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Natural Sterols
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Natural Sterols

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 49900

Special Issue Editor

Prof. Dr. Yasunori Yaoita

E-Mail Website
Guest Editor
Pharmaceutical Education Center, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan
Interests: natural product chemistry; isolation; structure determination; sterols; terpenoids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Sterols are among the most studied groups of natural products with interest commencing in the 19th century and continuing through to the present. Sterols occur in all major groups of organisms, from fungi to humans, as secondary metabolites. We now plan to edit this Special Issue on “Natural Sterols”. Please submit your recent results of the following areas: Isolation, analytical method, structure determination, synthesis, biosynthesis, enzymatic process, biotransformation, and biological activity. We aim to provide a platform to present the valuable results of your research in these areas.

Assoc. Prof. Dr. Yasunori Yaoita
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • sterols
  • isolation
  • analytical method
  • structure
  • synthesis
  • biosynthesis
  • biotransformation
  • bioactivity

Published Papers (6 papers)

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Research

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14 pages, 4141 KiB  
Article
Inhibition of Phytosterol Biosynthesis by Azasterols
by Sylvain Darnet, Laetitia B B Martin, Pierre Mercier, Franz Bracher, Philippe Geoffroy and Hubert Schaller
Molecules 2020, 25(5), 1111; https://doi.org/10.3390/molecules25051111 - 2 Mar 2020
Cited by 8 | Viewed by 4474
Abstract
Inhibitors of enzymes in essential cellular pathways are potent probes to decipher intricate physiological functions of biomolecules. The analysis of Arabidopsis thaliana sterol profiles upon treatment with a series of azasterols reveals a specific in vivo inhibition of SMT2, a plant sterol-C-methyltransferase acting [...] Read more.
Inhibitors of enzymes in essential cellular pathways are potent probes to decipher intricate physiological functions of biomolecules. The analysis of Arabidopsis thaliana sterol profiles upon treatment with a series of azasterols reveals a specific in vivo inhibition of SMT2, a plant sterol-C-methyltransferase acting as a branch point between the campesterol and sitosterol biosynthetic segments in the pathway. Side chain azasteroids that modify sitosterol homeostasis help to refine its particular function in plant development. Full article
(This article belongs to the Special Issue Natural Sterols)
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17 pages, 6562 KiB  
Article
OcUGT1-Catalyzing Glycodiversification of Steroids through Glucosylation and Transglucosylation Actions
by Yan-Li Xu and Jian-Qiang Kong
Molecules 2020, 25(3), 475; https://doi.org/10.3390/molecules25030475 - 22 Jan 2020
Cited by 9 | Viewed by 2719
Abstract
Steroidal glycosides are important sources of innovative drugs. The increased diversification of steroidal glycosides will expand the probability of discovering active molecules. It is an efficient approach to diversify steroidal glycosides by using steroidal glycosyltransferases. OcUGT1, a uridine diphosphate-d-glucose (UDP-Glc)-dependent glycosyltransferase [...] Read more.
Steroidal glycosides are important sources of innovative drugs. The increased diversification of steroidal glycosides will expand the probability of discovering active molecules. It is an efficient approach to diversify steroidal glycosides by using steroidal glycosyltransferases. OcUGT1, a uridine diphosphate-d-glucose (UDP-Glc)-dependent glycosyltransferase from Ornithogalum caudatum, is a multifunctional enzyme, and its glycodiversification potential towards steroids has never been fully explored. Herein, the glycodiversification capability of OcUGT1 towards 25 steroids through glucosylation and transglucosylation reactions were explored. Firstly, each of 25 compounds was glucosylated with UDP-Glc. Under the action of OcUGT1, five steroids (testosterone, deoxycorticosterone, hydrocortisone, estradiol, and 4-androstenediol) were glucosylated to form corresponding mono-glucosides and biosides. Next, OcUGT1-mediated transglucosylation activity of these compounds with another sugar donor ortho-nitrophenyl-β-d-glucopyranoside (oNPGlc) was investigated. Results revealed that the same five steroids could be glucosylated to generate mono-glucosides and biosides by OcUGT1 through transglucosylation reactions. These data indicated that OcUGT1-assisted glycodiversification of steroids could be achieved through glucosylation and transglucosylation reactions. These results provide a way to diversify steroidal glycosides, which lays the foundation for the increase of the probability of obtaining active lead compounds. Full article
(This article belongs to the Special Issue Natural Sterols)
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19 pages, 3784 KiB  
Article
Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
by Masatoshi Nakakuni, Yoshimi Yamasaki, Nonoka Yoshitake, Keiko Takehara and Shuichi Yamamoto
Molecules 2019, 24(22), 4040; https://doi.org/10.3390/molecules24224040 - 7 Nov 2019
Cited by 4 | Viewed by 4656
Abstract
Sterols are widely distributed in nature from lipids in organisms to sediments. As a conventional method, extraction and derivatization with TMS have been applied for sterol analysis, requiring a long preparation time for gas chromatography–mass spectrometry analysis. In this study, for sterol analysis, [...] Read more.
Sterols are widely distributed in nature from lipids in organisms to sediments. As a conventional method, extraction and derivatization with TMS have been applied for sterol analysis, requiring a long preparation time for gas chromatography–mass spectrometry analysis. In this study, for sterol analysis, thermochemolysis using tetramethylammonium hydroxide (TMAH) was applied. This method performs hydrolysis and methylation simultaneously; thus, free and ether-bonding sterols can be analyzed as sterol methyl ethers in a relatively short time period. A sediment sample from a tideland (the Yatsu tideland, Japan) was analyzed using the TMAH method, and we detected more than 10 sterols, which include cholest-5-en-3β-ol (cholesterol), 24-ethylcholest-5-en-3β-ol (sitosterol), 24-methylcholesta-5,22E-3β-ol (brassicasterol), 24-ethylcholesta-5,24(28)Z-dien-3β-ol (isofucosterol), 4α,23,24-trimethyl-5α(H)-cholest-22E-en-3β- ol (dinosterol), and 5β(H)-cholestan-3β-ol (coprostanol). The detection of the various sterols can be attributed to multiple natural and artificial sources around the Yatsu tideland. In this paper, the mass spectra of these sterols are provided together with an interpretation of their fragmentation patterns. Additionally, the fecal pollution in the Yatsu tideland is discussed in the context of the detection of coprostanol. Full article
(This article belongs to the Special Issue Natural Sterols)
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17 pages, 3150 KiB  
Article
Comparison of Strategies for the Determination of Sterol Sulfates via GC-MS Leading to a Novel Deconjugation-Derivatization Protocol
by Julia Junker, Isabelle Chong, Frits Kamp, Harald Steiner, Martin Giera, Christoph Müller and Franz Bracher
Molecules 2019, 24(13), 2353; https://doi.org/10.3390/molecules24132353 - 26 Jun 2019
Cited by 11 | Viewed by 4944
Abstract
Sulfoconjugates of sterols play important roles as neurosteroids, neurotransmitters, and ion channel ligands in health and disease. In most cases, sterol conjugate analysis is performed with liquid chromatography-mass spectrometry. This is a valuable tool for routine analytics with the advantage of direct sterol [...] Read more.
Sulfoconjugates of sterols play important roles as neurosteroids, neurotransmitters, and ion channel ligands in health and disease. In most cases, sterol conjugate analysis is performed with liquid chromatography-mass spectrometry. This is a valuable tool for routine analytics with the advantage of direct sterol sulfates analysis without previous cleavage and/or derivatization. The complementary technique gas chromatography-mass spectrometry (GC-MS) is a preeminent discovery tool in the field of sterolomics, but the analysis of sterol sulfates is hampered by mandatory deconjugation and derivatization. Despite the difficulties in sample workup, GC-MS is an indispensable tool for untargeted analysis and steroid profiling. There are no general sample preparation protocols for sterol sulfate analysis using GC-MS. In this study we present a reinvestigation and evaluation of different deconjugation and derivatization procedures with a set of representative sterol sulfates. The advantages and disadvantages of trimethylsilyl (TMS), methyloxime-trimethylsilyl (MO-TMS), and trifluoroacetyl (TFA) derivatives were examined. Different published procedures of sterol sulfate deconjugation, including enzymatic and chemical cleavage, were reinvestigated and examined for diverse sterol sulfates. Finally, we present a new protocol for the chemical cleavage of sterol sulfates, allowing for simultaneous deconjugation and derivatization, simplifying GC-MS based sterol sulfate analysis. Full article
(This article belongs to the Special Issue Natural Sterols)
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Review

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13 pages, 1487 KiB  
Review
Plants are Capable of Synthesizing Animal Steroid Hormones
by Danuše Tarkowská
Molecules 2019, 24(14), 2585; https://doi.org/10.3390/molecules24142585 - 16 Jul 2019
Cited by 34 | Viewed by 8175
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Natural Sterols)
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28 pages, 1322 KiB  
Review
Isoflavones
by Ludmila Křížová, Kateřina Dadáková, Jitka Kašparovská and Tomáš Kašparovský
Molecules 2019, 24(6), 1076; https://doi.org/10.3390/molecules24061076 - 19 Mar 2019
Cited by 437 | Viewed by 24331
Abstract
Phytoestrogens are naturally occurring nonsteroidal phenolic plant compounds that, due to their molecular structure and size, resemble vertebrate steroids estrogens. This review is focused on plant flavonoids isoflavones, which are ranked among the most estrogenic compounds. The main dietary sources of isoflavones for [...] Read more.
Phytoestrogens are naturally occurring nonsteroidal phenolic plant compounds that, due to their molecular structure and size, resemble vertebrate steroids estrogens. This review is focused on plant flavonoids isoflavones, which are ranked among the most estrogenic compounds. The main dietary sources of isoflavones for humans are soybean and soybean products, which contain mainly daidzein and genistein. When they are consumed, they exert estrogenic and/or antiestrogenic effects. Isoflavones are considered chemoprotective and can be used as an alternative therapy for a wide range of hormonal disorders, including several cancer types, namely breast cancer and prostate cancer, cardiovascular diseases, osteoporosis, or menopausal symptoms. On the other hand, isoflavones may also be considered endocrine disruptors with possible negative influences on the state of health in a certain part of the population or on the environment. This review deals with isoflavone classification, structure, and occurrence, with their metabolism, biological, and health effects in humans and animals, and with their utilization and potential risks. Full article
(This article belongs to the Special Issue Natural Sterols)
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