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

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

Marine Drugs ◽

10.3390/md19060324 ◽

2021 ◽

Vol 19 (6) ◽

pp. 324

Author(s):

Valery M. Dembitsky ◽

Tatyana A. Gloriozova ◽

Vladimir V. Poroikov

Keyword(s):

Confidence Level ◽

Marine Invertebrates ◽

Biological Activities ◽

Cyclopropane Ring ◽

Fungal Endophytes ◽

Marine Sponges ◽

Lymphocytic Leukemia ◽

Moderate Activity ◽

Activity Levels ◽

Wide Range

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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The Extracts of Some Marine Invertebrates and Algae Collected off the Coast Waters of Vietnam Induce the Inhibitory Effects on the Activator Protein-1 Transcriptional Activity in JB6 Cl41 Cells

Journal of Chemistry ◽

10.1155/2013/896709 ◽

2013 ◽

Vol 2013 ◽

pp. 1-6 ◽

Cited By ~ 3

Author(s):

S. N. Fedorov ◽

V. B. Krasokhin ◽

L. K. Shubina ◽

S. A. Dyshlovoy ◽

N. H. Nam ◽

...

Keyword(s):

Transcriptional Activity ◽

Marine Invertebrates ◽

Biological Activities ◽

Marine Sponges ◽

Marine Organisms ◽

Biologically Active ◽

Luciferase Reporter ◽

Nuclear Factor ◽

Inhibitory Effects ◽

Luciferase Reporter Gene

It has previously been shown that inhibition of the transcriptional activity of the oncogenic nuclear factor AP-1 can result in cancer prevention. Marine invertebrates and alga are a rich source of natural compounds that possess various biological activities. The inhibitory effects of the extracts of Vietnamese marine organisms in relation to the AP-1 transcriptional activity were examined by the luciferase method using JB6 Cl41 cells stably expressing a luciferase reporter gene controlled by AP-1 DNA binding sequence. As was found, 71 species of marine sponges out of 148 species studied contain inhibitors of the AP-1 transcriptional activity. Therefore, marine organisms as a source of biologically active compounds have a great potential for isolation of the new cancer preventive compounds that inhibit the oncogenic AP-1 nuclear factor.

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Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms

Marine Drugs ◽

10.3390/md19060327 ◽

2021 ◽

Vol 19 (6) ◽

pp. 327

Author(s):

Valentin A. Stonik ◽

Sophia A. Kolesnikova

Keyword(s):

Biological Activity ◽

Tumor Cells ◽

Biological Activities ◽

Structural Diversity ◽

Marine Sponges ◽

Terrestrial Plants ◽

Taxonomic Distribution ◽

Tricyclic Core ◽

High Cytotoxicity ◽

Rare Group

In this review, we discuss structural diversity, taxonomic distribution, biological activities, biogenesis, and synthesis of a rare group of terpenoids, the so-called malabaricane and isomalabaricane triterpenoids, as well as some compounds derived from them. Representatives of these groups were found in some higher and lower terrestrial plants, as well as in some fungi, and in a relatively small group of marine sponges. The skeletal systems of malabaricanes and isomalabaricanes are similar to each other, but differ principally in the stereochemistry of their tricyclic core fragments, consisting of two six-membered and one five-membered rings. Evolution of these triterpenoids provides variety of rearranged, oxidized, and glycoconjugated products. These natural compounds have attracted a lot of attention for their biosynthetic origin and biological activity, especially for their extremely high cytotoxicity against tumor cells as well as promising neuroprotective properties in nanomolar concentrations.

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Structural and Bioactive Studies of Halogenated Constituents from Sponges

Current Medicinal Chemistry ◽

10.2174/0929867325666181112092159 ◽

2020 ◽

Vol 27 (14) ◽

pp. 2335-2360 ◽

Cited By ~ 2

Author(s):

Chao Li ◽

Dayong Shi

Keyword(s):

Microbial Communities ◽

Organic Compounds ◽

Biological Activities ◽

Marine Sponges ◽

Nitrogen Compounds ◽

Halogenated Organic Compounds ◽

Bioactive Natural Products ◽

The Past ◽

Tyrosine Derivatives ◽

Polyunsaturated Lipids

: Marine organisms are abundant sources of bioactive natural products. Among metabolites produced by sponges and their associated microbial communities, halogenated natural compounds accounted for an important part due to their potent biological activities. The present review updates and compiles a total of 258 halogenated organic compounds isolated in the past three decades, especially brominated derivatives derived from 31 genera of marine sponges. These compounds can be classified as the following classes: brominated polyunsaturated lipids, nitrogen compounds, brominated tyrosine derivatives and other halogenated compounds. These substances were listed together with their source organisms, structures and bioactivities. For this purpose, 84 references were consulted.

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Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

Marine Drugs ◽

10.3390/md19060330 ◽

2021 ◽

Vol 19 (6) ◽

pp. 330

Author(s):

Timofey V. Malyarenko ◽

Alla A. Kicha ◽

Valentin A. Stonik ◽

Natalia V. Ivanchina

Keyword(s):

Marine Invertebrates ◽

Biological Activities ◽

Complete Information ◽

Structural Features ◽

Marine Organisms ◽

Structural Components ◽

Chemical Structures ◽

The Past ◽

Complex Lipids ◽

Complex Sphingolipids

Sphingolipids are complex lipids widespread in nature as structural components of biomembranes. Commonly, the sphingolipids of marine organisms differ from those of terrestrial animals and plants. The gangliosides are the most complex sphingolipids characteristic of vertebrates that have been found in only the Echinodermata (echinoderms) phylum of invertebrates. Sphingolipids of the representatives of the Asteroidea and Holothuroidea classes are the most studied among all echinoderms. In this review, we have summarized the data on sphingolipids of these two classes of marine invertebrates over the past two decades. Recently established structures, properties, and peculiarities of biogenesis of ceramides, cerebrosides, and gangliosides from starfishes and holothurians are discussed. The purpose of this review is to provide the most complete information on the chemical structures, structural features, and biological activities of sphingolipids of the Asteroidea and Holothuroidea classes.

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Natural Products from Tongan Marine Organisms

Molecules ◽

10.3390/molecules26154534 ◽

2021 ◽

Vol 26 (15) ◽

pp. 4534

Author(s):

Taitusi Taufa ◽

Ramesh Subramani ◽

Peter Northcote ◽

Robert Keyzers

Keyword(s):

Natural Products ◽

Pacific Ocean ◽

Biological Activities ◽

Marine Sponges ◽

Marine Organisms ◽

Biologically Active ◽

Geographic Variability ◽

South Pacific Ocean ◽

New Novel ◽

Rich Diversity

The islands of the South Pacific Ocean have been in the limelight for natural product biodiscovery, due to their unique and pristine tropical waters and environment. The Kingdom of Tonga is an archipelago in the central Indo-Pacific Ocean, consisting of 176 islands, 36 of which are inhabited, flourishing with a rich diversity of flora and fauna. Many unique natural products with interesting bioactivities have been reported from Indo-Pacific marine sponges and other invertebrate phyla; however, there have not been any reviews published to date specifically regarding natural products from Tongan marine organisms. This review covers both known and new/novel Marine Natural Products (MNPs) and their biological activities reported from organisms collected within Tongan territorial waters up to December 2020, and includes 109 MNPs in total, the majority from the phylum Porifera. The significant biological activity of these metabolites was dominated by cytotoxicity and, by reviewing these natural products, it is apparent that the bulk of the new and interesting biologically active compounds were from organisms collected from one particular island, emphasizing the geographic variability in the chemistry between these organisms collected at different locations.

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Chromatography-Independent Fractionation and Newly Identified Molecular Features of the Adzuki Bean (Vigna angularis Willd.) β-vignin Protein

International Journal of Molecular Sciences ◽

10.3390/ijms22063018 ◽

2021 ◽

Vol 22 (6) ◽

pp. 3018

Author(s):

Biane Philadelpho ◽

Victória Souza ◽

Fabiani Souza ◽

Johnnie Santos ◽

Fabiana Batista ◽

...

Keyword(s):

Metal Binding ◽

Cardiovascular Health ◽

Binding Capacity ◽

Biological Activities ◽

Electrophoretic Analysis ◽

Adzuki Bean ◽

Molecular Features ◽

Health Promoting ◽

High Degree

Adzuki seed β-vignin, a vicilin-like globulin, has proven to exert various health-promoting biological activities, notably in cardiovascular health. A simple scalable enrichment procedure of this protein for further nutritional and functional studies is crucial. In this study, a simplified chromatography-independent protein fractionation procedure has been optimized and described. The electrophoretic analysis showed a high degree of homogeneity of β-vignin isolate. Furthermore, the molecular features of the purified protein were investigated. The adzuki bean β-vignin was found to have a native size of 146 kDa, and the molecular weight determined was consistent with a trimeric structure. These were identified in two main polypeptide chains (masses of 56–54 kDa) that are glycosylated polypeptides with metal binding capacity, and one minor polypeptide chain with a mass 37 kDa, wherein these features are absent. The in vitro analysis showed a high degree of digestibility of the protein (92%) and potential anti-inflammatory capacity. The results lay the basis not only for further investigation of the health-promoting properties of the adzuki bean β-vignin protein, but also for a possible application as nutraceutical molecule.

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Biogenic Iodine and Iodine-Containing Metabolites

Natural Product Communications ◽

10.1177/1934578x0600100210 ◽

2006 ◽

Vol 1 (2) ◽

pp. 1934578X0600100 ◽

Cited By ~ 2

Author(s):

Valery M Dembitsky

Keyword(s):

Marine Invertebrates ◽

Biological Activities ◽

Biological Significance ◽

Covalent Bond ◽

Minor Components ◽

Marine Area ◽

The Future ◽

Comprehensive Survey ◽

Living Organisms

This review is intended as a comprehensive survey of iodinated metabolites possessing carbon–iodine covalent bond, which have been obtained from living organisms. Generally thought to be minor components produced by many different organisms these interesting compounds now number more than 110. Many from isolated and identified iodine-containing metabolites showed high biological activities. Recent research, especially in the marine area, indicates this number will increase in the future. Sources of iodinated metabolites include microorganisms, algae, marine invertebrates, and some animals. Their origin and possible biological significance have also been discussed.

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Sulfated and Sulfur-Containing Steroids and Their Pharmacological Profile

Marine Drugs ◽

10.3390/md19050240 ◽

2021 ◽

Vol 19 (5) ◽

pp. 240

Author(s):

Tatyana A. Pounina ◽

Tatyana A. Gloriozova ◽

Nick Savidov ◽

Valery M. Dembitsky

Keyword(s):

Antitumor Activity ◽

Confidence Level ◽

Biological Activities ◽

Marine Sponges ◽

Bioactive Lipids ◽

Pharmacological Profile ◽

Wide Range ◽

Sulfated Steroids ◽

Strong Antitumor Activity ◽

Sulfur Containing

The review focuses on sulfated steroids that have been isolated from seaweeds, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. Sulfur-containing steroids and triterpenoids are sourced from sedentary marine coelenterates, plants, marine sediments, crude oil, and other geological deposits. The review presents the pharmacological profile of sulfated steroids, sulfur-containing steroids, and triterpenoids, which is based on data obtained using the PASS program. In addition, several semi-synthetic and synthetic epithio steroids, which represent a rare group of bioactive lipids that have not yet been found in nature, but possess a high level of antitumor activity, were included in this review for the comparative pharmacological characterization of this class of compounds. About 140 steroids and triterpenoids are presented in this review, which demonstrate a wide range of biological activities. Therefore, out of 71 sulfated steroids, thirteen show strong antitumor activity with a confidence level of more than 90%, out of 50 sulfur-containing steroids, only four show strong antitumor activity with a confidence level of more than 93%, and out of eighteen epithio steroids, thirteen steroids show strong antitumor activity with a confidence level of 91% to 97.4%.

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A Statistical Predictive Model to Prioritize Site Selection for Stress Corrosion Cracking Direct Assessment

Volume 2: Integrity Management; Poster Session; Student Paper Competition ◽

10.1115/ipc2006-10573 ◽

2006 ◽

Cited By ~ 1

Author(s):

Anthony Merle ◽

P. F. Ehlers

Keyword(s):

Stress Corrosion ◽

Stress Corrosion Cracking ◽

Environmental Parameters ◽

Predictive Modelling ◽

Corrosion Cracking ◽

Direct Assessment ◽

Degree Of Certainty ◽

Regression Techniques ◽

Selection For ◽

High Degree

Pipeline stress-corrosion cracking (SCC) is an ongoing integrity concern for pipeline operators. A number of different strategies are currently employed to locate and mitigate SCC. Ultrasonic in-line inspection tools have proven capable of locating SCC, but reliability of these tools in gas pipelines remains in question. Rotating hydrotest programs are effectively employed by some companies but may not provide useful information as to the location of SCC along the pipeline. NACE Standard RP0204-2004 (SCC Direct Assessment Methodology) outlines factors to consider and methodologies to employ to predict where SCC is likely to occur, but even this document acknowledges that there are no well-established methods for predicting the presence of SCC with a high degree of certainty. Predictive modelling attempts to date have focused on establishing quantitative relationships between environmental factors and SCC formation and growth; these models have achieved varying degrees of success. A statistical approach to SCC predictive modelling has been developed. In contrast to previous models that attempted to determine direct correlations between environmental parameters and SCC, the new model statistically analyzed data from dig sites where SCC was and was not found. Regression techniques were used to create a multi-variable logistic regression model. The model was applied to the entire pipeline and verification digs were performed. The dig results indicated that the model was able to predict locations of SCC along the pipeline.

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