Photochemical Transformations of Chalcone-Vitamin E Hybrids

Abstract. Chalcone-vitamin E hybrids 6’-O-tosyl-3,4,5-trimethoxy-δ-tocopherol-chalcone (1), 3,4,5-trimethoxy-δ-tocopherol-chalcone (2), 6’-O-tosyl-3,4,5-trimethoxy-δ-tocopherol-retrochalcone (3) and 3,4,5-trimethoxy-δ-tocopherol-retrochalcone (4) were synthesized as part of a search for new biological activities in these types of derivatives. We report herein on the photoisomerization products of hybrids 1-4, and the effects of the solvent and substitution patterns in producing secondary products such as flavanone 6, 3-deoxyanthocyanidin 8, and hemiketal 10. Photochemically-induced changes are considered important since structural modifications and/or the presence of additional products can affect the biological activity of this type of semisynthetic hybrids. Resumen. Los híbridos de chalcona-vitamina E, 6’-O-tosil-3,4,5-trimetoxi-δ-tocoferol-chalcona (1), 3,4,5-trimetoxi-δ-tocoferol-chalcona (2), 6’-O-tosil-3,4,5-trimetoxi-δ-tocoferol-retrochalcona (3) y 3,4,5-trimetoxi-δ-tocoferol-retrochalcona (4), fueron sintetizados como parte de la búsqueda de nuevos perfiles de actividad biológica para este tipo de derivados. En este trabajo reportamos los productos de fotoisomerización de los híbridos 1-4, y los efectos del disolvente, así como de distintos patrones de sustitución en la generación de productos secundarios como la flavanona 6, la 3-deoxiantocianidina 8, y el hemicetal 10. Los cambios fotoinducidos son considerados de gran importancia debido a que la modificación en la estructura y/o la presencia de productos adicionales puede afectar la actividad biológica de este tipo de híbridos semisintéticos.

Download Full-text

Current Advances in the Biological Activity of Polysaccharides in Dendrobium with Intriguing Therapeutic Potential

Current Medicinal Chemistry ◽

10.2174/0929867324666170227114648 ◽

2018 ◽

Vol 25 (14) ◽

pp. 1663-1681 ◽

Cited By ~ 9

Author(s):

Chun-Ting Lee ◽

Heng-Chun Kuo ◽

Yung-Hsiang Chen ◽

Ming-Yen Tsai

Keyword(s):

Biological Activity ◽

Therapeutic Potential ◽

Biological Activities ◽

Biological Effects ◽

Herbal Medicines ◽

Research Field ◽

Protective Effects ◽

Pharmacological Effects ◽

The Family ◽

Anti Tumor Activity

The polysaccharides in many plants are attracting worldwide attention because of their biological activities and medical properties, such as anti-viral, anti-oxidative, antichronic inflammation, anti-hypertensive, immunomodulation, and neuron-protective effects, as well as anti-tumor activity. Denodrobium species, a genus of the family orchidaceae, have been used as herbal medicines for hundreds of years in China due to their pharmacological effects. These effects include nourishing the Yin, supplementing the stomach, increasing body fluids, and clearing heat. Recently, numerous researchers have investigated possible active compounds in Denodrobium species, such as lectins, phenanthrenes, alkaloids, trigonopol A, and polysaccharides. Unlike those of other plants, the biological effects of polysaccharides in Dendrobium are a novel research field. In this review, we focus on these novel findings to give readers an overall picture of the intriguing therapeutic potential of polysaccharides in Dendrobium, especially those of the four commonly-used Denodrobium species: D. huoshanense, D. offininale, D. nobile, and D. chrysotoxum.

Download Full-text

Naphthoquinone Derivatives Isolated from Plants: Recent Advances in Biological Activity

Mini-Reviews in Medicinal Chemistry ◽

10.2174/1389557520666200818212020 ◽

2020 ◽

Vol 20 (19) ◽

pp. 2019-2035

Author(s):

Esmaeil Sheikh Ahmadi ◽

Amir Tajbakhsh ◽

Milad Iranshahy ◽

Javad Asili ◽

Nadine Kretschmer ◽

...

Keyword(s):

Clinical Trials ◽

Biological Activity ◽

Small Molecules ◽

Anticancer Activity ◽

Clinical Significance ◽

Phase Ii ◽

Biological Activities ◽

Phase Ii Clinical Trials ◽

Naturally Occurring ◽

The Subject

Naturally occurring naphthoquinones (NQs) comprising highly reactive small molecules are the subject of increasing attention due to their promising biological activities such as antioxidant, antimicrobial, apoptosis-inducing activities, and especially anticancer activity. Lapachol, lapachone, and napabucasin belong to the NQs and are in phase II clinical trials for the treatment of many cancers. This review aims to provide a comprehensive and updated overview on the biological activities of several new NQs isolated from different species of plants reported from January 2013 to January 2020, their potential therapeutic applications and their clinical significance.

Download Full-text

Synthesis and Biological Activity of Hydrazones and Derivatives: A Review

Mini-Reviews in Medicinal Chemistry ◽

10.2174/1389557519666191014142448 ◽

2020 ◽

Vol 20 (5) ◽

pp. 342-368 ◽

Cited By ~ 5

Author(s):

Juliana de Oliveira Carneiro Brum ◽

Tanos Celmar Costa França ◽

Steven R. LaPlante ◽

José Daniel Figueroa Villar

Keyword(s):

Biological Activity ◽

Medicinal Chemistry ◽

Biological Activities ◽

New Drugs ◽

New Drug ◽

Cancer Inflammation

Hydrazones and their derivatives are very important compounds in medicinal chemistry due to their reported biological activity for the treatment of several diseases, like Alzheimer’s, cancer, inflammation, and leishmaniasis. However, most of the investigations on hydrazones available in literature today are directed to the synthesis of these molecules with little discussion available on their biological activities. With the purpose of bringing lights into this issue, we performed a revision of the literature and wrote this review based on some of the most current research reports of hydrazones and derivatives, making it clear that the synthesis of these molecules can lead to new drug prototypes. Our goal is to encourage more studies focused on the synthesis and evaluation of new hydrazones, as a contribution to the development of potential new drugs for the treatment of various diseases.

Download Full-text

Quantitative structure-activity relationship model, molecular docking simulation and computational design of some novel compounds against DNA gyrase receptor.

Current Computer - Aided Drug Design ◽

10.2174/1573409916666200625142447 ◽

2020 ◽

Vol 16 ◽

Author(s):

Shola Elijah Adeniji

Keyword(s):

Biological Activity ◽

Molecular Docking ◽

Binding Energy ◽

Biological Activities ◽

Docking Simulation ◽

Dna Gyrase ◽

Computational Design ◽

Multi Drug Resistance ◽

Drug Candidate ◽

Standard Drug

Introduction: Mycobacterium tuberculosis has instigated a serious challenge toward the effective treatment of tuberculosis. The reoccurrence of the resistant strains of the disease to accessible drugs/medications has mandate for the development of more effective anti-tubercular agents with efficient activities. Time expended and costs in discovering and synthesizing new hypothetical drugs with improved biological activity have been a major challenge toward the treatment of multi-drug resistance strain M. tuberculosis (TB). Meanwhile, to solve the problem stated, a new approach i.e. QSAR which establish connection between novel drugs with a better biological against M. tuberculosis is adopted. Methods: The anti-tubercular model established in this study to forecast the biological activities of some anti-tubercular compounds selected and to design new hypothetical drugs is subjective to the molecular descriptors; MATS7s, SM1_DzZ, SpMin4_Bhv, TDB3v and RDF70v. Ligand-receptor interactions between quinoline derivatives and the receptor (DNA gyrase) was carried out using molecular docking technique by employing the PyRx virtual screening software and discovery studio visualizer software. Furthermore, docking study indicates that compounds 20 of the derivatives with promising biological activity have the utmost binding energy of -17.79 kcal/mol. Results: Meanwhile, the interaction of the standard drug; isoniazid with the target enzyme was observed with the binding energy -14.6 kcal/mol which was significantly lesser than the binding energy of the ligand (compound 20).Therefore, compound 20 served as a template structure to designed compounds with more efficient activities. Among the compounds designed; compounds 20p was observed with better anti-tubercular activities with more prominent binding affinities of -24.3kcal/mol. Conclusion: The presumption of this research aid the medicinal chemists and pharmacist to design and synthesis a novel drug candidate against the tuberculosis. Moreover, in-vitro and in-vivo test could be carried out to validate the computational results.

Download Full-text

Synthesis and biological properties of cholecystokinin heptapeptide analogues containing D- and L-forms of tert-leucine or neopentylglycine in position 5

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19912209 ◽

1991 ◽

Vol 56 (10) ◽

pp. 2209-2217 ◽

Cited By ~ 8

Author(s):

Jan Hlaváček ◽

Jana Pírková ◽

Jan Pospíšek ◽

Jiřina Slaninová ◽

Lenka Maletínská

Keyword(s):

Gall Bladder ◽

Solid Phase ◽

Biological Activities ◽

Biological Properties ◽

Phase Synthesis ◽

Structural Modifications ◽

Bladder Contraction ◽

Anorectic Effect ◽

Carboxy Terminal ◽

Anorectic Activity

Using solution or solid-phase synthesis we prepared the cholecystokinin fragment Boc-CCK-7 (Boc-Tyr-(SO3-.Na+)-Met-Gly-Trp-Met-Asp-PheNH2) and its four analogues in which the methionine moiety (Met) in the carboxy-terminal part is replaced by tert-leucine (Tle) or neopentylglycine (Neo) residue or D-enantiomers of these non-coded amino acids. These structural modifications led to reduction of the studied biological activities (gall bladder contraction, anorectic activity, analgetic and sedation activity) of all prepared analogues except Boc[Neo5]-CCK-7 which, being less analgetically active, retains full gall bladder and sedation activity of CCK-8. Moreover, its anorectic activity is substantially higher (400%). This analogue is very interesting particularly for its selectively increased (4x) anorectic effect compared with that of CCK-8.

Download Full-text

Interaction mechanism of aloe-emodin with trypsin: molecular structure–affinity relationship and effect on biological activities

RSC Advances ◽

10.1039/d0ra02712j ◽

2020 ◽

Vol 10 (35) ◽

pp. 20862-20871

Author(s):

Guoyan Ren ◽

He Sun ◽

Gen Li ◽

Jinling Fan ◽

Lin Du ◽

...

Keyword(s):

Molecular Structure ◽

Biological Activity ◽

Biological Activities ◽

Interaction Mechanism ◽

Mechanism Of Interaction ◽

Development And Utilization ◽

Aloe Emodin

The mechanism of interaction between AE and trypsin was studied firstly. The biological activity of both decreased after the interaction. These results provide a basis for the development and utilization of AE.

Download Full-text

Chemical Diversity and Biological Activity of Secondary Metabolites from Soft Coral Genus Sinularia since 2013

Marine Drugs ◽

10.3390/md19060335 ◽

2021 ◽

Vol 19 (6) ◽

pp. 335

Author(s):

Xia Yan ◽

Jing Liu ◽

Xue Leng ◽

Han Ouyang

Keyword(s):

Biological Activity ◽

Secondary Metabolites ◽

Coral Species ◽

Soft Coral ◽

Biological Activities ◽

Vital Role ◽

Chemical Diversity ◽

Pharmacological Activities ◽

Lead Compounds ◽

Coral Genus

Sinularia is one of the conspicuous soft coral species widely distributed in the world’s oceans at a depth of about 12 m. Secondary metabolites from the genus Sinularia show great chemical diversity. More than 700 secondary metabolites have been reported to date, including terpenoids, norterpenoids, steroids/steroidal glycosides, and other types. They showed a broad range of potent biological activities. There were detailed reviews on the terpenoids from Sinularia in 2013, and now, it still plays a vital role in the innovation of lead compounds for drug development. The structures, names, and pharmacological activities of compounds isolated from the genus Sinularia from 2013 to March 2021 are summarized in this review.

Download Full-text

Methodologies in the Analysis of Phenolic Compounds in Roselle (Hibiscus sabdariffa L.): Composition, Biological Activity, and Beneficial Effects on Human Health

Horticulturae ◽

10.3390/horticulturae7020035 ◽

2021 ◽

Vol 7 (2) ◽

pp. 35

Author(s):

Bety W. Hapsari ◽

Manikharda ◽

Widiastuti Setyaningsih

Keyword(s):

Biological Activity ◽

Phenolic Compounds ◽

Human Health ◽

Analytical Methods ◽

Environmental Influence ◽

Biological Activities ◽

Research Progress ◽

Hibiscus Sabdariffa ◽

Beneficial Effects ◽

Positive Effects

Roselle (Hibiscus sabdariffa L.), as an edible flower, has long provided an array of positive effects on human health. This benefit is a result of phenolic compounds that are naturally present mainly in the calyx. Plentiful medicinal remedies and functional foods based on this flower are available worldwide, as supported by the studies of phenolic compounds in recent decades. This paper aims to provide a comprehensive review of the composition, biological activity, and beneficial effects on human health of phenolic compounds in roselle. This review was performed in accordance with the Preferred Reporting Items for Systematic reviews and Meta-Analyses (PRISMA) guidelines. A structured search in the published literature for phenolics compositions in roselle was required prior to the evaluation on the validity of the reported analytical methods. Reliable identification and quantification of phenolic compounds in roselle can be achieved by employing the proper extraction and separation methods. With ample alternative analytical methods discussed here, this review provided an aid for comprehending and selecting the most appropriate method for a particular study. The applications of the analytical methods highlighted indicated that phenolic acids, flavonoids, and their derivatives have been identified and quantified in roselle with a range of biological activities and beneficial effects on human health. It was also disclosed that the composition and concentration of phenolic compounds in roselle vary due to the growth factors, cultivars, and environmental influence. Finally, apart from the research progress carried out with roselle during the last ten years, this review also proposed relevant future works.

Download Full-text