmán, and Csaba Koncz. "Control of cell elongation and stress responses by steroid hormones and carbon catabolic repression in plants." Philosophical Transactions of the Royal Society of London. Series B: Biological Sciences 353, no. 1374 (September 29, 1998): 1517–20. http://dx.doi.org/10.1098/rstb.1998.0307.

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Molecular analysis of Arabidopsis mutants displaying hypocotyl elongation defects in both the dark and light revealed recently that steroids play an essential role as hormones in plants. Deficiencies in brassinosteroid biosynthesis and signalling permit photomorphogenic development and light––regulated gene expression in the dark, and result in severe dwarfism, male sterility and de–repression of stress–induced genes in the light. A cytochrome P450 steroid hydroxylase (CYP90) controls a rate limiting step in brassinosteroid biosynthesis and appears to function as a signalling factor in stress responses. Another key step in steroid biosynthesis is controlled by the Arabidopsis SNF1 kinases that phosphorylate the 3–hydroxy–3methylglutaryl–CoA reductase. The activity of SNF1 kinases is regulated by PRL1, an evolutionarily conserved α–importin–binding nuclear WD–protein. The prl1 mutation results in cell elongation defects, de–repression of numerous stress–induced genes, and augments the sensitivity of plants to glucose, cold stress and several hormones, including cytokinin, ethylene, auxin, and abscisic acid.

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Kaleta, Michal, Jana Oklestkova, Ondřej Novák, and Miroslav Strnad. "Analytical Methods for the Determination of Neuroactive Steroids." Biomolecules 11, no. 4 (April 9, 2021): 553. http://dx.doi.org/10.3390/biom11040553.

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Neuroactive steroids are a family of all steroid-based compounds, of both natural and synthetic origin, which can affect the nervous system functions. Their biosynthesis occurs directly in the nervous system (so-called neurosteroids) or in peripheral endocrine tissues (hormonal steroids). Steroid hormone levels may fluctuate due to physiological changes during life and various pathological conditions affecting individuals. A deeper understanding of neuroactive steroids’ production, in addition to reliable monitoring of their levels in various biological matrices, may be useful in the prevention, diagnosis, monitoring, and treatment of some neurodegenerative and psychiatric diseases. The aim of this review is to highlight the most relevant methods currently available for analysis of neuroactive steroids, with an emphasis on immunoanalytical methods and gas, or liquid chromatography combined with mass spectrometry.

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27

Bacila, Irina-Alexandra, Charlotte Elder, and Nils Krone. "Update on adrenal steroid hormone biosynthesis and clinical implications." Archives of Disease in Childhood 104, no. 12 (June 7, 2019): 1223–28. http://dx.doi.org/10.1136/archdischild-2017-313873.

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Steroid biosynthesis is a complex process in which cholesterol is converted to steroid hormones with the involvement of multiple enzymes and cofactors. Inborn conditions affecting adrenal steroidogenesis are relatively common in paediatric practice and have serious implications on patient mortality and morbidity. This paper provides an overview of novel insights into human adrenal steroid biosynthesis. Inborn errors of steroidogenesis associated with congenital adrenal hyperplasia are discussed, with a particular focus on the pathophysiology and clinical features of 21-hydroxylase deficiency. The final section of the review presents more recent findings and clinical implications of adrenal-specific androgen biosynthesis.

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28

Summons, Roger E., Alexander S. Bradley, Linda L. Jahnke, and Jacob R. Waldbauer. "Steroids, triterpenoids and molecular oxygen." Philosophical Transactions of the Royal Society B: Biological Sciences 361, no. 1470 (May 17, 2006): 951–68. http://dx.doi.org/10.1098/rstb.2006.1837.

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There is a close connection between modern-day biosynthesis of particular triterpenoid biomarkers and presence of molecular oxygen in the environment. Thus, the detection of steroid and triterpenoid hydrocarbons far back in Earth history has been used to infer the antiquity of oxygenic photosynthesis. This prompts the question: were these compounds produced similarly in the past? In this paper, we address this question with a review of the current state of knowledge surrounding the oxygen requirement for steroid biosynthesis and phylogenetic patterns in the distribution of steroid and triterpenoid biosynthetic pathways. The hopanoid and steroid biosynthetic pathways are very highly conserved within the bacterial and eukaryotic domains, respectively. Bacteriohopanepolyols are produced by a wide range of bacteria, and are methylated in significant abundance at the C2 position by oxygen-producing cyanobacteria. On the other hand, sterol biosynthesis is sparsely distributed in distantly related bacterial taxa and the pathways do not produce the wide range of products that characterize eukaryotes. In particular, evidence for sterol biosynthesis by cyanobacteria appears flawed. Our experiments show that cyanobacterial cultures are easily contaminated by sterol-producing rust fungi, which can be eliminated by treatment with cycloheximide affording sterol-free samples. Sterols are ubiquitous features of eukaryotic membranes, and it appears likely that the initial steps in sterol biosynthesis were present in their modern form in the last common ancestor of eukaryotes. Eleven molecules of O 2 are required by four enzymes to produce one molecule of cholesterol. Thermodynamic arguments, optimization of function and parsimony all indicate that an ancestral anaerobic pathway is highly unlikely. The known geological record of molecular fossils, especially steranes and triterpanes, is notable for the limited number of structural motifs that have been observed. With a few exceptions, the carbon skeletons are the same as those found in the lipids of extant organisms and no demonstrably extinct structures have been reported. Furthermore, their patterns of occurrence over billion year time-scales correlate strongly with environments of deposition. Accordingly, biomarkers are excellent indicators of environmental conditions even though the taxonomic affinities of all biomarkers cannot be precisely specified. Biomarkers are ultimately tied to biochemicals with very specific functional properties, and interpretations of the biomarker record will benefit from increased understanding of the biological roles of geologically durable molecules.

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Meccariello, Rosaria, Natalia Battista, Heather B. Bradshaw, and Haibin Wang. "Updates in Reproduction Coming from the Endocannabinoid System." International Journal of Endocrinology 2014 (2014): 1–16. http://dx.doi.org/10.1155/2014/412354.

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The endocannabinoid system (ECS) is an evolutionarily conserved master system deeply involved in the central and local control of reproductive functions in both sexes. The tone of these lipid mediators—deeply modulated by the activity of biosynthetic and hydrolyzing machineries—regulates reproductive functions from gonadotropin discharge and steroid biosynthesis to the formation of high quality gametes and successful pregnancy. This review provides an overview on ECS and reproduction and focuses on the insights in the regulation of endocannabinoid production by steroids, in the regulation of male reproductive activity, and in placentation and parturition. Taken all together, evidences emerge that the activity of the ECS is crucial for procreation and may represent a target for the therapeutic exploitation of infertility.

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John, Maliyakal E., Takashi Okamura, Albert Dee, Beverly Adler, Manorama C. John, Perrin C. White, Evan R. Simpson, and Michael R. Waterman. "Bovine steroid 21-hydroxylase: regulation of biosynthesis." Biochemistry 25, no. 10 (May 20, 1986): 2846–53. http://dx.doi.org/10.1021/bi00358a016.

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Bishop, Gerard J. "Refining the plant steroid hormone biosynthesis pathway." Trends in Plant Science 12, no. 9 (September 2007): 377–80. http://dx.doi.org/10.1016/j.tplants.2007.07.001.

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32

ALBRECHT, EUGENE D., and GERALD J. PEPE. "Placental Steroid Hormone Biosynthesis in Primate Pregnancy*." Endocrine Reviews 11, no. 1 (February 1990): 124–50. http://dx.doi.org/10.1210/edrv-11-1-124.

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33

Spencer, Thomas A. "The squalene dioxide pathway of steroid biosynthesis." Accounts of Chemical Research 27, no. 3 (March 1994): 83–90. http://dx.doi.org/10.1021/ar00039a004.

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Duarte, Alejandra, Cecilia Poderoso, Mariana Cooke, Gastón Soria, Fabiana Cornejo Maciel, Vanesa Gottifredi, and Ernesto J. Podestá. "Mitochondrial Fusion Is Essential for Steroid Biosynthesis." PLoS ONE 7, no. 9 (September 21, 2012): e45829. http://dx.doi.org/10.1371/journal.pone.0045829.

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Meseguer, A., C. Puche, and A. Cabero. "Sex Steroid Biosynthesis in White Adipose Tissue." Hormone and Metabolic Research 34, no. 11/12 (November 2002): 731–36. http://dx.doi.org/10.1055/s-2002-38249.

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36

Taylor, David R., Lea Ghataore, Lewis Couchman, Royce P. Vincent, Ben Whitelaw, Dylan Lewis, Salvador Diaz-Cano, et al. "A 13-Steroid Serum Panel Based on LC-MS/MS: Use in Detection of Adrenocortical Carcinoma." Clinical Chemistry 63, no. 12 (December 1, 2017): 1836–46. http://dx.doi.org/10.1373/clinchem.2017.277624.

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Abstract BACKGROUND Adrenocortical carcinoma (ACC) is a rare malignancy, with an annual incidence of 1 or 2 cases per million. Biochemical diagnosis is challenging because up to two-thirds of the carcinomas are biochemically silent, resulting from de facto enzyme deficiencies in steroid hormone biosynthesis. Urine steroid profiling by GC-MS is an effective diagnostic test for ACC because of its capacity to detect and quantify the increased metabolites of steroid pathway synthetic intermediates. Corresponding serum assays for most steroid pathway intermediates are usually unavailable because of low demand or lack of immunoassay specificity. Serum steroid analysis by LC-MS/MS is increasingly replacing immunoassay, in particular for steroids most subject to cross-reaction. METHODS We developed an LC-MS/MS method for the measurement of serum androstenedione, corticosterone, cortisol, cortisone, 11-deoxycorticosterone, 11-deoxycortisol, 21-deoxycortisol, dehydroepiandrosterone sulfate, pregnenolone, 17-hydroxypregnenolone, progesterone, 17-hydroxyprogesterone, and testosterone. Assay value in discriminating ACC from other adrenal lesions (phaeochromocytoma/paraganglioma, cortisol-producing adenoma, and lesions demonstrating no hormonal excess) was then investigated. RESULTS In ACC cases, between 4 and 7 steroids were increased (median = 6), and in the non-ACC groups, up to 2 steroids were increased. 11-Deoxycortisol was markedly increased in all cases of ACC. All steroids except testosterone in males and corticosterone and cortisone in both sexes were of use in discriminating ACC from non-ACC adrenal lesions. CONCLUSIONS Serum steroid paneling by LC-MS/MS is useful for diagnosing ACC by combining the measurement of steroid hormones and their precursors in a single analysis.

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Dashbaldan, Soyol, Agata Rogowska, Cezary Pączkowski, and Anna Szakiel. "Distribution of Triterpenoids and Steroids in Developing Rugosa Rose (Rosarugosa Thunb.) Accessory Fruit." Molecules 26, no. 17 (August 25, 2021): 5158. http://dx.doi.org/10.3390/molecules26175158.

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Triterpenoids and steroids are considered to be important for the fruit quality and health-promoting properties for the consumers. The aim of the study was the determination of the changes in triterpenoid and steroid biosynthesis and the accumulation in hypanthium and achenes of rugosa rose (Rosa rugosa Thunb.) hip during fruit development and ripening at three different phenological stages (young fruits, fully developed unripe fruits, and matured fruits). Triterpenoids and steroids were also determined in the peel and the pulp of the matured hips. The obtained results indicated that the distribution of the analyzed compounds in different fruit tissues is a selective process. The increased rate of hydroxylation of triterpenoids, the deposition of hydroxylated acids in fruit surface layer, and the continuous biosynthesis of phytosterols in achenes versus its gradual repression in hypanthium accompanied by the accumulation of their biosynthetic intermediates and ketone derivatives seem to be characteristic metabolic features of maturation of rugosa rose accessory fruit. These observations, apart from providing the important data on metabolic modifications occurring in developing fruits, might have a practical application in defining fruit parts, particularly rich in bioactive constituents, to enable the development of novel functional products.

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Freeman, M. R., A. Dobritsa, P. Gaines, W. A. Segraves, and J. R. Carlson. "The dare gene: steroid hormone production, olfactory behavior, and neural degeneration in Drosophila." Development 126, no. 20 (October 15, 1999): 4591–602. http://dx.doi.org/10.1242/dev.126.20.4591.

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Steroid hormones mediate a wide variety of developmental and physiological events in insects, yet little is known about the genetics of insect steroid hormone biosynthesis. Here we describe the Drosophila dare gene, which encodes adrenodoxin reductase (AR). In mammals, AR plays a key role in the synthesis of all steroid hormones. Null mutants of dare undergo developmental arrest during the second larval instar or at the second larval molt, and dare mutants of intermediate severity are delayed in pupariation. These defects are rescued to a high degree by feeding mutant larvae the insect steroid hormone 20-hydroxyecdysone. These data, together with the abundant expression of dare in the two principal steroid biosynthetic tissues, the ring gland and the ovary, argue strongly for a role of dare in steroid hormone production. dare is the first Drosophila gene shown to encode a defined component of the steroid hormone biosynthetic cascade and therefore provides a new tool for the analysis of steroid hormone function. We have explored its role in the adult nervous system and found two striking phenotypes not previously described in mutants affected in steroid hormone signaling. First, we show that mild reductions of dare expression cause abnormal behavioral responses to olfactory stimuli, indicating a requirement for dare in sensory behavior. Then we show that dare mutations of intermediate strength result in rapid, widespread degeneration of the adult nervous system.

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Li, Xiao Jing, Xiao Jie Wang, and Yun Zhe Ji. "Applications of Chemical Factors in Steroid Bioconversion." Advanced Materials Research 1073-1076 (December 2014): 159–64. http://dx.doi.org/10.4028/www.scientific.net/amr.1073-1076.159.

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Microbial conversion is a key process in the biosynthetic routes of steroid medicine.The whole process of bioconversion includes two essential steps: (1) enzymatic reaction step where the enzyme-catalyzed substrate transformation takes place inside the cells, and (2) diffusion step that includes the diffusion of substrate molecules from the surface of solid substrate particles into bulk media (i.e., the solubilization of solid substrate), the diffusion of solubilized substrate molecules from bulk media into cells, and the diffusion of formed product molecules from inside cells into bulk media. In this review, the applications of three chemical factors (growth regulator,surfactant and cyclodextrin), and their effects on steroid microbial enzymatic conversion were extensively discussed, which provides insights into the development of novel approaches to cost-effectively improve biosynthesis efficiency in steroid medicine.

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Panin, L. Ye, O. M. Khoshchenko, and I. F. Usynin. "Role of apolipoprotein A-I in the anabolic effect of steroid hormones." Problems of Endocrinology 48, no. 6 (December 15, 2002): 45–48. http://dx.doi.org/10.14341/probl11727.

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As early shown, a portion of steroid hormones binds to blood lipoproteins, primarily to high-density lipoproteins (HDL) [Panin et al. 1988]. Steroid hormones together with HDL are captured by resident macrophages of the liver where in secondary lysosomes HDL are degraded to form apoA-I and steroid hormones restore a ∆4, 3-keto group with the participation of 5-α and 5β- reductases to give rise to tetrahydro compounds. In this study, an attempt was undertaken to show a role of a complex of some steroid hormones with apo A-I in realization of the anabolic action of these steroid hormones by using the cultured hepatocytes and concurrently cultured hepatocytes and Kupffer’s cells isolated from the liver of male Wistar rats weighing 180-200 g. Steroid hormones having an anabolic action, such as androsterone, dehydroepiandrosterone, dehydroepiandrosterone sulfate and tetrahydrocortisol as ingredients of a complex with apolipoprotein A-I (apoA-I), increased the rate of protein biosynthesis and dehydroepiandrosterone sulfate and tetrahydrocortisol also did the rate of DNA synthesis in the cultured hepatocytes. All the hormones had a restored ∆4,3-keto group in the A ring structure. Restoration of this group of steroid hormones and formation of their complex with apoA-I are associated with the action of resident macrophages (Kupffer’s cells). That is the reason that addition of HDL (a source of apoA-I) and cortisol (a source of the restored form - tetrahydrocortisol) to the coculture of hepatocytes and macrophages, by concurrently stimulating the latter by lipopolysaccharide led to a significant increase in the rate of protein and DNA biosynthesis. The findings show an important role of a ∆4,3-keto group of the A ring of steroid hormones and their complex with apo A-I in realizing the anabolic action of steroids.

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41

Hampl, Richard, Jana Kubátová, Vladimír Sobotka, and Jiří Heráček. "Steroids in semen, their role in spermatogenesis, and the possible impact of endocrine disruptors." Hormone Molecular Biology and Clinical Investigation 13, no. 1 (January 1, 2013): 1–5. http://dx.doi.org/10.1515/hmbci-2013-0003.

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AbstractThe data on hormonal steroids in the human seminal plasma and their role in spermatogenesis are summarized. The seminal steroid levels need not correlate with the blood plasma levels. The recent reports showed that androgen, especially dihydrotestosterone, and the estrogen levels in the seminal fluid may be used as the markers of spermatogenesis impairment. The estradiol concentration in the seminal plasma was higher than in the blood plasma, and its levels were significantly increased in men with impaired spermatogenesis. A good indicator for predicting the normal spermatogenesis, therefore, seems to be the testosterone/estradiol ratio. The seminal plasma also contains significant amounts of cortisol, which influences the androgen biosynthesis through its receptors in the Leydig cells. The local balance between cortisol and inactive cortisone is regulated by 11β-hydroxysteroid dehydrogenase, the activity of which may be affected by the environmental chemicals acting as the endocrine disruptors (EDCs). These compounds are believed to participate in worsening the semen quality – the sperm count, motility, and morphology, as witnessed in the recent last decades. As to the steroids’ role in the testis, the EDCs may act as antiandrogens by inhibiting the enzymes of testosterone biosynthesis, as the agonists or antagonists through their interaction with the steroid hormone receptors, or at the hypothalamic-pituitary-gonadal axis. Surprisingly, though the EDCs affect the steroid action in the testis, there is no report of a direct association between the concentrations of steroids and the EDCs in the seminal fluid. Therefore, measuring the steroids in the semen, along with the various EDCs, could help us better understand the role of the EDCs in the male reproduction.

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Tarkowská, Danuše. "Plants are Capable of Synthesizing Animal Steroid Hormones." Molecules 24, no. 14 (July 16, 2019): 2585. http://dx.doi.org/10.3390/molecules24142585.

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As a result of the findings of scientists working on the biosynthesis and metabolism of steroids in the plant and animal kingdoms over the past five decades, it has become apparent that those compounds that naturally occur in animals can also be found as natural constituents of plants and vice versa, i.e., they have essentially the same fate in the majority of living organisms. This review summarizes the current state of knowledge on the occurrence of animal steroid hormones in the plant kingdom, particularly focusing on progesterone, testosterone, androstadienedione (boldione), androstenedione, and estrogens.

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Papadopoulos, Vassilios. "From benzodiazepines to peripheral and brain steroid biosynthesis." Pharmacological Research 64, no. 4 (October 2011): 330–32. http://dx.doi.org/10.1016/j.phrs.2011.05.024.

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44

Bruynseels, J., R. De Coster, P. Van Rooy, W. Wouters, M. C. Coene, E. Snoeck, A. Raeymaekers, et al. "R 75251, a new inhibitor of steroid biosynthesis." Prostate 16, no. 4 (1990): 345–57. http://dx.doi.org/10.1002/pros.2990160409.

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45

Ferraldeschi, Roberta, Nima Sharifi, Richard J. Auchus, and Gerhardt Attard. "Molecular Pathways: Inhibiting Steroid Biosynthesis in Prostate Cancer." Clinical Cancer Research 19, no. 13 (March 7, 2013): 3353–59. http://dx.doi.org/10.1158/1078-0432.ccr-12-0931.

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46

Sewer, Marion B., and Donghui Li. "Regulation of Steroid Hormone Biosynthesis by the Cytoskeleton." Lipids 43, no. 12 (August 26, 2008): 1109. http://dx.doi.org/10.1007/s11745-008-3221-2.

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47

Engelhardt, D., and M. M. Weber. "Therapy of Cushing's syndrome with steroid biosynthesis inhibitors." Journal of Steroid Biochemistry and Molecular Biology 49, no. 4-6 (June 1994): 261–67. http://dx.doi.org/10.1016/0960-0760(94)90267-4.

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48

Pelletier, G., S. Li, V. Luu-The, Y. Tremblay, A. Belanger, and F. Labrie. "Immunoelectron microscopic localization of three key steroidogenic enzymes (cytochrome P450(scc), 3 beta-hydroxysteroid dehydrogenase and cytochrome P450(c17)) in rat adrenal cortex and gonads." Journal of Endocrinology 171, no. 2 (November 1, 2001): 373–83. http://dx.doi.org/10.1677/joe.0.1710373.

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The biosynthesis of steroid hormones in endocrine steroid-secreting glands results from a series of successive steps involving both cytochrome P450 enzymes, which are mixed-function oxidases, and steroid dehydrogenases. So far, the subcellular distribution of steroidogenic enzymes has been mostly studied following subcellular fractionation, performed in placenta and adrenal cortex. In order to determine in situ the intracellular distribution of some steroidogenic enzymes, we have investigated the ultrastructural localization of the three key enzymes: P450 side chain cleavage (scc) which converts cholesterol to pregnenolone; 3 beta-hydroxysteroid dehydrogenase (3 beta-HSD) which catalyzes the conversion of 3 beta-hydroxy-5-ene steroids to 3-oxo-4-ene steroids (progesterone and androstenedione); and P450(c17) which is responsible for the transformation of C(21) into C(19) steroids (dehydroepiandrosterone and androstenedione). Immunogold labeling was used to localize the enzymes in rat adrenal cortex and gonads. The tissues were fixed in 1% glutaraldehyde and 3% paraformaldehyde and included in LR gold resin. In the adrenal cortex, both P450(scc) and 3 beta-HSD immunoreactivities were detected in the reticular, fascicular and glomerular zones. P450(scc) was exclusively found in large mitochondria. In contrast, 3 beta-HSD antigenic sites were mostly observed in the endoplasmic reticulum (ER) with some gold particles overlying crista and outer membranes of the mitochondria. P450(c17) could not be detected in adrenocortical cells. In the testis, the three enzymes were only found in Leydig cells. Immunolabeling for P450(scc) and 3 beta-HSD was restricted to mitochondria, while P450(c17) immunoreactivity was exclusively observed in ER. In the ovary, P450(scc) and 3 beta-HSD immunoreactivities were found in granulosa, theca interna and corpus luteum cells. The subcellular localization of the two enzymes was very similar to that observed in adrenocortical cells. P450(c17) could also be detected in theca interna cells of large developing and mature follicles. As observed in Leydig cells, P450(c17) immunolabeling could only be found in the ER. These results indicate that in different endocrine steroid-secreting cells P450(scc), 3 beta-HSD and P450(c17) have the same association with cytoplasmic organelles (with the exception of 3 beta-HSD in Leydig cells), suggesting similar intracellular pathways for biosynthesis of steroid hormones.

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Gizard, F., E. Teissier, I. Dufort, G. Luc, V. Luu-The, B. Staels, and DW Hum. "The transcriptional regulating protein of 132 kDa (TReP-132) differentially influences steroidogenic pathways in human adrenal NCI-H295 cells." Journal of Molecular Endocrinology 32, no. 2 (April 1, 2004): 557–69. http://dx.doi.org/10.1677/jme.0.0320557.

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Steroid hormones synthesized from cholesterol in the adrenal gland are important regulators of many physiological processes. It is now well documented that the expression of many genes required for steroid biosynthesis is dependent on the coordinated expression of the nuclear receptor steroidogenic factor-1 (SF-1). However, transcriptional mechanisms underlying the species-specific, developmentally programmed and hormone-dependent modulation of the adrenal steroid pathways remain to be elucidated. Recently, we demonstrated that the transcriptional regulating protein of 132 kDa (TReP-132) acts as a coactivator of SF-1 to regulate human P450scc gene transcription in human adrenal NCI-H295 cells. The present study shows that overexpression of TReP-132 increases the level of active steroids produced in NCI-H295 cells. The conversion of pregnenolone to downstream steroids following TReP-132 expression showed increased levels of glucocorticoids, C(19) steroids and estrogens. Correlating with these data, TReP-132 increases P450c17 activities via the induction of transcript levels and promoter activity of the P450c17 gene, an effect that is enhanced in the presence of cAMP or SF-1. In addition, P450aro activity and mRNA levels are highly induced by TReP-132, whereas 3beta-hydroxysteroid dehydrogenase type II and P450c11aldo transcript levels are only slightly modulated. Taken together, these results demonstrate that TReP-132 is a trans-acting factor of genes involved in adrenal glucocorticoid, C(19) steroid and estrogen production.

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Saloniemi, Taija, Heli Jokela, Leena Strauss, Pirjo Pakarinen, and Matti Poutanen. "The diversity of sex steroid action: novel functions of hydroxysteroid (17β) dehydrogenases as revealed by genetically modified mouse models." Journal of Endocrinology 212, no. 1 (November 1, 2011): 27–40. http://dx.doi.org/10.1530/joe-11-0315.

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Disturbed action of sex steroid hormones, i.e. androgens and estrogens, is involved in the pathogenesis of various severe diseases in humans. Interestingly, recent studies have provided data further supporting the hypothesis that the circulating hormone concentrations do not explain all physiological and pathological processes observed in hormone-dependent tissues, while the intratissue sex steroid concentrations are determined by the expression of steroid metabolising enzymes in the neighbouring cells (paracrine action) and/or by target cells themselves (intracrine action). This local sex steroid production is also a valuable treatment option for developing novel therapies against hormonal diseases. Hydroxysteroid (17β) dehydrogenases (HSD17Bs) compose a family of 14 enzymes that catalyse the conversion between the low-active 17-keto steroids and the highly active 17β-hydroxy steroids. The enzymes frequently expressed in sex steroid target tissues are, thus, potential drug targets in order to lower the local sex steroid concentrations. The present review summarises the recent data obtained for the role of HSD17B1, HSD17B2, HSD17B7 and HSD17B12 enzymes in various metabolic pathways and their physiological and pathophysiological roles as revealed by the recently generated genetically modified mouse models. Our data, together with that provided by others, show that, in addition to having a role in sex steroid metabolism, several of these HSD17B enzymes possess key roles in other metabolic processes: for example, HD17B7 is essential for cholesterol biosynthesis and HSD17B12 is involved in elongation of fatty acids. Additional studiesin vitroandin vivoare to be carried out in order to fully define the metabolic role of the HSD17B enzymes and to evaluate their value as drug targets.

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