Suresh D. Bagul

Outlooks on Medicinal Properties of Eugenol and its Synthetic Derivatives

Eugenol is found in essential oils of many plants. It belongs to a class of naturally occurring phenolic monoterpenoids, chemically it is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class and is remarkably versatile molecule incorporated as a functional ingredient in several products and has found applications in the pharmaceutical, agricultural, fragrance, flavor, cosmetic and various other industries. Its vast range of pharmacological activities has been well-researched which include antimicrobial, anti-inflammatory, analgesic, antioxidant and anticancer activities. In present review we shortly summarize medicinal properties of Eugenol and its derivatives.

Design, synthesis and biological activities of novel 5-isopropyl-2-methylphenolhydrazide-based sulfonamide derivatives

Sulfonamides have enormous importance in biological sciences. In the present investigation, the fundamental energetic group, hydrazide-based sulfonamide, has been incorporated into a naturally occurring phenolic monoterpenoid, carvacrol (5-isopropyl-2-methylphenol) moiety, with the aim of combining the active groups in order to generate more potent antimicrobial and anti-oxidant agents. Series of hydrazide-based sulfonamide derivatives (IV a–g) have been synthesized and characterized by modern sophisticated techniques such as 1H NMR, 13C NMR and LC–MS. The newly synthesized derivatives were screened for their antimicrobial activities against three fungal (Aspergillus niger, A. flavus and A. fumigatus) and three bacterial (Escherichia coli, Staphylococcus aureus and Bacillus subtilis) species, of which compounds IVc and IVd were found to have good antifungal activity and compounds IVd and IVg exhibited decent antibacterial activities. antioxidant activity was performed by DPPH radical scavenging assay. Compound IVd has been found to be more active in comparison to standard ascorbic acid and compounds IVa, IVb, and IVc demonstrated excellent antioxidant activity.Graphical Abstract

Design, Synthesis and Biological Evaluation of Novel Class DiindolylMethanes (DIMs) Derived from Naturally Occurring PhenolicMonoterpenoids

Several Diindolyl alkanes and their derivatives have been isolated from plant and marine sources. Among the various derivatives of indoles, Diindolyl methanes have wide medicinal applications such as to induce apoptosis in human cancer cells, antibacterial, Anti-inflammatory, antiviral and hormonal control activities. Therefore, they play essential role in marine as well as terrestrial living systems. In present studies we report novel class of Diindolyl methanes prepared from natural phenolic monoterpenoids, via ortho formylation of phenolic monoterpenoids (Carvacrol, Thymol and Eugenol), followed by synthesis, characterization, anticancer, antioxidant and α-amylase inhibitory activities. All the synthesized derivatives show moderate anticancer activities against human breast cell line MCF7, good antioxidant and α-amylase inhibitory activities using DPPH and α-amylase assay respectively.

Synthesis, crystal structures, biological screening and electrochemical analysis of some salen-based transition metal complexes

A new series of transition metal complexes with (1) Mn(III), (2) Co(II), (3) Ni(II) and (4) Cu(II) have been synthesized by the reaction of [6,6′-((1E,1′E)-(propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(5-isopropyl-2-methylphenol)] with suitable metal salts. The synthesized complexes have been characterized by elemental analysis and spectroscopic techniques. The results of single crystal structures show that the metal is bonded to the ligand through the phenolic oxygens and imino nitrogens. Synthesized complexes have been evaluated for antibacterial activity and antioxidant activity, which shows considerable results.

Comparative Anti-Proliferative Studies of Natural PhenolicMonoterpenoids on Human Malignant Tumour Cells

In present study we report prominent effect of carvacrol (5-isopropyl-2-methyl phenol), thymol (2-isopropyl-5- methyl phenol) and eugenol (4 allyl-2-methoxyphenol) on Human melanoma cells. These three compounds were screened for Anti-proliferative test by using Sulforhodamine B (SRB) assay. For this investigation we used human breast melanoma cell line MCF-7, human skin melanoma cell line SK-MEL-2, human colon melanoma cell line HCT-15 and human pancreatic melanoma cell line MIAPaCa-2. Carvacrol was identified as most potent molecule with low GI50 value as 0.1 μL for selected human cancer cell lines; which is comparatively equal to standard drug 14 Adriamycin (ADR). Thymol and Eugenol also exhibited remarkable GI50 for human cancer cell 15 lines.

Perspectives on medicinal properties of natural phenolic monoterpenoids and their hybrids

Carvacrol, thymol and eugenol belong to a class of naturally presenting phenols with a ten-carbon unit, which are present in essential oils of many plants. These versatile molecules are incorporated as useful ingredients in many food products and find applications in agricultural, pharmaceutical, fragrance, cosmetic, flavor and other industries. They are wide ranging of biological and pharmaceutical activities: anti-inflammatory, antimicrobial, analgesic, anticancer and antioxidant. This review summarizes pharmacological and medicinal activities of these phytochemicals and their synthetic hybrids.Graphical Abstract

Design, synthesis, biological screenings and docking simulations of novel carvacrol and thymol derivatives containing acetohydrazone linkage

Carvacrol and thymol are well-known phenolic monoterpenoids present as functional ingredients in numerous products. Keeping the diverse therapeutic activities of phenolic monoterpenes in mind, we attempted to synthesize a new series of acetohydrazone linkage containing carvacrol and thymol derivatives. All synthesized derivatives were characterized by spectroscopic techniques. Finally, all the derivatives were screened for their anti-oxidant activities by using DPPH assay, and anticancer activities by using SRB assay against pancreatic cancer with the MIAPaCa-2 cell line and colon cancer with the HCT-15 cell line. Themolecular docking studies of all the synthesized derivatives were carried out on the cyclooxygenase-2 (COX-2) protein enzyme. In the anti-oxidant test, EC50 values of all the compounds showed excellent anti-oxidant potency, and similarly the values of GI50 in the anticancer test displayed that most of the compounds possess good anticancer potency. Total docking results suggested that all the synthesized compounds exhibit good binding affinity towards receptors.Graphical Abstract

Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage

In the present work, we report the synthesis of six new azomethine linkage containing dihydroxy derivatives of carvacrol, thymol, and eugenol. All the synthesized derivatives have been characterized by spectroscopic techniques and their structures were confirmed by X-ray single crystallography. Synthesized derivatives were screened for anti-oxidant activity using DPPH radical scavenging assay, and anticancer activity by using SRB assay against pancreatic cancer with MIAPaCa-2 and colon cancer with HCT-15 cell lines. The molecular docking studies of all the synthesized derivatives were performed on cyclooxygenases (COX-2) protein enzyme. In the anti-oxidant test, the values of EC50 indicated that all the compounds show excellent anti-oxidant potency, and similarly the GI50 values in anticancer tests indicated that most of the compounds possess good anticancer efficacy. The overall docking score suggested that all the synthesized compounds exhibit good binding affinity towards cyclooxygenases (COX-2) protein enzyme.Graphical Abstract

Synthesis, biological activities and molecular docking simulation of hydrazone scaffolds of carvacrol, thymol and eugenol

In present work, we report the synthesis of 12 new hydrazones and sulfonyl hydrazones linkage containing carvacrol, thymol and eugenol derivatives by simple condensation reactions. Synthesized derivatives have been characterized by 1H NMR, 13C NMR, LC–MS, and X-ray single crystallography techniques, and these derivatives were screened for anticancer testing by using sulforhodamine B assay and anti-oxidant testing by using DPPH assay. Docking studies of all the derivatives against the active site of human heme oxygenase-1 indicated that interaction with the maximum site of the amino acid residue of human heme oxygenase-1 was crucial for anti-oxidant activity. The results show that all derivatives possess interesting biological activities.

Controlled release study of phenol formaldehyde based microcapsules containing various loading percentage of core cypermethrin at different agitation rates

AbstractsCypermethrin is a synthetic pyrethroid that acts as a neurotoxin and is used on large scale in both agricultural and domestic purposes. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. Sometimes it develops tingling, burning, dizziness, and itching to the operator which is why there is a need to develop a safe and effective formulation, which can release cypermethrin under controlled conditions. In this communication, we report a successful encapsulation of cypermethrin within shell of phenol formaldehyde (PF). A series of PF microcapsules have been prepared at various loading percentage and varying agitation rates by in situ polymerization. The formulation consists of mainly two parts, namely emulsification of the oil and wall formation. The morphology of formulated microcapsules was confirmed initially by observing under optical microscope and further with FESEM, which indicated spherical shape, smooth surface, and rigid nature to the microcapsules. The microcapsules were characterized by FTIR, TGA, and particle size analyzer. Release rate of cypermethrin from polymeric microcapsules was calculated by UV spectrophotometer and also by a simple gravimetric method. The stable, safe, and controlled release formulation of easily degradable, highly burning and etching cypermethrin is the success of our present work.Graphical abstract