INFLUENTIAL FACTORS OF PICTET-SPENGLER REACTION IN TOTAL SYNTHESIS OF CANTHIN-6-ONE

2015 ◽  
Vol 77 (2) ◽  
Author(s):  
Julenah Ag Nuddin ◽  
Nur Aini Azib ◽  
Aishah Adam ◽  
Ahmad Sazali Hamzah
Keyword(s):  
Secondary Metabolites ◽  
Total Synthesis ◽  
Structural Modification ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Influential Factors ◽  
The Family

The family of Simaroubaceae is known to contain quassinoids and canthin-6-ones, secondary metabolites that have been reported to possess numerous biological activities such as anticancer. A biomimetic total synthesis of canthin-6-one using Pictet-Spengler condensation according to the procedure by Czerwinski et al. (2003) was explored. The aim of this study was to determine the viability of this reaction for structural modification. In this report, influential factors of carboxyl mediated Pictet-Spengler condensation reaction would be discussed.

scholarly journals Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

2020 ◽  
Vol 21 (19) ◽  
pp. 7078
Author(s):  
Mariola Zielińska-Błajet ◽  
Joanna Feder-Kubis
Keyword(s):  
Biological Activity ◽  
Secondary Metabolites ◽  
Essential Oils ◽  
Structural Modification ◽  
Biological Activities ◽  
Plant Secondary Metabolites ◽  
Biologically Active ◽  
Pivotal Role ◽  
Medical Applications ◽  
Biological And Medical Applications

Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

Ascidian halogen-containing secondary metabolites from the family didemnidae

2019 ◽  
Vol 17 (2) ◽  
pp. 97-130
Author(s):  
Miljana Djordjevic ◽  
Niko Radulovic
Keyword(s):  
Secondary Metabolites ◽  
Total Synthesis ◽  
Current Knowledge ◽  
Structural Complexity ◽  
Structural Diversity ◽  
Pharmacological Properties ◽  
Pharmacological Activities ◽  
The Family ◽  
Biological Tests ◽  
Brominated Compounds

This review summarizes current knowledge concerning the isolation, structural elucidation, biological/pharmacological activities, and total synthesis of halogen-containing secondary metabolites isolated from ascidians of the family Didemnidae. Overall, 81 compounds are presented, displaying great structural diversity and possessing a number of significant biological/pharmacological properties. In addition to the most numerous brominated compounds, chlorinated and iodinated ones were also found. The most prolific genus in regard to the number of published papers and isolated molecules is the genus Didemnum, which was treated separately from the rest of the genera of the ascidian family. The structural complexity of the isolated metabolites prompted a number of synthetic endeavors that not only provided conclusive proof of the structure of the metabolites but also enabled the biological tests and the possible application of these metabolites.

The chemistry and biology of guanidine secondary metabolites

2020 ◽  
Author(s):  
Roberto G. S. Berlinck ◽  
Darlon I. Bernardi ◽  
Taicia Fill ◽  
Alessandra A. G. Fernandes ◽  
Igor D. Jurberg
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Total Synthesis ◽  
Marine Invertebrates ◽  
Biological Activities ◽  
Ecological Roles

Guanidine metabolites isolated from microorganisms, marine invertebrates, terrestrial animals and plants are reviewed, as well as the biosynthesis, total synthesis, biological activities and ecological roles of guanidine natural products.

scholarly journals Eriosema (Fabaceae) Species Represent a Rich Source of Flavonoids with Interesting Pharmacological Activities

2015 ◽  
Vol 10 (7) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Maurice Ducret Awouafack ◽  
Pierre Tane ◽  
Michael Spiteller ◽  
Jacobus Nicolaas Eloff
Keyword(s):  
Erectile Dysfunction ◽  
Chemical Composition ◽  
Secondary Metabolites ◽  
Total Synthesis ◽  
Biological Activities ◽  
Chemical Diversity ◽  
Pharmacological Properties ◽  
Pharmacological Activities ◽  
Natural Sources ◽  
Synthetic Derivatives

Many flavonoids have so far been isolated as main secondary metabolites in plant species of the genus Eriosema (Fabaceae), which contains approximately 160 species. A total of 52 flavonoids including isoflavones, dihydroflavonols, flavonols, flavanones, dihydrochalcones, isoflavanone and their pyrano or glucoside derivatives were isolated and characterized from the five species of this genus investigated to date. Total synthesis and semi-synthesis (acetylation, methylation, hydrogenation, and cyclization) of some isolated flavonoids were reported. Due to several significant pharmacological properties (antimicrobial, cytotoxicity, anti-mycobacterial, antioxidant, antiviral, erectile-dysfunction, vasodilatory and hypoglycemic) of the isolated flavonoids and derivatives, more scientists should be interested in investigating Eriosema species. The present review is the first to document all flavonoids that have been reported from the genus Eriosema to date together with their synthetic and semi-synthetic derivatives, and their pharmacological properties. Dihydrochalcones, which are precursors of other classes of flavonoids, are very rare in natural sources and their isolation from Eriosema species may explain the large number of flavonoids found in this genus. It appears that isoflavone could be a marker for species in this genus. The 83 flavonoids (1–83) documented include 52 isolates, 31 semi-synthetic and 3 totally synthetic derivatives. Data were obtained from Google scholar, Pubmed, Scifinder, Sciencedirect, and Scopus. With 52 different flavonoids isolated from only 5 of the approximately 160 species it shows the remarkable chemical diversity of this genus. This compilation of the biological activities and chemical composition may renew the interest of pharmacologists and phytochemists in this genus.

scholarly journals Qualitative analysis of Phytochemical studies on Sargassum wightii and Padina gymnospora

2021 ◽  
pp. 161-175
Author(s):  
Maria Puspham Grace ◽  
M Rajithra R ◽  
V.Ilakkiya ◽  
Dr.B.Dhanalakshmi
Keyword(s):  
Secondary Metabolites ◽  
Biological Activities ◽  
Binary Compound ◽  
Screening Tests ◽  
Phytochemical Analysis ◽  
Alcohol Extract ◽  
Sargassum Wightii ◽  
Therapeutic Uses ◽  
The Family ◽  
Padina Gymnospora

In recent years, the secondary metabolites are extensively investigated as a supply of healthful agents. The sample for the study constitutes Sargassum wightii and Padina gymnospora and it was collected from the Mandapam coast, Rameswaram, TamilNadu, India. Sargassum wightii is belonging to the family Sargassum wightii and Padina gymnospora belonging to the family Dictyotaceae are 2 brown seaweeds better-known for varied biological activities like bactericide, antiviral, inhibitor, opposed cancer, medicine, etc. Five totally different extracts of Sargassum wightii and Padina gymnospora were subjected to phytochemical analysis of secondary metabolites of qualitatively phytochemical screening tests of twelve different chemical compounds (alkaloids, terpenoids, steroids, tannins, saponins, flavonoids, phenols, coumarins, proteins, sugars, quinones, and glycosides). Among the solvent extracts of alga Sargassum wightii and Padina gymnospora showed the utmost presence of saponins, carbohydrates, proteins, and quinines in 3 completely different extracts (ethanol, methanol, water) except solvent and chloroform. So the present study on extractive values of methyl alcohol extract and the binary compound extract was most in each the seaweeds, however, were significantly a lot of in P. gymnopora than S. wightii. Considering their therapeutic uses, like alternative healthful plants there’s a requirement to try pharmacognostic studies of those 2 seaweeds. KEYWORDS: Seaweeds, Coumarins, Phytochemicals, Sargassum wightii and Padina gymnospora

scholarly journals A Recent Review on Chemistry and Biological Activities of Bryophyllum Pinatum (Lam.) Oken Family: Crassulaceae

2021 ◽  
Vol 37 (2) ◽  
pp. 269-280
Author(s):  
Priyanka Yadav ◽  
Arun Kumar Mishra ◽  
Harpreet Singh
Keyword(s):  
Secondary Metabolites ◽  
Biological Activities ◽  
Biological Effects ◽  
Human Beings ◽  
Pharmacological Activities ◽  
Medicinal Uses ◽  
Herbal Formulation ◽  
The Family ◽  
Web Science ◽  
Phytochemical Constituents

Bryophyllum pinnatum (Lam.) Oken belongs to the family Crassulaceae, one of the important medicinal plants which has great significances to treat various disorders, ailments in human beings. This study tells phytochemical constituents and pharmacological activities of extracts of Bry.pin(Lam.) Oken. The aim of this review is to emphasise the recent and advanced research on different parts of plant extracts used. The forty secondary metabolites were isolated by different researchers where the most important includes flavonoids, terpenoids, glycosides, steroids and these secondary metabolites were responsible for various biological actions as antioxidant, anticancer, antidiabetic, anti-inflammatory, analgesics, wound healing and hepatoprotective actions which are incorporated. All this information gathered into this review were collected by using electronic search as PubMed, Research gate, Elsevier, Google scholar and Web science. Further studies also required on extracts for getting more information about mechanism of action, biological effects, safety, dosage required. By observing the medicinal uses and pharmacological profile of Bry.pin(Lam.) Oken might be transferred into a new various herbal formulation and can report for future.

Total Synthesis of the Antitumor Depsipeptide FE399 and its S-Benzyl Derivative: A Macrolactamization Approach

2020 ◽  
Author(s):  
Takayuki Tonoi ◽  
Miyuki Ikeda ◽  
Teruyuki Sato ◽  
Ryo Kawahara ◽  
Takatsugu Murata ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Condensation Reaction ◽  
Practical Method ◽  
Equilibrium Mixture ◽  
Conformational Isomers ◽  
Single Isomer

<div>An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.</div>

10-step Synthesis of 20-nor-Salvinorin A by Dynamic Strategic Bond Analysis

2017 ◽  
Author(s):  
Jeremy Roach ◽  
Yusuke Sasano ◽  
Cullen Schmid ◽  
Saheem Zaidi ◽  
Vsevolod Katritch ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Opioid Receptors ◽  
Structural Modification ◽  
High Selectivity ◽  
Therapeutic Potential ◽  
Salvinorin A ◽  
High Affinity ◽  
Plant Metabolite ◽  
Complex Architecture ◽  
Property Modification

Salvinorin A (SalA) is a plant metabolite that agonizes the human <i>kappa</i>-opioid receptor (κ-OR) with high affinity and high selectivity over <i>mu- </i>and <i>delta-</i>opioid receptors. Its therapeutic potential has stimulated extensive semi-synthetic studies and total synthesis campaigns. However, structural modification of SalA has been complicated by its instability, and efficient total synthesis has been frustrated by its dense, complex architecture. Treatment of strategic bonds in SalA as dynamic and dependent on structural perturbation enabled the identification of an efficient retrosynthetic pathway. Here we show that deletion of C20 simultaneously stabilizes the SalA skeleton, simplifies its synthesis and retains its high affinity and selectivity for the κ-OR. The resulting 10-step synthesis now opens the SalA scaffold to deep-seated property modification.

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

2018 ◽  
Vol 25 (14) ◽  
pp. 1663-1681 ◽  
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.

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