SYNTHESIS AND COMPARATIVE STUDY OF CURCUMINOID ANALOGUES BY CONVENTIONAL AND NON-CONVENTIONAL METHODS

Conventionally, Starting as an vanillin condensed with acetyl acetone by using tributyl borate, boric anhydride and butyl amine then reaction mixture was allowed to stand for overnight at room temperature, after workup it convert yellowish product. Similarly, Non-conventionally, Acetyl acetone, boric acid, anhydrous Sodium sulfate mixed in toluene then substituted aromatic aldehydes added with n-BuNH2, formed mixture irradiated to MWI, after workup, final compound was collected. Second method is environmentally benign gives good yields of curcumin analogues under microwave condition. The reaction performed in less time of reaction, cleaner, no side product, good to excellent yield of product.

Phytochemical analysis and biological activities of ethanolic extract of Curcuma longa rhizome / Análise fitoquímica e atividades biológicas do extrato etanólico do rizoma de Curcuma longa

Abstract Curcuma longa is an important dietary plant which possess several pharmacological activities, including antioxidant, antimicrobial, anti-inflamatory, anticancer and anti clotting etc. The aim of the present study was to determine the phenolic profile of Curcuma longa and in vitro antioxidant and antidiabetic activities. In HPLC chromatogram of Curcuma longa rhizome extract 15 phenolic compounds were identified namely Digalloyl-hexoside, Caffeic acid hexoside, Curdione, Coumaric, Caffeic acid, Sinapic acid, Qurecetin-3-D-galactoside, Casuarinin, Bisdemethoxycurcumin, Curcuminol, Demethoxycurcumin, and Isorhamnetin, Valoneic acid bilactone, Curcumin, Curcumin-O-glucuronide respectively. The ethanolic extract displayed an IC50 value of 37.1±0.3 µg/ml against alpha glucosidase. The IC50 value of DPPH radical scavenging activity was 27.2 ± 1.1 μg/mL. It is concluded that ethanolic extract of Curcuma long is rich source of curcumin and contain several important phenolics. The in vitro antioxidant and alpha glucosidase inhibitory effect of the plant justifies its popular use in traditional medicine.

Resumo A Curcuma longa é uma importante planta presente na dieta da população, pois possui diversas atividades farmacológicas, incluindo antioxidante, antimicrobiana, anti-inflamatória, anticancerígena, anticoagulante etc. O objetivo do presente estudo foi elucidar o perfil fenólico da Curcuma longa e determinar as atividades antioxidante e antidiabética in vitro do extrato. No cromatograma por HPLC do extrato de rizoma de Curcuma longa, foram identificados 15 compostos fenólicos: digaloil-hexosídeo, hexosídeo de ácido cafeico, curdiona, cumárico, ácido cafeico, ácido sinápico, quercetina-3-D-galactosídeo, casuarinina, bisdemetoxicurcumina, curcuminol, demetoxicurcumina, isoramnetina, bilactona de ácido valônico, curcumina e curcumina-O-glicuronídeo. O extrato etanólico apresentou um valor de IC50 de 37,1 ± 0,3 µg / mL em relação à alfa-glucosidase. O valor de IC50 da atividade de eliminação de radicais DPPH foi de 27,2 ± 1,1 μg / mL. Conclui-se que o extrato etanólico de Curcuma longa é uma rica fonte de curcumina e contém várias substâncias fenólicas importantes. O efeito antioxidante in vitro e inibidor da alfa-glucosidase da planta justifica seu uso popular na medicina tradicional.

High water-soluble curcuminoids-rich extract regulates osteogenic differentiation of MC3T3-E1 cells: Involvement of Wnt/β-catenin and BMP signaling pathway / 中草药·英文版

Objective: The present study aimed to evaluate the effect of a high water-soluble curcuminoids-rich extract (CRE) in a solid dispersion form (CRE-SD) using polyvinylpyrrolidone K30 on osteogenic induction of MC3T3-E1 cells. Methods: CRE was pre-purified using a microwave assisted extraction couple with a Diaion® HP-20 column chromatography. The osteoblastic cell proliferation and differentiation potentials of CRE-SD in MC3T3-E1 cells were tested by cell viability, alkaline phosphatase (ALP) activity, and Alizarin red S activity assays. The mRNA expressions of osteoblast-specific genes and underline mechanisms were assessed by a real time PCR and western blot analysis. Results: CRE-SD 50 µg/mL increased alkaline phosphatase (ALP) activity, an early differentiation marker of osteoblasts in both MC3T3-E1 cells and non-osteogenic mouse pluripotent cell line, C3H10T1/2, indicating the action of CRE-SD was not cell-type specific. Alizarin red S activity showed a significant amount of calcium deposition in cells treated with CRE-SD. CRE-SD also upregulated the mRNA expression levels of transcription factors that favor osteoblast differentiation including Bmp-2, Runx2 and Collagen 1a, in a dose dependent manner. Western blot analysis revealed that noggin attenuated CRE-SD-promoted expressions of Bmp-2 and Runx2 proteins. siRNA mediated blocking of Wnt/β-catenin signaling pathway also annulled the influence of CRE-SD, indicating Wnt/β-catenin dependent activity. Inhibition of the different signaling pathways abolished the influence of CRE-SD on ALP activity, confirming that CRE-SD induced MC3T3-E1 cells into osteoblasts through Wnt/β-catenin and BMP signaling pathway. Conclusion: These results collectively demonstrate that CRE-SD may be a potential therapeutic agent for the treatment of osteoporosis.

Effects of a mucoadhesive formulation containing Curcuma longa L. on oral wound healing

Introduction: The aim of this study was to investigate the effects of a topical mucoadhesive formulation with Curcuma longa L. extract (MFC) on oral wound healing. Methods: Seventy-two Wistar rats were randomly assigned to 3 groups: Control, Vehicle, and MFC. Traumatic ulcers were made on the dorsum of the tongue with a 3-mm diameter punch. Vehicle and MFC groups received application of the products twice a day, while animals in the control group were cared for in identical conditions but received no product application. Six rats in each group were euthanized at days 3, 5, 10, and 14. Percentage of repair was calculated based on wound area. HE-stained histological sections were obtained for semi-quantitative analysis of re-epithelization and inflammation. Results: Clinical findings revealed that at days 3 and 5, animals from the MFC group exhibited a significantly higher percentage of wound repair. At day 5, animals from this group also demonstrated a significant increase in the degree of re-epithelization and inflammation. Conclusions: MFC is capable of accelerating oral wound repair in an in vivo model by modulating the inflammatory process and stimulating epithelial proliferation. (AU)

Phytochemical analysis and biological activities of ethanolic extract of Curcuma longa rhizome

Abstract Curcuma longa is an important dietary plant which possess several pharmacological activities, including antioxidant, antimicrobial, anti-inflamatory, anticancer and anti clotting etc. The aim of the present study was to determine the phenolic profile of Curcuma longa and in vitro antioxidant and antidiabetic activities. In HPLC chromatogram of Curcuma longa rhizome extract 15 phenolic compounds were identified namely Digalloyl-hexoside, Caffeic acid hexoside, Curdione, Coumaric, Caffeic acid, Sinapic acid, Qurecetin-3-D-galactoside, Casuarinin, Bisdemethoxycurcumin, Curcuminol, Demethoxycurcumin, and Isorhamnetin, Valoneic acid bilactone, Curcumin, Curcumin-O-glucuronide respectively. The ethanolic extract displayed an IC50 value of 37.1±0.3 µg/ml against alpha glucosidase. The IC50 value of DPPH radical scavenging activity was 27.2 ± 1.1 g/mL. It is concluded that ethanolic extract of Curcuma long is rich source of curcumin and contain several important phenolics. The in vitro antioxidant and alpha glucosidase inhibitory effect of the plant justifies its popular use in traditional medicine.

Resumo A Curcuma longa é uma importante planta presente na dieta da população, pois possui diversas atividades farmacológicas, incluindo antioxidante, antimicrobiana, anti-inflamatória, anticancerígena, anticoagulante etc. O objetivo do presente estudo foi elucidar o perfil fenólico da Curcuma longa e determinar as atividades antioxidante e antidiabética in vitro do extrato. No cromatograma por HPLC do extrato de rizoma de Curcuma longa, foram identificados 15 compostos fenólicos: digaloil-hexosídeo, hexosídeo de ácido cafeico, curdiona, cumárico, ácido cafeico, ácido sinápico, quercetina-3-D-galactosídeo, casuarinina, bisdemetoxicurcumina, curcuminol, demetoxicurcumina, isoramnetina, bilactona de ácido valônico, curcumina e curcumina-O-glicuronídeo. O extrato etanólico apresentou um valor de IC50 de 37,1 ± 0,3 µg / mL em relação à alfa-glucosidase. O valor de IC50 da atividade de eliminação de radicais DPPH foi de 27,2 ± 1,1 g / mL. Conclui-se que o extrato etanólico de Curcuma longa é uma rica fonte de curcumina e contém várias substâncias fenólicas importantes. O efeito antioxidante in vitro e inibidor da alfa-glucosidase da planta justifica seu uso popular na medicina tradicional.

Use of Curcuma longa in cosmetics: extraction of curcuminoid pigments, development of formulations, and in vitro skin permeation studies

Curcuma longa is a ginger family aromatic herb (Zingiberaceae) whose rhizomes contain curcuminoid pigments, including curcumin, a compound known for its anti-inflammatory effects. The objective of this study was to obtain curcuminoid-rich extracts, develop topical formulations thereof, and assess the stability and skin permeation of these formulations. Curcuma longa extracts were obtained and used to develop formulations. Skin permeation studies were conducted in a modified Franz diffusion cell system, and skin retention of curcuminoid pigments was quantified in pig ear membrane. Prepared urea-containing gel-cream formulations were unstable, whereas all others had satisfactory stability and pseudoplastic rheological behavior. The amount of curcuminoid pigments recovered from the receptor solution was negligible. The skin concentration of curcuminoid pigments retained was positive (>20 µg/g of skin, mostly in the stratum corneum), considering the low skin permeability of curcumin. We conclude that development of topical formulations containing curcumin or Curcuma longa extract is feasible, as long as adjuvants are added to improve preservation and durability. The formulations developed in this study enabled penetration of curcumin limited to the superficial layers of the skin and then possibly without a risk of systemic action, thus permitting local use as a topical anti-inflammatory.

Curcuma longa é uma erva aromática, pertencente à família Zingiberaceae e seus rizomas contêm pigmentos curcuminoides, dentre eles a curcumina, conhecida por seu efeito anti-inflamatório. O objetivo deste trabalho foi obter extratos ricos nestes pigmentos, desenvolver e avaliar a estabilidade de formulações tópicas e realizar o estudo da penetração cutânea. Extratos de Curcuma longa foram obtidos e utilizados no desenvolvimento de formulações. A penetração e retenção cutâneas de pigmentos curcuminoides foi avaliada em pele de orelha de porco, utilizando célula de difusão de Franz modificada. As formulações de gel creme preparadas que continham ureia foram instáveis e as demais apresentaram estabilidade satisfatória e comportamento reológico pseudoplástico. A quantidade de pigmentos curcuminoides encontrada na solução receptora foi insignificante, enquanto que a quantidade retida na pele foi superior a 20 µg/g de pele. Concluiu-se como possível o desenvolvimento de formulações tópicas contendo curcumina ou extrato de Curcuma longa, conciliando a adição de adjuvantes para a preservação e maior durabilidade da mesma. As formulações promoveram a penetração da curcumina limitada às camadas superiores da pele, possivelmente sem o risco de ocorrência de ação sistêmica sendo possível a sua utilização para ação local com atividade anti-inflamatória.

Atividade antimicrobiana in vitro do rizoma em pó, dos pigmentos curcuminóides e dos óleos e dos essenciais da Curcuma longa L. / In vitro antimicrobial activity of the ground rhizome, curcuminoid pigments and essential oil of Curcuma longa L.

Este trabalho teve como objetivo avaliar a atividade antimicrobiana da cúrcuma em pó, da curcumina disponível no comércio, dos pigmentos curcuminóides purificados e dos óleos essenciais da cúrcuma. As amostras foram analisadas quanto aos teores de pigmentos curcuminóides por cromatografia líquida de alta eficiência. O óleo essencial foi também analisado quanto à densidade, índice de refração e perfil das substâncias voláteis por cromatografia gasosa e detector de ionização de chamas. A atividade antimicrobiana in vitro foi determinada pelo método de difusão em ágar com discos de papel estéreis, impregnados com os extratos, sendo os diâmetros dos halos de inibição medidos com paquímetro. Os extratos etanólicos da cúrcuma, da curcumina comercial, e dos pigmentos curcumina e desmetoxicurcumina não inibiram o crescimento de Staphylococcus aureus, Bacillus subtilis, Salmonella choleraesuis, Escherichia coli, Aspergillus niger, Saccharomyces cerevisiae, e Candida albicans. Apenas o extrato etanólico da bisdesmetoxicurcumina apresentou atividade antimicrobiana em relação ao B. subtilis. O óleo essencial da cúrcuma apresentou atividade antimicrobiana para o B. subtilis, S. choleraesuis, E. coli, A. niger e S. cerevisiae, sendo que essa atividade aumentou em função do aumento da concentração. Os halos de inibição, obtidos com o óleo essencial, foram significativos, quando comparados aos respectivos antibióticos tradicionais, cloranfenicol e anfotericina, indicando ser o óleo essencial da cúrcuma um agente antimicrobiano em potencial.

The objective of this work was to investigate the antimicrobial activity of ground turmeric, commercially available curcumin, purified curcuminoid pigments and turmeric essential oils. The samples were analyzed for the levels of curcuminoid pigments by high performance liquid chromatography. The essential oil was also analyzed for density, refractive index and profile of volatile compounds by gas chromatography-flame ionization detection. The in vitro antimicrobial activity was determined by the agar diffusion method using sterile disks impregnated with the extracts and the diameters of the inhibition zones were measured using a caliper. The ethanolic extracts of turmeric, commercial curcumin, and the purified pigments curcumin and demethoxycurcumin did not inhibit the growth of Staphylococcus aureus, Bacillus subtilis, Salmonella choleraesuis, Escherichia coli, Aspergillus niger, Saccharomyces cerevisiae, and Candida albicans. Only the ethanolic extract of bisdemethoxycurcumin showed in vitro antimicrobial activity on B. subtilis. The essential oil of turmeric inhibited the growth of B. subtilis, S. choleraesuis, E. coli, A. niger and S. cerevisiae. The antimicrobial activity increased with an increase in the concentration of the essential oil. The inhibitory effects on the microorganisms were significant when compared to the respective traditional antibiotics chloranphenicol and anphotericin. This result indicates that the essential oil from turmeric is a potential antimicrobial agent.

Primary study on hepatoprotective effect of curcuminoid in mice

Background: Curcuminoid in crocus has a wide spectrum of therapeutic effects such as antitumor and anti-inflammatory effects, including antibacterial, antiviral, antifungal, and antispasmodic activities. Curcuminoid \ufffd?biofavonoid, a component of Cucuma longa L is attracting attention of researchers because of their effects and low toxicity. Objectives:To evaluate the hepatoprotective effect of curcuminoid on acute liver injury induced by carbon tetraclorid (CCl4 and paracetamol (PAR) in mice.) Subjects and method: Curcuminoid at doses of 60mg/kg and 120mg/kg were used in 8 consecutive days before hepatotoxins ( CCl4 0.5ml/kg in olive oil or PAR 400mg/kg) in mice.Results & Conclusion: Curcuminoid has hepatoprotective effect, expressed by reductions of serum levels of ALT, AST and liver histopathological injuries, in comparison with the control group ( which didn\u2019t use any drug). Curcuminoid at doses of 60mg/kg and 120mg/kg have hepatoprotective effect on acute liverinjury induced by carbon tetraclorid and paracetamol in mice. Curcuminoid at two different doses and silymarin at a dose 67mg/kg. The result showed that just low dose of curcuminoid (60mg/kg in mice) was enough to protect liver. It was just cheaper and safer than using high dose when using high dose the effect was not increase much.\r\n', u'\r\n', u'