Synthesis of Biologically Active Carvacrol Compounds using Different Solvents and Supports

More, Uttam B.; Narkhede, Hemant P.; Dalal, Dipak S.; Mahulikar, Pramod P.

doi:10.1080/00397910701354608

Cited by 6 publications

(8 citation statements)

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“…Isopropoxy‐carvacrol (known as carvacrol isopropyl ether) was synthesized by Dr. Damião Pergentino de Sousa (Federal University of Paraíba, Department of Pharmaceutical Sciences) from the alkylation of carvacrol, as described previously . The chemical structure of IPC is shown in Fig.…”

Section: Methodsmentioning

confidence: 99%

Isopropoxy‐Carvacrol, a Derivative Obtained from Carvacrol, Reduces Acute Inflammation and Nociception in Rodents

Bonfim

Paiva-Souza

Moraes

et al. 2014

Basic Clin Pharma Tox

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Monoterpenes, compounds mainly presented in essential oils, have important pharmacological actions. Isopropoxy-carvacrol (IPC) is a derivative of the monoterpene carvacrol, and its pharmacological properties have not yet been investigated. The aim of this study was to analyse the acute anti-inflammatory and antinociceptive properties of IPC. Mice (25-30 g) and rats (150-230 g) were pre-treated (i.p.) with IPC at the doses of 10, 30 or 100 mg/kg or vehicle (Tween 80, 0.5%), 30 min. before injection of the phlogistic agents. Both the first and the second phases of formalin-induced nociception were significantly reduced by IPC (100 mg/kg). Injection of carrageenan in mice paw reduced the threshold of stimulus intensity, applied with an analgesymeter, necessary to cause paw withdrawal, which was significantly reduced by 100 mg/kg of IPC. The area under curve (0-4 hr) of rat paw oedema induced by injection of carrageenan was also significantly diminished by the administration of IPC (100 mg/kg). Administration of 12-O-tetradecanoylphorbol-13-acetate (TPA) markedly increased mice ear oedema and myeloperidase (MPO) activity. Topical co-administration of IPC (0.3-3 mg/ear) during the induction did not affect TPA-induced ear oedema, but significantly decreased MPO activity in the ears, when compared with the vehicle. In in vitro experiments, IPC reduced lipoperoxidation induced by different stimuli, showed nitric oxide scavenger activity and did not interfere with murine macrophage viability in concentrations up to 100 lg/mL. These results demonstrate that IPC exerts acute anti-inflammatory and antinociceptive activities, suggesting that it may represent an alternative in the development of new future therapeutic strategies.

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Section: Methodsmentioning

confidence: 99%

Isopropoxy‐Carvacrol, a Derivative Obtained from Carvacrol, Reduces Acute Inflammation and Nociception in Rodents

Bonfim

Paiva-Souza

Moraes

et al. 2014

Basic Clin Pharma Tox

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“…The reactions were rapid, and the Lit. [11,13,16] isolation of products was very simple. The synthesized compounds were characterized by their physical constants, comparative TLC, and spectroscopic proton magnetic resonance (PMR) and infra-red (IR) techniques with the products prepared by conventional routes.…”

Section: Resultsmentioning

confidence: 99%

“…The routine synthetic methods suffer from some disadvantages such as low yields, high temperature conditions, long reaction times, and formation of by-products in addition to tedious reaction workup. [10] In continuation of our work on structural modification of monoterpenoids [11][12][13] and microwave technique, [14] we report herein a simple, rapid, efficient, and environmentally friendly synthesis of carvacrol compounds Scheme 1. The present work includes microwave-mediated alkylation, acylation, and dimerization of carvacrol using solid supports such as silica gel, alumina, and fly ash (a waste generated by thermal power stations by burning coal).…”

Section: Introductionmentioning

confidence: 99%

Solid-Supported Synthesis of Bio-active Carvacrol Compounds Using Microwaves

Narkhede¹,

More²,

Dalal

et al. 2008

Synthetic Communications

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The most abundant and potent natural products having a broad spectrum of biological activity against various pests are terpenoids, especially monoterpenoids. The chemical modification of natural monoterpenoids has been reported to result in modified biological activity. The present work emphasizes the structural modification of carvacrol, a phenolic monoterpenoid, through the synthesis of different ether and ester derivatives that are useful for structure-activity relationship studies to exploit the potent molecules. The carvacrol was reacted with alkyl halides and acid chlorides under microwaves using solid supports such as silica gel, alumina, and fly ash to give ethers and esters, respectively. The synthesis of dimeric ether and ester compounds using dihalides and acid dichlorides was conducted with novel reactions. Additional features of the methodology include very fast reactions, higher yields and purities of the products, and an ecofriendly approach.

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“…Carvacrol is a component of some medicinal plants, such as black cumin (Nigella sativa), oregano (Origanum compactum), Monarda didyma, Origanum dictamnus, Origanum microphyllum, Origanum onites, Origanum scabrum, Origanum vulgare, thyme (Thymus glandulosus), savory (Satureja hortensis) (Aligiannis et al, 2001;De Vincenzi et al, 2004;Coskun et al, 2008;Liolios et al, 2009;Figiel et al, 2010). Also, carvacrol has been produced by chemical and biotechnological synthesis via metabolic engineered microorganisms (More et al, 2007).…”

Section: Carvacrol Sourcesmentioning

confidence: 99%

“…Friedman et al 2002, Sokovic et al (2002), Nastro et al (2004), and Baser (2008) found antimicrobial influences of carvacrol against many species of microbes such as Pseudomonas, Aspergillus, Salmonella, Streptococci, Listeria, Bacillus andFusarium. Burt et al (2005 and2007) observed that carvacrol supplement as antimicrobial component has a significant impact on harmful bacteria including Escherichia coli and Salmonella numbers in chickens, this effect may be attributed to inhibit the growth of pathogenic bacteria by carvacrol vapour. Johny et al (2010) postulated that carvacrol and eugenol decreased (P≤ 0.05) Salmonella Enteritidis and C. jejuni counts in chicken cecal contents to <1.0 log 10 cfu/ml at 50 and 75 mM and 20 and 30 mM, respectively.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Biological Effects and Modes of Action of Carvacrol in Animal and Poultry Production and Health - A Review

Alagawany¹

2015

Adv. Anim. Vet. Sci.

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The carvacrol compound is an antioxidant nutrient, used to enhance growth and productive performance via modification and activation of gastrointestinal tract structure and function and to inhibit/prevent cancer initiations. Numerous studies performed on animal diets supplemented with phytogenic supplements/feed additives containing natural antioxidants such as carvacrol demonstrated its capability to improve performance indices, feed utilization, immune functions and health of livestock as well as reducing the risks of different animal diseases like cancer and other diseases. Such properties could be due to its ability as antimicrobial, antioxidant, antifungal, immunomodulatory, anticancer and anti-inflammatory agents by preventing free radicals and hazardous compounds from interacting with cellular DNA and its ability to change the gut microflora, improving digestion coefficient and absorption of nutrient compounds. The present review illustrates the chemical and physical proprieties, modes of action, metabolism and excretion, biological properties, natural sources and beneficial aspects of carvacrol in animal and poultry production and health.

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Synthesis of Biologically Active Carvacrol Compounds using Different Solvents and Supports

Cited by 6 publications

References 1 publication

Isopropoxy‐Carvacrol, a Derivative Obtained from Carvacrol, Reduces Acute Inflammation and Nociception in Rodents

Isopropoxy‐Carvacrol, a Derivative Obtained from Carvacrol, Reduces Acute Inflammation and Nociception in Rodents

Solid-Supported Synthesis of Bio-active Carvacrol Compounds Using Microwaves

Biological Effects and Modes of Action of Carvacrol in Animal and Poultry Production and Health - A Review

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