Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

Vil, Vera A.; Gloriozova, Tatyana A.; Terent’ev, Alexander O.; Zhukova, Natalia V.; Dembitsky, Valery M.

doi:10.1002/vjch.201960001

Cited by 5 publications

(3 citation statements)

References 71 publications

(91 reference statements)

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“…Nakiterpiosinone (165) and nakiterpiosin (166), two related C-nor-D homosteroids, were identified in MeOH extracts of the sponge Terpios hoshinota. These compounds have shown potential as anti-cancer agents, particularly in tumors resistant to existing anti-mitotic agents and dependent on Hedgehog pathway responses for growth [196,197]. Their discovery highlights the importance of exploring marine sources for novel compounds with therapeutic potential.…”

Section: Halogenated Steroids Derived From Marine Sourcesmentioning

confidence: 99%

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Dembitsky

2023

Molecules

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This review delves into the investigation of the biological activity and structural diversity of steroids and related isoprenoid lipids. The study encompasses various natural compounds, such as steroids with aromatic ring(s), steroid phosphate esters derived from marine invertebrates, and steroids incorporating halogen atoms (I, Br, or Cl). These compounds are either produced by fungi or fungal endophytes or found in extracts of plants, algae, or marine invertebrates. To assess the biological activity of these natural compounds, an extensive examination of referenced literature sources was conducted. The evaluation encompassed in vivo and in vitro studies, as well as the utilization of the QSAR method. Numerous compounds exhibited notable properties such as strong anti-inflammatory, anti-neoplastic, anti-proliferative, anti-hypercholesterolemic, anti-Parkinsonian, diuretic, anti-eczematic, anti-psoriatic, and various other activities. Throughout the review, 3D graphs illustrating the activity of individual steroids are presented alongside images of selected terrestrial or marine organisms. Additionally, the review provides explanations for specific types of biological activity associated with these compounds. The data presented in this review hold scientific interest for academic science as well as practical implications in the fields of pharmacology and practical medicine. The analysis of the biological activity and structural diversity of steroids and related isoprenoid lipids provides valuable insights that can contribute to advancements in both theoretical understanding and applied research.

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Section: Halogenated Steroids Derived From Marine Sourcesmentioning

confidence: 99%

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Dembitsky

2023

Molecules

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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%

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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“…Both compounds showed broad cytotoxic activity when evaluated against a panel of human cancer cell lines [82]. (41) was found from Cimicifuga foetida [83]. This compound demonstrated antitumor activity against cancerous MCF-7, HepG2/ADM, HepG2 and HELA cell lines.…”

Section: Cyclopropane Containing Steroids and Triterpenoidsmentioning

confidence: 99%

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

2021

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This review focuses on the rare group of carbon-bridged steroids (CBS) and triterpenoids found in various natural sources such as green, yellow-green, and red algae, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in amoebas, fungi, fungal endophytes, and plants. For convenience, the presented CBS and triterpenoids are divided into four groups, which include: (a) CBS and triterpenoids containing a cyclopropane group; (b) CBS and triterpenoids with cyclopropane ring in the side chain; (c) CBS and triterpenoids containing a cyclobutane group; (d) CBS and triterpenoids containing cyclopentane, cyclohexane or cycloheptane moieties. For the comparative characterization of the antitumor profile, we have added several semi- and synthetic CBS and triterpenoids, with various additional rings, to identify possible promising sources for pharmacologists and the pharmaceutical industry. About 300 CBS and triterpenoids are presented in this review, which demonstrate a wide range of biological activities, but the most pronounced antitumor profile. The review summarizes biological activities both determined experimentally and estimated using the well-known PASS software. According to the data obtained, two-thirds of CBS and triterpenoids show moderate activity levels with a confidence level of 70 to 90%; however, one third of these lipids demonstrate strong antitumor activity with a confidence level exceeding 90%. Several CBS and triterpenoids, from different lipid groups, demonstrate selective action on different types of tumor cells such as renal cancer, sarcoma, pancreatic cancer, prostate cancer, lymphocytic leukemia, myeloid leukemia, liver cancer, and genitourinary cancer with varying degrees of confidence. In addition, the review presents graphical images of the antitumor profile of both individual CBS and triterpenoids groups and individual compounds.

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Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

Cited by 5 publications

References 71 publications

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

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

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

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