Naturally occurring marine α,β‐epoxy steroids: Origin and biological activities

Dembitsky, Valery M.; Gloriozova, Tatyana A.; Poroikov, Vladimir

doi:10.1002/vjch.201800025

Cited by 12 publications

(21 citation statements)

References 77 publications

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“…Highly oxygenated steroids are a large group of steroids and triterpenoids found in plant, fungal, and invertebrate extracts, and many of them exhibit a wide range of biological activities. This group of lipids includes secosteroids, epoxy steroids and peroxy steroids, and triterpenoids, which demonstrate a high degree of activity as potential regulators of lipid metabolism [119][120][121][122][123].…”

Section: Highly Oxygenated Natural Steroids and Triterpenoidsmentioning

confidence: 99%

“…α,α-epoxyand/or β,β-steroids are found in lipid extracts of marine invertebrates, including sponges, soft corals, starfish, and nudibranchs (Mollusca) [123,[155][156][157][158][159]. Two cytotoxic epoxysteroids, 5α,6α-epoxystigmasta-7,22-en-3β-ol (41) and 5α,6α-epoxystigmasta-7-en-3β-ol (42) were isolated from the ethanolic extract of the marine sponge Ircinia aruensis [160].…”

Section: Natural Epoxy Steroids Derived From Marine Sourcesmentioning

confidence: 99%

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In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

Dembitsky

2021

Marine Drugs

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This review focuses on a rare group of steroids and triterpenoids that share common properties as regulators of lipid metabolism. This group of compounds is divided by the type of chemical structure, and they represent: aromatic steroids, steroid phosphate esters, highly oxygenated steroids such as steroid endoperoxides and hydroperoxides, α,β-epoxy steroids, and secosteroids. In addition, subgroups of carbon-bridged steroids, neo steroids, miscellaneous steroids, as well as synthetic steroids containing heteroatoms S (epithio steroids), Se (selena steroids), Te (tellura steroids), and At (astatosteroids) were presented. Natural steroids and triterpenoids have been found and identified from various sources such as marine sponges, soft corals, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in fungi, fungal endophytes, and plants. The pharmacological profile of the presented steroids and triterpenoids was determined using the well-known computer program PASS, which is currently available online for all interested scientists and pharmacologists and is currently used by research teams from more than 130 countries of the world. Our attention has been focused on the biological activities of steroids and triterpenoids associated with the regulation of cholesterol metabolism and related processes such as anti-hyperlipoproteinemic activity, as well as the treatment of atherosclerosis, lipoprotein disorders, or inhibitors of cholesterol synthesis. In addition, individual steroids and triterpenoids were identified that demonstrated rare or unique biological activities such as treating neurodegenerative diseases, Alzheimer’s, and Parkinson’s diseases with a high degree of certainty over 95 percent. For individual steroids or triterpenoids or a group of compounds, 3D drawings of their predicted biological activities are presented.

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Section: Highly Oxygenated Natural Steroids and Triterpenoidsmentioning

confidence: 99%

Section: Natural Epoxy Steroids Derived From Marine Sourcesmentioning

confidence: 99%

In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

Dembitsky

2021

Marine Drugs

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“…The soft coral S. flexibilis appears to be one of the few corals most studied and described in the scientific literature. The structures of the steroids (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36) are shown in Figure 2 and the potential biological activities are shown in Table 2. Yu and co-workers have used this organism to study steroids.…”

Section: Steroids Derived From the Genus Sinulariamentioning

confidence: 99%

“…Kobayashi and co-workers conducted studies of the soft coral S. mayi, S. gibberosa, S. dissecta and Sinularia sp. collected off the coast of Japan and identified a series of steroids (35)(36)(37)(38)(39)(40)(41)(42) but the biological activity of the isolated steroids was not determined [74][75][76][77][78]. The structures of the steroids are shown in Figure 3 and the potential biological activities are shown in Table 3.…”

Section: Steroids Derived From the Genus Sinulariamentioning

confidence: 99%

“…In addition, photosynthetic corals are successfully cultivated in artificial conditions and are the subject of chemical and biomedical investigation [3,4]. Soft corals produce more than 5800 secondary metabolites [5], including rare and unusual fatty acids [6][7][8][9][10][11][12][13], terpenoids [14][15][16], quinones [17], alkaloids [18][19][20][21][22][23], glycosides [24][25][26][27][28][29][30][31] and steroids [18,[32][33][34][35][36][37]. It is known that many secondary metabolites isolated from marine invertebrates including soft corals, exhibit anticancer and other pharmacological activities [38][39][40][41][42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

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Chemical Diversity of Soft Coral Steroids and Their Pharmacological Activities

et al. 2020

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The review is devoted to the chemical diversity of steroids produced by soft corals and their determined and potential activities. There are about 200 steroids that belong to different types of steroids such as secosteroids, spirosteroids, epoxy- and peroxy-steroids, steroid glycosides, halogenated steroids, polyoxygenated steroids and steroids containing sulfur or nitrogen heteroatoms. Of greatest interest is the pharmacological activity of these steroids. More than 40 steroids exhibit antitumor and related activity with a confidence level of over 90 percent. A group of 32 steroids shows anti-hypercholesterolemic activity with over 90 percent confidence. Ten steroids exhibit anti-inflammatory activity and 20 steroids can be classified as respiratory analeptic drugs. Several steroids exhibit rather rare and very specific activities. Steroids exhibit anti-osteoporotic properties and can be used to treat osteoporosis, as well as have strong anti-eczemic and anti-psoriatic properties and antispasmodic properties. Thus, this review is probably the first and exclusive to present the known as well as the potential pharmacological activities of 200 marine steroids.

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First Synthesis, Confirmation of Stereochemistry, and Cytotoxic Activity of Oxyfungiformin

et al. 2022

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The relative configuration of the marine sesquiterpenoid oxyfungiformin, isolated from the soft coral Capnella fungiformis, was confirmed by synthesis using the natural product guaiol as chiral precursor. The absolute configuration of oxyfungiformin could be assigned by combination of X-ray diffraction and comparison of the values for the specific optical rotation. Oxyfungiformin and a diastereoisomer showed cytotoxic activity in cells originating from cancers of the lung, breast, and cervix.Recently, we have isolated the sesquiterpenoid oxyfungiformin (1) with a 1,2 : 3,4-diepoxide moiety from the soft coral Capnella fungiformis (Figure 1). [3] The constitution of 1 was assigned by a combination of 1D and 2D NMR techniques and

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Naturally occurring marine α,β‐epoxy steroids: Origin and biological activities

Cited by 12 publications

References 77 publications

In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

Chemical Diversity of Soft Coral Steroids and Their Pharmacological Activities

First Synthesis, Confirmation of Stereochemistry, and Cytotoxic Activity of Oxyfungiformin

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