scholarly journals Marine Terpenic Endoperoxides

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 661
Author(s):  
Irene Torres-García ◽  
Josefa L. López-Martínez ◽  
Manuel Muñoz-Dorado ◽  
Ignacio Rodríguez-García ◽  
Miriam Álvarez-Corral
Keyword(s):  
Total Synthesis ◽  
Marine Invertebrates ◽  
Biological Activities ◽  
Structural Features ◽  
Naturally Occurring ◽  
Organic Extracts ◽  
Pharmaceutical Uses ◽  
Potential Use ◽  
Dioxane Ring

Organic extracts of marine invertebrates, mainly sponges, from seas all over the world are well known for their high in vitro anticancer and antibiotic activities which make them promising sources of compounds with potential use as pharmaceutical leads. Most of the structures discovered so far have a peculiar structural feature in common: a 1,2-dioxane ring. This is a highly reactive heterocycle that can be considered as an endoperoxide function. Together with other structural features, this group could be responsible for the strong biological activities of the substances present in the extracts. Numerous research programs have focused on their structural elucidation and total synthesis since the seventies. As a consequence, the number of established chiral centres and the similarity between different naturally occurring substances is increasingly higher. Most of these compounds have a terpenoid nature, mainly diterpene and sesterterpene, with several peculiar structural features, such as the loss of one carbon atom. Although there are many reviews dealing with the occurrence of marine peroxides, their activities, or potential pharmaceutical uses, no one has focused on those having a terpene origin and the endoperoxide function. We present here a comprehensive review of these compounds paying special attention to their structural features and their biological activity.

scholarly journals Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

Marine Drugs ◽  
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.

scholarly journals Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

Antibiotics ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 620
Author(s):  
Anne Ardaillou ◽  
Jérôme Alsarraf ◽  
Jean Legault ◽  
François Simard ◽  
André Pichette
Keyword(s):  
Biological Activities ◽  
Biological Evaluation ◽  
Pharmacological Properties ◽  
Cytotoxic Potential ◽  
Naturally Occurring

Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel–Crafts alkylation of the readily available aglycon moiety of neohesperidin dihydrochalcone was performed using cinnamyl, benzyl, and isoprenyl alcohols. This procedure provided a straightforward access to a series of derivatives that were structurally related to natural balsacones, uvaretin, and erioschalcones, respectively. The antibacterial and cytotoxic potential of these novel analogs was evaluated in vitro and highlighted some relations between the structure and the pharmacological properties of alkylated dihydrochalcones.

scholarly journals In vitro cytotoxicity of Aspilia pluriseta Schweinf. extract fractions

2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Sospeter N. Njeru ◽  
Jackson M. Muema
Keyword(s):  
Biological Activities ◽  
Vero Cells ◽  
In Vitro Cytotoxicity ◽  
Root Extract ◽  
Lack Of Information ◽  
Information Gap ◽  
Diphenyltetrazolium Bromide ◽  
Potential Use

Abstract Objectives We and others have shown that Aspilia pluriseta is associated with various biological activities. However, there is a lack of information on its cytotoxicity. This has created an information gap about the safety of A. pluriseta extracts. As an extension to our recent publication on the antimicrobial activity and the phytochemical characterization of A. pluriseta root extracts, here we report on cytotoxicity of tested solvent fractions. We evaluated the potential cytotoxicity of these root extract fractions on Vero cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Results We show that all solvent extract fractions (except methanolic solvent fractions) had cytotoxic concentration values that killed 50% of the Vero cells (CC50) greater than 20 µg/mL and selectivity index (SI) greater than 1.0. Taken together, we demonstrate that, A. pluriseta extract fractions’ earlier reported bioactivities are within the acceptable cytotoxicity and selective index limits. This finding scientifically validates the potential use of A. pluriseta in the discovery of safe therapeutics agents.

Tanshinone IIA: Pharmacology, total synthesis, and progress in structure-modifications

2021 ◽  
Vol 28 ◽  
Author(s):  
Xing Huang ◽  
Hao Deng ◽  
Qing-kun Shen ◽  
Zhe-Shan Quan
Keyword(s):  
Herbal Medicine ◽  
Total Synthesis ◽  
Chinese Herbal Medicine ◽  
Biological Activities ◽  
Structural Features ◽  
Tanshinone Iia ◽  
Structural Modifications ◽  
Chinese Herbal ◽  
Bioactive Constituent

: Tanshinone IIA, a major bioactive constituent of Danshen, a Chinese herbal medicine, has gained extensive exploration owing to its unique structural features and multiple promising biological activities. This review focuses on the pharmacology, total synthesis, and structural modifications of tanshinone IIA. We hope this review will contribute to a better understanding of the progress in the field and provide constructive suggestions for further study of tanshinone IIA.

scholarly journals Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review

2018 ◽  
Vol 15 (1) ◽  
pp. 3-20 ◽  
Author(s):  
Vahideh Zadsirjan ◽  
Majid M. Heravi
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Conjugate Addition ◽  
Chiral Auxiliary ◽  
Addition Reactions ◽  
Chiral Auxiliaries ◽  
Complex Molecules ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Wide Range

Background: The most frequently used chiral auxiliaries, oxazolidinones (Evans' oxazolidinones) have been employed in 1,4-congugate addition reactions to α,β-unsaturated carbonyl compounds. Supplementary to our previous reports in this mini-review, we attempted to underscore the applications of this strategy in a step (steps) in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Objective: In this mini-review, we try to underscore the applications of oxazolidinones (Evans’ oxazolidinones) in 1,4-congugate addition reactions to α,β-unsaturated carbonyl in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Conclusion: In spite of well-known superiority of asymmetric catalyzed reactions, the use of auxiliarycontrolled reactions are still considered as commanding, vital and sometimes as only tools in the generation of stereogenic centers during the construction of complex molecules and total synthesis of naturally occurring compounds. The commercial availability, or readily accessibility of a wide variety of chiral amino alcohols as starting materials to synthesize a wide range of oxazolidinones is the merits of them. In addition, the ease of removal and subjection to various and diverse stereoselective reactions make oxazolidinones as the ideal and superior chiral auxiliaries. In this regard, they were successfully used in asymmetric 1,4-conjugate addition reactions with high stereoselectivities. The high degree of asymmetric induction can be attributed to the rigid chelation of N-acyloxazolidinones with metal ions, as well as the covering of one face of the system by the bulkiness of 4-substituent. In summary, in this report, the importance of the applications of chiral oxazolidinones as suitable chiral auxiliaries in the stereoselective, 1,4-conjugate addition reactions in asymmetric synthesis and in particular, the total synthesis of naturally occurring compounds and some complex molecules were underscored. Noticeably, in these total syntheses, this chiral auxiliary is controlling the stereochemistry of a newly created stereogenic center as well as preserving the configuration of other chiral centers, which already have been presented in the precursor. General methods have been established for the attachment of the chiral auxiliary as a moiety to the substrate molecule in high to excellent yields. At the end of these reactions, this auxiliary can be easily removed leaving various desired reactive motifs for the next step in multi-step synthesis.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

scholarly journals Design and synthesis of multi-target directed 1,2,3-triazole-dimethylaminoacryloyl-chromenone derivatives with potential use in Alzheimer's disease

BMC Chemistry ◽  
2020 ◽  
Vol 14 (1) ◽  
Author(s):  
Hajar Karimi Askarani ◽  
Aida Iraji ◽  
Arezoo Rastegari ◽  
Syed Nasir Abbas Bukhari ◽  
Omidreza Firuzi ◽  
...  
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Biological Activities ◽  
Neuroprotective Effects ◽  
Design And Synthesis ◽  
Catalytic Active Site ◽  
Aβ Aggregation ◽  
Multifunctional Agents ◽  
Potential Use

Abstract To discover multifunctional agents for the treatment of Alzheimer's disease (AD), a new series of 1,2,3-triazole-chromenone derivatives were designed and synthesized based on the multi target-directed ligands approach. The in vitro biological activities included acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition as well as anti-Aβ aggregation, neuroprotective effects, and metal-chelating properties. The results indicated a highly selective BuChE inhibitory activity with an IC50 value of 21.71 μM for compound 10h as the most potent compound. Besides, compound 10h could inhibit self-induced Aβ1–42 aggregation and AChE-induced Aβ aggregation with 32.6% and 29.4% inhibition values, respectively. The Lineweaver–Burk plot and molecular modeling study showed that compound 10h targeted both the catalytic active site (CAS) and peripheral anionic site (PAS) of BuChE. It should be noted that compound 10h was able to chelate biometals. Thus, the designed scaffold could be considered as multifunctional agents in AD drug discovery developments.

scholarly journals Ramalin, a Novel Phenyl Hydrazide from the Lichen Ramalina Terebrata; Isolation, Total Synthesis and Biological Activities

2016 ◽  
Vol 30 (2) ◽  
pp. 35-42
Author(s):  
Durga Prasad Pandey ◽  
Hari Datta Bhattarai
Keyword(s):  
Total Synthesis ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Cost Effective ◽  
Scale Production ◽  
In Vivo Test ◽  
The Antarctic ◽  
Industrial Scale Production

Ramalin, a new L-glutamic acid derivative of phenylhydrazide (Y-glutamyl-N'-(2-hydroxyphenyl) hydrazide, 1) was isolated from the Antarctic lichen, Ramalina terebrata after a series of bioactivity guided fractionation of crude aqueous methanolic extract. Ramalin showed stronger antioxidant activities than commercially available standards, ascorbic acid, trolox, BHA, kojic acid in both, in vitro and in vivo test systems. In addition, ramalin showed no/less toxicity effects against two human cell lines; fibroblast (CCD-986SK) cells and keratinocyte (HaCaT). Thus, realign merits for cosmetic application and industrial scale production were needed. We developed a cost effective total synthesis of ramalin with 71.5% yield and described here.

Total synthesis of indole and dihydroindole alkaloids. X.1,2 The preparation of novel oxygenated catharanthine derivatives

1977 ◽  
Vol 55 (18) ◽  
pp. 3227-3234 ◽  
Author(s):  
James P. Kutney ◽  
Gordon H. Bokelman ◽  
Masahiro Ichikawa ◽  
Edwin Jahngen ◽  
Alummoottil V. Joshua ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Osmium Tetroxide ◽  
Electrophilic Attack ◽  
Naturally Occurring ◽  
Derivatives Of ◽  
Potential Use

Detailed investigations involving the electrophilic attack of various reagents on the 3,4-double bond of catharanthine derivatives (e.g. 3, R = O) furnished a series of novel derivatives of potential use in the syntheses of naturally occurring bisindole alkaloids. These studies include such reagents as peracid, osmium tetroxide, and positive iodine.

Gluten protein functionality in wheat flour processing: a review

2001 ◽  
Vol 52 (12) ◽  
pp. 1311 ◽  
Author(s):  
P. W. Gras ◽  
R. S. Anderssen ◽  
M. Keentok ◽  
F. Békés ◽  
R. Appels
Keyword(s):  
Structural Features ◽  
Protein Functionality ◽  
Gluten Protein ◽  
Physical Processes ◽  
Naturally Occurring ◽  
Wheat Flours ◽  
Insight Into

Gluten protein functionality remains the basis of any understanding of the end-product quality of wheat flours. Information about this functionality has been obtained by both in vivo and in vitro studies. Recent advances include structure/function studies of deletion mutants and transformed genotypes, where the genes incorporated were both naturally occurring genes and genes which have been desired to provide specific structural features. The contributions of these specific changes in structure to the rheology of the resulting doughs allow insight into the underlying physical processes that determine dough and end-product properties.

Sign in / Sign up

Export Citation Format

Share Document